US6096273A
Expired / Lapsed
US
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Electrodes linked via conductive oligomers to nucleic acids
Assignee: Roche Molecular Systems Inc
•
Filing: 1996-11-05
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Granted: 2000-08-01
•
Expires: 2016-11-05
Abstract
Abstract The invention relates to nucleic acids covalently coupled to electrodes via conductive oligomers. More particularly, the invention is directed to the site-selective modification of nucleic acids with electron transfer moieties and electrodes to produce a new class of biomaterials, and to methods of making and using them.
Inventors
- 👤 Jon F. Kayyem
- 👤 Stephen D. O'Connor
- 👤 Michael Gozin
- 👤 Changjun Yu
- 👤 Thomas J. Meade
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 18:49
CPC Classifications
C; C07; C07H; C07H21/00; C12; C12Q; C12Q1/00; C12Q1/68; C12Q1/6813; C12Q1/6816; C12Q1/6825
Claims Analysis
Total Claims: 43
Claim 1
Independent Claim
138 words
A composition comprising: a) an electrode; b) at least one nucleoside; and c) a conductive oligomer covalently attached to both said electrode and said nucleoside, wherein said conductive oligomer has the formula: ##STR38## wherein Y is an aromatic group; n is an integer from 1 to 50; g is either 1 or zero; e is an integer from zero to 10; and m is zero or 1; wherein when g is 1, B-D is a conjugated bond selected from --C.tbd.C--, --CH═CH--, --CR═CR--, --CH═CR--, --CR═CH--, --NH--CO--, --NR--CO--, --CO--NH--, --CO--NR--, --N═N--, --CO--O--, --O--CO--, --CS--O--, --O--CS--, --CH═N--, --CR═N--, --N═CH-- and --N═CR--, --SiH═SiH--, --SiR═SiH--, --SiR═SiH--, --SiR═SiR--, --SiH═CH--, --SiR═CH--, --SiH═CR--, --SiR═CR--, --CH═SiH--, --CR═SiH--, --CH═SiR--, --CR═SiR--, wherein R is a substitution group; and wherein when g is zero, e is 1 and D is carbonyl or a moiety comprising oxygen, sulfur, nitrogen or phosphorus.
Claim 2
Dependent Claim
138 words
A composition comprising: a) an electrode; b) at least one nucleoside; and c) a conductive oligomer covalently attached to both said electrode and said nucleoside, wherein said conductive oligomer has the formula: ##STR38## wherein Y is an aromatic group; n is an integer from 1 to 50; g is either 1 or zero; e is an integer from zero to 10; and m is zero or 1; wherein when g is 1, B-D is a conjugated bond selected from --C.tbd.C--, --CH═CH--, --CR═CR--, --CH═CR--, --CR═CH--, --NH--CO--, --NR--CO--, --CO--NH--, --CO--NR--, --N═N--, --CO--O--, --O--CO--, --CS--O--, --O--CS--, --CH═N--, --CR═N--, --N═CH-- and --N═CR--, --SiH═SiH--, --SiR═SiH--, --SiR═SiH--, --SiR═SiR--, --SiH═CH--, --SiR═CH--, --SiH═CR--, --SiR═CR--, --CH═SiH--, --CR═SiH--, --CH═SiR--, --CR═SiR--, wherein R is a substitution group; and wherein when g is zero, e is 1 and D is carbonyl or a moiety comprising oxygen, sulfur, nitrogen or phosphorus.
Claim 3
Dependent Claim
109 words
A composition comprising: a) an electrode; b) at least one nucleoside; and c) a conductive oligomer covalently attached to both said electrode and said nucleoside, wherein said conductive oligomer has the formula: ##STR39## wherein n is an integer from 1 to 50; m is 0 or 1; C is carbon; J is carbonyl or a moeity comprising nitrogen, silicon, phosphorus, sulfur; and G is a bond selected from single, double or triple bonds, wherein when G is a single bond, two R groups are attached to each C, and when G is a double bond, one R group is attached to each C, wherein R is a substitution group.
