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US 2007/0178512 A1Published application
Modified carbocyanine dyes and their conjugates
AssigneeInvitrogen Corporation
InventorsWai-Yee LEUNG, Ching-Ying CHEUNG, Stephen YUE
Life of this patent
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Abstract
Chemically reactive carbocyanine dyes incorporating an indolium ring moiety that is substituted at the 3-position by a reactive group or by a conjugated substance, and their uses, are described. Conjugation through this position results in spectral properties that are uniformly superior to those of conjugates of spectrally similar dyes wherein attachment is at a different position. The invention includes derivative compounds having one or more benzo nitrogens.
Claims26
1-17. (canceled)
A compound having the Formula:
- and its salts, wherein,
- R2 is alkyl or sulfoalkyl;
- R12 is alkyl or sulfoalkyl;
- R3 is carboxyalkyl or —(CH2)d(CONH(CH2)e)z′—Rx, wherein Rx is a carboxylic acid, a succinimidyl ester of a carboxylic acid, a hydrazide, or a maleimide;
- d is 0-5;
- e is 1-5;
- and z′ is 0 or 1;
- R4 is alkyl;
- R13 is alkyl or sulfoalkyl;
- R14 is alkyl or sulfoalkyl;
- R6 is selected from hydrogen or sulfo;
- R7 is selected from hydrogen or sulfo;
- R8 is selected from hydrogen or sulfo;
- R9 is selected from hydrogen or sulfo;
- R16 is selected from hydrogen or sulfo;
- R17 is selected from hydrogen or sulfo;
- R18 is selected from hydrogen or sulfo;
- R19 is selected from hydrogen or sulfo;
- wherein sulfo is sufonic acid or sulfonate;
- and
- n is 1, 2, or 3.
18 more elements
A compound having the formula:
- and its salts, wherein,
- R2 is alkyl or sulfoalkyl;
- R12 is alkyl or sulfoalkyl;
- R3 is carboxyalkyl or —(CH2)d(CONH(CH2e)z′—Rx, wherein Rx is a carboxylic acid, a succinimidyl ester of a carboxylic acid, a hydrazide, or a maleimide;
- d is 0-5;
- e is 1-5;
- and z′ is 0 or 1;
- R13 is sulfoalkyl;
- wherein sulfo is sufonic acid or sulfonate;
- and
- n is 1, 2 or 3.
8 more elements
A compound having the formula:
- or a salt thereof, wherein,
- R2 is alkyl or sulfoalkyl;
- R12 is alkyl or sulfoalkyl;
- R13 is alkyl or sulfoalkyl;
- wherein sulfo is sufonic acid or sulfonate;
- and
- n is 1, 2 or 3.
4 more elements
A method of staining a biological sample, comprising:
- combining a dye solution comprising a compound having the formula:
- and its salts, wherein,
- R2 is alkyl or sulfoalkyl;
- R12 is alkyl or sulfoalkyl;
- R3 is carboxyalkyl or —(CH2)d(CONH(CH2)e)z′—Rx, wherein Rx is a carboxylic acid, a succinimidyl ester of a carboxylic acid, a hydrazide, or a maleimide;
- d is 0-5;
- e is 1-5;
- and z′ is 0 or 1;
- R4 is alkyl;
- R13 is alkyl or sulfoalkyl;
- R14 is alkyl or sulfoalkyl;
- R6 is selected from hydrogen or sulfo;
- R7 is selected from hydrogen or sulfo;
- R8 is selected from hydrogen or sulfo;
- R9 is selected from hydrogen or sulfo;
- R16 is selected from hydrogen or sulfo;
- R17 is selected from hydrogen or sulfo;
- R18 is selected from hydrogen or sulfo;
- R19 is selected from hydrogen or sulfo;
- wherein sulfo is sufonic acid or sulfonate;
- and
- n is 1, 2, or 3;
- with a biological sample in a concentration sufficient to yield a detectable optical response under desired conditions.
20 more elements
A method for forming a dye-conjugate of a protein, peptide, or a nucleic acid polymer, said method comprising:
- combining a dye solution comprising a compound of the formula:
- and its salts, wherein,
- R2 is alkyl or sulfoalkyl;
- R12 is alkyl or sulfoalkyl;
- R3 is carboxyalkyl or —(CH2)d(CONH(CH2)e)z′—Rx, wherein Rx is a carboxylic acid, a succinimidyl ester of a carboxylic acid, a hydrazide, or a maleimide;
- d is 0-5;
- e is 1-5;
- and z′ is 0 or 1;
- R4 is alkyl;
- R13 is alkyl or sulfoalkyl;
- R14 is alkyl or sulfoalkyl;
- R6 is selected from hydrogen or sulfo;
- R7 is selected from hydrogen or sulfo;
- R8 is selected from hydrogen or sulfo;
- R9 is selected from hydrogen or sulfo;
- R16 is selected from hydrogen or sulfo;
- R17 is selected from hydrogen or sulfo;
- R18 is selected from hydrogen or sulfo;
- R19 is selected from hydrogen or sulfo;
- wherein sulfo is sufonic acid or sulfonate;
- and
- n is 1, 2, or 3;
- with a sample comprising a protein, peptide, or a nucleic acid polymer whereby a dye conjugate is formed.
20 more elements
A kit for fluorescent labeling of a biological sample, comprising:
- a dye solution comprising a compound having the formula:
- and its salts, wherein,
- R2 is alkyl or sulfoalkyl;
- R12 is alkyl or sulfoalkyl;
- R3 is carboxyalkyl or —(CH2)d(CONH(CH2)e)z′—Rx, wherein Rx is a carboxylic acid, a succinimidyl ester of a carboxylic acid, a hydrazide, or a maleimide;
- d is 0-5;
- e is 1-5;
- and z′ is 0 or 1;
- R4 is alkyl;
- R13 is alkyl or sulfoalkyl;
- R14 is alkyl or sulfoalkyl;
- R6 is selected from hydrogen or sulfo;
- R7 is selected from hydrogen or sulfo;
- R8 is selected from hydrogen or sulfo;
- R9 is selected from hydrogen or sulfo;
- R16 is selected from hydrogen or sulfo;
- R17 is selected from hydrogen or sulfo;
- R18 is selected from hydrogen or sulfo;
- R19 is selected from hydrogen or sulfo;
- wherein sulfo is sufonic acid or sulfonate;
- and
- n is 1, 2, or 3;
- and a buffer.
20 more elements
A composition comprising a compound having the formula:
- and its salts, wherein,
- R2 is alkyl or sulfoalkyl;
- R12 is alkyl or sulfoalkyl;
- R3 is carboxyalkyl or —(CH2)d(CONH(CH2)e)z′—Rx, wherein Rx is a carboxylic acid, a succinimidyl ester of a carboxylic acid, a hydrazide, or a maleimide;
- d is 0-5;
- e is 1-5;
- and z′ is 0 or 1;
- R4 is alkyl;
- R13 is alkyl or sulfoalkyl;
- R14 is alkyl or sulfoalkyl;
- R6 is selected from hydrogen or sulfo;
- R7 is selected from hydrogen or sulfo;
- R8 is selected from hydrogen or sulfo;
- R9 is selected from hydrogen or sulfo;
- R16 is selected from hydrogen or sulfo;
- R17 is selected from hydrogen or sulfo;
- R18 is selected from hydrogen or sulfo;
- R19 is selected from hydrogen or sulfo;
- wherein sulfo is sufonic acid or sulfonate;
- and
- n is 1, 2, or 3;
- and a protein, peptide, or a nucleic acid polymer.
19 more elements
Dependencies are inferred from the claim text.