Xanthene dyes comprising a sulfonamide group

• US 8,436,170 B2
• Filed: 02/03/2010
• Issued: 05/07/2013
• Est. Priority Date: 02/03/2009
• Status: Active Grant

• Current Assignee: Biotium, Inc.
• Original Assignee: Biotium, Inc.
• Inventors: Mao, Fei, Leung, Wai-Yee, Cheung, Ching-Ying
• Primary Examiner(s): Bianchi, Kristin
• Application Number:
  US12/699,778
• Publication Number:
  US 20100197030A1
• Time in Patent Office: 1,189 Days
• Field of Search: 436/73, 549/227, 548/525, 548/418, 546/48, 546/256, 546/37, 544/405, 536/23.1, 536/54, 530/408, 530/350, 530/391.3
• US Class Current: 544/405
• CPC Class Codes: C07D 311/88 Nitrogen atoms
• CPC Class Codes: C07D 405/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 405/14 containing three or more hetero rings
• CPC Class Codes: C07D 491/147 the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
• CPC Class Codes: C07D 491/22 in which the condensed system contains four or more hetero rings
• CPC Class Codes: C07K 1/13 Labelling of peptides
• CPC Class Codes: C09B 11/24 Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
• CPC Class Codes: G01N 33/57484 involving compounds serving as markers for tumor, cancer, neoplasia, e.g. cellular determinants, receptors, heat shock/stress proteins, A-protein, oligosaccharides, metabolites
• CPC Class Codes: G01N 33/582 with fluorescent label

Abstract

The present invention relates to fluorescent dyes in general. The present invention provides a wide range of fluorescent dyes and kits containing the same, which are applicable for labeling a variety of biomolecules, cells and microorganisms. The present invention also provides various methods of using the fluorescent dyes for research and development, forensic identification, environmental studies, diagnosis, prognosis, and/or treatment of disease conditions.

Claims

1. A compound of Formula Ia or Ib:

2. The compound of claim 1,

wherein the compound comprises at least one reactive sulfonamide of Formula IIa:

3. The compound of claim 2, wherein R₁₀ is H, sulfopropyl or sulfobutyl.

4. The compound of claim 2 having the structure of Formula IIIa:

5. The compound of claim 4 wherein:

R₃ is H or —

SO₃⁻

; and

L is Q_n, wherein at least one, two, three or four Q are —

(CH₂CH₂O)—

.

6. The compound of claim 2 having the structure of Formula IV:

7. The compound of claim 2 having the structure of Formula V:

8. A compound having the structure of Formula VI:

9. A compound of Formula Ia or Ib:

10. The compound of claim 9, wherein R_m and R_n are each independently H or a C₁-C₁₂ alkyl.

11. The compound of claim 9, wherein the unreactive sulfonamide is positively charged.

12. The compound of claim 9 having the structure of Formula IIIb: