CA2302360C - Fluorination of proteins and peptides for f-18 positron emission tomography - Google Patents
Fluorination of proteins and peptides for f-18 positron emission tomography Download PDFInfo
- Publication number
- CA2302360C CA2302360C CA002302360A CA2302360A CA2302360C CA 2302360 C CA2302360 C CA 2302360C CA 002302360 A CA002302360 A CA 002302360A CA 2302360 A CA2302360 A CA 2302360A CA 2302360 C CA2302360 C CA 2302360C
- Authority
- CA
- Canada
- Prior art keywords
- labeled peptide
- group
- gly
- peptide
- maleimide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title claims abstract description 95
- 102000004196 processed proteins & peptides Human genes 0.000 title claims abstract description 22
- 238000002600 positron emission tomography Methods 0.000 title claims abstract description 8
- 102000004169 proteins and genes Human genes 0.000 title description 10
- 108090000623 proteins and genes Proteins 0.000 title description 10
- 238000003682 fluorination reaction Methods 0.000 title description 6
- KRHYYFGTRYWZRS-BJUDXGSMSA-N ac1l2y5h Chemical compound [18FH] KRHYYFGTRYWZRS-BJUDXGSMSA-N 0.000 claims abstract description 94
- 238000000034 method Methods 0.000 claims abstract description 49
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 36
- 238000002372 labelling Methods 0.000 claims abstract description 32
- 125000003396 thiol group Chemical class [H]S* 0.000 claims abstract description 32
- 108010021625 Immunoglobulin Fragments Proteins 0.000 claims abstract description 23
- 102000008394 Immunoglobulin Fragments Human genes 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 150000003923 2,5-pyrrolediones Chemical group 0.000 claims abstract description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 16
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000001540 azides Chemical group 0.000 claims abstract description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 16
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 16
- SPXOTSHWBDUUMT-UHFFFAOYSA-M 4-nitrobenzenesulfonate Chemical group [O-][N+](=O)C1=CC=C(S([O-])(=O)=O)C=C1 SPXOTSHWBDUUMT-UHFFFAOYSA-M 0.000 claims abstract description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 15
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims abstract description 15
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 14
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims abstract description 14
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 14
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 12
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 12
- BYKGZWMDFQXYHG-UHFFFAOYSA-N 2,5-dioxopyrrole-3-sulfonic acid Chemical compound OS(=O)(=O)C1=CC(=O)NC1=O BYKGZWMDFQXYHG-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 125000001424 substituent group Chemical group 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000000163 radioactive labelling Methods 0.000 claims abstract description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 5
- WPBXOELOQKLBDF-UHFFFAOYSA-N cyanogen iodide Chemical group IC#N WPBXOELOQKLBDF-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000001336 alkenes Chemical class 0.000 claims description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000004697 chelate complex Chemical class 0.000 claims description 7
- 229910052688 Gadolinium Inorganic materials 0.000 claims description 4
- 125000000539 amino acid group Chemical group 0.000 claims description 4
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 4
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 4
- 229910006069 SO3H Inorganic materials 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 101100080277 Caenorhabditis elegans ncr-1 gene Proteins 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 24
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- 239000013598 vector Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 150000003573 thiols Chemical class 0.000 description 12
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- -1 F-18 ion Chemical class 0.000 description 9
- 235000018102 proteins Nutrition 0.000 description 9
- 239000012634 fragment Substances 0.000 description 8
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
