Silane molecules with pre-activated and protein-resistant functionalities and silane films comprising such molecules
View Patent ↗The present invention provides a silane molecule which combines pre-activated and protein-resistant functionalities in one molecule; the molecule has a general formula: A-(CH 2 ) n —(O[CH 2 ] t ) m —(CH 2 ) v —Y (1) wherein A is a functional group for binding to a substrate and Y is a functional group for binding to biomolecules. The invention furthermore provides a method for the synthesis of such a silane molecule and a method for depositing a monolayer of such silane molecules onto a substrate. Such a monolayer of silane molecules may be used in biosensors, DNA/protein micro-arrays or other sensor applications. For further lowering the protein binding to the surface of the biosensor, the monolayer may furthermore comprise second silane molecules with formula: B—(CH 2 ) o —(OCH 2 CH 2 ) r —Z. (4)
1. A silane molecule having the general formula:
A-(CH 2 ) n —(O(CH 2 ) t ) m —(CH 2 ) v —Y (1)
wherein
A is selected from the group consisting of X 3 Si, X 2 R 1 Si, and XR 1 R 2 Si, wherein X is a halo group or an alkoxy group, and R 1 and R 2 are each independently an alkyl chain,
Y is a conjugated carbonyl, and
n is an integer from 6 to 22, m is an integer from 0 to 50, v is an integer from 0 to 5, and t is an integer from 1 to 10.
2. The silane molecule according to claim 1 , wherein Y is a conjugated carbonyl selected from the group consisting of fluoro substituted benzoate, pentafluorophenylester, N-hydroxysuccinimide ester, acid halogenide, and maleimide.
3. The silane molecule according to claim 1 , wherein A is Cl 3 Si— or EtO 3 Si—.
4. The silane molecule according to claim 1 , wherein at least one pair of adjacent —CH 2 — moieties in the group (CH 2 ) n are separated from each other by at least one heteroatom, such that the group (CH 2 ) n comprises p heteroatoms, with p being such that n+p is an integer from 6 to 22.
5. The silane molecule according to claim 1 , wherein at least one pair of adjacent —CH 2 — moieties in the group (CH 2 ) v are separated from each other by at least one heteroatom, wherein (CH 2 ) v is a spacer and comprises q heteroatoms, with q being such that v+q is an integer from 0 to 5.
6. A method for synthesizing a silane molecule, the method comprising:
reacting an alcohol of formula (2)
H 2 C═(CH 2 ) n−1 —(O—(CH 2 ) t ) m —OH (2)
wherein n is an integer from 6 to 22, m is an integer from 0 to 50, and t is an integer from 0 to 5, with a compound of a formula selected from the group consisting of Cl—(CH 2 ) v —Y and Br—(CH 2 ) v —Y, wherein v is an integer from 0 to 5 and Y is a conjugated carbonyl, whereby an intermediate of formula (3) is obtained; and
H 2 C═(CH 2 ) n−1 —(O—(CH 2 ) t ) m —(CH 2 ) v —Y (3)
reacting the intermediate of formula (3) with a compound of formula A-H, wherein A is selected from the group consisting of X 3 Si, X 2 R 1 Si, and XR 1 R 2 Si, X is a halo group or an alkoxy group, and R 1 and R 2 are each independently an alkyl chain, whereby a silane of formula (1) is obtained:
A-(CH 2 ) n —(O(CH 2 ) t ) m —(CH 2 ) v —Y (1).
7. The method according to claim 6 , wherein Y is a conjugated carbonyl selected from the group consisting of fluoro substituted benzoate, pentafluorophenylester, N-hydroxysuccinimide ester, acid halogenide, and maleimide.
8. The method according to claim 6 , wherein A is Cl 3 Si— or EtO 3 Si—.
9. The method according to claim 6 , wherein at least one pair of adjacent —CH 2 — moieties in the group (CH 2 ) n are separated from each other by at least one heteroatom, such that the group (CH 2 ) n comprises p heteroatoms, with p being such that n+p is an integer from 0 to 30.
10. The method according to claim 6 , wherein at least one pair of adjacent —CH 2 — moieties in the group (CH 2 ) v are separated from each other by at least one heteroatom, wherein (CH 2 ) v is a spacer and comprises q heteroatoms, with q being such that v+q is an integer from 0 to 5.
11. The silane molecule according to claim 1 , wherein Y is fluoro substituted benzoate.
12. The silane molecule according to claim 1 , wherein Y is pentafluorophenylester.
13. The silane molecule according to claim 1 , wherein Y is N-hydroxysuccinimide ester.
14. The silane molecule according to claim 1 , wherein Y is acid halogenide.
15. The silane molecule according to claim 1 , wherein Y is maleimide.
16. The silane molecule according to claim 1 , wherein A is X 3 Si, wherein X is a halo group or an alkoxy group.
17. The silane molecule according to claim 1 , wherein A is X 2 R 1 Si, wherein X is a halo group or an alkoxy group, and R 1 is an alkyl chain.
18. The silane molecule according to claim 1 , wherein A is XR 1 R 2 Si, wherein X is a halo group or an alkoxy group, and R 1 and R 2 are each independently an alkyl chain.
19. The method according to claim 6 , wherein Y is fluoro substituted benzoate.
20. The method according to claim 6 , wherein Y is pentafluorophenylester.
21. The method according to claim 6 , wherein Y is N-hydroxysuccinimide ester.
22. The method according to claim 6 , wherein Y is acid halogenide.
23. The method according to claim 6 , wherein Y is maleimide.
24. The method according to claim 6 , wherein A is X 3 Si, wherein X is a halo group or an alkoxy group.
25. The method according to claim 6 , wherein A is X 2 R 1 Si, wherein X is a halo group or an alkoxy group, and R 1 is an alkyl chain.
26. The method according to claim 6 , wherein A is XR 1 R 2 Si, wherein X is a halo group or an alkoxy group, and R 1 and R 2 are each independently an alkyl chain.
27. The silane molecule according to claim 1 , wherein t is an integer from 1 to 5 and in is an integer from 3 to 22.
28. The method according to claim 6 , wherein t is an integer from 1 to 5 and m is an integer from 3 to 22.