Claim 4
Dependent Claim
109 words
A composition comprising: a) an electrode; b) at least one nucleoside; and c) a conductive oligomer covalently attached to both said electrode and said nucleoside, wherein said conductive oligomer has the formula: ##STR39## wherein n is an integer from 1 to 50; m is 0 or 1; C is carbon; J is carbonyl or a moeity comprising nitrogen, silicon, phosphorus, sulfur; and G is a bond selected from single, double or triple bonds, wherein when G is a single bond, two R groups are attached to each C, and when G is a double bond, one R group is attached to each C, wherein R is a substitution group.
Claim 5
Dependent Claim
20 words
A composition according to claim 1 or 2 wherein said nucleoside is part of a first single stranded nucleic acid.
Claim 6
Dependent Claim
20 words
A composition according to claim 3 further comprising a plurality of conductive oligomers each covalently attached to a nucleic acid.
Claim 7
Dependent Claim
14 words
A composition according to claim 4 wherein said nucleic acids are all the same.
Claim 8
Dependent Claim
16 words
A composition according to claim 4 wherein at least one of said nucleic acids is different.
Claim 9
Dependent Claim
35 words
A composition according to claim 1 or 2 wherein said nucleoside contains a ribose-phosphate backbone and said covalent attachment of said conductive oligomer to said nucleoside is to the ribose or phosphate of said nucleoside.
Claim 10
Dependent Claim
26 words
A composition according to claim 1 or 2 wherein said covalent attachment of said conductive oligomer to said nucleoside is to the base of said nucleoside.
Claim 11
Dependent Claim
18 words
A composition according to claim 1 or 2 wherein said electrode further comprises at least one passavation agent.
Claim 12
Dependent Claim
18 words
A composition according to claim 1 or 2 wherein said electrode further comprises a monolayer of passavation agents.
Claim 13
Dependent Claim
71 words
A composition comprising: a) a first electron transfer moiety comprising an electrode; b) a first single stranded nucleic acid; c) a second electron transfer moiety covalently attached to said first nucleic acid; and d) a conductive oligomer covalently attached to both said electrode and said first nucleic acid, wherein one of said first and second electron transfer moieties is an electron donor moiety and the other is an electron acceptor moiety.
Claim 14
Dependent Claim
71 words
A composition comprising: a) a first electron transfer moiety comprising an electrode; b) a first single stranded nucleic acid; c) a second electron transfer moiety covalently attached to said first nucleic acid; and d) a conductive oligomer covalently attached to both said electrode and said first nucleic acid, wherein one of said first and second electron transfer moieties is an electron donor moiety and the other is an electron acceptor moiety.
Claim 15
Dependent Claim
108 words
A composition comprising: a) an electrode; b) at least one metallocene; and c) a conductive oligomer covalently attached to both said electrode and said metallocene, wherein said conductive oligomer has the formula: ##STR40## wherein n is an integer from 1 to 50; m is 0 or 1; C is carbon; J is carbonyl or a comprising nitrogen, silicon, phosphorus, sulfur; and G is a bond selected from single, double or triple bonds, wherein when G is a single bond, two R groups are attached to each C, and when G is a double bond, one R group is attached to each C. wherein R is a substitution group.
Claim 16
Dependent Claim
108 words
A composition comprising: a) an electrode; b) at least one metallocene; and c) a conductive oligomer covalently attached to both said electrode and said metallocene, wherein said conductive oligomer has the formula: ##STR40## wherein n is an integer from 1 to 50; m is 0 or 1; C is carbon; J is carbonyl or a comprising nitrogen, silicon, phosphorus, sulfur; and G is a bond selected from single, double or triple bonds, wherein when G is a single bond, two R groups are attached to each C, and when G is a double bond, one R group is attached to each C. wherein R is a substitution group.
