NO176668B - Immobilisering av ligander med radioderiverte polymerer - Google Patents
Immobilisering av ligander med radioderiverte polymerer Download PDFInfo
- Publication number
- NO176668B NO176668B NO911564A NO911564A NO176668B NO 176668 B NO176668 B NO 176668B NO 911564 A NO911564 A NO 911564A NO 911564 A NO911564 A NO 911564A NO 176668 B NO176668 B NO 176668B
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- Prior art keywords
- acid
- polymer
- rdp
- irradiated
- conjugate
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- KIRKGWILHWJIMS-UHFFFAOYSA-K trisodium;1-amino-4-[4-[[4-chloro-6-(2-sulfonatoanilino)-1,3,5-triazin-2-yl]amino]-3-sulfonatoanilino]-9,10-dioxoanthracene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(S([O-])(=O)=O)C=C1NC(C=C1S([O-])(=O)=O)=CC=C1NC(N=1)=NC(Cl)=NC=1NC1=CC=CC=C1S([O-])(=O)=O KIRKGWILHWJIMS-UHFFFAOYSA-K 0.000 description 1
- 229960003732 tyramine Drugs 0.000 description 1
- 229960004441 tyrosine Drugs 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 description 1
- 235000012711 vitamin K3 Nutrition 0.000 description 1
- 239000011652 vitamin K3 Substances 0.000 description 1
- 229940041603 vitamin k 3 Drugs 0.000 description 1
- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
Oppfinnelsen angår fremgangsmåte til fremstilling av radio-derivert polymer ved sammenføring av en radiolyserbar polymer og en ikke-polymerbar konjugand hvor enten den radiolyserbare polymer og/eller konjuganden bestråles med høyenergi-gammastråling for å binde konjuganden til polymeren.
Det er behov for kovalent modifisering av polymere overflater som anvendes som bærere for molekyler, som støtte for celler eller som sorbenter i separasjonsfremgangsmåter. Begrensningene ved adsorptiv belegging av polystyren, heretter betegnet med PS bioanalyser, er generelt kjent og behovet for kovalente koblingsfremgangsmåter er anerkjent i fagområdet.
Funksjonalisert PS egnet til kovalent fastgjøring av ligander og antistoffer er oppnådd ved følgende tre fremgangsmåter: kopolymerisasjon av monomerer som inneholder funksjonelle grupper, som beskrevet i Lloyd og Durscher, J. Appl. Polymer. Sei., Vol. 7, 1963, pp. 2025-2037; kjemisk modifikasjon av PS-produkter, som vist av Chu og Tarcha, P.J., J. Appl. Polymer. Sei., Vol. 34, 1987, pp. 1912-1924, og pode-polymerisasjon av umettede monomerer, som demonstrert i EP 0 106 169. Et problem med disse fremgangsmåten er at de resulterende produkter har svekkede optiske kvaliteter og/eller høy bakgrunnsstøy i bindingsanalyser.
Bare den siste fremgangsmåten som omfatter pode-polymerisasjon av umettede monomerer anvender stråling for å initiere dannelse av kovalent binding mellom støttematerialet og avstandsmoleky-let eller molekylene som skal immobiliseres. Strålings-pode-polymerisasjon anvender polymeriserbare monomerer for å bygge opp en kjede i en strålingsinitiert eller fri radikal polymeri-sasjonsreaksjon. Ulempene assosiert med stråling-pode-polymerisasjon er som følger: 1) Pode-polymerisasjon er teknisk vanskelig å utføre og er ikke lett å kontrollere, dvs. lengden av det podede polymer er variabel; 2) Under utføringen av pode-polymerisasjon kan andre reaksjoner, såsom tverrbinding av de podede polymerkjedene, ta plass i tillegg til polymerisasjon og resultere i et stivt strålingspodet lag av polymer; 3) I tilfeller hvor den ligerende gruppe er festet bare til avslutningen av den podede kjede, ventes ikke pode-polymerisasjon å gi høy grad av støtte; 4) Siden avstandsmolekyler på tilnærmet 10 Å lengde er funnet å være optimal i ligand-antistoffinteraksjoner, se Lowe et al., Biochem. J. , Vol. 133, 1973, pp. 499-514, er de lange (hundre til tusen ganger monomerlengden) podede kjeder oppnådd i EP O 106 769 sub-optimale; 5) I de fleste pode-polymerisasjonsfremgangsmåter er store områder av ladede og/eller hydrofobe overflater intro-dusert, som fører til høye nivåer av ikke-spesifikke interaksjoner og uakseptabel bakgrunnsstøy, se Lowe og Dean, P.D.G. Affinity Chromatography, J. Wiley and Sons, N.Y. 1974. Disse ulemper ved strålings-pode-polymerisasjon kan overkommes ved å anvende ikke-polymeriserbare molekyler til strålingsmediert derivering av polymerer som beskrevet nedenfor.
Det er en hensikt med den foreliggende oppfinnelse å fremstille faststoff støttemateriale med lavt støynivå som har fordelak-tige adsorpsjonsegenskaper for bindingsanalyser. De fleste RDP kan fremstilles uten svekkelse av den optiske kvalitet til transparente polymerer, f.eks. PS, og vil derved gjøre deriverte mikrotiterplater egnet for kolometriske analyser. RDP i partikkelform er egnet til fremstilling av affinitetsor-benter, f.eks. affinitetskromatografi med høy ytelsesevne og immobiliseringen av enzymer.
Denne hensikt er oppnådd med foreliggende oppfinnelse kjenne-tegnet ved det som fremgår av kravene.
Oppfinnelsen angår en fremgangsmåte til å anvende ikke-polymeriserbare små molekyler i strålingsmediert derivering (radioderivering) av polymerer. Når polymerer, såsom støpte PS-produkter (f.eks. mikrotiterplater) eller latekspartikler bestråles med høyenergi (1-10 Mrads) gammastråler i nærvær av ikke-polymeriserbare små molekyler, såsom aromatiske aminer, inkorporeres noen av disse molekyler i polymeren og fører til dannelse av radioderivert polymer, som i det følgende er betegnet RDP. Idet de har forbedrede adsorpsjons- og ionebin-dende egenskaper kan RDP anvendes direkte som celle/vevs-kultursubstrater, ionebyttere eller sorbenter for kromatografi.
Denne oppfinnelse angår videre RDP egnet for innføring av forankringsgrupper til anvendelse for kovalent immobilisering eller fiksering av molekyler på polymere overflater. To klasser av RDP kan identifiseres med hensyn på sin evne til kovalent immobilisering av biologisk viktige molkyler: 1) reaktive RDP, som er istand til å danne kovalente bindinger med molekyler, såsom proteiner, uten hjelp av tverrbindere og 2) funksjonaliserte RDP, som kan anvendes til immobilisering av molekyler med aktivatorer (f.eks. karbodiimider) eller med tverrbindere. Fig. 1 viser det grunnleggende prinsipp ved radioderivering i henhold til foreliggende oppfinnelse og de fire fremgangsmåter hvormed radioderiverte polymerer kan oppnås. Fig. 2 viser virkningene av radioderivering av polystyren på EDC-mediert opptak av fem karboksylsyrer, betegnet A til E. I det øverste panel, betegnet (a) , viser skraverte histogram opptak av radioaktivitet uten etyldietylaminopropyl-karbodiimid (EDC). Det nederste panel (b), viser relativt opptak av radioaktivitet, som er forholdet av opptak oppnådd med bestrålte plater versus ikke-bestrålte plater i nærvær av EDC.
Fig. 2 er beskrevet mer detaljert i eksempel 4.
Prinsippene ved den foreliggende oppfinnelse er illustrert på fig. 1. Betegnelsen radio-derivert beskriver den strålings-medierte stabile fastgjøring av ikke-polymeriserbare molekyler til polymerer. Betegnelsen "radio-" omfatter bestråling på samme måte som stråleterapi (radiotherapy). I skjemaene A,B og C på fig. 1, kan [P] være hvilken som helst polymer som inneholder radiolyserbare bindinger. Konjugander, betegnet som [Cj], kan være hvilken som helst forbindelse som inneholder radiolyserbare bindinger. Spesielt er aromatiske forbindelser egnet med polystyren. Radioaktiverte mellomprodukter [P]<*> og [Cj]<*> kan være frie radikaler og/eller andre reaktive mellomprodukter av [P] og [Cj], som ved rekombinasjoner, kondensa-sjoner eller andre reaksjonstyper fører til dannelsen av radioderiverte produkter.
Det radioderiverte polymer (RDP) er betegnet som [P]-[Cj], som er en felles betegnelse for å beskrive sammenbindingen av [P] og [Cj] ved antatt dannelse av kovalent binding. Selv om ikke-kovalente interaksjoner, såsom innfanging av Cj i P, bidrar til dannelsen av noen av radioderivatene, er disse vist å være stabile nok for immobilisering av molekyler til å være praktisk nyttig i fast-fase analyser. (Eksempel 22). Reaktive RDP er de RDP som er istand til å danne stabile binding(er) med molekyler av praktisk viktighet, såsom ligander, antistoffer og enzymer, i fravær av aktivatorer eller tverrbindere. Funksjonaliserte RDP er RDP som bærer funksjonelle grupper såsom nukleofiler. Tilleggsstoffer, såsom aktivatorer eller tverrbindere er nødvendig for kovalent fastgjøring av molekyler av praktisk viktighet til funksjonaliserte RDP.
Radioderivasjon kan utføres etter fire forskjellige fremgangsmåter, som hver er antatt å resultere i dannelsen av det samme RPD. To fremgangsmåter er vist i fig. IA, den første omfatter simultan radioderivasjon hvori [P] og [Cj] bestråles i nær kontakt med hverandre (dvs. mikrotiterplatebrønner som inneholder en oppløsning av Cj) og, den andre omfatter separat radioderivasjon hvori [P] og [Cj] bestråles separat for å danne [P]<*> og [Cj]<*>, som deretter bringes i kontakt med hverandre. En tredje fremgangsmåte er vist i fig. IB, hvori bare [P] bestråles for å danne [P]<*> som deretter eksponeres til [Cj]. Fig. 1C viser den fjerde måte hvori bare [Cj] bestråles for å danne [Cj]<*>, som deretter eksponeres til [P].
Mens de beskrevne eksempler alle ble utført ved å anvende simultanfremgangsmåten (fig. IA), kan hvilken som helst av de tre andre fremgangsmåtene benyttes. Dannelse av stabile, lenge levende radikaler og/eller andre reaktive mellomprodukter under høyenergibestråling er velkjent (heksadienylradikaler), dannet fra polystyren med høyenergi gammastråling kan de overleve i måneder, dvs. halveringstiden for disse radikaler er tilnærmet et halvt år. Se Wilske og Heusinger, J. Polymer. Sei., Vol. 7, 1969, pp. 995-1010). Den (de) sekvensielle fremgangsmåte(r) kan foretrekkes når den strukturelle integritet til [Cj] eller [P] skal bevares.
Polymerene i foreliggende oppfinnelse er de polymerer som inneholder radiolyserbare bindinger, som gjennomgår radiolyse under betingelsene til radioderivering. I forbindelse med denne oppfinnelse betyr radiolyserbar tilstrekkelig følsomhet for radiolyse til å fremskaffe aktiverte fokuser på polymeroverfla-ten, med stor nok tetthet til å tillate belegging av platen med tilnærmet 100 p. mol/cm<2> forankringsfunksjonaliteter ved bestråling med doser på 1-10 Mrad. Skjønt det foretrukne polymer i foreliggende oppfinnelse er polystyren og dets kopolymer, inkluderer andre egnede radiolyserbare polymerer, acetalharpikser, akryler og deres kopolymerer, alkylharpiks, celluloseacetat, cumaronindenharpikser, epoksyharpikser, furanharpikser, melaminharpikser, paracumaronindenharpikser,' pentaerytritolharpikser, fenoler og deres kopolymerer, polyestere og deres kopolymerer, polyetylen og dens kopolymerer, polypropylen og dens kopolymere, polyamid (nylon, etc), polybutadiener og deres kopolymerer (butadienstyren), polyety-lenglykoler, polyvinylalkohol og dens kopolymerer, polyvinyl-klorid og dens kopolymerer, polyvinylacetat og dens kopolymerer, polyftalater og deres kopolymerer, polyuretan og dens kopolymerer, polyisopren og dens kopolymerer, silikoner og ureaformaldehydpolymerer.
