Intermediate for and fluorescent cyanine dyes containing carboxylic acid groups

• US 4,981,977 A
• Filed: 06/09/1989
• Issued: 01/01/1991
• Est. Priority Date: 06/09/1989
• Status: Expired due to Term

• Current Assignee: Carnegie Mellon University
• Original Assignee: Carnegie Mellon University
• Inventors: Southwick, Philip L., Waggoner, Alan S.
• Primary Examiner(s): Springer, David B.
• Application Number:
  US07/364,773
• Time in Patent Office: 571 Days
• Field of Search: 548/455, 548/510
• US Class Current: 548/455
• CPC Class Codes: C07D 209/08 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
• CPC Class Codes: C09B 23/06 three >CH- groups, e.g. carbocyanines

Abstract

(2,3,3-Trimethyl-3-H-indol-5-yl)-acetic acid has been synthesized. Additionally, derivatives of (2,3,3-Trimethyl-3-H-indol-5-yl)-acetic acid have been prepared as intermediates for preparation of fluorescent cyanine biolabels. A derived dye, 5.5'"'"'-Dicarboxymethyl-3,3,3'"'"',3'"'"'-tetramethyl-1,1'"'"'-diethylindocarboc yanine, is a biolabeling substance with a brilliant red fluorescence.

Claims

1. The compound having the formula ##STR7##

2. The compound having the formula ##STR8## where R₁ is --(CH₂)_m CH₃, m ranging from 0 to 25, or arylalkyl and X^- is a counterion to N⁺.

3. The compound of claim 2 wherein said counterion consists of F^-, Cl^-, Br^- or I^-.

4. The compound of claim 2 wherein said counterion consists of R₂ SO₃^- where R₂ is alkyl, aryl, arylalkyl, or OH.

5. The compound of claim 2 wherein said counterion is an internal carboxylate salt.

6. The compound having the formula ##STR9## where R₃ is --(CH₂)_m COOH Y^-, m ranging from 1 to 5, -(CH₂)_n SO₃^-, n ranging from 2 to 6 , or -(CH₂)_k N⁺ (R₄)₃ Z, k ranging from 1 to 4 and R₄ is -(CH₂)_j CH₃, j ranging from 0 to 25, or H,

where Y^- and Z^- are appropriate counterions to N⁺.

7. The compound of claim 6 wherein said Y^- counterion consists of F^-, Cl^-, Br^- or I^-.

8. The compound of claim 6 wherein said Y^- counterion consists of R₅ SO₃^- where R₅ is alkyl, aryl, arylalkyl or OH.

9. The compound of claim 6 where said Z^- counterion is F^-, Cl^-, Br^-, I'"'"' or RSO₃^-.

10. The compound having the formula ##STR10##

11. The compound having the formula ##STR11##

12. The compound having the formula ##STR12##