Violet laser excitable dyes and their method of use

• US 9,644,099 B2
• Filed: 06/13/2016
• Issued: 05/09/2017
• Est. Priority Date: 09/26/2005
• Status: Active Grant

• Current Assignee: Life Technologies Corporation (Thermo Fisher Scientific Incorporated)
• Original Assignee: Life Technologies Corporation (Thermo Fisher Scientific Incorporated)
• Inventors: Buller, Gayle, Liu, Jixiang, Yue, Stephen, Bradford, Jolene Ann
• Primary Examiner(s): Aulakh, Charanjit
• Application Number:
  US15/180,516
• Publication Number:
  US 20160355682A1
• Time in Patent Office: 330 Days
• Field of Search: 5462714, 546167, 435 4, 436546
• CPC Class Codes: C07D 409/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 413/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 413/14 containing three or more hetero rings
• CPC Class Codes: C07D 417/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C09B 23/0075 the polymethine chain being part of an heterocyclic ring
• CPC Class Codes: G01N 2021/6441 with two or more labels
• CPC Class Codes: G01N 21/6486 Measuring fluorescence of biological material, e.g. DNA, RNA, cells G01N21/6428 takes precedence
• CPC Class Codes: G01N 33/52 Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper and including single- and multilayer analytical elements immunological elements G01N33/54386; involving labelled immunochemicals G01N33/58; for haemoglobin or occult blood G01N33/72
• CPC Class Codes: G01N 33/582 with fluorescent label

Abstract

The present invention provides dye compounds optimally excited at about 400 nm and have a Stokes shift of at least about 80 nm. These dyes find use in detection of analyte in a sample and the preparation of dye-conjugates.

Claims

1. A compound according to the formula:

2. The compound according to claim 1, wherein R³ is alkoxy.

3. The compound according to claim 1, wherein at least two of R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸ or R⁹ comprises a sulfo group.

4. The compound according to claim 1, wherein at least three of R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸ or R⁹ comprises a sulfo group.

5. The compound according to claim 1 wherein at least one of R¹, R², R³, R⁵, R⁶, R⁷, or R⁹ comprises a reactive group, carrier molecule or solid support.

6. The compound according to claim 1, wherein R³ comprises a reactive group, carrier molecule or solid support.

10. A kit for detecting an analyte in a sample, wherein the kit comprises:

a. a compound according to claim 1; and

b. instructions for detecting the analyte.

11. A kit for forming a dye conjugate, wherein the kit comprises:

a. a compound according to claim 1, wherein the compound comprises a reactive group; and

b. instructions for forming the dye conjugate with a carrier molecule or solid support.

7. A method for detecting an analyte in a sample, wherein the method comprises

a. combining a compound with a sample to form a combined sample, wherein the compound has the formula

8. The method according to claim 7, wherein the illumination and/or detecting step comprises a flow cytometer.

9. A method for evaluating the viability of cells in a sample, comprising

a. combining a compound with a sample to form a combined sample, wherein the compound comprises an amine reactive group and has the formula