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DK1812031T3 - Sammensætninger og fremgangsmåder til modificering af biomolekyler - Google Patents

Sammensætninger og fremgangsmåder til modificering af biomolekyler Download PDF

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DK1812031T3
DK1812031T3 DK05823231.5T DK05823231T DK1812031T3 DK 1812031 T3 DK1812031 T3 DK 1812031T3 DK 05823231 T DK05823231 T DK 05823231T DK 1812031 T3 DK1812031 T3 DK 1812031T3
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ester
compound
nitro
sulfonyl
azide
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Carolyn R Bertozzi
Jeremy Michael Baskin
Nicholas J Agard
Jennifer A Prescher
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Univ California
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Claims (27)

1. Forbindelse med formlen:
hvor: hvert af X og X' uafhængigt er: (a) et eller to halogenatomer (e.g., bromo, chlor, fluor, iodo); (b) -W-(CH2)n-Z, hvor n er et helt tal fra 1-4; hvor W, hvis til stede, er O, N eller S; og hvor Z er nitro, cyano, sulfonsyre eller et halogen; (c) -(CH2)n-W-(CH2)m-Z, hvor n og m hver især uafhængigt er 1 eller 2; hvor W er O, N, S eller sulfonyl; forudsat at hvis W er O, N eller S, så er Z nitro, cyano eller halogen; og forudsat at hvis W er sulfonyl, så er Z H; eller (d) -(CH2)n-Z, hvor n er et helt tal fra 1 -4; og hvor Z er nitro, cyano, sulfonsyre eller et halogen; Y er H; en reaktiv gruppe udvalgt fra et carboxyl, en amin, en ester, en thioester, et sulfonylhalid, en alkohol, en thiol, en succinimidylester, et isothiocyanat, et iodoacetamid, et maleimid og et hydrazin; eller en detekter-bar markering, et lægemiddel, et toksin, et peptid, et polypeptid, en epitop-tag eller et medlem af et specifikt bindingspar; og Ri er udvalgt fra en carboxylsyre, en alkylester, en arylester, en substitueret arylester, et aldehyd, et amid, et arylamid, et alkylhalid, en thioester, en sul-fonylester, en alkylketon, en arylketon, en substitueret arylketon, et halosul-fonyl, en nitril og et nitro; eller hvert af X og X' uafhængigt er: (a) H; (b) et eller to halogenatomer (f.eks. bromo, chlor, fluor, iodo); (c) -W-(CH2)n-Z, hvor n er et helt tal fra 1-4; hvor W, hvis til stede, er O, N eller S; og hvor Z er nitro, cyano, sulfonsyre eller et halogen; (d) -(CH2)n-W-(CH2)m-Z, hvor n og m hver især uafhængigt er 1 eller 2; hvor W er O, N, S eller sulfonyl; forudsat at hvis W er O, N eller S, så er Z nitro, cyano eller halogen; og forudsat at hvis W er sulfonyl, så er Z H; eller (e) -(CH2)n-Z, hvor n er et helt tal fra 1 -4; og hvor Z er nitro, cyano, sulfonsyre eller et halogen; Y er et carboxyl, et amin, en thioester, et sulfonylhalid, en alkohol, en thiol, en succinimidylester, et isothiocyanat, et iodoacetamid, et maleimid eller et hydrazin; eller en fluorescerende markering, et lægemiddel, et toksin, et peptid, et polypeptid, et epitop-tag eller et medlem af et specifikt bindingspar; og Ri er udvalgt fra en carboxylsyre, en alkylester, en arylester, en substitueret arylester, et aldehyd, et amid, et arylamid, et alkylhalid, en thioester, en sul-fonylester, en alkylketon, en arylketon, en substitueret arylketon, et halosul-fonyl, en nitril og et nitro.
