Chemical reagents for attaching affinity molecules on surfaces

Patent metadata

Field	Value
Publication number	US-9981997-B2
Application number	US-201415033004-A
Country	US
Kind code	B2
Filing date	Oct 28, 2014
Priority date	Oct 31, 2013
Publication date	May 29, 2018
Grant date	May 29, 2018

Abstract

Chemical linkage reagents, methods of making and method of using the same are provided. Chemical linkage reagents according to at least some of the embodiments of the present disclosure may be incorporated into or operatively-linked with affinity molecules for attachment to silicon oxide surfaces to, for example, measure interactions between an affinity molecule and its targeting biomolecules.

First claim

What is claimed is:

1. A compound of Formula I:

wherein:
X is O, CH 2 , NH or NCH 3 ;
Y is O, CH 2 , NH or NCH 3 ;
P is CH 2 or O; and
s and t are each independently 0, 1, 2, 3, 4, or 5.

2. The compound of claim 1 , wherein the compound is

3. A compound of Formula III:

wherein:
A is CH 2 or O; and
u is any integer ranging from 1 to 36.

4. The compound of claim 3 , wherein A is O.

5. The compound of claim 3 , wherein u is 12.

6. The compound of claim 3 , wherein the compound is a compound of Formula IV:

7. A composition comprising

8. A method for preparing a compound according to Formula I, comprising contacting a silatrane to a functionalized acid in the presence of a coupling reagent.

9. The method of claim 8 , further comprising an organic solvent.

10. The method of claim 8 , where the organic solvent is dichloromethane.

11. The method of claim 8 , wherein the silatrane is 1-(3-aminopropyl)silatrane (APS).

12. The method of claim 8 , wherein the functionalized acid is 2-(cyclooct-2-yn-1-yloxy)acetic acid.

13. The method of claim 8 , wherein the coupling agent is 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC).

14. The method of claim 8 , wherein the compound of Formula I is

15. A method of preparing compound 6a, comprising:
a. mixing hexatheylene glycol and

in the presence of a first base to form

and
b. mixing divinyl sulfone,

and a second base, to form

16. The method of claim 15 , wherein the first base is sodium hydride.

17. The method of claim 15 , wherein the second base is a tert-butoxide.

18. The method of claim 17 , wherein the tert-butoxide is potassium tert-butoxide.

19. A method for preparing immobilized affinity molecules attached to a functionalized AFM tip, comprising a step of mixing AFM tip with a compound of claim 1 .

20. A method of functionalizing an AFM tip, comprising reacting the silatrane moiety of a compound of claim 1 with silanol on the surface of the AFM tip.

Assignees

• Univ Arizona State

Inventors

• Zhang Peiming
• Senapati Subhadip
• Manna Saikat

Classifications

• C07F7/07

  Cyclic esters · CPC title

• G01Q60/42

  Functionalisation · CPC title

• C07F7/10 Primary

  containing nitrogen {having a Si-N linkage} · CPC title

• C07F7/1804 Primary

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title

• G01Q70/18

  Functionalisation · CPC title