IP Library › Granted Patent US 6,974,873
Granted Patent B2
US 6,974,873 · App. 09/969,853 · Granted Dec 13, 2005

Modified carbocyanine dyes and their conjugates

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Quick Facts
Patent No.
US 6,974,873
App. No.
09/969,853
Granted
Dec 13, 2005
Kind
B2
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.

Claims (105)

1. A method of staining a biological sample, comprising:

combining a dye solution comprising a compound having the formula

or its salts, wherein

R 2 is alkyl or sulfoalkyl;

R 12 is alkyl or sulfoalkyl;

R 3 is carboxyalkyl;

R 4 is alkyl;

R 13 is alkyl;

R 14 is alkyl;

R 6 is hydrogen or sulfo;

R 7 is hydrogen or sulfo;

R 8 is hydrogen or sulfo;

R 9 is hydrogen or sulfo;

R 16 is hydrogen or sulfo;

R 17 is hydrogen or sulfo;

R 18 is hydrogen or sulfo;

R 19 is hydrogen or sulfo;

wherein sulfo is sulfonic 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.

2. A method of staining a biological sample, comprising:

combining a dye solution comprising a compound having the formula

or its salts, wherein

R 2 is alkyl or sulfoalkyl;

R 12 is alkyl or sulfoalkyl;

R 4 is alkyl;

R 13 is alkyl;

R 14 is alkyl;

R 6 is hydrogen or sulfo;

R 7 is hydrogen or sulfo;

R 8 is hydrogen or sulfo;

R 9 is hydrogen or sulfo;

R 16 is hydrogen or sulfo;

R 17 is hydrogen or sulfo;

R 18 is hydrogen or sulfo;

R 19 is hydrogen or sulfo;

wherein sulfo is sulfonic 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.

3. A method of staining a biological sample, comprising:

combining a dye solution comprising a compound having the formula

or its salts, wherein;

R 2 is alkyl or sulfoalkyl;

R 12 is alkyl or sulfoalkyl;

R 4 is alkyl;

R 19 is alkyl;

R 14 is alkyl;

R 6 is hydrogen or sulfo;

R 7 is hydrogen or sulfo;

R 8 is hydrogen or sulfo;

R 9 is hydrogen or sulfo;

R 16 is hydrogen or sulfo;

R 17 is hydrogen or sulfo;

R 18 is hydrogen or sulfo;

R 19 is hydrogen or sulfo;

wherein sulfo is sulfonic 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.

4. A method of staining a biological sample, comprising:

combining a dye solution comprising a compound having the formula

or its salts, wherein;

R 2 is alkyl or sulfoalkyl;

R 12 is alkyl or sulfoalkyl;

wherein sulfo is sulfonic 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.

5. 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

or its salts, wherein;

R 2 is alkyl or sulfoalkyl;

R 12 is alkyl or sulfoalkyl;

R 4 is alkyl;

R 13 is alkyl;

R 14 is alkyl;

R 6 is hydrogen or sulfo;

R 7 is hydrogen or sulfo;

R 8 is hydrogen or sulfo;

R 9 is hydrogen or sulfo;

R 16 is hydrogen or sulfo;

R 17 is hydrogen or sulfo;

R 18 is hydrogen or sulfo;

R 19 is hydrogen or sulfo;

wherein sulfo is sulfonic 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.

6. A method of staining a biological sample, comprising:

combining a dye solution comprising a compound having the formula

or its salts, wherein

R 2 is alkyl or sulfoalkyl;

R 12 is alkyl or sulfoalkyl;

R 3 is a protein, peptide or a nucleic acid polymer;

R 4 is alkyl;

R 13 is alkyl;

R 14 is alkyl;

R 6 is hydrogen or sulfo;

R 7 is hydrogen or sulfo;

R 8 is hydrogen or sulfo;

R 9 is hydrogen or sulfo;

R 16 is hydrogen or sulfo;

R 17 is hydrogen or sulfo;

R 18 is hydrogen or sulfo;

R 19 is hydrogen or sulfo;

wherein sulfo is sulfonic 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.

Assignments (1)
LIEN RELEASE Recorded Apr 8, 2013
From: BANK OF AMERICA, N.A.
To: MOLECULAR PROBES, INC.
Reel/Frame 030173/0561 →