2. Forbindelse ifølge krav 1, hvor: hvert af X og X' uafhængigt er: (a) et eller to halogenatomer (e.g., bromo, chlor, fluor, iodo); (b) -W-(CH2)n-Z, hvor n er et helt tal fra 1-4; hvor W, hvis til stede, er O, N eller S; og hvor Z er nitro, cyano, sulfonsyre eller et halogen; (c) -(CH2)n-W-(CH2)m-Z, hvor n og m hver især uafhængigt er 1 eller 2; hvor W er O, N, S eller sulfonyl; forudsat at hvis W er O, N eller S, så er Z nitro, cyano eller halogen; og forudsat at hvis W er sulfonyl, så er Z H; eller (d) -(CH2)n-Z, hvor n er et helt tal fra 1 -4; og hvor Z er nitro, cyano, sulfonsyre eller et halogen; Y er H; en reaktiv gruppe udvalgt fra et carboxyl, en amin, en ester, en thioester, et sulfonylhalid, en alkohol, en thiol, en succinimidylester, et isothiocyanat, et iodoacetamid, et maleimid og et hydrazin; eller en detekter-bar markering, et lægemiddel, et toksin, et peptid, et polypeptid, en epitop-tag eller et medlem af et specifikt bindingspar; og Ri er udvalgt fra en carboxylsyre, en alkylester, en arylester, en substitueret arylester, et aldehyd, et amid, et arylamid, et alkylhalid, en thioester, en sul-fonylester, en alkylketon, en arylketon, en substitueret arylketon, et halosul-fonyl, en nitril og et nitro.
3. Forbindelse ifølge krav 1, hvor: hvert af X og X' uafhængigt er: (a)H; (b) et eller to halogenatomer (f.eks. bromo, chlor, fluor, iodo); (c) -W-(CH2)n-Z, hvor n er et helt tal fra 1-4; hvor W, hvis til stede, er O, N eller S; og hvor Z er nitro, cyano, sulfonsyre eller et halogen; (d) -(CH2)n-W-(CH2)m-Z, hvor n og m hver især uafhængigt er 1 eller 2; hvor W er O, N, S eller sulfonyl; forudsat at hvis W er O, N eller S, så er Z nitro, cyano eller halogen; og forudsat at hvis W er sulfonyl, så er Z H; eller (e) -(CH2)n-Z, hvor n er et helt tal fra 1 -4; og hvor Z er nitro, cyano, sulfonsyre eller et halogen; Y er et carboxyl, et amin, en thioester, et sulfonylhalid, en alkohol, en thiol, en succinimidylester, et isothiocyanat, et iodoacetamid, et maleimid eller et hydrazin; eller en fluorescerende markering, et lægemiddel, et toksin, et peptid, et polypeptid, et epitop-tag eller et medlem af et specifikt bindingspar; og Ri er udvalgt fra en carboxylsyre, en alkylester, en arylester, en substitueret arylester, et aldehyd, et amid, et arylamid, et alkylhalid, en thioester, en sul-fonylester, en alkylketon, en arylketon, en substitueret arylketon, et halosul-fonyl, en nitril og et nitro.