Betegnelsen "konjugand" slik den er anvendt her, er en fellesbetegnelse som refererer seg til den ikke-polymeriserbare forbindelse som initielt bindes til polymeren for å danne RDP ved radioderivering. Disse ikke-polymeriserbare forbindelser er kjemisk rene og inneholder radiolyserbare bindinger. Betegnelsen radiolyserbar er definert ovenfor og betegnelsen ikke-polymer iserbar, som benyttet her, betyr en forbindelse som ikke gjennomgår polymerisasjon, eller dersom den gjør det, skjer polymerisasjon som en uventet bireaksjon, under eksponering til høyenergistråling.
Avhengig av hvilken type konjugand som anvendes fremstiller den foreliggende oppfinnelse to klasser av RDP: reaktive RDP og funksjonaliserte RDP. Reaktive RDP kan anvendes til immobili-sasjon av molekyler, såsom proteiner, uten aktivatorer eller tverrbindere. De kan fremstilles ved generering av reaktive grupper på polymerene, fra ikke-reaktive komponenter under utføringen av radioderivering som i eksempel 3, tabell 3. Den nøyaktige kjemiske natur og mekanismer for dannelse av disse produkter er ukjent. Uten å være bundet av teori er det imidlertid antatt at under bestråling av polystyren i nærvær av vann, oksygen og aromatiske forbindelser, såsom p-aminofenol eller 2-amino-4-Cl-fenol, blir protein-reaktive grupper, såsom aldehyd og/eller kinoner generert. Reaktive RDP kan også oppnås ved radioderivering med strålingsresistente syrehalogenider, syreazider eller aktive estere som er istand til å reagere med passende funksjoner, såsom nukleofile grupper tilstede på proteiner, og andre biologisk viktige molekyler. Reaktive RDP kan også fremstilles ved aktivering av funksjonaliserte RDP.
Reaktive RDP kan fremstilles ved å bestråle polymerer i nærvær av ikke-polymeriserbare konjugander, som er kinoner eller forbindelser fra hvilke kinoner eller kinoidstrukturer genereres ved radioderivering. Generelle eksempler på slike konjugander er aromatiske polyoler, aminofenoler, og visse aromatiske diaminer. Spesielt foretrukne konjugander i denne klasse er p-aminofenol, 2-amino-4-Cl-fenol og 5-I-2-aminopyrimidin. Spesifikke eksempler på reaktiv RDP-dannende konjugander som er kinoner eller forbindelser fra hvilke kinoner genereres er: acenaftenkinon, acetylpyrokatekol, 4-acetylpyrogallol, alizarin, 3-amino-alizarin, 4-aminoaliza-rin, 2,3-dihydroksyanilin, 3,4-dihydroksyanilin, 1,2-dihydroksyantracen, 9,10-dihydroksyantracen, 9,10-antrakinon, 1-amino-9,10-antrakinon, 2-amino-9,10-antrakinon, l-brom-9,10-antrakinon, 2-brom-9,10-antrakinon, l-klor-9,10-antrakinon, 2-klor-9,10-antrakinon, 1-hydroksyantrakinon, 2-hydroksyantrakinon, 1,4-dihydroksyantrakinon, 4,5-dihydroksyantrakinon, 3,4-dihydroksybenzaldehyd, l-klor-2,3-dihydroksybenzen, 4-klor-l,2-dihydroksybenzen, 1,2-diaminobenzen, 1,4-diaminobenzen, o-aminofenol, p-aminofenol, 3,4-diamino-benzensvovelsyre, 2,3-diaminobenzosyre, 2,3-dihydroksybenzosyre, 3,4-diaminobifenyl, 3,4-dihydroksybenzosyre, 2,3-dihydroksybenzofenon, kloranil, kloranilsyre, katechol, 2,5-dihydroksyfenyleddiksyre (homogentistic acid), hydrokinon, 2-acetylhydrokinon, isatin, 9,10-naftacenkinon, 9,11-naftacenkinon, 1,4-diamino-naftalen, 1,2-diaminonaftalen, 2,3-diaminonaftalen, 1,4-diamono-2-metylnaftalen, 1,2-dihydroksynaftalen, 1,4-dihydroksyfaftalen, 2, 3-dihydroksy-naftalen, 1,2-naftokinon, 3-brom-l,2-naftokinon, 4-brom-l,2-naftokinon, 6-brom-l,2-naftokinon, 3-klor-l,2-naftokinon, 3,6-dibrom-l,2-naftokinon, 4,6-dibrom-l,2-naftokinon, 6-hydroksy-l,2-naftokinon, 7-hydroksy-1,2-naftokinon, 3-metyl-1,2-naftokinon, 4-mety1-1,2-naftokinon, 1,4-naftokinon, 2-klor-l,4-naftokinon, 5-klor-l,4-naftokinon, 6-klor-l,4-naftokinon, 2,6-diklor-l,4-naftokinon, 5,6-diklor-l,4-naftokinon, 5,8-diklor-l,4-naftokinon, 5,8-dihydroksy-l,4-naftokinon, 2,5-dimetyl-l,4-naftokinon, 2,6-dimetyl-l,4-naftokinon, 2,8-dimetyl-l,4-naftokinon, 2-etyl-l,4-naftokinon, 2-hydroksy-1,4-naftokinon, 5-hydroksy-l,4-naftokinon, 6-hydroksy-l,4-naftokinon, menadion, 2-fenyl-l,4-naftokinon, nitranilinsyre, naftopurpurin, 3,4-dihydroksy-fenantren, 9,10-fenantrakinon, 1,2-dihydroksy-9,10-fenantrakinon, 2-hydroksy-9,10-fenantrakinon, 4,5-dihydroksy-9,10-fenantrakinon, 3-hydroksy-9,10-fenantrakinon, o-kinon, 3-klor-o-kinon, 4-klor-o-kinon, p-kinon, 2-klor-p-kinon, tolxikinon, fenyl-p-kinon, 2,3-benzotiofenkinon, tiosatin, 2,3-dihydroksytoluen, og 3,4-dihydroksytoluen.
I tillegg til de ovennenvte kan konjugander som er protein-modifiserende reagenser benyttes til å fremstille reaktive
RDP.
Generelt kan proteinmodifiserende reagenser, som er kjent blant fagfolk, tjene som konjugander ved fremstilling av reaktive RDP. Spesifikke eksempler på egnede proteinmodifiserende reagenser er: eddiksyreanhydrid, acetaldehyd, acetaldehyd-bis(2-kloretyl)acetal, acetaldehyd-diacetal, acetaldehyd-dimetylacetal, trikloracetal, acetaldehydbromidetylacetal, acetaldehyd-klordietylacetal, dikloracetaldehyd, triklor-acetaldehyd, acetylaceton, kloracetonkloroform, acetylbromid, acetylklorid, acetylfluorid, eddiksyrebrometylester, eddik-syrekloretylester, adipaldehyd, adamantylfluorformat, 4-amino-4•-dimetylaminobenzen, 5-aminotetrazol, 3-amino-l,2,4-triazol, azobenzen-l-sulfenylbromid, 1-acetylimidazol, 3-aminofenylbor-syrehemisulfat, N-acetyl-DL-cystein, N-acetyl-DL-homocystein-tiolacton, 4-amino-fenylmercur-acetat, N-(4-anilin-l-naftyl)maleimid, azobenzen-2-sulfenylbromid, 4-azidfenancylbromid, l-amino-5-azidnaftalen, 4-azidanilin, 4(5)-azidfluorescein-diacetat, 5-azid-2-nitrobenzosyre, 4-azidfenacyl-bromid, 4-azidfenylisotiocyanat, 4-acetamido-4<1->isotiocyanatstilben-2,2•-disulfonsyre, N-(4-aminobutyl)-N-etylisoluminol, 4-aminofluorescein, 5-aminofluorescein, 7-amino-4-metylcumarin, 8-anilin-naftalen-l-sulfonsyre, auramin 0, benzonitril, 4-benzylamino-7-nitrobenzofurazan, benzyl-klorformat, 4-(B0C-2-aminometyl)fenylisotiocyanat, 5-BOC-2-merkapto-4,6-dimetylpyrimidin, 2-(BOC-oksimino)-2-fenylacetonitril, t-butylkarbazat, (2-bromoktyl)-klorformat, 3-brompropionsyre, bromeddiksyre, 4-bromfenacylbro-mid, 2,3-butandion, 3-brom-3-metyl-2-(2-nitrofenylmerkapto)3H-indol, N-(4-(2-benzimidazolyl)fenylmaleimid, 4,4'-bis-(dimetylamino)-difenylkarbinol, brompyrodruesyre, N-butylmaleimid, omega-brom-4-nitroacetofenon, benzofenon-3,3<1>,4,4<1->tetrakarbok-syldianhydrid, (+)-biotin-4-nitrofenyster, (+)-biotin-4-nitrofenylester, 2,2<1->bikinolon-4,4<1->dikarboksylsyre, bis(4-fluor-3-nitrofenyl)sulfon, 1,5-bis(succinimidooksykarbonylok-sy)-pentan, 4-(BOC-aminoetyl)fenylisotiocyanat, N-BOC-1,6-diaminoheksan, N-(4-(2-benzimidazolyl)fenylmaleimid, 2',4'-bis(di(karboksymetyl)aminoetyl)fluorescein, 4,4'-bis(dimetylamino)difenylkarbinol, 4-brommetyl-7-metoksy-cormarin, BOC-L-tyrosinhydrosuccinimidester, benzaldehyd, 2-amino-benzaldehyd, 3-amino-benzaldehyd, 4-amino-benzaldehyd, 2-brom-benzaldehyd, 3-brom-benzaldehyd, 4-brom-benzaldehyd, 2-klor-benzaldehyd, 3-klor-benzaldehyd, 4-klor-benzaldehyd, 2-hydroksy-benzaldehyd, 3-hydroksy-benzaldehyd, 4-hydroksy-benzaldehyd, benzensulfin-syreklorid, benzen-sulfonsyreklorid, benzensulfonsyrefluorid, benzoylbromid, benzoylklorid, benzoylfluorid, 2-klor-ben-zosyreanhydrid, 3-klorbenzosyreanhydrid, 3-klorbenzoylklorid, 4-klorbenzosyreanhydrid, 4-klorbenzoylklorid, bioksiran, 1,2-butylenoksid, smørsyreanhydrid, butyrylbromid, bis(2-nitrofe-nyl)disulfid, (bis(trifluoracetoksy)iod)benzen, kloral, kloralalkoholat, kloreddiksyreanhydrid, klordifenylacetylklo-rid, cumaldehyd, 1,2-epoksy-cykloheksan, kaprylsyreanhydrid, kaprylklorid, cyklamen-aldehyd, 2-klor-3,5-dinitropyridin, klor-etansulfonsyre, 4-klor-7-nitrobenzofurazan, citraconsyre anhydrid, 2-cyanopyridin, 1,2-cykloheksandion, 1,1'-karbonyl-diimidazol, 1,1'-karbonyl-di(1,2,4-triazil), N-cykloheksyl-N•-(2-morfolinoetyl)karbodiimidmeto-p-toluensulfonat, kamforkinon-10-sulfonsyre, kloramin B, kloramin