Claim 17
Dependent Claim
138 words
A composition comprising: a) an electrode; b) at least one metallocene; and c) a conductive oligomer covalently attached to both said electrode and said metallocene, wherein said conductive oligomer has the formula: ##STR41## wherein Y is an aromatic group; n is an integer from 1 to 50; g is either 1 or zero; e is an integer from zero to 10; and m is zero or 1; wherein when g is 1, B-D is a conjugated bond selected from --C.tbd.C--, --CH═CH--, --CR═CR--, --CH═CR--, --CR═CH--, --NH--CO--, --NR--CO--, --CO--NH--, --CO--NR--, --N═N--, --CO--O--, --O--CO--, --CS--O--, --O--CS--, --CH═N--, --CR═N--, --N═CH-- and --N═CR--, --SiH═SiH--, --SiR═SiH--, --SiR═SiH--, --SiR═SiR--, --SiH═CH--, --SiR═CH--, --SiH═CR--, --SiR═CR--, --CH═SiH--, --CR═SiH--, --CH═SiR--, --CR═SiR--, wherein R is a substitution group; and wherein when g is zero, e is 1 and D is carbonyl or a moiety comprising oxygen, sulfur, nitrogen or phosphorus.
Claim 18
Dependent Claim
138 words
A composition comprising: a) an electrode; b) at least one metallocene; and c) a conductive oligomer covalently attached to both said electrode and said metallocene, wherein said conductive oligomer has the formula: ##STR41## wherein Y is an aromatic group; n is an integer from 1 to 50; g is either 1 or zero; e is an integer from zero to 10; and m is zero or 1; wherein when g is 1, B-D is a conjugated bond selected from --C.tbd.C--, --CH═CH--, --CR═CR--, --CH═CR--, --CR═CH--, --NH--CO--, --NR--CO--, --CO--NH--, --CO--NR--, --N═N--, --CO--O--, --O--CO--, --CS--O--, --O--CS--, --CH═N--, --CR═N--, --N═CH-- and --N═CR--, --SiH═SiH--, --SiR═SiH--, --SiR═SiH--, --SiR═SiR--, --SiH═CH--, --SiR═CH--, --SiH═CR--, --SiR═CR--, --CH═SiH--, --CR═SiH--, --CH═SiR--, --CR═SiR--, wherein R is a substitution group; and wherein when g is zero, e is 1 and D is carbonyl or a moiety comprising oxygen, sulfur, nitrogen or phosphorus.
Claim 19
Dependent Claim
15 words
A composition according to claim 3 wherein said nucleic acid is a nucleic acid analog.
Claim 20
Dependent Claim
16 words
A composition according to claim 14 wherein said nucleic acid analog is a peptide nucleic acid.
Claim 21
Dependent Claim
18 words
A composition according to claim 3 wherein said first nucleic acid further comprises a second electron transfer moiety.
Claim 22
Dependent Claim
21 words
A composition according to claim 3 wherein said composition further comprises a second nucleic acid comprising a second electron transfer moiety.
Claim 23
Dependent Claim
71 words
A composition comprising: a) a first electron transfer moiety comprising an electrode; b) a first single stranded nucleic acid; c) a conductive oligomer covalently attached to both said electrode and said first nucleic acid; and d) a second single stranded nucleic acid comprising a second electron transfer moiety, wherein one of said first and second electron transfer moieties is an electron donor moiety and the other is an electron acceptor moiety.
Claim 24
Dependent Claim
71 words
A composition comprising: a) a first electron transfer moiety comprising an electrode; b) a first single stranded nucleic acid; c) a conductive oligomer covalently attached to both said electrode and said first nucleic acid; and d) a second single stranded nucleic acid comprising a second electron transfer moiety, wherein one of said first and second electron transfer moieties is an electron donor moiety and the other is an electron acceptor moiety.
Claim 25
Dependent Claim
13 words
A composition according to claim 1 wherein Y is phenyl or substituted phenyl.
Claim 26
Dependent Claim
13 words
A composition according to claim 1 wherein g=1, e=1, and B-D is acetylene.
Claim 27
Dependent Claim
8 words
A composition according to claim 1 wherein n+m=3.
