Polymers and DNA copolymer coatings

Patent metadata

Field	Value
Publication number	US-11447582-B2
Application number	US-202016739679-A
Country	US
Kind code	B2
Filing date	Jan 10, 2020
Priority date	Oct 31, 2014
Publication date	Sep 20, 2022
Grant date	Sep 20, 2022

Abstract

Some embodiments described herein relate to new polymer coatings for surface functionalization and new processes for grafting pre-grafted DNA-copolymers to surface(s) of substrates for use in DNA sequencing and other diagnostic applications.

First claim

What is claimed is:

1. A polymer for surface functionalization, comprising a recurring unit of Formula (V):

wherein
each R 1d and R 2d is independently hydrogen, optionally substituted alkyl or optionally substituted phenyl;
R 3d is hydrogen, optionally substituted alkyl, optionally substituted phenyl, or optionally substituted C 7-14 aralkyl;
R B is azido, substituted amino, Boc-protected amino, hydroxy, thiol, alkynyl, alkenyl, halo, epoxy, tetrazinyl, or aldehyde;
L 4 is an optionally substituted alkylene linker or an optionally substituted heteroalkylene linker; and
L 5 is

and wherein n is an integer of 1 to 50.

2. The polymer of claim 1 , wherein R 1d is hydrogen or alkyl.

3. The polymer of claim 1 , wherein each R 2d and R 3d is hydrogen.

4. The polymer of claim 1 , wherein R B is azido, or Boc-protected amino, or a combination thereof.

5. The polymer of claim 1 , wherein L 4 is a methylene linker.

6. The polymer of claim 1 , wherein the recurring unit of Formula (V) is also represented by Formula (Va) or (Vb), or both:

wherein each R 1d is independently hydrogen or methyl, and n is 1, 2, or 3.

7. The polymer of claim 1 , further comprises a recurring unit of Formula (VIa) or (VIb), or both:

wherein each R 1e , R 2e R 1f and R 2f is independently hydrogen, optionally substituted alkyl or optionally substituted phenyl.

8. The polymer of claim 7 , wherein each R 1e and R 1f is hydrogen or alkyl; and each R 2e and R 2f is hydrogen.

9. A substrate having a first surface comprising a polymer of claim 1 covalently bonded thereto.

10. The substrate of claim 9 , further comprising one or more recurring units selected from the group consisting of polyacrylamides, polyacrylates, polyurethanes, polysiloxanes, silicones, polyacroleins, polyphosphazenes, polyisocyanates, poly-ols, and polysaccharides, and combinations thereof.

11. The substrate of claim 9 , wherein the polymer is covalently bonded to the first surface of the substrate through reaction with a first plurality of functional groups covalently attached thereto the first surface, wherein the first plurality of functional groups comprise vinyl, acryloyl, alkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, cycloalkynyl, heterocycloalkynyl, nitrene, aldehyde, hydrazinyl, glycidyl ether, epoxy, carbene, isocyanate or maleimide, or optionally substituted variants or combinations thereof.

12. The substrate of claim 11 , wherein the first plurality of functional groups comprise optionally substituted norbornene, glycidyl ether, or epoxy, or combinations thereof.

13. The substrate of claim 11 , wherein the covalent bonding between the polymer and the first surface of the substrate comprises the structure moiety

or combinations thereof, wherein * indicates the polymer's point of connection with the first surface of the substrate.

14. The substrate of claim 11 , wherein the covalent bonding between the polymer and the first surface comprises the structure moiety

or combinations thereof, wherein * indicates the polymer's point of connection with the first surface of the substrate.

15. The substrate of claim 9 , further comprising functionalized oligonucleotides covalently bonded to the polymer.

16. The substrate of claim 15 , wherein the functionalized oligonucleotides are covalently bonded to the polymer through reaction of one or more functional moieties of the functionalized oligonucleotides with the epoxy groups of the polymer, and wherein said one or more functional moieties of the oligonucleotides comprises optionally substituted amino, hydroxy, thiol, carboxyl, acid anhydride, or combinations thereof.

17. The substrate of claim 15 , wherein the covalent bonding between the functionalized oligonucleotide and the polymer comprises the structure moiety

or combinations thereof, wherein * indicates the polymer's point of connection with the functionalized oligonucleotide.

18. A method for immobilizing a polymer to a first surface of a substrate, comprising:
contacting a polymer comprising a recurring unit of Formula (V) with the first surface of the substrate, said first surface comprising a first plurality of functional groups covalently attached thereto; and
reacting the first plurality of functional groups of the first surface with the polymer, thereby covalently bonding the polymer to the first surface of the substrate;

wherein
each R 1d and R 2d is independently hydrogen, optionally substituted alkyl or optionally substituted phenyl;
R 3d is hydrogen, optionally substituted alkyl, optionally substituted phenyl, or optionally substituted C 7-14 aralkyl;
R B is azido, substituted amino, Boc-protected amino, hydroxy, thiol, alkynyl, alkenyl, halo, epoxy, tetrazinyl, or aldehyde;
L 4 is an optionally substituted alkylene linker or an optionally substituted heteroalkylene linker; and
L 5 is

and wherein n is an integer of 1 to 50.

19. The method of claim 18 , wherein the first plurality of functional groups of the first surface comprise vinyl, acryloyl, alkenyl, cycloalkenyl, heterocycloalkenyl, alkynyl, cycloalkynyl, heterocycloalkynyl, nitrene, aldehyde, hydrazinyl, glycidyl ether, epoxy, carbene, isocyanate or maleimide, or optionally substituted variants, or combinations thereof.

20. The method of claim 19 , wherein the first plurality of functional groups comprise norbornene, glycidyl ether or epoxy, or combinations thereof.

21. The method of claim 20 , wherein R B is azido, or Boc-protected amino, or a combination thereof.

Assignees

• Illumina Cambridge Ltd

Inventors

• Brown Andrew A
• George Wayne N
• Richez Alexandre
• Dingwall Anne-Cecile
• Von Hatten Xavier

Classifications

• C08F8/32 Primary

  by reaction with amines · CPC title

• C08F2438/03

  Use of a di- or tri-thiocarbonylthio compound, e.g. di- or tri-thioester, di- or tri-thiocarbamate, or a xanthate as chain transfer agent, e.g . Reversible Addition Fragmentation chain Transfer [RAFT] or Macromolecular Design via Interchange of Xanthates [MADIX] · CPC title

• C40B50/18

  using a particular method of attachment to the solid support · CPC title

• C08F20/60 Primary

  containing nitrogen in addition to the carbonamido nitrogen · CPC title

• C08F220/20

  of polyhydric alcohols or phenols {, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate} · CPC title