T, N-klorsuccinimid, cyanur-fluorid, kloranil, kloretansulfonsyre, 4-(klormerkuri)-benzensulfonsyre, 4-(klormerkuri)benzosyre, 4-klor-7-sulfoben-zofurazan, l-cyan-4-dimetylaminopyridintetrafluorborat, cystamin, cibacron blått 3G-A, karbetoksymetylisotiocyanat, difenyletanal, difenyleddiksyreanhydrid, difenylacetylklorid, difenylkarbodiimid, 1,2-diacetylbenzen, N,S-diacetylcysteamin, di-t-butyldikarbonat, N,N-dietyl-2,4-dinitro-5-fluoranilin, dietylpyrokarbonat, 4-dimetylamino-benzen-4•-isotiocyanat, 4-dimetylaminoazobenzen-4•-sulfonyl-klorid, 4-(5-dimetylaminonaf-talen-l-sulf onylamino) f enylisocyanat, 5-dimetylamino-l-naftalensulfonylklorid, dimetylmaleinsyreanhydrid, 3,5-dimetyl-1-pyrazolyl-formamidiniumnitrat, 2,4-dinitro-5-fluoranilin, 2,4-dinitro-l-fluorbenzen, N,N'-di-t-butylkarbodiimid, N,N'-dicykloheksylkarbodiimid, N-(dimetylaminopropyl)-N'-etyl-karbodiimid, 2-etoksy-l-etoksykarbonyl-l,2-dihydrokinolin, 1,4-ditioerytritol, (-)1,4-ditio-L-treitol, 1,4-ditio-DL-treitol, diisopropylfluorfosfat, 4-dimetylaminoazobenzen-4•-sulfonylklo-rid, 5-dimetylamino-l-naftalensulfonylklorid, 4-dimetylamino-benzaldehyd, dietylpyrokarbonat, 1,2-diiodoetan, N-(4-dimetyl-aminoazobenzen-4')iodoacetamid, N-(7-dimetylamino-4-metyl-3-cumarinyl)maleimid, 2,2'-difenyl-l-picrylhydrazyl, 2,2'-ditiobis(4-metyltiazol), 5,5•-ditiobis(2-nitrobenzosyre), (3,3',6)-2,2'-ditiobis(5-nitropyridin), 2,2'-ditio dibenzosyre, 2,2'-ditiodipyridin, 4,4'-diazidostilben-2,2'-disulfonsyre, dietylentriaminpentaeddiksyredianhydrid, dietylenpyrokarbonat, 1,5-difluor-2,4-dinitrobenzen, 1,6-diisocyanatheksan, dimetyl-adipimidat-N-(dimetylaminopropyl)-N•-etylkarbodiimid, dimetyl-3,3'-ditiodipropionimidat, dimetylpimelindiimidat, dimetyl-suberimidat, 3,3'-ditiodipropionsyre-bis(N-hydroksy-suc-cinimidester), dansylkadaverin, dansylhydrazin, 4-(4,6-diklor-s-triazin-2-ylamin)fluorescein, 4-(5-dimetylaminonaftalen-1-sulfonylamino)fenylisocyanat, dimetyloksyran, 4-dimetylamino-l-naftylisotiocyanat, difenylborsyre-anhydrid, (diacetoksy-iod)benzen, 6-diazo-5-okso-5,6-dihydro-l-naftalensulfonylklorid, 2,3-dimerkapto-l-propanol, 2,4-dinitrofenylhydrazin, 1,6-difenyl-1,3,5-heksatrien, 1-dodekanetiol, epibromhydrin, alfa-epiklorhydrin, beta-epiklorhydrin, epiiodhydrin, epicyanohyd-rin, etansylfonylklorid, N-etoksykarbonyl-ftalimid, etylacet-imidat, N-etylmaleimid, etyl-trifluoracetat, etanetiol, etyldiazoacetat, furfural, 9-fluorenylmetylklorformat, 5'-(4-fluorosulfonylbenzoyl)adenosin, formaldehyd, 4-formyl-l-metylpyridiniumbenzensulfonat, fluoresceinmerkur-acetat, fluoresceinisotiocyanat, fluoresceinisotiocyanat isomer I, 4-fluor-3-nitrofenyl azid, N-(3-fluorantyl)maleimid, fluor-esceinamin, 4-fluor-7-nitrobenzofurazan, fluram, glykolaldehyd, glyoksysyre, glykolsyreanhydrid, glycidsyre, glycidol, glycinamid, glyoksal, L-glutation (oksidert), glutaraldehyd, glutarylklorid, glutarnitril, 2-hydroksy-5-nitrobenzylbromid, 6-hydroksy-2-naftyl-disulfid, heksametylendiisocyanat, 3-(4-hydroksy-fenyl)propionsyre-N-hydroksysuccinimidester, N-hydroksy-sulfosuccinimid, DL-homocysteintiolakton, 2'-(4-hydroksy-fenylazo)benzosyre, iodeddiksyre, iodacetamid, iodeddisyreetylester, isobutyrylklorid, isonikotin-aldehyd, isonikotinsyreanhydrid, 2-iminotiolan, N-iodosuccinimid, N-(iodacetaminoetyl)-1-naftylamin-5•-sulfonsyre, iodacetonitril, iodmetan, 2-iodbenzosyre, isatin, isoftalaldehyd, Lucifer gult CH, Lucifer gult VS, metoksyacetylklorid, metaldehyd, 5,5'-metylendisalicylaldehyd, metansulfonylklorid, metyloksiran, maleinsyreanhydrid, mersalylsyre, N-metoksykarbonylmaleimid, 2-(2-(2-(2)-metoksyetoksy)etoksy) eddiksyre, metylisotiocyanat, S-metylisotioureasulfat, O-metylisotioureasulfat, O-metyliso-tioureahydrogensulfat, metyl-4-nitrobenzensulfonat, 2-metoksy-5-nitrobenzylbromid, 4-maleimidosmørsyre, 6-maleimidokaproin-syre, N-maleoyl-beta-alanin, N-(2-merkaptopropionyl)glycin, kvikksølvorange, 0-metyl-N,N'-diisopropylisourea, N-metyl-maleimid, S-metylmetan-tiosulfonat, metyl-4-nitrobenzensul-fonat, malononitril, metyl-4-hydroksybenzimidat, N-metyl-merkaptoacetamid, N-metylfenazonmetylsulfat, 0-acetylman-delylklorid, metylglyoksal, 2-nitrobenzen-sulfenylklorid, 4-nitrofenyliodoacetat, 2-nitro-5-tiocyanatbenzosyre, 4-nitro-L-tyrosinetylester, 1-naftaldehyd, 2-naftaldehyd, 2-hydroksy-l-naftaldehyd, alfanaftyltiocyanat, betanaftyl-tiocyanat, ninhydrin, 4-nitrofenylacetat, 4-nitrofenylformat, N-nitros-N-metyl-4-toluensulfonamid, 2-nitrobenzensulfenylklorid, 1-hydroksy-2-naftaldehyd, naftalinsyreanhydrid, naftalensvovel-syreklorid, naftosulton, 1-naftonsyreanhydrid, 1-naftonsyreklorid, 2-naftonsyreanhydrid, 2-naftonsyreklorid, oktanal, 2-oksoglutarsyre, fenoksyeddiksyreanhydrid, fenoksyacetylklorid, fenyleddiksyreanhydrid, fenylacetylklorid, o-fenacylbromid, m-klor-p-fenacylbromid, p-klor-p-fenacylbromid, p-brom-p-fenacylklorid, fenacylklorid, fenylmaleinsyreanhydrid, paImitaldehyd, paraldehyd, pentanal, 4-hydroksy-pentanal, 3-hydroksy-2-metylpentanal, 2-oksopentanal, 4-metyl-2-oksopentanal, 4-oksopentanal, 2-fenylpentandioinsyre, 2-fenylpentandioinsyreanhydrid, 3-fenylpentandioinsyreanhydrid, ftalal-dehyd, ftaldialdehyd, ftalaldehydsyre, ftalsyreanhydrid, ftalsyre-diklorid, propanal, propanaldietylacetal, 2-brom-propanal, 2-klorpropanal, 3-klorpropanal, 2-klor-2-metylpropa-nal, 2,3-dibrompropanal, 2,2-diklor-propanal, 2,3-diklorpropa-nal, 2-fenoksypropanal, 2-fenylpropanal, 3-fenylpropanal, pivaldehyd, propanolonal, propionsyreanhydrid, propionylbromid, propionylklorid, fenylglycidol, fenylrodanat, pentafluor-fenylacetat, fenylisotiocyanat, fenylmetansulfonylfluorid, ftalonitril, pyridoksalhydroklorid, pyromellitinsyredian-hydrid, 9,10-fenantren-kinon, fenylglyoksal, fenylmetansul-fonylf luorid, D-penicillamin, fenylarsinoksid, N,N'-(1,2-fenylen) dimaleimid, N,N'-(l,4-fenylen)dimaleimid, N-fenyl-maleimid, N-propylmaleimid, N-(3-pyrenyl)maleimid, polyetylen-glycol 600 disyre, fenacylbromid, fotobiotin, 9,10-fenantren-kinon, pyridin-4-carboksaldehyd, benzylrodanat, fenylrodanat, p-tolyl-rodanat, rodamin b isotiocyanat, ravsyreanhydrid, ravsyremonoklorid, benzylsulfonylklorid, salicylaldehyd, N-succinimidyl-3-(2-pyridyltio)-propionat, 2-sulfobenzosyre syklisk anhydrid, 4-sulfofenylisotiocyanat, N-succinimidyl-3-maleimidbenzoat, N-succinimidyl-4-maleimidbutyrat, N-suc-cinimidyl-6-maleimidokaproat, N-succinimidyl-3-maleimidopropio-nat, sebaconitril, sulforodamin 101 syre, sulforodamin 101 syreklorid, styrenoksid, tereftalaldehyd, p-toluensulfinyl-klorid, o-toluensulfonylklorid, p-toluensulfonylklorid, 3-tosyloksypropylisocyanat, trifluoreddiksyreanhydrid, 3-trifluormetylfenylisocyanat, 2,2,6-trimetyl-l,3-dioksin-4-on, 2,4,6-trinitrobenzensulfonsyre, trietoksoniumtetrafluorborat, trimetyloksoniumtetrafluorborat, 1-tioglycerol, tioglycolsyre-tributylfosfin, N-tosyl-L-lysinklormetylketon, tosyl-L-fenylalaninklormetylketon, tiodietylen-glykol, toluylen-2,4-diisocyanat, tetrametylrodamin B isotiocyanat, 6-(4-toluidin)-2-naftalensulfonsyre, 2,2,2-trikloretanol, toluensulfonsyre, vanilin, veratrylaldehyd, valerianaldehyd, valerylklorid, m-xylylendiisocyanat, N-acetyl-beta-glykosamin-fenylisotiocyanat, alfa-glukopyranosylfenyl-isotiocyanat, beta-glycopyranosyl-fenylisotiocyanat, beta-galktopyranosylfenylisotiocyanat og alfa-mannopyranosylfenylisotiocyanat.
Funksjonaliserte RDP kan oppnås ved å velge en konjugand med den korrekte funksjonelle gruppe for radioderivering. F.eks. kan nukleofiliserte RDP oppnås ved å anvende nukleofil-inneholdende konjugander. Dette prinsipp er vist på fig. 2. Når polystyren er radioderivert i nærvær av aromatiske aminer, såsom p-aminofenol, DL-2-amino-l (p-hydroksyfenyl)-etanol-1 eller benzylestere av aminosyrer, kan de resulterende RDP anvendes for kobling av karboksylinneholdende forbindelser med karbodiimid.
