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EP0808829A1
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Fluorescent group-containing carbodiimide compound
Assignee: Nisshinbo Holdings Inc
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Filing: 1997-05-20
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Granted: —
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Expires: 2017-05-20
Abstract
Abstract Using the fluorescent group-containig carbodiimide compound represented by the following formula (I) as the label and the like in the nucleic acid detection method, immunoassay, or chemiluminescence assay, labeling can be made efficiently for a short time, a nucleic acid derived from nature can be labelled, and highly sensitive assay is enabled. B-Y 3 -N=C=N-Y 2 -W-Y 1 -[A] n -F (I) wherein F represents a fluorescent group; A represents a moiety selected from the group consisting of -CH 2 -, -NHCO-, -CONH-, -O-, -S-, -NR- wherein R is an alkyl group, -COO-, -OCO-, -NHSO 2 -, and - SO 2 NH-; n is 0 or 1; W represents a direct bond or a quaternary ammonium group; Y 1 , Y 2 and Y 3 each represents an alkylene group which may have a functional group in its main chain; and B represents H or a monovalent organic group which may be the same as or different from that represented by -W-Y 1 -[A] n -F.
Inventors
- 👤 Osamu c/o Nisshinbo Ind. Inc. Suzuki
- 👤 Gen c/o Nisshinbo Ind. Inc. Masuda
- 👤 Namiko c/o Nisshinbo Ind. Inc. Shiohata
- 👤 Kazuko c/o Nisshinbo Ind. Inc. Matsumoto
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-29 10:11
CPC Classifications
C; C07; C07H; C07H21/00; C07C; C07C267/00; G; G01; G01N; G01N33/00; G01N33/48; G01N33/50; G01N33/58; G01N33/582
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
177 words
A fluorescent group-containing carbodiimide compound represented by the formula (I): B-Y 3 -N=C=N-Y 2 -W-Y 1 -[A] n -F (I) wherein F represents a fluorescent group; A represents a moiety selected from the group consisting of -CH 2 -, -NHCO-, -CONH-, -O-, -S-, -NR-, wherein R is an alkyl group, -COO-, -OCO-, -NHSO 2 -, and - SO 2 NH-; n is 0 or 1; W represents a direct bond or a quaternary ammonium group; Y 1 , Y 2 and Y 3 each represents a group having the formula (L): -(CH 2 ) p -L-(CH 2 ) q - (L) wherein L is a direct bond or a moiety selected from the group consisting of -NHCO-, -CONH-, -O-, -S-, -NR-, -N + RR'-, wherein R' is an alkyl group, -COO-, and -OCO-; p and q each represents an integer of from 1 to 12; and B represents a hydrogen atom or a monovalent organic group which may be the same as or different from that represented by -W-Y 1 -[A] n -F in the formula (I).
Claim 2
Dependent Claim
113 words
The fluorescent group-containing carbodiimide compound as claimed in Claim 1, which is a compound represented by the formula (II): wherein R 1 and R 2 each represents a straight-chain or branched, saturated or unsaturated aliphatic hydrocarbon group having from 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, or a nitrogen-containing heterocyclic group formed by R 1 and R 2 which are bound to each other; X - represents a halogen atom or a sulfonate ion; and B, Y 1 , Y 2 , Y 3 , A and F have the same definition as in the formula (I).
Claim 3
Dependent Claim
54 words
The fluorescent group-containing carbodiimide compound as claimed in Claim 2, wherein the compound represented by the formula (II) is a compound represented by the formula (III): wherein R 1 , R 2 , X - , Y 1 , Y 2 , A and F have the same definition as in the formula (II).
Claim 4
Dependent Claim
70 words
The fluorescent group-containing carbodiimide compound as claimed in Claim 1, which is a compound represented by the formula (IV): B-Y 3 -N=C=N-F' (IV) wherein B and Y 3 have the same definition as in the formula (I); F' represents a moiety selected from the group consisting of a coumarin derivative, a pyrene derivative, a perylene derivative, a rhodamine derivative, a dansyl derivative, an oxazole derivative, and a thiazole orange derivative.