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- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 125000002346 iodo group Chemical group I* 0.000 description 4
- OKJPEAGHQZHRQV-UHFFFAOYSA-N iodoform Chemical compound IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 4
- 230000000269 nucleophilic effect Effects 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- 235000018417 cysteine Nutrition 0.000 description 3
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 3
- 238000006073 displacement reaction Methods 0.000 description 3
- 125000006575 electron-withdrawing group Chemical group 0.000 description 3
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- 230000007935 neutral effect Effects 0.000 description 3
- 239000012038 nucleophile Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000007974 sodium acetate buffer Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 108010047041 Complementarity Determining Regions Proteins 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 108010016076 Octreotide Proteins 0.000 description 2
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- 108010008281 Recombinant Fusion Proteins Proteins 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- HMSWAIKSFDFLKN-UHFFFAOYSA-N hexacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC HMSWAIKSFDFLKN-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 2
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
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- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
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- 238000004809 thin layer chromatography Methods 0.000 description 2
- BUTXNGJCCCGNMV-REOHCLBHSA-N (2s)-2-amino-3-sulfanylpropanethioic s-acid Chemical group SC[C@H](N)C(S)=O BUTXNGJCCCGNMV-REOHCLBHSA-N 0.000 description 1
- DEQANNDTNATYII-OULOTJBUSA-N (4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-19-[[(2r)-2-amino-3-phenylpropanoyl]amino]-16-benzyl-n-[(2r,3r)-1,3-dihydroxybutan-2-yl]-7-[(1r)-1-hydroxyethyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxa Chemical compound C([C@@H](N)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC=CC=2)NC1=O)C(=O)N[C@H](CO)[C@H](O)C)C1=CC=CC=C1 DEQANNDTNATYII-OULOTJBUSA-N 0.000 description 1
- PBFKSBAPGGMKKJ-UHFFFAOYSA-N 1-[6-(2,5-dioxopyrrolidin-1-yl)hexyl]pyrrolidine-2,5-dione Chemical compound O=C1CCC(=O)N1CCCCCCN1C(=O)CCC1=O PBFKSBAPGGMKKJ-UHFFFAOYSA-N 0.000 description 1
- DPPDFTAXNOTIJG-UHFFFAOYSA-N 1-amino-3-[[1-(fluoromethyl)-9h-carbazol-4-yl]oxy]propan-2-ol Chemical compound N1C2=CC=CC=C2C2=C1C(CF)=CC=C2OCC(O)CN DPPDFTAXNOTIJG-UHFFFAOYSA-N 0.000 description 1
- WWHZZMHPRRFPGP-UHFFFAOYSA-N 2,2,2-triiodoacetic acid Chemical compound OC(=O)C(I)(I)I WWHZZMHPRRFPGP-UHFFFAOYSA-N 0.000 description 1
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 1
- AUFVJZSDSXXFOI-UHFFFAOYSA-N 2.2.2-cryptand Chemical compound C1COCCOCCN2CCOCCOCCN1CCOCCOCC2 AUFVJZSDSXXFOI-UHFFFAOYSA-N 0.000 description 1
- ZLPORNPZJNRGCO-UHFFFAOYSA-N 3-methylpyrrole-2,5-dione Chemical compound CC1=CC(=O)NC1=O ZLPORNPZJNRGCO-UHFFFAOYSA-N 0.000 description 1
- 102100037328 Chitotriosidase-1 Human genes 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical group F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 206010018338 Glioma Diseases 0.000 description 1
- 101000879661 Homo sapiens Chitotriosidase-1 Proteins 0.000 description 1
- 101000904173 Homo sapiens Progonadoliberin-1 Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 108060003951 Immunoglobulin Proteins 0.000 description 1
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- 102000001706 Immunoglobulin Fab Fragments Human genes 0.000 description 1
- 101100370002 Mus musculus Tnfsf14 gene Proteins 0.000 description 1
- 102000057297 Pepsin A Human genes 0.000 description 1
- 108090000284 Pepsin A Proteins 0.000 description 1
- 102100024028 Progonadoliberin-1 Human genes 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 101000996723 Sus scrofa Gonadotropin-releasing hormone receptor Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
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- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
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- LEVWYRKDKASIDU-IMJSIDKUSA-N cystine group Chemical group C([C@@H](C(=O)O)N)SSC[C@@H](C(=O)O)N LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 description 1