Valget av konjugand for å fremstille en funksjonalisert RDP avhenger av den spesielle funksjonalitet som er ønsket. F.eks. kan aromatiske aminer anvendes hvis en funksjonell gruppe som er istand til å bli diazotert er ønsket. Når en nukleofil funksjonalisert RDP er ønsket bør forbindelser som inneholder nukleofile grupper, såsom amino, hydroksyl eller merkaptogrup-per, anvendes som konjugand. De foretrukne konjugander i denne klasse er aminer som inneholder aromatiske strukturer, men ikke nødvendigvis aromatiske aminer. Eksempler på disse foretrukkede konjugander er anilin og dets derivater (dvs. m-fenylendiamin), aminofenoler (dvs., p-aminofenol), naftylaminer (dvs., l,2,naftylendiamin) aromatiske estere av aminosyrer (dvs., li-ser inbenzy lester) og forbindelser som inneholder forskjellige nukleofiler, såsom 2-amino-l(4-hydroksyfenyl)-etanol-1 (AHE). Spesifikke eksempler på egnede nukleofilinneholdende konjugander til fremstilling av nukleofile funksjonaliserte RDP er: tionalid, tioglycolsyreanilid, p-acetylfenol, o-merkapto-anilin, m-merkapto-anilin, p-merkapto-anilin, 1-hydroksyantracen, 2-hydroksyantracen, 9-hydroksyantracen, 3-hydroksyazobenzen, 4-hydroksyazobenzen, m,m'-metylen-difenol, p,p'-metylendifenol, 1,5-dihydroksynaftalen, 1,6-dihydroksynaftalen, 1,7-dihydroksynaftalen, 1,8-dihydroksynaftalen, 2,6-dihydroksynaftalen, 2,7-dihydroksynaftalen, 1-hydroksynaftalen, 2-hydroksynaftalen, 2-hydroksyfenantren, 3-hydroksyfenantren, 9-hydroksyfenantren, fenol, 2-bromfenol, 3-bromfenol, 4-bromfenol, 3-brom-5-klorfenol, 4-brom-2-klorfenol, 2-klorfenol, 3-klorfenol, 4-klorfenol, 2,4-dibromfenol, 2,6-dibrom-fenol, 2,3-diklorfenol, 2,4-diklorfenol, 2,5-diklorfenol, 2,6-diklorfenol, 3,4-diklorfenol, 3,5-diklorfenol, 2-iodfenol, 3-iodfenol, 4-iodfenol, 2-merkaptofenol, 3-merkaptofenol, 4-merkaptofenol, 2-pyridol, 3-pyridol, 4-pyridol, saligenin, alfa-3-dihydroksytoluen, alfa,2-dihydroksytoluen, alfa-4-dihydroksytoluen, 2,4-dihydroksytoluen, 2,5-dihydroksytoluen, 3,5-dihydroksytoluen, 2-hydroksytoluen, 3-hydroksytoluen, 4-hydroksytoluen, tyrosin, og DL-2-amino-l(4-hydroksyfenyl)-etanol-1.
Spesifikke ekempler på egnede aminogruppeinneholdende konjugander til fremstilling av funksjonaliserte RDP som er reaktive med karboksyl-inneholdende forbindelser i nærvær av aktivatorer, såsom karbodiimider er: n-butylamin, s-butylamin, t-butylamin, putrescin, cykloheksylamin, etylamin, etylen-diamin, heksametylen-diamin, 1-amino-pentan, 2-amino-pentan, 3-amino-pentan, kadaverin, fenylalanin, propylamin, isopropyl-amin, amfetamin, 1,2-propandiamin, trimetylendiamin, DL-alanin, beta-alanin, benzylamin, m-brombenzylamin, p-brombenzylamin, og trietylentetramin.
De foretrukne aminogruppe-inneholdende konjugander egnet til kobling av forskjellige karboksylforbindelser i nærvær av en EDC aktivator, er DL-2-amino-l(4-hydroksyfenyl)-etan-l-ol, p-aminofenol, 3,4-diaminopyridin, 1-alaninbenzylester, li-ser inbenzy lester (se eksempel 4, fig. 2).
Betegnelsen aktivatorer, som benyttet her, refererer seg til de typer av stoffer egnet til aktivering av karboksylgrupper for peptidsyntese, som omfatter blandede anhydridtyper, aktive estertyper, hydroksylamintyper og forskjellige koblingsreagen-ser (se M. Bodanszky: Principles of Peptide Synthesis, Springer Verlag, New York, 1984). I tillegg til å være reaktive med aminogrupper og egnet for peptidbindingsdannelse, kan disse aktivatorer aktivere karboksylgrupper til å reagere med andre funksjonaliteter såsom SH og OH. Spesifikke eksempler på passende aktivatorer er: acyl-klorider, såsom valerylklorid, fosforsyreklorider, arsensyreklorider, fosforsyreklorider, pyridinfosforsyreklorider, acylfosfoniumsalter, svovelsyre-derivater, tiolsyre, Leuchs anhydrider, aktive estere, såsom fenylestere, nitrofenylestere, dinitrofenylestere, metok-syfenylestere, klorfenylestere, fluorfenylestere, reaktive hydroksylaminderivater, såsom hydroksyftalamidestere, N-hydroksysuccinimidestere, N-hydroksypiperidinestere; koblinas-rea<g>enser: spesifikke karbodiimider såsom dicykloheksyl-karbodiimid, etyl-dimetylaminopropyl-karbodiimid (EDC), 1-etoksykarbonyl-2-etoksy-l,2-dihydrokinolin (EEDQ), 1-isobutyok-sykarbonyl-2-isobutyloksy-l,2-dihydrokinolin (IIDO), difenylke-tener, acyloksy-fosfoniumsalter. Hjelpenukleofiler kan anvendes som additiver i koblingsreaksjoner (primært med karbodiimider) såsom N-hydroksysuccinimid, 1-hydroksybenztriazol, 3-hydroksy-3,4-dihydro-l,2,3,-benztriazin-4-on (HOObt).
En viktig gruppe av RDP er de oppnådd med konjugander som er aromatiske aminer. Fortrinnsvis aromatiske aminer, såsom fenylendiaminer, aminopyrimidin, naftylamin eller 5-1-2-aminopyrimidin gir RDP som kan diazotiseres, hvorved diazonium-saltderivatet kan anvendes videre for å koble egnede molekyler såsom proteiner, med fenolsidegrupper (eksempel 5, tabell 4). De foretrukne aromatiske aminer, som er funnet spesielt egnet til fremstilling av diazotiserbare RDP, passende for å gi relativt stor grad av kobling av RNase eller hemoglobin, er 2-naftylamin, 5-I-2-aminopyrimidin, 1,2-naftylendiamin, 1-5-naftylendiamin, m-fenylendiamin, og 2,6-diaminopyridin (fra tabell 4).
Spesifikke eksempler på egnede aromatiske aminer som kan anvendes til fremstilling av funksjonaliserte RDP eller diazotiserte RDP er: 2-aminoazobenzen, 3-amino-azobenzen, 4-aminoazobenzen, 2,2'diaminoazobenzen, 2,4-diaminoazobenzen, 4,4<*->diaminoazobenzen, l-klor-2,4-diaminobenzen, l-klor-3,5 diaminobenzen, 2-klor-l,3-diaminobenzen, 2-klor-1,4-diaminobenzen, 4-klor-l,2-diaminobenzen, 1,3-diaminobenzen, 1,4-diaminobenzen, ortanilinsyre, metanilinsyre, sulfanilinsyre, 3,5-diaminobenzensulfonsyre, 2-aminobenzimidazol, antranilinsyre, 3-aminobenzosyre, 4-aminobenzosyre, 2,4-diaminobenzosyre, 2,5-diaminobenzosyre, 3,4-diaminobenzosyre, 3,5-diaminobenzosyre, 2-aminobenzofenon, 3-aminobenzofenon, 4-aminobenzofenon, 2,2'-diaminobenzofenon, 3,3'-diaminobenzofenon, 2-aminobifenyl, 3-aminobifenyl, 4-aminobifebyl, 2,2'-diaminobifenyl, 2,4'-diaminobifenyl, 3,3'-diaminobifenyl, 4,4'-diaminobifenyl, o-benzhydranilin, m-benzhydranilin, p-benzhydranilin, 4,4'-diaminoditan, 4,4'-diaminotritan, pararosanilin, 1-naftylamin, 2-naftylamin, 1,2-diaminonaftalen, 1,5-diaminonaftalen, 2,6-diaminonaftalen, 1,7-diaminonaftalen, 1,8-diaminonaftalen, 2,6-diaminonaftalen, 3-aminofenantren, 9-aminofenantren, o-hydroksyanilin, m-hydroksyanilin, p-hydroksyanilin, o-acetylanilin, m-acetylanilin, p-acetylanilin, p-aminofenacylklorid, 2-aminoakridin, 3-aminoakridin, 4-aminoakridin, 9-aminoakridin,
3,6-diaminoakridin, anilin, 3-acetamidoanilin, 4-acetamidoanilin, 2-bromanilin, 3-bromanilin, 4-bromanilin, 2-kloranilin, 3-kloranilin, 4-kloranilin, 2,3-dibromanilin, 2,4-dibromanilin, 2,5-dibromanilin, 2,6-dibromanilin, 3,5-dibromanilin, 2,3-
dikloranilin, 2,4-dikloranilin, 2,5-dikloranilin, 3,4-dikloranilin, 3,5-dikloranilin, o-butylanilin, p-butylanilin, 4-dimetylaminoanilin, o-etylanilin, m-etylanilin, p-etylanilin, o-fenetidin, m-fenetidin, p-fenetidin, 2-fenoksyanilin, 3-fenoksyanilin, 4-fenoksyanilin, 1-aminoantracen, 2-aminoantracen, 9-aminoantracen, 1,2-diaminoantrakinon, 1,3-diaminoantrakinon, 1,4-diaminoantrakinon, 1,5-diaminoantrakinon, 1,6-diaminoantrakinon, 1,7-diaminoantrakinon, 1,8-diaminoantrakinon, 2,3-diaminoantrakinon, 2,6-diamionoantrakinon, 2,7-diaminoantrakinon, 5-iod-o-toluidin, 4-iod-o-toluidin, 2-iod-m-toluidin, 6-iod-m-toluidin, 5-iod-m-toluidin, 3-iod-p-toluidin, 2-iod-p-toluidin, 4-iod-m-toluidin, 2,3-diaminotoluen, 2,4-diaminotoluen, 2,5-diaminotoluen, 2,6-diaminotoluen, 3,4-diaminotoluen, 3-5-diaminotoluen, og tyramin.
I tillegg til å fremstille diazotiserbare RDP kan de aromatiske aminer oppført ovenfor også anvendes til å fremstille RDP som har andre reaktive egenskaper, nemlig RDP som er reaktive med karboksyl-inneholdende forbindelser i nærvær av aktivatorer, RDP som er reaktive med bifunksjonelle reagenser og de som er reaktive med nukleofil-funksjonaliserte RDP. I tillegg til aminogrupper kan andre relativt radioresistente nukleofiler eller nukleofiler som overlever bestråling under radiosterilisering i tilstrekkelig antall til å bli anvendt for belegging av flaten, med adekvat tetthet av nukleofiler, f.eks. SH eller OH, bindes til polymerer for å fremstille nukleofiliserte RDP.
