Electrically conductive electroactive functionalized conjugated polymers, and uses thereof

• US 6,096,825 A
• Filed: 02/06/1996
• Issued: 08/01/2000
• Est. Priority Date: 04/22/1994
• Status: Expired due to Fees

• Current Assignee: Bio Merieux
• Original Assignee: Bio Merieux
• Inventors: Garnier, Francis
• Primary Examiner(s): Nutter, Nathan M.
• Application Number:
  US08/564,246
• Time in Patent Office: 1,638 Days
• Field of Search: 525/54.1, 530/402, 530/403, 530/405, 530/409, 530/810, 530/812, 530/815, 530/816, 530/817, 210/656, 210/660, 210/690, 210/692, 205/149, 205/152, 427/58, 436/518, 436/528, 436/531, 436/532
• US Class Current: 525/54.1
• CPC Class Codes: C08G 61/124 with a five-membered ring containing one nitrogen atom in the ring
• CPC Class Codes: C12Q 1/002 Electrode membranes
• CPC Class Codes: C12Q 1/6825 Nucleic acid detection involving sensors
• CPC Class Codes: G01N 33/5438 Electrodes
• CPC Class Codes: H01B 1/127 comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
• CPC Class Codes: Y10S 530/81 Carrier - bound or immobilized peptides or proteins and the preparation thereof, e.g. biological cell or cell fragment as carrier
• CPC Class Codes: Y10S 530/812 Peptides or proteins is immobilized on, or in, an organic carrier
• CPC Class Codes: Y10S 530/815 Carrier is a synthetic polymer
• CPC Class Codes: Y10S 530/816 Attached to the carrier via a bridging agent
• CPC Class Codes: Y10S 530/817 Entrapped within the carrier, e.g. gel, hollow fibre

Abstract

There are electrically conductive, electroactive functionalized conjugated polymers having formula (I): ##STR1## These electrically conducive, electroactive conjugated polymers may be covalently bonded to a first biological molecule or antiligand. Polymers bonded to a first biological molecule or antiligand may be used to form an electrode and may be used to assay for, detect and/or extract a second biological molecule or ligand.

Claims

1. An electrically conductive, electroactive conjugated polymer of formula (II):

##STR7## wherein n is a non-zero integer and i is an integer ranging from 2 to n-1, and

each R'"'"' of R'"'"'¹, R'"'"'ⁱ and R'"'"'ⁿ, which may be identical or different, represents H or a functional group capable of covalently bonding with, or covalently bonded to, a first biological molecule or an antiligand, provided that at least one said R'"'"' represents a functional group that is covalently bonded to a first biological molecule or antiligand,

wherein said first biological molecule comprises a polynucleotide or peptide sequence.

2. The polymer as claimed in claim 1, wherein each said functional group, before being bonded to a biological molecule or antiligand, is selected from the group consisting of:

Y_p --C--X, where X represents H, OH, a substituted or unsubstituted lower O-alkyl radical, or a halogen;

Y_p --NHZ, where Z represents H or an alkyl radical;

Y_p --NH--CO--CF₃ ;

Y_p --X, where X represents H, OH, a substituted or unsubstituted lower O-alkyl radical, or a halogen;

--Si (alkyl)₃ ;

--Si (alkoxyl)₃ ; and

an activated ester group;

wherein p is an integer less than or equal to three.

3. The polymer as claimed in claim 2, wherein Y is selected from the group consisting of:

alkyls having from 1 to 5 carbon atoms, alkoxyls having from 1 to 5 carbon atoms, and polyethers corresponding to the formula (CH₂ --CH₂ --O)_m --(CH₂)_m'"'"' --, m representing an integer ranging from 1 to 3 and m'"'"' representing an integer equal to 1 or 2.

4. The polymer as claimed in claim 1, wherein each said functional group bonded to a biological molecule or antiligand, before reaction with the first biological molecule or antiligand, is --(CH₂)--COOH.

5. The conjugated polymer as claimed in claim 1, wherein each said first biological molecule is selected from the group consisting of:

peptides, peptide derivatives and polynucleotides.

6. An electrode comprising a conductive substrate and a polymer as defined in any claim 1.

7. A self-supporting film of a polymer comprising a polymer as defined in claim 1.

8. The polymer as claimed in claim 2, wherein p is an integer selected from the group consisting of 0, 1 and 2.

9. The polymer as claimed in claim 2, wherein the activated ester group is N-hydroxysuccinimide.

10. The polymer as claimed in claim 2, wherein the halogen is chlorine.

11. The conjugated polymer as claimed in claim 5, wherein the peptide is selected from the group consisting of Gly-Phe, Phe-Pro and Phe-Hea-Pro.

12. The conjugated polymer as claimed in claim 5, wherein the polynucleotide is CCTAAGAGGGAGTG.

13. A method for at least one of detecting, assaying and extracting a second biological molecule or ligand in an in vitro or in vivo solution, comprising:

bringing a conjugated polymer as claimed in claim 1, which contains at least one said first biological molecule or antiligand that is different from and specifically interacts with said second biological molecule or ligand, into contact with said solution; and

at least one of determining whether the specific interaction occurs and extracting said second biological molecule or ligand.

14. The method of claim 13, wherein said second biological molecule or ligand is detected or assayed by at least one of observation and measurement of a potential difference or a variation in current between the conjugated polymer not bonded to the second biological molecule or ligand and the conjugated polymer bonded to the second biological molecule or ligand.

15. The method as claimed in claim 13, wherein the second biological molecule or ligand is an enzyme.

16. The method as claimed in claim 13, wherein the second biological molecule or ligand is a polynucleotide.

17. The method as claimed in claim 13, wherein the conjugated polymer is deposited on a conductive substrate or is in the form of a self-supporting film.

18. The method of claim 13, wherein said process determines whether said specific interaction occurs.

19. The method of claim 13, wherein said second biological molecule or ligand is extracted.

20. The conjugated polymer as claimed in claim 1, wherein said antiligand is able to form an antiligand/target molecule complex.

21. The conjugated polymer as claimed in claim 20, wherein said complex is selected from the group consisting of peptide/antibody, antibody/haptene, hormone/receptor, polynucleotide hybrids/polynucleotide and polynucleotide/nucleic acid couple.