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 125000002228 disulfide group Chemical group 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- OSTIHFXUTPZJQL-UHFFFAOYSA-N fluoro benzoate Chemical compound FOC(=O)C1=CC=CC=C1 OSTIHFXUTPZJQL-UHFFFAOYSA-N 0.000 description 1
- 125000004175 fluorobenzyl group Chemical group 0.000 description 1
- VPLALCFPHOLSTP-UHFFFAOYSA-N fluoromethyl benzoate Chemical compound FCOC(=O)C1=CC=CC=C1 VPLALCFPHOLSTP-UHFFFAOYSA-N 0.000 description 1
- PREZBOFRYJAPOC-UHFFFAOYSA-N fluoromethylsulfanylmethylbenzene Chemical compound FCSCC1=CC=CC=C1 PREZBOFRYJAPOC-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
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- XLXSAKCOAKORKW-UHFFFAOYSA-N gonadorelin Chemical compound C1CCC(C(=O)NCC(N)=O)N1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)CNC(=O)C(NC(=O)C(CO)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C(CC=1NC=NC=1)NC(=O)C1NC(=O)CC1)CC1=CC=C(O)C=C1 XLXSAKCOAKORKW-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
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- 229910052588 hydroxylapatite Inorganic materials 0.000 description 1
- 230000002163 immunogen Effects 0.000 description 1
- 102000018358 immunoglobulin Human genes 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
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- 239000011630 iodine Substances 0.000 description 1
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- IYYQIFHXKAKJPU-UHFFFAOYSA-N n-ethyl-n-(fluoromethyl)ethanamine Chemical compound CCN(CC)CF IYYQIFHXKAKJPU-UHFFFAOYSA-N 0.000 description 1
- 229960002700 octreotide Drugs 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 1
- 229940111202 pepsin Drugs 0.000 description 1
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- TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K16/00—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies
- C07K16/18—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from animals or humans
- C07K16/28—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from animals or humans against receptors, cell surface antigens or cell surface determinants
- C07K16/30—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from animals or humans against receptors, cell surface antigens or cell surface determinants from tumour cells
- C07K16/3007—Carcino-embryonic Antigens
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
- A61K51/083—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins the peptide being octreotide or a somatostatin-receptor-binding peptide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
- A61K51/088—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins conjugates with carriers being peptides, polyamino acids or proteins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
- A61K51/10—Antibodies or immunoglobulins; Fragments thereof, the carrier being an antibody, an immunoglobulin or a fragment thereof, e.g. a camelised human single domain antibody or the Fc fragment of an antibody
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/008—Peptides; Proteins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/107—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides
- C07K1/1072—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides by covalent attachment of residues or functional groups
- C07K1/1077—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides by covalent attachment of residues or functional groups by covalent attachment of residues other than amino acids or peptide residues, e.g. sugars, polyols, fatty acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/13—Labelling of peptides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K16/00—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies
- C07K16/46—Hybrid immunoglobulins
- C07K16/468—Immunoglobulins having two or more different antigen binding sites, e.g. multifunctional antibodies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2123/00—Preparations for testing in vivo
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Immunology (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Optics & Photonics (AREA)
- Physics & Mathematics (AREA)