Konjugander som er karbohydrater eller derivater derav kan anvendes til å derivere polymerer under bestråling og fremstille glykofase RDP. Betegnelsen "glykofase RDP", slik den er benyttet her, refererer seg til en faststoff støtte som bærer vicinale dioler, vanligvis i form av kovalent festet karbohydrat til glass (Corning, Pierce), til Sephadez, Sepharose (Pharmacia) eller andre lignende produkter. Glykofase RDP'er kan aktiveres med cyanogenbromid som vist i Ceska et al., J. Allerg. Clin. Immunol. Vol. 49, 1972, pp. 1-9, eller med periodat som vist i Varg, Methods Enzymol., Vol. 112, 1985,
pp. 259-269, eller med andre egnede aktiverende stoffer. De
spesielt foretrukne konjugander, anvendt ved fremstilling av glykofase RDP, er fenol-alfa-D-glaktosid, fenol-beta-D-galaktosid og fenol-beta-D-glykosid. Ytterligere egnede konjugander som kan anvendes til fremstilling av glykofase RDP omfatter: 2-acetamido-2,6-benzyliden-2-deoksy-beta-glukopyranose, N-acetyl-beta-glukosaminnaftol, p-aminobenzyl-l-tio-2-acetamido-2-deoksy-beta-glykopyranosid, p-aminofenyl-2-acetamido-2-deoksy-1-tio-beta-glukopyranosid, p-aminofenyl-alfa-fukopyranosid, p-aminofenyl-alfa-galaktopyranosid, p-aminofenyl-beta-galaktopyranosid, p-aminofenyl-alfa-glykopyranosid, p-aminofenyl-beta-glukopyranosid, o-aminofenyl-alfa-glukuronid, p-aminofenyl-l-tio-beta-glukoronid, p-aminofenyl-beta-laktopyranosid, p-aminofenyl-alfa-mannopyranosid, p-aminofenyl-beta-tiofykopyr-anosid, p-aminofeny1-1-tio-beta-galaktopyranosid, p-aminofenyl-1- tio-beta-glukopyranosid, p-aminofenyl-l-tio-beta-xylopyranosid, p-aminofenyl-beta-xylopyranosid, D-amygdalin, N-benzoyl-alfa-glykosamin, benzyl-2-acetamido-6-0-(2-acetamido-2-deoksy-beta-glukopyranosyl)-2-deoksy-alfa-glukopyranosid, benzy1-2-acetamido-2-deoksy-alfa-galaktopyranosid, benzy1-2-acetamido-2-deoksy-3-0-beta-galaktopyranosyl-alfa-galaktopyranosid, benzyl-2- acetamido-2-deoksy-alfa-glukopyranosid, benzy1-2-acetamido-2-deoksy-beta-glukopyranosid, benzy1-2-acetamido-2-deoksy-3-0-beta-glukopyranosid, benzyl-N-CBZ-glukosamidin, benzyl-4-0-beta-galaktopyranosyl-beta-glykopyranosid, 4,6-0-benzylidengly-kopyranosid, 4,6-0-benzylidenglukose, 6-brom-2-naftylgalak-topyranosid, 6-brom-2-naftyl-glukopyranosid, 6-brom-2-naf-tylglykopyranosid, n-butyl 4-0-galaktopyranosyl-beta-glykopyranosid, 6,7-dihydroksy-kumarin-6-glucosid, n-dodecylbeta-glykopyranosid, n-dodecylbeta-maltosid, eskulin, fluoreceindi-(beta-galaktopyranosid), beta-galaktosenaftol, heptanoyl-N-metylglukamid, n-heptylbeta-glukopyranosid, hesperidin, 2-heksanedekanoylamino-4-nitofenyl-beta-galaktopyranosid, 2-heksadekanoylamin-4-nitrofenyl-beta-glykopyranosid, n-heksyl-beta-glukopyranosid, 8-hydroksykinolin-beta-glukopyranosid, 8-hydroksykinolinglykuronid, mandelnitril-beta-glukosid, mandenitrilglukoronsyre, alfa-naftyl-alfa-galaktopyranosid, alfa-naftyl-beta-galaktopyranosid, beta-naftyl-beta-galaktopyranosid, beta-naftyl-alfa-glukopyranosid, beta-naftyl-beta-glykopyranosid, beta-naftyl-alfa-glukosid, alfa-naftyl-beta-glucuronid, naringin, n-nonylglukosid, n-nonylglukopyranosid, oktadecyltioetyl-4-0-alfa-galaktopyranosyl-beta-galaktopyranosid, octanoyl-N-metylglycamid, n-octylalfa-glukopyranosid, n-oktyl-beta-glukopyranosid, fenolftaleinglukuronsyre, fenolfta-leinmono-beta-glukosiduronsyre, fenolftaleinmono-beta-glukuron-syre, fenyl-2-acetamido-2-deoksy-alfa-galaktopyranosid, fenyl-2-acetamido-2-deoksy-alfa-glykopyranosid, alfa-fenyl-N-acetylglukosaminid, beta-fenyl-N-acetylglukosaminid, fenyletyl-beta-galaktosid, fenyl-beta-galaktosid, fenyl-beta-galaktopyranosid, fenyl-alfa-glukopyranosid, fenyl-beta-glukopyranosid, fenyl-alfa-glukosid, fenyl-beta-glukosid, fenyl-beta-glukuronid, fenyl-alfa-mannopyranosid, fenyl-beta-tiogalakto-pyranosid, fenyl-beta-tiogalaktosid, og salicin.
Ved å anvende karboksyl-inneholdende forbindelser som konjugand, kan et karboksylert RDP fremstilles, som videre kan aktiveres med karbodiimider eller andre egnede aktivatorer, anført her. For aktivering av faststoff fase-bundet karboksyler, se Sott, L. T., et al., (J. Am. Chem. Soc, Vol. 99, 1977, pp. 625-626). Betegnelsen karboksyl-inneholdende forbindelse, som benyttet her, betyr konjugander som inneholder minst en karboksylgruppe og minst en aromatisk struktur i det samme molekyl, men ikke nødvendigvis aromatiske karboksyler. Eksempler på spesielt foretrukne karboksyl-inneholdende konjugander er benzosyre, naftalenkarboksylsyre og dets derivater, fenyleddiksyre og fenylnaftalenkarboksylsyre og deres derivater. Ytterligere karboksylinneholdende forbindelser som kan tjene som konjugander til fremstilling av karboksylerte RDP omfatter: eddiksyre, o-brom-toluensyre, m-brom-toluensyre, o-klor-toluensyre, m-klor-toluensyre, p-klor-toluensyre, 2,5-dihydroksybenzeneddiksyre, difenyleddiksyre, benzylsyre, fenylglykolsyre, o-hydroksy-alfa-toluensyre, m-hydroksy-alfa-toluensyre, p-hydroksy-alfa-toluensyre, tiogly-kolsyre, metoksyfenyleddiksyre, 1-naftoksyeddiksyre, 2-naftoksyeddiksyre, 1-naftaleneddiksyre, N-benzoyl-aspartinsyre, o-azobenzosyre, m-azobenzosyre, p-azobensosyre, ftalsyre, isoftalsyre, tereftalsyre, 2-amino-l,3-benzen-dikarboksylsyre, 4-amino-l,3-benzen-dikarboksylsyre, 5-amino-l,3-benzen-dikarboksylsyre, 2-amino-l,4-benzen-dikarboksylsyre, 4-amino-1,4-benzen-dikarboksylsyre, 5-amino-l,4-benzen-dikarboksylsyre, hemimellitsyre, trimellitsyre, trimessyre, benzosyre, 2-klor-benzosyre, 3-klor-benzosyre, 4-klor-benzosyre, anilineddiksyre, N-benzoylleucin, N-benzoyllysin, 1-naftalenkarboksylsyre, 2-naftalenkarboksylsyre, 1,2-naftalendikarboksylsyre, 1,4-naftalendikarboksylsyre, 1,5-naftalendikarboksylsyre, 1,6-naftalendikarboksylsyre, 1,7-naftalen-dikarboksylsyre, 1,8-naftalendikarboksylsyre, 2,3-naftalendikarboksylsyre, 2,6-naftalendikarboksylsyre, 2,7-naftalendikarboksylsyre, 2-fenylpentan-dioidsyre, valeriansyre, 1-fenantrenkarboksylsyre, 2- fenantrenkarboksylsyre, 3-fenantrenkarboksylsyre, ftalsyre, prolin, propionsyre, 2,2-difenyl-propionsyre, 2,3-difenylpro-pionsyre, 3,3-difenyl-propionsyre, 2,3-difenyl-2-hydrok-sypropionsyre, 3,3-difenyl-2-hydroksypropionsyre, 3,3-difenyl-3- hydroksy-propionsyre, benzoylglycolsyre, alfa-hydroksy-hydrocynnamsyre, 3-hydroksy-2-fenylpropionsyre, 3-hydroksy-3-fenylpropionsyre, melilotsyre, 2-metyl-3-fenyl-propionsyre, 3(1-naftyl)-propionsyre, 3(2-naftyl)-propionsyre, fenyl-pyrodruesyre, benzoyl-eddiksyre, 2-fenoksypropionsyre, 3-fenoksypropionsyre, 2-fenylpropionsyre, 3-fenylpropionsyre, pikolinsyre, nitotinsyre, isonikotinsyre, kinolinsyre, lutidinsyre, dipikolinsyre, dinikotinsyre og benzylravsyre.
Proteinmodifiserende reagenser, som er kjent av fagfolk (se Lundblad, L.L., Noues, CM.: Chemical reagents for protein modififation, CRC Press, Boca Raton, 1984), kan tjene som konjugander for fremstilling av RDP som er nukleofile reaktive polymerer. De foretrukkene protein-modifiserende reagenser er de som inneholder minst en proteinreaktiv gruppe og minst en aromatisk struktur, såsom Bolton-Hunter reagens, OPA, TNBSA, Dansylklorid, Dabsylklorid, DABITC, SBF-klorid, Ellmans reagens, p-hydroksyfenylglyoksal, BTI, Ninhydrin, (se Pierce 1988, Handbook for forkortelsene) eller fluorescamin, FITC, RITC FLUOS, RESOS, RHODOS, og Resornfin fra Sigma Co. Ytterligere egnede proteinmodifiserende reagenser er tidligere oppført her, under konjugander til fremstilling av reaktive
RDP.
Bifunksjonelle reagenser kan brukes til å reagere med funksjonaliserte RDP, spesifikke nukleofil-funksjonaliserte RDP og RDP dannet av konjugander som inneholder aminogrupper eller vann. Betegnelsen bifunksjonell reagens, slik den er brukt her, refererer seg til tverrbindende reagenser som er i stand til å kombinere eller brobinde RDP med minst en ligand. Betegnelsen bifunksjonelle reagenser omfatter polyfunksjonelle reagenser eller tverrbindingsreagenser som inneholder et flertall av funksjonelle grupper. De foretrukne bifunksjonelle reagenser er EDC, BDE og TDI (Se tabell 5). Ytterligere eksempler på bifunksjonelle eller tverrbindende reagenser benyttet i denne oppfinnelse omfatter: dialdehyder, fortrinnsvis glutaraldehyd, diisotiocyanater, fortrinnsvis fenylen-l,4-diisotiocyanat, diisocyanater, fortrinnsvis toluylen-2,4-diisocyanat, bis-diazo-benzidiner, bis-diazo-o-anisidin, biepoksider og klor-5-triaziner.
En viktig side ved foreliggende oppfinnelse er at det er betydelig overlapping mellom de forskjellige klasser av konjugander anvendt til å fremstille de forskjellige klasser av RDP. F.eks. konjuganden p-aminofenol er både et aromatisk amin som kan diazotiseres og den kan også omsettes til et kinon, hvilket forklarer hvorfor denne spesielle konjugand kan anvendes til å fremstille funksjonaliserte RDP og reaktive RDP. Aromatiske amin-konjugander er diazotiserbare og samtidig er de nukleofil-inneholdende; således, i tillegg til diazotise-ring er de funksjonaliserte og egnet for kobling med bifunksjonelle reagenser og aktivatorer. Tilsvarende kan noen av de reaktive RDP også tjene som funksjonaliserte RDP.
Det er funnet at konjugander som inneholder aromatiske strukturer gir høyere inkorporasjonsnivåer i polystyren enn alifatiske konjugander (eksempel 1, tabell 1). Følgelig er de aromatiske forbindelser foretrukne konjugander for radioderivering av polystyren. I prinsippet behøver dette ikke å gjelde andre polymerer, såsom polyetylen.
En av de enkleste RDP-produkter i foreliggende oppfinnelse er dannet med vann som konjuganden. Som vist i tabell 2 inkorporeres relativt store mengder vann i polystyren under radioderivering. Reaktiviteten til polystyren-vann-RDP antyder dannelsen av reaktive nukleofiler (eksempel 7-11). De er istand til å danne kovalente bindinger med DNP-aminosyrer i karbodiimid-medierte reaksjoner, og den immobiliserte ligand kan benyttes i meget reproduserbare immunoanalyser (eksempel 22). I tillegg kan vann-RDP dannes som biprodukter når radioderivering utføres i en vandig oppløsning.
RDP fremstilt i foreliggende oppfinnelse har mange anvendelser. De kan benyttes f.eks. som sådan uten videre modifikasjoner, f.eks., som substrater for cellekulturer med forbedret adherens og vekstunderstøttende egenskaper, eller som sorbenter for kromatografi ved anvendelse av, f.eks., radioaromatiserte, radioalkylerte, radiokarboksylerte partikler. Disse RDP kan være spesielt nyttige når ikke undertrykkbare materialer er nødvendig f.eks. for HPLC og affinitetskromatografi med høy ytelsesevne.
