Method for direct photopatterning of molecules on surfaces

Patent metadata

Field	Value
Publication number	US-10124312-B2
Application number	US-201514729976-A
Country	US
Kind code	B2
Filing date	Jun 3, 2015
Priority date	Jun 3, 2014
Publication date	Nov 13, 2018
Grant date	Nov 13, 2018

Abstract

The disclosure relates to methods of photopatterning molecules directly on a surface by photochemical means.

First claim

What is claimed is:

1. A method for preparing a covalent linked structure of Formula II:

wherein the method comprises:
exposing a reaction mixture to ultraviolet radiation to produce the covalent linked structure of Formula II,
wherein the reaction mixture comprises a reactive component and a functionalized surface, wherein the reactive component functionalized surface are each independently selected from the group consisting of:

and
wherein
R 1 and R 2 and each independently selected from the group consisting of a surface, a polypeptide, a protein, and oligonucleotide, and antibody, a capsid, or a combination thereof,
wherein one of R 1 and R 2 is the surface, and wherein one of R 1 and R 2 is selected from the group consisting of the polypeptide, the protein, the oligonucleotide, the antibody, the capsid, or a combination thereof, and

L 1 and L 2 are each independently linking groups.

2. The method of claim 1 , comprising:
a) contacting the surface with a functionalizing agent under conditions sufficient to form the functionalized surface;
b) depositing a layer comprising the reactive component on top of the functionalized surface to provide the reaction mixture,
wherein the reactive component comprises the structure of Formula I,

and
c) exposing the reaction mixture to ultraviolet radiation to produce the covalently linked structure of Formula II

wherein
X is a binding group attached directly to the surface;
R 1 comprises the polypeptide, the protein, the oligonucleotide, the antibody, the capsid, or a combination thereof; and
L 1 and L 2 are each independently linking groups comprising from one to fifteen carbon atoms, and optionally substituted with one to three heteroatoms selected from the group consisting of oxygen, nitrogen, and sulfur.

3. The method of claim 2 , wherein the surface is a glass surface.

4. The method of claim 2 , wherein the functionalizing agent comprises the structure

and the functionalized surface comprises the structure:

wherein
X′ is absent or an activated binding group.

5. The method of claim 4 , wherein the functionalizing agent comprises the structure

6. The method of claim 4 , wherein the functionalizing agent is present in a mixture comprising ethanol and aqueous acetate buffer.

7. The method of claim 2 , wherein the functionalizing agent comprises the structure

and the functionalized surface comprises the structure

wherein m is an integer from 1 to 3.

8. The method of claim 7 , wherein the functionalized surface is further treated with an aqueous solution comprising tris-(2-carboxyethyl)phosphine (TCEP) prior to depositing the layer of the reactive component, to form the functionalized surface:

9. The method of claim 2 , wherein L 1 comprises the structure

wherein
n is an integer from 1 to 3;
m is an integer from 5 to 8;
wherein * represents the attachment point to

and
wherein ** represents the attachment point of R 1 .

10. The method of claim 9 , wherein R 1 comprises an oligonucleotide selected from the group consisting of DNA and RNA.

11. The method of claim 10 , wherein R 1 comprises ssDNA.

12. The method of claim 2 , wherein the reactive component is present in a solution of water and methanol.

13. The method of claim 2 , wherein the method further comprises:
adding methanol to the reaction mixture prior to exposing the reaction mixture to ultraviolet radiation; and
distributing the methanol on the surface.

14. The method of claim 13 , wherein the distributing is performed by spin coating.

15. The method of claim 2 , wherein the method further comprises contacting the reaction mixture with a mask containing at least one region that is transparent to ultraviolet radiation.

16. The method of claim 2 , wherein the method comprises:
a) contacting the surface with the functionalizing agent having the structure

in a solution comprising ethanol and aqueous acetate buffer to provide the functionalized surface comprising the structure:

b) depositing the reactive component in a solution of water and methanol on top of the functionalized surface to provide a thin film of the reaction mixture,
wherein the reactive component comprises a structure of Formula III,

and
c) exposing the reaction mixture to ultraviolet radiation to produce a structure of Formula IV:

wherein R 1 is 5′-TGT GTG TGT GTG TGT GTG TG-3′.

17. The method of claim 2 , wherein the method comprises:
a) contacting the surface with a functionalizing agent having the structure

in a solution comprising ethanol, water, and acetic acid to provide the functionalized surface comprising the structure:

treating the functionalized surface with an aqueous solution comprising tris-(2-carboxyethyl)phosphine (TCEP) to provide the functionalized surface comprising the structure

b) depositing the reactive component in a solution of water and methanol on top of the functionalized surface to provide a thin film of the reaction mixture,
wherein the reactive component comprises a structure of Formula III,

and
c) exposing the reaction mixture to ultraviolet radiation to produce a structure of Formula V

wherein R 1 is 5′-TGT GTG TGT GTG TGT GTG TG-3′.

Assignees

• Univ California

Inventors

• Francis Matthew B B
• Twite Amy A
• El Muslemany Kareem

Classifications

• G03F7/008

  Azides (G03F7/075 takes precedence) · CPC title

• B01J2219/0881

  Two or more materials · CPC title

• B01J2219/1203

  Incoherent waves · CPC title

• G03F7/0125

  characterised by the polymeric binder or the macromolecular additives other than the macromolecular azides · CPC title

• G03F7/0755

  Non-macromolecular compounds containing Si-O, Si-C or Si-N bonds (G03F7/0752 takes precedence) · CPC title