DK2222686T3 - Polyviologenboronsyredeaktivatorer til anvendelse i analytsensorer - Google Patents
Polyviologenboronsyredeaktivatorer til anvendelse i analytsensorer Download PDFInfo
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- DK2222686T3 DK2222686T3 DK08826232.4T DK08826232T DK2222686T3 DK 2222686 T3 DK2222686 T3 DK 2222686T3 DK 08826232 T DK08826232 T DK 08826232T DK 2222686 T3 DK2222686 T3 DK 2222686T3
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- amide
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- 239000008103 glucose Substances 0.000 claims description 32
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 2
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
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- 229910052786 argon Inorganic materials 0.000 description 10
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 5
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- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 3
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- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 3
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- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 2
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 2
- KXXXUIKPSVVSAW-UHFFFAOYSA-K pyranine Chemical class [Na+].[Na+].[Na+].C1=C2C(O)=CC(S([O-])(=O)=O)=C(C=C3)C2=C2C3=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1 KXXXUIKPSVVSAW-UHFFFAOYSA-K 0.000 description 2
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
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- 229910006069 SO3H Inorganic materials 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- 159000000021 acetate salts Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
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- 239000003570 air Substances 0.000 description 1
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- 238000000429 assembly Methods 0.000 description 1
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 1
- XFOZBWSTIQRFQW-UHFFFAOYSA-M benzyl-dimethyl-prop-2-enylazanium;chloride Chemical compound [Cl-].C=CC[N+](C)(C)CC1=CC=CC=C1 XFOZBWSTIQRFQW-UHFFFAOYSA-M 0.000 description 1
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- PCPIANOJERKFJI-UHFFFAOYSA-N ethyl 5-bromopyridine-3-carboxylate Chemical compound CCOC(=O)C1=CN=CC(Br)=C1 PCPIANOJERKFJI-UHFFFAOYSA-N 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- GSMAWUZTAIOCPL-UHFFFAOYSA-N methyl 3,5-dibromobenzoate Chemical compound COC(=O)C1=CC(Br)=CC(Br)=C1 GSMAWUZTAIOCPL-UHFFFAOYSA-N 0.000 description 1
- 239000012982 microporous membrane Substances 0.000 description 1
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- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
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- 125000000565 sulfonamide group Chemical group 0.000 description 1
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- UZNHKBFIBYXPDV-UHFFFAOYSA-N trimethyl-[3-(2-methylprop-2-enoylamino)propyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)NCCC[N+](C)(C)C UZNHKBFIBYXPDV-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0627—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only one nitrogen atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/142222—Hetero-O [e.g., ascorbic acid, etc.]
- Y10T436/143333—Saccharide [e.g., DNA, etc.]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/142222—Hetero-O [e.g., ascorbic acid, etc.]
- Y10T436/143333—Saccharide [e.g., DNA, etc.]
- Y10T436/144444—Glucose
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polymerisation Methods In General (AREA)
Claims (14)
1. Forbindelse, som omfatter to eller flere 3,3'-N,N'bis(benzyl)bipyridiniumdiha-logenid-dele, som er sammenkoblet ved hjælp af en koblingsgruppe, der er indsubstitueret på mindst én af ringene i 3,3'-N,N'bis(benzyl)bipyridiniumdihaloge-nid-delene, hvor hver del indbefatter mindst to boronsyrefunktionelle grupper, med undtagelse af forbindelsen
2. Forbindelse ifølge krav 1
, som har følgende struktur: hvor Z enten er en reaktiv, ethylenisk umættet gruppe eller en reaktiv funktionel gruppe, som kan danne en kovalent binding med en polymer eller matrix; Y er en trivalent forbindelsesgruppe valgt blandt
, hvor R er H eller en lavere alkylgruppe, og
; X' er en modion; X1 og X2 er -O- eller -NH-; og L1, L2 og L3 er valgt fra gruppen bestående af en direkte binding og en lavere alkylengruppe med 1 til 8 carbonatomer, eventuelt termineret med eller afbrudt af en eller flere divalente forbindelsesgrupper valgt fra gruppen bestående af sulfonamid (-SO2NH-), amid -(C=0)N-, ester -(C=0)-0-, ether -O-, sulfid -S-, sulfon (-SO2-), phenylen -CeFU-, urethan -NH(C=0)-0-, urea -NH(C=0)NH-, thiourea -NH(C=S)-NH-, amid -(C=0)NH- og amin -NR- (hvor R er defineret som alkyl med 1 til 6 carbonatomer) eller kombinationer deraf.