Reaktive og funksjonaliserte RDP har flere anvendelser. Et stort antal støpte polymerer, hovedsakelig polystyren og dens kopolymerer, kan fremstilles for å benyttes som mikrotiterplater, vevskulturplater eller pipetter. Den adsorptive bin-dingsevne og/eller reaktive evne til disse produkter kan fordelaktig modifiseres ved radioderivering, fulgt av immobilisering av egnede ligander. Sammenlignet med fremgangsmåter som nå anvendes, har den foreliggende fremgangsmåte med radioderivering klare fortrinn når det er behov for transparente støttematerialer (mikrotiterplater, vevskulturlabora-torieutstyr), og når disse produkter er eksponert for høyener-getisk stråling ved sterilisering. I dette tilfellet kan RDP med fordelaktig adsorptiv og/eller kovalent bindingskapasitet oppnås med relativt liten ekstra fremstillingsinnsats foruten strålingen anvendt til radiosterilisering. De resulterende RDP kan deretter benyttes i flere anvendelser 1) metoden er generelt egnet for fremstilling av polymere overflater med kovalent festede ligander til bindingsanalyser, inkludert immunoanalyser. Fremgangsmåten kan være spesielt fordelaktig ved koiorimetriske analyser, siden optisk gjennomsiktighet hos RDP ikke er påvirket. I tillegg kan fremgangsmåten fordelaktig anvendes på andre måter, såsom radiometriske eller fluoromet-riske analyser på grunn av den lave bakgrunnsstøyen som oppnås ved radioderivering. 2) RDP kan benyttes til kovalent binding av adhesjonsmolekyler, antistoff eller biologisk aktive molekyler for massekultivering av celler og panorering (pan-ning). 3) Radioderiverte polymerer i form av folie og/eller ark som kan benyttes til immunblotting og hybridisering. 4) Radioderiverte polymerpartikler (såsom polystyren "lateks" kuler) kan anvendes for fremstilling av affinitetssorbenter, ionebyttere eller hydrofobe sorbenter som er ufølsomme for baser og ikke undertrykkbare, og dermed er egnet for HPLC-kolonner; "reaktive polymerer" til organisk syntese; fast fundament for peptid-, oligonukleotid- og oligosakkaridsyntese; immobiliserte enzymer for "enzymreaktorer"; immobiliserte antigener til produksjon av vaksiner; immobiliserte transpor-tører. 5) RDP i væske, gel eller granulær form kan anvendes som bærere for legemidler. 6) Radioderiveringsfremgangsmåten kan vurderes for fremstilling av molekylære trykte kretser i fremstilling av mikrobrikker.
Type av molekyler, partikler eller stoffer som er immobilisert ved anvendelsene beskrevet ovenfor er heretter betegnet ligander. Ligandene i den foreliggende oppfinnelse kan være organisk eller uorganisk stoff. Som eksempel og uten derved å være begrensende kan ytterligere ligander, som kan immobiliseres, fikseres eller videre bindes til radioderiverte polymerer fremstilt i denne oppfinnelse, omfatte kofaktorer, koenzymer, gelatdannere, ioner, hormoner, legemidler, fargestoffer, lipider, lektiner, karbohydrater, nukleinsyrer, enzymer, haptener, antigener, allergener, antistoffer, viruser, mikroorganismer, eukariote celler og bestanddeler av disse.
Ved immobilisering av ligander på RDP med tverrbindere og aktiverende midler, er standardmetoder til kobling av ligander og proteiner til karbohydratbaserte (f.eks. "Sepharose") eller polyakrylamid, og andre (f.eks. uorganiske) fundamenter generelt kjent av fagfolk. Følgende hovedtyper av kovalen-tekoblingsfremgangsmåter kan tas i betraktning, avhengig av naturen til det funksjonaliserte RDP og liganden som skal immobiliseres: a) karboksylinneholdende molekyler kan kon-verteres til nukleofil-reaktive derivater (dvs. med karbodiimid) og eksponeres til nukleofiliserte RDP (eksempel 4, fig. 2). Den samme fremgangsmåte kan benyttes med proteiner (eksempel 6, tabell 5). Angående denne generelle fremgangsmåte kan andre reagenser, såsom symmetriske eller blandede syreanhydrider, Leuch's anhydrider, syreazider, eller reaktive hydroksylaminderivater benyttes. Utbyttet av disse typer av koblingsreaksjoner kan økes med inklusjon av "hjelpenukleofiler", såsom 1-hydroksybenzotriazol, andre benzotriazin-der ivater og hydroksysuccinimid, etc; b) Diazoniumsalt-reaktive forbindelser (f.eks. fenol-RDP) kan anvendes for å binde diazotiserte molekyler; c) Homo- eller heterobifunksjo-nelle tverrbindere kan benyttes, som er i stand til å reagere med funksjonelle grupper tilstede på RDP og molekyler som skal immobiliseres (tabell 2); d) RDP kan videre modifiseres med "avstandsmolekyler" ved å bruke Leuch's anhydrider, beta-alanin, oligoglycin, etc, ved å anvende f.eks., aminofunksjo-naliserte RDP og aminoblokkerte avstandsmolekyler. Amino-avstandsmolekyl-RDP kan oppnås etter avblokkering.
Denne oppfinnelsen er ikke begrenset til bindingsfremgangsmå-tene diskutert ovenfor, idet tallrike andre fremgangsmåter kjent av fagfolk kan anvendes for å binde molekyler til funksjonaliserte RDP.
De resulterende RDP dannet av konjuganden og polymeren, og de endelige RDP bundet til ligander kan identifiseres ved radiometri, ved å benytte radiomerkede konjugander (eksempel 1, tabell 1). Radiomerkede ligander eller ligandbindende proteiner
(fig. 2, tabell 3-5) kan benyttes til å identifisere det ligandbindende protein til RDP. Andre fremgangsmåter kjent av fagfolk kan også anvendes.
Skjønt alle typer av polymerer som inneholder radiolyserbare bindinger kan anvendes for radioderivering, har den foretrukne utføring av foreliggende oppfinnelse og alle eksemplene beskrevet nedenfor blitt utført med polystyren. Konjugandene ble satt til polystyren (PS) mikrotiterplater (ikke-sterile ubestrålte, anskaffet fra Greiner GmbH, Kremsmunster, Østerrike; 100 jul/brønn) , 100 mM (med mindre annet er notert) i vann (pH-verdi 9, NaOH). Platene ble forseglet med klebefilm (Nunc nr. 236269) og hermetisk pakket med en varmeforsegler (Krups Co., FRG) av polyetylenfilm, deretter eksponert til en gammakilde som beskrevet ovenfor. Ikke-bestrålte (kontroll) plater ble holdt ved værelsestemperatur like lenge og med de samme stoffer som de bestrålte, og i det følgende behandlet på samme måte som de bestrålte plater. Oppløsningene ble fjernet fra platene ved kraftig risting og platene ble vasket i følgende trinn: 10 ganger med springvann, deretter ble 200 /il NaHC03 (0,1 M) tilsatt og holdt ved romtemperatur i 5 min, oppløsningen ble fjernet og 200 ul KC1 (2 M i glycinbuffer 0,2 M, pH-verdi 3) ble tilsatt og holdt ved værelsestemperatur; de siste to vasketrinn ble gjentatt fire ganger etterfulgt av ti gangers vasking med springvann og dobbelt antall ganger med destillert vann; platene ble øyeblikkelig anvendt for bin-dingsstudier eller de ble lagret i vakuum ved værelsestemperatur. Under disse betingelser var det intet signifikant tap av reaktivitet på 1 måned.
Konjugander som av fagfolk er kjent for å hydrolysere, eller på annen måte reagere med vann under betingelser for radioderivering, nødvendiggjør en alternativ vaskefremgangsmåte. Platene bør vaskes fem ganger med vannfritt formamid etter radioderivering, istedenfor den ovenfor beskrevne vaskefremgangsmåten, og benyttes øyeblikkelig for immobilisering av molekyler. Generelle eksempler på konjugander som ville hydrolysere ved betingelsene for radioderivering (i vandig alkalisk oppløsning) er syreanhydrider, syrehalogenider, isotiocyanater, karbodiimider, oksyraner og nitroaromatiske halogenider.
Konjugander som hydrolyserer i vann er fortrinnsvis benyttet i ufortynnet form når konjuganden er i væskeform ved værelsestemperatur. Både væske og faste hydrolyserbare konjugander kan anvendes i oppløsning i vannfritt formamid eller andre oppløsningsmidler, såsom DMSO, som ikke oppløser polymeren, dvs. polystyren, og ikke lyserer konjuganden.
Generelt er fortrinnsvis konjugander som ikke hydrolyserer benyttet i vannfri, alkalisk oppløsning, men de kan også benyttes i oppløsning med andre oppløsningsmidler enn vann, forutsatt at slike oppløsningsmidler ikke løser opp polymeren (dvs. polystyren) og ikke lyserer konjuganden, såsom formamid. Ikke-hydrolyserbare konjugander som er i væskeform ved værelsestemperatur kan også anvendes ufortynnet. Bruk av væskeformige ikke-hydrolyserbare konjugander i ufortynnet tilstand er foretrukket når konjuganden har lav oppløselighet i vann og/eller formamid. Blant eksemplene beskrevet her ble 1,3-diamino-2-hydroksypropan benyttet ufortynnet.
Opptak av radiomerkede konjugander ble målt med samme fremgangsmåte som radioderivering beskrevet ovenfor, med følgende modifikasjoner: 0,1-3 juCi radiomerket konjugand ble tilsatt som sporstoff til det umerkede stoffet, og etter bestråling og vasketrinnene, ble brønnene i mikrotiterplatene skåret ut med et rødglødende barberblad, oppløst med Bioflour (NEN) emul-gerende cocktail og tellet i en væske-sintillasjonsteller (LKB/Wallac 1215).
Bestråling ble utført ved å benytte en <60>Co gammakilde (ca. 17.000 Ci) med en intensitet på 0,1-0,2 Mrad/h til en total dose på 1-15 Mrad, fortrinnsvis 3-5 Mrad, ved normalt atmos-færetrykk og værelsestemperatur. Eksklusjon av oksygen under bestråling har generelt en gunstig effekt på reaktiviteten til RDP. Selv om bestråling i nærvær av oksygen gir RDP med lavere reaktivitet, er de imidlertid tilstrekkelig reaktive for immobilisering av ligander til immunoanalyser, se eksempel 22. Skjønt bestråling fra ovennevnte gammakilde ble benyttet i foreliggende eksempler, kan hvilken som helst høyenergibestrå-ling (dvs. elektronbestråling) som er istand til radiolyse av polymer og/eller konjugand benyttes i foreliggende oppfinnelse.
Etyldietylaminopropyl-karbodiimid eller EDC-mediert binding ble utført for små molekyler ved å tilsette 50 /il oppløsninger
(2 mM i NaCl, 0,1 M, pH-verdi 5, eller pH-verdi 3 for DNP-Gly)
av molekylene som skulle bindes til brønnene i radioderiverte mikrotiterplater, fulgt av 50 /il EDC-oppløsning (2 mg/ml i NaCl, 0,1 M, pH-verdi 5 eller pH-verdi 3 for DNP-Gly). Bindingsreaksjonen ble tillatt å foregå ved værelsestemperatur i 2 timer i mørke med lysfølsomme materialer; ikke bundet materiale ble fjernet ved vasking og opptak av merkede forbindelser ble målt.
For EDC-mediert binding av proteiner ble 1 mg/ml proteinopp-løsninger med tilnærmet 100000 cpm spor-[<125>I] merkede proteiner anvendt ved værelsestemperatur i 2 timer i mørke med lysfølsomme materialer og med 10 mg/ml EDC-oppløsning, med pH-verdi justert til 5. Ikke bundede proteiner ble fjernet som beskrevet ovenfor, med unntak av at vaskeoppløsninger ble suplementert med 0,05% Tween 20 og PBS ble anvendt istedenfor KCl/glycin-oppløsning. Radioaktiviteten ble tellet i en gammateller (LKB/Wallac CliniGamma). Proteinene ble merket med <125>j ve<j å benytte "Enzymobead"-fremgangsmåten til Bio Rad, Richmond, California.