4. Forbindelse ifølge krav 3, hvor X er to fluoratomer, og X' er H.
5. Forbindelse ifølge krav 3, hvor X og X' begge er H.
6. Forbindelse ifølge et af kravene 1 til 3, hvor X og X' begge er fluor.
7. Forbindelse et af kravene 1 til 6, hvor Y er et fluorphor.
8. Forbindelse ifølge et af kravene 1 til 6, hvor Y er et medlem af et specifikt bindingspar.
9. Forbindelse ifølge et af kravene 1 til 6, hvor Y er biotin.
10. Forbindelse ifølge krav 9, hvor forbindelsen har strukturen:
11. Forbindelse ifølge et af kravene 1 til 6, hvor Y er et epitop-tag.
12. Forbindelse til anvendelse i en fremgangsmåde til diagnosticering eller en fremgangsmåde til terapi, hvor forbindelsen er et modificeret cycloalkyn med formel
j hvor: hvert af X og X' uafhængigt er: (a) H; (b) et eller to halogenatomer (f.eks. bromo, chlor, fluor, iodo); (c) -W-(CH2)n-Z, hvor n er et helt tal fra 1-4; hvor W, hvis til stede, er O, N eller S; og hvor Z er nitro, cyano, sulfonsyre eller et halogen; (d) -(CH2)n-W-(GH2)m-Z, hvor n og m hver især uafhængigt er 1 eller 2; hvor W er O, N, S eller sulfonyl; forudsat at hvis W er O, N eller S, så er Z nitro, cyano eller halogen; og forudsat at hvis W er sulfonyl, så er Z H; eller (e) -(CH2)n-Z, hvor n er et helt tal fra 1 -4; og hvor Z er nitro, cyano, sulfonsyre eller et halogen; Y er en detekterbar markering, et lægemiddel, et toksin, et peptid, et po-lypeptid, et epitop-tag eller et medlem af et specifikt bindingspar; og Ri er udvalgt fra en carboxylsyre, en alkylester, en arylester, en substitueret arylester, et aldehyd, et amid, et arylamid, et alkylhalid, en thioester, en sul- fonylester, en alkylketon, en arylketon, en substitueret arylketon, et halosul-fonyl, en nitril og et nitro.
13. Forbindelse til anvendelse ifølge krav 12, hvor fremgangsmåden omfatter trinnene med at omsætte et azid af et målmolekyle med det modificerede cycloalkyn, og omsætningen frembringer et konjugat mellem azidet af målmolekylet og det modificerede cycloalkyn.
14. Forbindelse til anvendelse ifølge krav 12, hvor fremgangsmåden er til syntetisk modificering af en cellekomponent, hvilken fremgangsmåde omfatter: indføring af en azidenhed i en cellekomponent, hvorved der frembringes en azid-modificeret cellekomponent; og det at bringe cellen, som omfatter den azid-modificerede cellekomponent, i kontakt med en reaktiv partner omfattende det modificerede cycloalkyn, hvor kontakten foregår under fysiologiske betingelser; og kontakten med den reaktive partner resulterer i en omsætning mellem azidgruppen af den azid-modificerede cellekomponent og cycloalkynet af den reaktive partner, hvorved cellekomponenten modificeres syntetisk og kovalent.
15. In wYro-fremgangsmåde til kemoselektiv ligation af et målmolekyle omfattende et azid, hvilken fremgangsmåde omfatter: omsætning af et azid af et målmolekyle med et modificeret cycloalkyn, og omsætningen frembringer et konjugat mellem azidet af målmolekylet og det modificerede cycloalkyn, hvor det modificerede cycloalkyn har formlen
hvor: hvert af X og X' uafhængigt er: (a) Η; (b) et eller to halogenatomer (f.eks. bromo, chlor, fluor, iodo); (c) -W-(CH2)n-Z, hvor n er et helt tal fra 1-4; hvor W, hvis til stede, er O, N eller S; og hvor Z er nitro, cyano, sulfonsyre eller et halogen; (d) -(CH2)n-W-(CH2)m-Z, hvor n og m hver især uafhængigt er 1 eller 2; hvor W er O, N, S eller sulfonyl; forudsat at hvis W er O, N eller S, så er Z nitro, cyano eller halogen; og forudsat at hvis W er sulfonyl, så er Z H; eller (e) -(CH2)n-Z, hvor n er et helt tal fra 1 -4; og hvor Z er nitro, cyano, sulfonsyre eller et halogen; Y er en detekterbar markering, et lægemiddel, et toksin, et peptid, et po-lypeptid, et epitop-tag eller et medlem af et specifikt bindingspar; og Ri er udvalgt fra en carboxylsyre, en alkylester, en arylester, en substitueret arylester, et aldehyd, et amid, et arylamid, et alkylhalid, en thioester, en sul-fonylester, en alkylketon, en arylketon, en substitueret arylketon, et halosul-fonyl, en nitril og et nitro.