- Animal Behavior & Ethology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Analytical Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Cell Biology (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5748597P | 1997-09-03 | 1997-09-03 | |
| US60/057,485 | 1997-09-03 | ||
| PCT/US1998/018268 WO1999011590A1 (en) | 1997-09-03 | 1998-09-03 | Fluorination of proteins and peptides for f-18 positron emission tomography |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2302360A1 CA2302360A1 (en) | 1999-03-11 |
| CA2302360C true CA2302360C (en) | 2005-11-15 |
Family
ID=22010853
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002302360A Expired - Lifetime CA2302360C (en) | 1997-09-03 | 1998-09-03 | Fluorination of proteins and peptides for f-18 positron emission tomography |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US6187284B1 (enExample) |
| EP (1) | EP1009726B1 (enExample) |
| JP (1) | JP3992923B2 (enExample) |
| AT (1) | ATE353864T1 (enExample) |
| AU (1) | AU9375698A (enExample) |
| CA (1) | CA2302360C (enExample) |
| DE (1) | DE69837095T2 (enExample) |
| WO (1) | WO1999011590A1 (enExample) |
Families Citing this family (71)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6136311A (en) | 1996-05-06 | 2000-10-24 | Cornell Research Foundation, Inc. | Treatment and diagnosis of cancer |
| US6962702B2 (en) * | 1998-06-22 | 2005-11-08 | Immunomedics Inc. | Production and use of novel peptide-based agents for use with bi-specific antibodies |
| US7387772B1 (en) | 1999-06-22 | 2008-06-17 | Immunimedics, Inc. | Chimeric, human and humanized anti-CSAP monoclonal antibodies |
| US7405320B2 (en) | 1998-06-22 | 2008-07-29 | Immunomedics, Inc. | Therapeutic and diagnostic conjugates for use with multispecific antibodies |
| US7833528B2 (en) * | 1998-06-22 | 2010-11-16 | Immunomedics, Inc. | Use of multispecific, non-covalent complexes for targeted delivery of therapeutics |
| JP4113670B2 (ja) * | 1998-06-22 | 2008-07-09 | イムノメディクス， インコーポレイテッド | プレターゲッティング診断およびプレターゲッティング治療のための二重特異性抗体の使用 |
| US7138103B2 (en) * | 1998-06-22 | 2006-11-21 | Immunomedics, Inc. | Use of bi-specific antibodies for pre-targeting diagnosis and therapy |
| US6998106B1 (en) * | 1998-12-01 | 2006-02-14 | Duke University | Radioconjugation of internalizing antibodies |
| DE10121741A1 (de) * | 2001-05-04 | 2002-11-14 | Forschungszentrum Juelich Gmbh | Verfahren zur Synthese trägerarmer ·18·F markierter Verbindungen |
| CA2474142C (en) * | 2002-02-06 | 2013-02-05 | The Johns Hopkins University | Non-invasive diagnostic imaging technology for mitochondria dysfunction using radiolabeled lipophilic salts |
| US7591994B2 (en) | 2002-12-13 | 2009-09-22 | Immunomedics, Inc. | Camptothecin-binding moiety conjugates |
| US8877901B2 (en) | 2002-12-13 | 2014-11-04 | Immunomedics, Inc. | Camptothecin-binding moiety conjugates |
| US20060099142A1 (en) * | 2002-03-14 | 2006-05-11 | Delaney Allen D | Cancer associated araf1 protein kinase and its uses |
| GB0206750D0 (en) | 2002-03-22 | 2002-05-01 | Amersham Plc | Radiofluorination methods |
| US7597876B2 (en) * | 2007-01-11 | 2009-10-06 | Immunomedics, Inc. | Methods and compositions for improved F-18 labeling of proteins, peptides and other molecules |
| US7993626B2 (en) | 2007-01-11 | 2011-08-09 | Immunomedics, Inc. | Methods and compositions for F-18 labeling of proteins, peptides and other molecules |
| US7563433B2 (en) * | 2007-01-11 | 2009-07-21 | Immunomedics, Inc. | Methods and compositions for F-18 labeling of proteins, peptides and other molecules |
| FR2841554B1 (fr) * | 2002-07-01 | 2008-01-18 | Commissariat Energie Atomique | Composes de maleimides marques, leur procede de preparation et leur utilisation pour le marquage de macromolecules |
| FR2841558B1 (fr) * | 2002-07-01 | 2004-08-13 | Commissariat Energie Atomique | Peptides marques ayant une affinite pour un phospholipide et utilisations |
| PL375183A1 (en) * | 2002-08-02 | 2005-11-28 | Mallinckrodt Inc. | Radioactively labelled amino acid analogues, their preparation and use |
| US9701754B1 (en) | 2002-10-23 | 2017-07-11 | City Of Hope | Covalent disulfide-linked diabodies and uses thereof |
| GB0305704D0 (en) | 2003-03-13 | 2003-04-16 | Amersham Plc | Radiofluorination methods |
| US7741524B2 (en) * | 2003-04-22 | 2010-06-22 | Solvay (Societe Anonyme) | Iodinated organic substances of low molecular mass and process for preparing them |