Diazo-binding ble oppnådd ved hjelp av følgende fremgangsmåte: radioderiverte (og kontroll) plater ble for-kjølet i isvann i 30 min; iskald NaN02-oppløsning (5 mg/ml i 2N HC1) ble tilsatt og holdt i isvann i 1 h. Væsken ble fjernet og platen vasket tre ganger med iskaldt vann. 100 /il protein-oppløsning [1 mg/ml (+ 0,1 /tCi spor-merket protein) i borat-buffer (0,1 M, pH-verdi 8,5)] ble satt til brønnene og bindingen foregikk natten over ved 4°C. Ikke-bundet protein ble fjernet; platene ble vasket og opptak av protein ble bestemt som beskrevet ovenfor.
Binding med tverrbindere ble oppnådd ved forbehandling av de radioderiverte platene med bifunksjonelle reagenser [100 /ul/brønn, 25 mg/ml i fosfatbuffer (0,2 M, pH-verdi 7,2)] i 2 h ved værelsestemperatur. Reagensene ble fjernet og protein-oppløsningene som inneholdt spormerkede proteiner ble tilsatt. Bindingen foregikk natten over ved 4°C. Ikke bundede proteiner ble fjernet og mengden av bundet stoff ble målt som beskrevet ovenfor.
De ovennevnte fremgangsmåter og materialer kan forandres uten å avvike fra oppfinnelsens ide og omfang, eller at fordelene ofres. De følgende eksempler er bare illustrerende og begrenser ikke oppfinnelsen.
Eksempel 1
Kommersielt tilgjengelige radiokjemikalier (ført opp i tabell 1) i mengder på 2-5 jiCi/50 /il/brønn, fortynnet med 1-100 mM kald substans i vandige oppløsninger (pH-verdi 9, NaOH) ble satt til ikke-bestrålte (Greiner nr. 651 101) mikrotiterplate-brønner og brønnene ble forseglet med plateklebrig folie (Nunc nr. 236 269). I tillegg ble platene individuelt forseglet med en polyetylenfolie varmeforsegler og bestrålt med Co gammakilde (ca. 17.000 Ci) med en intensitet på 0,1-0,2 Mrad/h til totalt 1-15 Mrad, fortrinnsvis 3-5 Mrad, ved normalt atmos-færetrykk og værelsestemperatur. De ikke-bestrålte (kontroll) platene som inneholder det samme stoffet ble holdt ved værelsestemperatur like lenge som de bestrålte plater, og i det følgende behandlet på samme måte som de bestrålte plater. Etter bestråling ble innholdet i brønnene fjernet med absorberende papir og platene ble vasket i følgende trinn: 10 ganger med springvann, deretter ble 200 jul NaHC03 (0,1 M) tilsatt og de ble holdt ved værelsestemperatur i 5 min, oppløsningen ble fjernet og 200 til KC1 (2 M i glycinbuf f er) (0,2 M, pH-verdi 3) ble tilsatt og holdt ved romtemperatur i 15 min. De to siste vasketrinn ble gjentatt fire ganger etterfulgt av vasking ti ganger med springvann og to ganger med destillert vann. Platene ble tørket i luft; brønnene ble skåret ut med et rødglødende barberblad, oppløst med "Biofluor" (NEN) emulgeringscocktail, og tellet i en LKB/Wallac 1215 væske-scintillasjonsteller. Resultatene er vist i tabell 1.
Eksempel 2: Polystyren-vann-RDP.
Vannfritt formamid, dimetylsulfoksid eller H2O ble tilsatt tritiert vann (sp. RA ca. 2000 Ci/ml) i økende konsentrasjoner; Plater som inneholdt oppløsninger (20 /ul/brønn) ble bestrålt, behandlet og kovalent bundet [3H] ble målt som beskrevet i eksempel 1; ikke-bestrålte kontrollplater ble eksponert for de samme oppløsninger like lenge som de bestrålte plater. Resultatene er vist i tabell 2.
Eksempel 3: Binding av proteiner til reaktive RDP.
Konjugander oppført i tabell 3 (10 mg/ml oppløsninger i 1 mM NaOH) ble satt til mikrotiterbrønner og behandlet som beskrevet i eksempel 1; 125I RNase eller 125I hemoglobin ble fortynnet med 1 mg/ml umerkede proteiner i boratbuffer (0,1 M,
pH-verdi 8,5), 100 /il/brønn ble satt til mikrotiterplater og holdt i 16 timer ved 4°C.
De ikke-bundne proteiner ble fjernet som beskrevet i eksempel 2, bortsett fra at vaskeoppløsninger ble supplementert med 0,05% Tween 20 og PBS ble benyttet isteden for KCl/glycin-oppløsning.
Opptaket av proteiner ble beregnet ut fra totalt antall tellinger (counts) tilsatt brønnene. Resultatene er vist i tabell 3.
AHE-DL-2-amino-l(4-Hydroksyfenyl)-etanol-1
*-Optisk kvalitet av PS ble svekket under radio-derivering ND-ikke bestemt
Tallene ble avrundet oppover til første desimal med 0,05 som grense.
Eksempel 4: EDC-mediert opptak av karboksylsyrer ved RDP.
Opptak av følgende karboksylsyrer ble målt: A) eddiksyre;
B) glycin; C) DNP-glycin; D) benzosyre; E) salicylsyre. Fig. 2 viser virkninger av radioderivering av polystyren på EDC-mediert opptak av disse karboksylsyrer. Bestrålingen ble utført i nærvær av følgende oppløsninger (tallene korresponderer til tallene på x-aksen i fig. 2) : 1) Ingen; 2) H20; 3) NH3, 25 %; 4) Ammoniumsulfat, mettet; 5) Etylamin-HCl, 90 %; 6) 1,3-diamino-2-hydroksypropan 99 % (ufortynnet); 7) 1,4-diaminobutanon.2HC1 20 % ImM NaOH; 8) etylendiamin.HCl 7,5% i 1 mM NaOH; 9) Isobutylamin.HCl 4 % i 1 mM NaOH; 10) DL-2-amino-l(4-hydroksyfenyl)-etan-l-ol, 4 % i 1 mM NaOH; 11) 1,6-diaminoheksan, 14 % i 1 mM NaOH; 12) p-aminofenol, 4 % i 1 mM NaOH; 13) 3,4-diaminopyridin 3,3% i 1 mM NaOH; 14) L-alaninbenzylester, 3,3% i 1 mM NaOH; 15) L-serinbenzylester, 4,4% i 1 mM NaOH;
16) Galaktosamin 11 % i H2O.
Resultatene er vist på fig. 2. I panel (a) viser skyggebelagte histogram opptak av radioaktivitet uten EDC, mens åpne histogram viser opptak av radioaktivitet med EDC. Nedre panel (b) viser det relative opptak: forholdet mellom opptak oppnådd med bestrålte plater og ikke-bestrålte plater i nærvær av EDC. For å oppsummere: resultatene i fig. 2 viser at polystyren mikrotiterplater bestrålt i nærvær av aromatiske aminer, såsom p-aminofenol, AHE, L-alanin og benzylester blir reaktive med eddiksyre, DNP-Gly eller benzosyre i EDC-medierte reaksjoner. Ingen signifikant EDC-mediert fiksering ble observert med glycin (B), mest sannsynlig fordi dannelse av peptidbinding var den foretrukne reaksjon. Lave bindingstettheter ble oppnådd med salicylsyre (E), unntagen med L-alaninbenzylester-konjugerte plater. Selvreaktiviteten av fenolhydroksyl i salicylsyre med det blandede EDC-karboksyanhydridderivat kan forklare bortfall av EDC-mediert binding av dette stoff til polystyren.
Eksempel 5: Binding av proteiner til diazotiserte RDP.
Radioderiveringer ble utført med konjugander oppført i tabell 4, som beskrevet i eksempel 2. De ble diazotisert i henhold til følgende fremgangsmåte: radioderiverte og (kontroll) plater ble for-kjølet i isvann i 30 min. Iskald NaN02-oppløsning (5 mg/ml i 2 N CH1) ble tilsatt og holdt i isvann i en time. Væsken ble fjernet og platen vasket tre ganger med iskaldt vann. 100 /xl proteinoppløsning [1 mg/ml (+ 0,1 /xCi spor-merket RNase og hemoglobinprotein) i boratbuffer (0,1 M, pH-verdi 8,5)] ble satt til brønnene og bindingen foregikk i løpet av natten ved 4°C; ikke-bundet protein ble fjernet; platene ble vasket som beskrevet i eksempel 3 og opptak av proteiner ble bestemt som beskrevet i eksempel 2. Resultatene er vist i tabell 4. Tallene ble avrundet oppover til neste første desimal med 0,05 som grense.
Eksempel 6: Binding av proteiner til p-aminofenol-polystyren RDP med EDC og bifunksjonelle reagenser.
P-aminofenol-polystyren RDP ble fremstilt og behandlet som beskrevet i eksempel 2. Bifunksjonelle reagenser oppført i tabell 5, nemlig etyldietylaminopropyl-karbodiimid (EDC); 1,4-butandiol diglycidyleter (BDE); toluylen-2,4-diisocyanat (TDI) ble satt til mikr ot it er brønner (100 /il/brønn, 25 mg/ml i K-fosfatbuffer(0,2 M, pH-verdi 7,2). Platene ble holdt i en time ved værelsestemperatur. De bindende oppløsninger ble rystet ut og resten fjernet ved banking på adsorberende papir over en hard overflate. Spormerkede proteiner (100 /Lii/brønn) ble tilsatt øyeblikkelig og holdt ved 4°C i seksten timer, og opptak av proteiner ble målt som beskrevet i eksempel 3. Ved EDC-mediert binding ble 50 /il spor-merkede proteiner satt til brønnene, etterfulgt av 50 fj. 1 EDC-oppløsning (10 mg/ml i 0,1 M NaCl, pH-verdi 5); Platene ble forseglet med heftebånd, holdt ved værelsestemperatur i fire timer og opptak av protein ble bestemt som beskrevet ovenfor. Resultatene er vist i tabell 5.
Tallene ble avrundet oppover til neste første desimal, med 0,05 som grense.
Eksempel 7: EDC-mediert binding av Penicillin G til vann-polystyren RDP.
Polystyren mikrotiterplater ble bestrålt i en vandig atmosfære som beskrevet i eksempel 1. Penicillin G (2 mM umerket +
0,1 /iCi [14C] penicillin G i 50 /il 0,1 M NaCl, pH-verdi 3) og det samme volum EDC (1 mg/ml i 0,1 M NaCl, pH-verdi 3) ble tilsatt og holdt ved romtemperatur i 2 timer. Det ikke-bundne penicillin G ble fjernet og platene ble behandlet som beskrevet i eksempel 1. Bindingstettheter ble oppnådd i området fra 50-100 pmol penicillin G/cm<2> ble oppnådd.
Eksempel 8: EDC-mediert binding av DNP-aminosyrer til vann-polystyren RDP.
Mikrotiterplater ble radioderivert som beskrevet i det foregående eksempel. DNP-glycin (1 mM + 0,1 /xCi DNP[3H]glycin i 50 /il 0,1 M NaCl, pH-verdi 3) og det samme volum EDC (1 mg/ml i 0,1 M NaCl, pH-verdi 3) ble inkubert i mikrotiterplatebrønnene ved værelsestemperatur i minst en time. Det ikke-bundne DNP-glycin ble fjernet og platene ble behandlet som beskrevet i eksempel 1. Bindingstettheter var i området fra 100-150 pmol/cm<2.>
Eksempel 9: Binding av myosin til vann-polystyren RDP med oksiraner.
Mikrotiterplater ble aktivert som beskrevet i det foregående eksempel. De ble deretter inkubert med BDE (25 mg/ml, i 100 fil fosfatbuffer, pH-verdi 7,2) i en time. Den bindende oppløsning ble fjernet; myosin (1 mg/ml + 1,0 /iCi <125>i myosin i 100 fil fosfatbuffer, pH-verdi 7,2) ble tilsatt og binding ble latt forløpe i 14-16 timer ved 4°C. Det ikke-bundne myosin ble fjernet og platene ble behandlet som beskrevet i eksempel 3. Bindingstettheter var i området fra 20-30 pmol myosin/cm<2>. Eksempel 10: Binding av myosin til vann-polystyren RDP med TDC.
