Preparation of a electronically conductive polymer/nucleotide copolymer

• US 5,837,859 A
• Filed: 09/22/1995
• Issued: 11/17/1998
• Est. Priority Date: 03/31/1993
• Status: Expired due to Term

• Current Assignee: Commissariat a L'Energie Atomique (AES Corporation)
• Original Assignee: CIS Bio International (Institut National Radio-Elements et D'Util Pub)
• Inventors: Roget, Andre, Livache, Thierry, Bidan, Gerard, Teoule, Robert, Barthet, Christelle
• Primary Examiner(s): Kunz, Gary L.
• Application Number:
  US08/525,506
• Time in Patent Office: 1,152 Days
• Field of Search: 536/25.3, 205/158, 204/165
• US Class Current: 536/25.3
• CPC Class Codes: B01J 2219/00713 Electrochemical synthesis
• CPC Class Codes: C07H 21/00 Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
• CPC Class Codes: C08G 61/124 with a five-membered ring containing one nitrogen atom in the ring
• CPC Class Codes: C12Q 1/6825 Nucleic acid detection involving sensors

Abstract

A copolymer of general formula (I), ##STR1## wherein unit A is a monomer of an electronically conductive polymer, unit B is a nucleotide, an oligonucleotide or an analogue thereof, x, y, z are integers of 1 or higher or y is 0, and l is a covalent bond, or a spacer arm. Methods for preparing said polymer and its use, in particular for nucleic acid synthesis, sequencing and hybridization, are also disclosed.

Claims

1. A process for preparing an electrically conductive copolymer represented by general formula (1):

##STR5## comprising copolymerizing a monomer represented by formula (IV);

##STR6## with a polymerizable monomer represented by the formula A, wherein said monomer A produces an electrically conductive polymer when polymerized, and represents a polymerized unit of said monomer A in the electrically conductive copolymer,

represents either (1) a nucleotide unit or an analog thereof, or (2) an oligonucleotide unit or an analog thereof,

x, y and z each, independently, represents an integer equal to or greater than 1, and l represents a covalent bond or a spacer arm.

2. The process of claim 1, wherein the copolymerization is an electrochemical copolymerization.

3. The process of claim 2, further comprising coupling additional units to the units of the copolymer.

4. The process of claim 3, wherein the coupling of additional units to the units of the copolymer comprises at least one electrochemical reaction.

5. The process of claim 4, wherein the copolymerization is conducted on the surface of an electrode.

6. The process of claim 1 wherein A is a pyrrole.

7. The method of claim 1, wherein A is acetylene, azine, p-phenylene, p-phenylene vinylene, pyrene, thiophene, furan, selenophene, pyridazine, carbazole or aniline.

8. The method of claim 1, wherein the ratio x/y is between 1/5 and 1/100,000.

9. The method of claim 1, wherein l is a spacer arm represented by the formula:

space="preserve" listing-type="equation">--R.sub.1 -- (CH.sub.2).sub.n --R.sub.2 !.sub.x -- CH.sub.2).sub.m --R.sub.3 !.sub.y --(CH.sub.2).sub.p --

wherein

n is an integer from 1 to 10;

m is 0 or an integer from 1 to 10;

p is 0 or an integer from 1 to 10;

x is 0 or an integer from 1 to 8;

y is 0 or an integer from 1 to 8;

R₁, R₂ and R₃, which may be identical or different, represent;

CH₂, O, S, NR'"'"', CO, CH═

CH, NR'"'"'CO, CONR'"'"', NHSO₂, or ##STR7## where R'"'"' represents a hydrogen atom or a C₁ to C₁₂ alkyl group.