3. Forbindelse ifølge krav 1,
hvor n er lig med 1,2, 3 eller 4.
4. Fremgangsmåde til fremstilling af forbindelsen ifølge krav 3, hvilken fremgangsmåde omfatter følgende trin: i
hvor n er lig med 1,2, 3 eller 4.
5. Fremgangsmåde til fremstilling af forbindelsen ifølge krav 3, hvilken fremgangsmåde omfatter følgende trin:
hvor n er lig med 4.
6. Forbindelse ifølge krav 1, som har følgende struktur:
hvor X' er en modion; L er en divalent linker valgt fra gruppen bestående af en direkte binding og en lavere alkylengruppe med 1 til 8 carbonatomer, eventuelt termineret med eller afbrudt af en eller flere divalente forbindelsesgrupper valgt fra gruppen bestående af sulfonamid (-SO2NH-), amid -(C=0)N-, ester -(0=0)-0-, ether -O-, sulfid -S-, sulfon (-SO2-), phenylen -C6H4-, urethan -NH(C=0)-0-, urea -NH(C=0)NH-, thiourea -NH(C=S)-NH-, amid -(C=0)NH- og amin -NR- (hvor R er defineret som alkyl med 1 til 6 carbonatomer) eller kombinationer deraf; Z enten er en reaktiv, ethylenisk umættet gruppe eller en reaktiv funktionel gruppe, som kan danne en kovalent binding med en polymer eller matrix; bindingen fra den centrale benzenring er til ortho-, meta- eller para-stillingen på pyridiniumringene i umiddelbar nærhed af den; og -β(ΟΗ)2 kan forefindes i ortho-, meta- eller para-stillingen.
7. Forbindelse ifølge krav 6, som har følgende struktur:
8. Fremgangsmåde til fremstilling af forbindelsen ifølge krav 7, hvilken fremgangsmåde omfatter følgende trin:
9. Forbindelse ifølge krav 1, som har følgende struktur:
hvor: Z enten er en reaktiv, ethylenisk umættet gruppe eller en reaktiv funktionel gruppe, som kan danne en kovalent binding med en polymer eller matrix; Y er en trivalent forbindelsesgruppe valgt blandt
, hvor R er H eller en lavere alkylgruppe, og
; X' er en modion; X1, X2, X3 og X4 er -O- eller -NH-; og L1, L2 og L3 er valgt fra gruppen bestående af en direkte binding og en lavere alkylengruppe med 1 til 8 carbonatomer, eventuelt termineret med eller afbrudt af en eller flere divalente forbindelsesgrupper valgt fra gruppen bestående af sulfonamid (-SO2NH-), amid -(C=0)N-, ester -(C=0)-0-, ether -O-, sulfid -S-, sulfon (-SO2-), phenylen -CeFU-, urethan -NH(C=0)-0-, urea -NH(C=0)NH-, thiourea -NH(C=S)-NH-, amid -(C=0)NH- og amin -NR- (hvor R er defineret som alkyl med 1 til 6 carbonatomer) eller kombinationer deraf.
10. Forbindelse ifølge krav 9, som har følgende struktur:
11. Fremgangsmåde til fremstilling af forbindelsen ifølge krav 10, hvilken fremgangsmåde omfatter følgende trin:
12. Analytsensor, som omfatter en hvilken som helst eller flere af forbindelserne ifølge krav 1-3, 6, 7, 9 og 10 og et fluorescerende farvestof.
13. Analytsensor ifølge krav 12, hvor analytten er glucose.
14. Stofsammensætning, som omfatter en fluorofor, der er tilbøjelig til at blive deaktiveret ved hjælp af en forbindelse ifølge krav 1, og en glucosepermeabel polymermatrix.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94914507P | 2007-07-11 | 2007-07-11 | |
| PCT/US2008/069855 WO2009009756A2 (en) | 2007-07-11 | 2008-07-11 | Polyviologen boronic acid quenchers for use in analyte sensors |
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| Publication Number | Publication Date |
|---|---|
| DK2222686T3 true DK2222686T3 (da) | 2015-09-21 |
Family
ID=40229502
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK08826232.4T DK2222686T3 (da) | 2007-07-11 | 2008-07-11 | Polyviologenboronsyredeaktivatorer til anvendelse i analytsensorer |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US7829341B2 (da) |
| EP (1) | EP2222686B1 (da) |
| JP (1) | JP5675350B2 (da) |
| DK (1) | DK2222686T3 (da) |
| WO (1) | WO2009009756A2 (da) |
Families Citing this family (94)
| Publication number | Priority date | Publication date | Assignee | Title |
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