| CA2538520C (en) | 2003-07-24 | 2015-02-10 | The Queen's Medical Center | Preparation and use of alkylating agents |
| CA2555305A1 (en) * | 2004-02-06 | 2005-08-18 | The University Of Alberta, Simon Fraser University, The University Of Vi Ctoria, The University Of British Columbia And Carleton University, Coll | Method of synthesizing compounds having a phosphorus-fluorine-18 bond |
| KR100808547B1 (ko) | 2005-06-22 | 2008-02-29 | 재단법인서울대학교산학협력재단 | 펩타이드 수용체 영상용 제제로 사용할 수 있는 ｆ－１８－플로로벤질리덴하이드라존－니코틴아마이드－펩타이드 유도체 및 펩타이드에 방사성불소를 효율적으로 표지하기 위한 방법 |
| US20070048803A1 (en) * | 2005-08-25 | 2007-03-01 | Lee Peter P | Immune profiling of lymph nodes associated with cancer |
| US20070092907A1 (en) * | 2005-10-21 | 2007-04-26 | Gambhir Sanjiv S | Methods of screening compound probes |
| GB0525949D0 (en) * | 2005-12-21 | 2006-02-01 | Hammersmith Imanet Ltd | Pet radiotracers |
| JP2009531324A (ja) * | 2006-03-20 | 2009-09-03 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | 癌標的化のための操作された抗前立腺幹細胞抗原（ｐｓｃａ）抗体 |
| US8153100B2 (en) * | 2007-01-11 | 2012-04-10 | Immunomedics, Inc. | Methods and compositions for F-18 labeling of proteins, peptides and other molecules |
| US8398956B2 (en) | 2007-01-11 | 2013-03-19 | Immunomedics, Inc. | In vivo copper-free click chemistry for delivery of therapeutic and/or diagnostic agents |
| EP2117604B1 (en) * | 2007-01-11 | 2017-07-26 | Immunomedics, Inc. | Methods and compositions for improved f-18 labeling of proteins, peptides and other molecules |
| US8709382B2 (en) | 2007-01-11 | 2014-04-29 | Immunomedics, Inc. | Methods and compositions for improved F-18 labeling of proteins, peptides and other molecules |
| US8545809B2 (en) | 2007-01-11 | 2013-10-01 | Immunomedics, Inc. | Methods and compositions for improved 18F labeling of proteins, peptides and other molecules |
| US8889100B2 (en) | 2007-01-11 | 2014-11-18 | Immunomedics, Inc. | Methods and compositions for improved F-18 labeling of proteins, peptides and other molecules |
| US8940298B2 (en) * | 2007-09-04 | 2015-01-27 | The Regents Of The University Of California | High affinity anti-prostate stem cell antigen (PSCA) antibodies for cancer targeting and detection |
| US8029743B2 (en) * | 2007-09-19 | 2011-10-04 | General Electric Company | Microfluidic device with vertical injection aperture |
| ES2531828T3 (es) * | 2008-03-31 | 2015-03-20 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Derivados de purina como agonistas selectivos de los receptores A3 de adenosina |
| US8916570B2 (en) | 2008-03-31 | 2014-12-23 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | A3 adenosine receptor agonists and antagonists |
| US9181253B2 (en) | 2008-08-01 | 2015-11-10 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Adenosine receptor agonists, partial agonists, and antagonists |
| EP2331542B1 (en) * | 2008-08-01 | 2016-07-27 | The United States of America, as Represented by The Secretary, Department of Health and Human Services | A3 adenosine receptor antagonists and partial agonists |
| US20100069616A1 (en) * | 2008-08-06 | 2010-03-18 | The Regents Of The University Of California | Engineered antibody-nanoparticle conjugates |
| US7927476B2 (en) * | 2008-12-22 | 2011-04-19 | General Electric Company | Injection method for microfluidic chips |
| PT3903829T (pt) | 2009-02-13 | 2023-06-02 | Immunomedics Inc | Imunoconjugados com uma ligação intracelular clivável |
| EP2398504B1 (en) | 2009-02-17 | 2018-11-28 | Cornell Research Foundation, Inc. | Methods and kits for diagnosis of cancer and prediction of therapeutic value |
| GB0905438D0 (en) * | 2009-03-30 | 2009-05-13 | Ge Healthcare Ltd | Radiolabelling reagents and methods |
| US8834839B2 (en) * | 2009-04-27 | 2014-09-16 | General Electric Company | Labeled molecular imaging agents, methods of making and methods of use |
| BR112012012887A2 (pt) | 2009-12-02 | 2017-05-02 | Imaginab Inc | minicorpo e cys-diabody (cysdb) codificados por sequência de nucleótidos, respectivo uso e métodos de diagnósticos e de tratamento de câncer associado com a expressão de psma num sujeito. |
| AU2010326004B2 (en) * | 2009-12-04 | 2016-04-21 | Immunomedics, Inc. | Methods and compositions for improved F-18 labeling of proteins, peptides and other molecules |