Claim 5
Dependent Claim
45 words
The fluorescent group-containing carbodiimide compound as claimed in Claim 1, which is a compound represented by the formula (V): B-Y 3 -N=C=N-Y 2 -A-F (V) wherein B, Y 2 , Y 3 , A and F have the same definition as in the formula (I).
Claim 6
Dependent Claim
40 words
The fluorescent group-containing carbodiimide compound as claimed in Claim 1, wherein F in the formula (I) is selected from the fluorescent group represented by the formula (F): wherein M is Eu 3+ , Sm 3+ , or Tb 3+ .
Claim 7
Dependent Claim
99 words
A process for producing the fluorescent group-containing carbodiimide compound as claimed in Claim 2, which comprises a step of reacting a carbodiimide group-containing compound represented by the formula (VI): B-Y 3 -N=C=N-Y 2 -W' (VI) wherein W' represents substituted or unsubstituted amino group; and B, Y 3 , and Y 2 have the same definition as in the formula (I), with a fluorescent group-containing compound represented by the formula (VII): F-A-Y 1 -X (VII) wherein F, A, and Y 1 have the same definition as in the formula (I); and X is a halogen atom or a sulfonate group.
Claim 8
Dependent Claim
109 words
A process for producing the fluorescent group-containing carbodiimide compound as claimed in Claim 4 which comprises a step of reacting an amino group-containing fluorescent compound represented by the formula (VIII): F'-NH 2 (VIII) wherein F' has the same definition as in the formula (IV), with an iso(thio)cyanate compound represented by the formula (IX): B-Y 3 -NCZ (IX) wherein Z represents an oxygen atom or a sulfur atom; and B and Y 3 have the same definition as in the formula (IV), to synthesize a (thio)urea compound represented by the formula (X): wherein B, F, Z, and Y 3 have the same definition as in the formulae (VIII) and (IX).
Claim 9
Dependent Claim
119 words
A process for producing the fluorescent group-containing carbodiimide compound as claimed in Claim 5, which comprises a step of reacting an amino group-containing fluorescent compound represented by the formula (XI): F-A-Y 2 -NH 2 (XI) wherein F, A, and Y 2 have the same definition as in the formula (V), with an iso(thio)cyanate compound represented by the formula (XII): B-Y 3 -NCZ (XII) wherein Z represents an oxygen atom or a sulfur atom; and B and Y 3 have the same definition as in the formula (V), to synthesize a (thio)urea compound represented by the formula (XIII): wherein A, B, F, Z, Y 2 , and Y 3 have the same definition as in the formulae (XI) and (XII).
Claim 10
Dependent Claim
30 words
A method for detecting a nucleic acid by hybridization using a labelled nucleic acid, wherein the fluorescent group-containing carbodiimide compound as claimed in Claim 1 is used as the label.
Claim 11
Dependent Claim
28 words
A method for immunoassay using a labelled antigen or a labelled antibody, wherein the fluorescent group-containing carbodiimide compound as claimed in Claim 1 is used as the label.
Claim 12
Independent Claim
103 words
A method for peroxalate ester chemiluminescence assay utilizing chemiluminescence due to a reaction between an oxalic acid derivative and a peroxide in the presence of a fluorescent substance, wherein the fluorescent substance is the fluorescent group-containing carbodiimide compound as claimed in any of Claims 1 to 6 having the fluorescent moiety selected from the group consisting of a coumarin derivative, a pyrene derivative, a perylene derivative, a rhodamine derivative, a dansyl derivative, an oxazole derivative, a thiazole orange derivative, a cyanine compound, a benzothiazole derivative, a benzoxazole derivative, a benzoxadiazol derivative, a dipyrromethene borondifluoride derivative, and a fluorescent rare earth metal chelate compound.
References Cited (Backward Citations)
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