Claim 28
Dependent Claim
8 words
A composition according to claim 1 wherein n+m=4.
Claim 29
Dependent Claim
8 words
A composition according to claim 1 wherein n+m=5.
Claim 30
Dependent Claim
20 words
A composition according to claim 11, 16 or 17 wherein said second electron transfer moiety comprises a transition metal complex.
Claim 31
Dependent Claim
21 words
A composition according to claim 11, 16 or 17 wherein said second electron transfer moiety comprises an organic electron transfer moiety.
Claim 32
Dependent Claim
33 words
A composition according to claim 11 wherein nucleic acid comprises a ribose-phosphate backbone and said covalent attachment of said second electron transfer moiety is to a ribose or phosphate of said nucleic acid.
Claim 33
Dependent Claim
24 words
A composition according to claim 11 wherein said covalent attachment of said second electron transfer moiety is to a base of said nucleic acid.
Claim 34
Dependent Claim
16 words
A composition according to claim 11 wherein said electrode further comprises at least one passavation agent.
Claim 35
Dependent Claim
18 words
A composition according to claim 1, 11, 18 wherein said electrode further comprises a monolayer of passavation agents.
Claim 36
Dependent Claim
121 words
A composition according to claim 11 or 18 wherein said conductive oligomer has the structure: ##STR42## wherein Y is an aromatic group; n is an integer from 1 to 50; g is either 1 or zero; e is an integer from zero to 10; and m is zero or 1; wherein when g is 1, B-D is a conjugated bond selected from --C.tbd.C--, --CH═CH--, --CR═CR--, --CH═CR--, --CR═CH--, --NH--CO--, --NR--CO--, --CO--NH--, --CO--NR--, --N═N--, --CO--O--, --O--CO--, --CS--O--, --O--CS--, --CH═N--, --CR═N--, --N═CH-- and --N═CR--, --SiH═SiH--, --SiR═SiH--, --SiR═SiH--, --SiR═SiR--, --SiH═CH--, --SiR═CH--, --SiH═CR--, --SiR═CR--, --CH═SiH--, --CR═SiH--, --CH═SiR--, --CR═SiR--, wherein R is a substitution group; and wherein when g is zero, e is 1 and D is carbonyl or a moiety comprising oxygen, sulfur, nitrogen or phosphorus.
Claim 37
Dependent Claim
92 words
A composition according to claim 11 or 18 wherein said conductive oligomer has the structure: ##STR43## wherein n is an integer from 1 to 50; m is 0 or 1; C is carbon; J is carbonyl or a moeity comprising nitrogen, silicon, phosphorus, sulfur; and G is a bond selected from single, double or triple bonds, wherein when G is a single bond, two R groups are attached to each C, and when G is a double bond, one R group is attached to each C, wherein R is a substitution group.
Claim 38
Dependent Claim
14 words
A composition according to claim 24 wherein said transition metal complex is a metallocene.
Claim 39
Dependent Claim
11 words
A composition according to claim 32 wherein said metallocene is ferrocene.
Claim 40
Dependent Claim
43 words
A composition comprising: a) a first electron transfer moiety comprising an electrode; b) a first single stranded nucleic acid; and c) a conductive oligomer covalently attached to both said electrode and said nucleic acid, wherein said electrode comprises a monolayer of passivation agent.
Claim 41
Dependent Claim
43 words
A composition comprising: a) a first electron transfer moiety comprising an electrode; b) a first single stranded nucleic acid; and c) a conductive oligomer covalently attached to both said electrode and said nucleic acid, wherein said electrode comprises a monolayer of passivation agent.
Claim 42
Dependent Claim
33 words
A method of making a composition according to claim 1, 2 or 11 comprising: a) providing a conductive oligomer covalently attached to a nucleoside; and b) attaching said conductive oligomer to said electrode.
Claim 43
Dependent Claim
33 words
A method of making a composition according to claim 1, 2 or 11 comprising: a) attaching a conductive oligomer to an electrode; and b) attaching at least one nucleotide to said conductive oligomer.
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