| CN103501825B (zh) | 2011-05-02 | 2017-03-15 | 免疫医疗公司 | 用于小体积施用的同种异型选择的抗体的超滤浓缩 |
| US8784774B2 (en) | 2011-09-16 | 2014-07-22 | General Electric Company | Labeled molecular imaging agents and methods of use |
| WO2013188740A1 (en) | 2012-06-14 | 2013-12-19 | Ambrx, Inc. | Anti-psma antibodies conjugated to nuclear receptor ligand polypeptides |
| US8937186B2 (en) | 2012-08-21 | 2015-01-20 | Uop Llc | Acids removal and methane conversion process using a supersonic flow reactor |
| EP2774930A1 (en) | 2013-03-07 | 2014-09-10 | Aptenia S.R.L. | Metallocene compounds and labeled molecules comprising the same for in vivo imaging. |
| US9468693B2 (en) | 2014-01-23 | 2016-10-18 | General Electric Company | Labeled molecular imaging agents and methods of use |
| US9468692B2 (en) | 2014-01-23 | 2016-10-18 | General Electric Company | Labeled molecular imaging agents and methods of use |
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| CA2968961A1 (en) | 2014-11-25 | 2016-06-02 | Bristol-Myers Squibb Company | Methods and compositions for 18f-radiolabeling of biologics |
| WO2016130549A1 (en) * | 2015-02-09 | 2016-08-18 | The Trustees Of Princeton University | Targeted, metal-catalyzed fluorination of complex compounds with fluoride ion via decarboxylation |
| CA2981543A1 (en) | 2015-04-22 | 2016-10-27 | Immunomedics, Inc. | Isolation, detection, diagnosis and/or characterization of circulating trop-2-positive cancer cells |
| MX2018001566A (es) | 2015-08-07 | 2019-04-25 | Imaginab Inc | Construcciones de union a antigeno para moleculas diana. |
| HRP20210644T8 (hr) | 2016-05-19 | 2021-06-25 | Bristol-Myers Squibb Company | Imunomodulatori za pet-snimanje |
| US10994033B2 (en) | 2016-06-01 | 2021-05-04 | Bristol-Myers Squibb Company | Imaging methods using 18F-radiolabeled biologics |
| WO2018147960A1 (en) | 2017-02-08 | 2018-08-16 | Imaginab, Inc. | Extension sequences for diabodies |
| US11655307B2 (en) | 2017-05-30 | 2023-05-23 | The Board Of Regents Of The University Of Oklahoma | Anti-doublecortin-like kinase 1 antibodies and methods of use |
| WO2019227490A1 (en) | 2018-06-01 | 2019-12-05 | Tayu Huaxia Biotech Medical Group Co., Ltd. | Compositions and methods for imaging |
| KR20210056288A (ko) | 2018-06-01 | 2021-05-18 | 타유 후아시아 바이오테크 메디컬 그룹 컴퍼니 리미티드 | 질환 또는 병태를 치료하기 위한 조성물 및 그의 용도 |
| WO2020151572A1 (en) | 2019-01-23 | 2020-07-30 | Tayu Huaxia Biotech Medical Group Co., Ltd. | Anti-pd-l1 diabodies and the use thereof |
| WO2022265912A1 (en) | 2021-06-16 | 2022-12-22 | Gundersen Lutheran Medical Foundation, Inc. | Antibodies targeting an amphiregulin-derived cell surface neo-epitope |
| CN115231995A (zh) * | 2022-06-14 | 2022-10-25 | 上海应用技术大学 | 一种单氟二溴代丙酮衍生物及其制备与应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69719529T2 (de) * | 1996-10-17 | 2003-12-11 | Immunomedics, Inc. | Nichtantigenes toxinkonjugat und fusionsprotein eines internalisierendes rezeptorsystems |
-
1998
- 1998-09-03 CA CA002302360A patent/CA2302360C/en not_active Expired - Lifetime
- 1998-09-03 JP JP2000508634A patent/JP3992923B2/ja not_active Expired - Fee Related
- 1998-09-03 AT AT98946820T patent/ATE353864T1/de not_active IP Right Cessation
- 1998-09-03 US US09/146,318 patent/US6187284B1/en not_active Expired - Lifetime
- 1998-09-03 WO PCT/US1998/018268 patent/WO1999011590A1/en not_active Ceased
- 1998-09-03 EP EP98946820A patent/EP1009726B1/en not_active Expired - Lifetime
- 1998-09-03 AU AU93756/98A patent/AU9375698A/en not_active Abandoned
- 1998-09-03 DE DE69837095T patent/DE69837095T2/de not_active Expired - Lifetime
-
2000
- 2000-08-24 US US09/644,706 patent/US6358489B1/en not_active Expired - Lifetime
-
2002
- 2002-02-11 US US10/071,247 patent/US6953567B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE69837095T2 (de) | 2007-11-22 |
| WO1999011590A1 (en) | 1999-03-11 |
| AU9375698A (en) | 1999-03-22 |
| CA2302360A1 (en) | 1999-03-11 |
| DE69837095D1 (de) | 2007-03-29 |
| EP1009726A1 (en) | 2000-06-21 |
| ATE353864T1 (de) | 2007-03-15 |
| JP3992923B2 (ja) | 2007-10-17 |
| US6187284B1 (en) | 2001-02-13 |
| EP1009726B1 (en) | 2007-02-14 |
| US6358489B1 (en) | 2002-03-19 |
| US20020119096A1 (en) | 2002-08-29 |
| US6953567B2 (en) | 2005-10-11 |
| JP2001515843A (ja) | 2001-09-25 |
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