Den samme fremgangsmåte som beskrevet i foregående eksempel ble benyttet, bortsett fra at TDC ble anvendt isteden for BDE. Bindingstettheter i området fra 15-20 pmol myosin/cm<2> ble oppnådd.
Eksempel 11; Binding av RNase til vann-polystyren RDP med TDC.
Samme fremgangsmåte som beskrevet i eksempel 10 ble brukt, bortsett fra at RNase [+<125>I-RNase] ble benyttet isteden for myosin. De oppnådde bindingstettheter varierte fra 2-2,5 nmol RNase/cm<2>.
Eksempel 12: Binding av hemoglobin til p-aminofenyl-polystyren
RDP.
Para-aminofenyl-polystyren RDP ble oppnådd som beskrevet i eksempel 4, og hemoglobin (1 mg/ml + 0,1 fiCi <l25>i hemoglobin i 100 fil 0,1 M NaCl, pH-verdi 3) ble tilsatt og holdt ved værelsestemperatur i 4 timer. Det ikke-bundne hemoglobin ble fjernet og platen ble behandlet som beskrevet i eksempel 3. Bindingstettheter på tilnærmet 1 nmol hemoglobin/cm<2> ble oppnådd.
Eksempel 13: EDC-mediert binding av pepsin til p-aminofenyl-polystyren RDP.
Para-aminofenyl-polystyren RDP ble oppnådd som beskrevet i eksempel 4 og pepsin (1 mg/ml + 0,1 /tCi <125>i pepsin i 100 /ul 0,1 M NaCl, pH-verdi 5) ble tilsatt, fulgt av tilsetting av det samme volum EDC (10 mg/ml i den samme oppløsning). Etter fire timers inkubasjon ved værelsestemperatur ble ikke-bundet pepsin fjernet og platen behandlet som beskrevet i eksempel 12. bindingstettheter på tilnærmet 1 nmol pepsin/cm<2> ble oppnådd.
Eksempel 14: EDC-mediert binding av penicillin G til para-aminof enyl-polystyren RDP.
Para-aminofenyl-polystyren RDP ble oppnådd som beskrevet i eksempel 4, penicillin G (2 mg/ml + 0,1 /iCi 14 C pencillin G i 100 fil i 0,1 M NaCl, pH-verdi 5) pluss det samme volum EDC
(10 mg/ml i 0,1 M NaCl, pH-verdi 5) ble tilsatt og holdt ved værelsestemperatur i fire timer. Det ikke-bundne pencillin ble fjernet og platen ble behandlet som beskrevet i eksempel 1. Bindingstettheter på tilnærmet 3 nmol/cm<2> ble oppnådd.
Eksempel 15: Binding av RNase til para-aminofenyl-polystyren
RDP.
Para-aminofenyl-polystyren RDP ble oppnådd som beskrevet i
eksempel 4; TDC ble anvendt som bindingsreagens som beskrevet i eksempel 10; RNase (1 mg/ml + 0,1 /xCi <125>I RNase i 100 /il 0,1 M boratbuffer, pH-verdi 8,5) ble tilsatt og holdt ved 4°C i 14-16 timer. Det ikke-bundne RNase ble fjernet og platen ble vasket
og behandlet som beskrevet i eksempel 12. Bindingstettheter på tilnærmet 1 nmol RNase/cm<2> ble oppnådd.
Eksempel 16: EDC-mediert binding av eddiksyre til AHE-polystyrol RDP.
AHE-polystyrol RDP ble oppnådd som beskrevet i eksempel 4 og
eddiksyre (0,1 M + 0,1 /iCi [3H] eddiksyre i 100 /il 0,1 M NaCl, pH-verdi 5) pluss det samme volum av EDC (20 mg/ml i den samme oppløsning) ble tilsatt og holdt ved værelsestemperatur i fire timer. Den ikke-bundne eddiksyre ble fjernet og platen ble
behandlet som beskrevet i eksempel 1. Bindingstettheter på tilnærmet 3 nmol acetat/cm<2> ble oppnådd.
Eksempel 17: EDC-mediert binding av penicillin G til AHE-polystyren RDP.
Den samme fremgangsmåte som beskrevet i det foregående eksempel ble benyttet, bortsett fra at penicillin G (20 mM) ble anvendt istedenfor eddiksyre. Bindingstettheter på tilnærmet 1,5 nmol penicillin G/cm<2> ble oppnådd.
Eksempel 18: EDC-mediert binding av benzosyre til AHE-polystyren RDP.
Fremgangsmåten beskrevet i eksempel 16 ble fulgt, bortsett fra at benzosyre (10 mM) ble anvendt istedenfor eddiksyre. Bindingstetthetene varierte fra 0,6 til 1 nmol benzosyre/cm<2>.
Eksempel 19: EDC-mediert binding av prostagladin El til AHE-polystyren RDP.
Samme fremgangsmåte som beskrevet i eksempel 16 ble fulgt, bortsett fra at prostaglandin El (1 mM) ble brukt istedenfor eddiksyre. Området av bindingstettheter var fra 0,5-1 nmol prostaglandin El/cm<2>.
Eksempel 20: EDC-mediert binding av DNP-aminosyrer til AHE-polystyren RDP.
Samme fremgangsmåte ble fulgt som beskrevet i eksempel 16, bortsett fra at DNP-glycin (10 mM + 0,1 nCi DNP[3H]gly) ble anvendt. Bindingstettheter på tilnærmet 5 nmol DNP-glycin/cm<2 >ble oppnådd.
Eksempel 21: EDC-mediert binding av pepsin til AHE-polystyren
RDP.
Den samme prosedyre som beskrevet i eksempel 16 ble fulgt for fremstilling av AHE-PS RDP, bortsett fra at pepsin (1 mg/ml + 0,1 /iCi <l25>i pepsin) ble benyttet istedenfor eddiksyre. Platene ble behandlet som beskrevet i eksempel 9. Bindingstetthetene varierte fra 0,8-1 nmol pepsin/cm<2>.
Eksempel 22: Til bindingsanalyser av DNP-spesifikt IgE antistoff ble det benyttet mikrotiterplater som inneholdt kovalent bundet DNP-glycin, oppnådd ved fremgangsmåter beskrevet i eksemplene 4,8 og 20. DNP-bindende muse-monoklonalt IgE (spormerket med <125>I) ble tilsatt og inkubert ved 4°C i 16 timer. Den ikke-bundne IgE ble fjernet og restradioaktiviteten (varierte mellom 30 og 40 % av totalt tilsatt IgE) ble bestemt. Intra- og interanalyse variasjonskoeffisient (CV) var mindre enn 3 %. Den samme bindingsanalyse har blitt benyttet til masseundersøkelse av store antall legemidler for multispesi-fikke interaksjoner med IgE i studier av legemiddelalergier (Varga, J.M., Klein, G. and Fritsch, P.:J. Invest. Dermatol., Vol. 92, 1989, pp 537).
Claims (20)
1. Fremgangsmåte for fremstilling av radioderivert polymer karakterisert ved at den omfatter sammenfø-ring av en radiolyserbar polymer og en ikke polymeriserbar konjugand, hvor minst en av nevnte radiolyserbare polymer og nevnte konjugand bestråles med en høyenergi-gamma-stråling i mengder på 1-15 Mrad, for derved å binde nevnte konjugand til nevnte polymer.
2. Fremgangsmåte i henhold til krav 1, karakterisert ved at nevnte radiolyserbare polymer er bestrålet.
3. Fremgangsmåte i henhold til krav 2, karakterisert ved at nevnte radiolyserbare polymer er bestrålt før nevnte sammenføringstrinn.
4. Fremgangsmåte i henhold til krav 1, karakterisert ved at nevnte konjugand er bestrålet.
5. Fremgangsmåte i henhold til krav 4, karakterisert ved at nevnte konjugand er bestrålt før nevnte sammenføringstrinn.
6. Fremgangsmåte i henhold til krav 1, karakterisert ved at både nevnte polymer og nevnte konjugand er bestrålt.
7. Fremgangsmåte i henhold til krav 6, karakterisert ved at nevnte radiolyserbare polymer og nevnte konjugand er bestrålt før nevnte sammen-føringstrinn.
8. Fremgangsmåte i henhold til krav 6, karakterisert ved at nevnte radiolyserbare polymer og nevnte konjugand er bestrålt etter nevnte sam-menf øringstrinn .
9. Fremgangsmåte i henhold til krav 1, karakterisert ved at nevnte konjugand er valgt fra gruppen som består av kinoner, forbindelser fra hvilke kinoner er dannet under bestråling, aromatiske forbindelser, nukleofilholdige stoffer, aminogruppeholdige forbindelser, aromatiske aminforbindelser, karbohydrater og derivater derav, karboksylholdige forbindelser, proteinmodifiserende reagenser og vann.
10. Fremgangsmåte i henhold til krav 1, karakterisert ved at nevnte radiolyserbare polymer er polystyren.
11. Fremgangsmåte i henhold til krav 1, karakterisert ved at det omfatter videre binding av nevnte radioderiverte polymer til en ligand valgt fra gruppen som består av proteiner, avstandsmolekyler, chelatdannere, ioner, kofaktorer, koenzymer, hormoner, legemidler, fargestoffer, lipider, karbohydrater, lektiner, nukleinsyrer, enzymer, haptener, antigener, allergener, antistoffer, viruser, mikroorganismer, eukariote celler og komponenter derav.
12. Fremgangsmåte i henhold til krav 1, karakterisert ved at konjuganden er vann og det radioderiverte produkt er reaktivt med minst en karboksylholdig forbindelse i nærvær av minst en aktivator.
13. Fremgangsmåte i henhold til krav 1, karakterisert ved at konjuganden er en aminogruppeholdig forbindelse og det radioderiverte produkt er reaktivt med karboksylholdige forbindelser i nærvær av minst en aktivator.
14. Fremgangsmåte i henhold til krav 1, karakterisert ved at konjuganden er et nukleofilholdig stoff og produktet er en nukleofil-funksjonalisert radio-derivert polymer.
15. Fremgangsmåte i henhold til krav 12,13 eller 14, karakterisert ved at den radioderiverte polymer er reaktiv med bifunksjonelle reagenser.
16. Fremgangsmåte i henhold til krav 1, karakterisert ved at konjuganden er et aromatisk amin og den radioderiverte polymer er diazotisert.
17. Fremgangsmåte i henhold til krav 1, karakterisert ved at konjuganden er et karbohydrat eller et derivat derav, derved dannende et glykofase radio-derivert polymer hvori nevnte glykofase radioderivert polymer er videre aktivert.
18. Fremgangsmåte i henhold til krav 1, karakterisert ved at konjuganden er en karboksylholdig forbindelse og den resulterende radioderiverte polymer er videre aktivert for å reagere med nukleofiler.
19. Fremgangsmåte i henhold til krav 18, karakterisert ved at nevnte karboksylerte radioderiverte produkt er videre aktivert med karbodiimider for å reagere med nukleofiler.
20. Fremgangsmåte i henhold til krav 1, karakterisert ved at konjuganden er et proteinmodifiserende reagens og den radio-deriverte polymer er en nukleofil-reaktiv polymer.
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Application Number | Priority Date | Filing Date | Title |
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AT0197689A AT397723B (de) | 1989-08-21 | 1989-08-21 | Verfahren zur herstellung radiokonjugierter polymerer und verwendung derselben |
US07/507,348 US5196478A (en) | 1989-08-21 | 1990-04-09 | Immobilization of ligands by radio-derivatized polymers |
PCT/EP1990/001362 WO1991002768A1 (en) | 1989-08-21 | 1990-08-18 | Immobilisation of ligands by radio-derivatized polymers |
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NO911564L NO911564L (no) | 1991-06-20 |
NO176668B true NO176668B (no) | 1995-01-30 |
NO176668C NO176668C (no) | 1995-05-10 |
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