16. Fremgangsmåde ifølge et af kravene 13-15, hvorved omsætningen udføres under vandige betingelser.
17. Fremgangsmåde ifølge et af kravene 13-15, hvorved omsætningen udføres under fysiologiske betingelser.
18. Forbindelse til anvendelse ifølge krav 12 eller 13 eller fremgangsmåderne ifølge et af kravene 15 til 17, hvor målmolekylet er et sukker.
19. Forbindelse til anvendelse ifølge krav 12 eller 13 eller fremgangsmåderne ifølge et af kravene 15 til 17, hvor sukkeret er et substrat af sialinsyrebiosyntese.
20. Forbindelse til anvendelse ifølge krav 12 eller 13 eller fremgangsmåderne ifølge et af kravene 15 til 17, hvor sukkeret er mannosamin eller acetyleret mannosamin.
21. Forbindelse til anvendelse ifølge krav 12 eller 13 eller fremgangsmåderne ifølge et af kravene 15 til 17, hvor målmolekylet er en aminosyre.
22. Forbindelse til anvendelse ifølge krav 12 eller 13 eller fremgangsmåderne ifølge et af kravene 15 til 17, hvor målmolekylet, som omfatter azidet, er ek-sprimeret på en celleoverflade.
23. In v/fro-fremgangsmåde til syntetisk modificering af en cellekomponent, hvilken fremgangsmåde omfatter: indføring af en azidenhed i en cellekomponent, hvorved der frembringes en azid-modificeret cellekomponent; og det at bringe cellen, som omfatter den azid-modificerede cellekomponent, i kontakt med en reaktiv partner omfattende et modificeret cycloalkyn, hvor kontakten foregår under fysiologiske betingelser; og kontakten med den reaktive partner resulterer i en omsætning mellem azidgruppen af den azid-modificerede cellekomponent og cycloalkynet af den reaktive partner, hvorved cellekomponenten modificeres syntetisk og kovalent, hvor det modificerede cycloalkyn har formlen
hvor: hvert af X og X' uafhængigt er: (a) H; (b) et eller to halogenatomer (f.eks. bromo, chlor, fluor, iodo); (c) -W-(CH2)n-Z, hvor n er et helt tal fra 1-4; hvor W, hvis til stede, er O, N eller S; og hvor Z er nitro, cyano, sulfonsyre eller et halogen; (d) -(CH2)n-W-(CH2)m-Z, hvor n og m hver især uafhængigt er 1 eller 2; hvor W er O, N, S eller sulfonyl; forudsat at hvis W er O, N eller S, så er Z nitro, cyano eller halogen; og forudsat at hvis W er sulfonyl, så er Z H; eller (e) -(CH2)n-Z, hvor n er et helt tal fra 1-4; og hvor Z er nitro, cyano, sulfonsyre eller et halogen; Y er en detekterbar markering, et lægemiddel, et toksin, et peptid, et po-lypeptid, et epitop-tag eller et medlem af et specifikt bindingspar; og Ri er udvalgt fra en carboxylsyre, en alkylester, en arylester, en substitueret arylester, et aldehyd, et amid, et arylamid, et alkylhalid, en thioester, en sul-fonylester, en alkylketon, en arylketon, en substitueret arylketon, et halosul-fonyl, en nitril og et nitro.
24. Forbindelse til anvendelse ifølge krav 14 eller fremgangsmåde ifølge krav 23, hvor cellekomponenten er et polypeptid.
25. Forbindelse til anvendelse ifølge krav 14 eller fremgangsmåde ifølge krav 23, hvor R-ι er en alkylester.
26. Forbindelse til anvendelse ifølge krav 14 eller fremgangsmåde ifølge krav 23, hvor alkylesteren er en methylester.
27. Forbindelse til anvendelse ifølge et af kravene 12 til 14 eller fremgangsmåderne ifølge et af kravene 15 til 24, hvor forbindelsen er ifølge et af kravene 1 til 11.
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