Rhodamine compounds and their use as fluorescent labels

• US 8,754,244 B1
• Filed: 03/08/2013
• Issued: 06/17/2014
• Est. Priority Date: 03/08/2013
• Status: Active Grant

• Current Assignee: Illumina Cambridge Ltd. (California) (Illumina Incorporated)
• Original Assignee: Illumina Cambridge Ltd. (California) (Illumina Incorporated)
• Inventors: Liu, Xiaohai, Romanov, Nikolai Nikolaevich
• Primary Examiner(s): SHAMEEM, GOLAM M
• Application Number:
  US13/790,776
• Time in Patent Office: 466 Days
• Field of Search: 549/356, 549/381, 549/385, 549/394, 436/800
• US Class Current: 549/394
• CPC Class Codes: C07D 311/82 Xanthenes
• 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 487/04 Ortho-condensed systems
• 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: C12Q 1/6869 Methods for sequencing

Abstract

The present invention relates to new rhodamine compounds and their use as fluorescent labels. The compounds may be used as fluorescent labels for nucleotides in nucleic acid sequencing applications.

Claims

1. A compound of formula (I) and mesomers thereof:

2. The compound of claim 1 wherein R₁₆ is alkyl and R₁₇ is alkyl.

3. The compound of claim 1 wherein R₁, R₄, R₅, R₆, R₈ and R₉ are all H, R₂ and R₃ are H or CH₃.

4. The compound of claim 1 wherein R₁₆ and R₁₇ are H.

5. The compound of claim 1 wherein R₁ is linked to R₂ or R₈ via a chain of CH₂ groups to form a ring, and R₄ is linked to R₃ or R₉ via a chain of CH₂ groups to form a ring.

6. The compound of claim 5 wherein R₁ and R₂ form a six membered ring, R₃ and R₄ form a six membered ring, R₅, R₆, R₈ and R₉ are H.

7. The compound of claim 1 wherein one or more of R₁, R₄, R₁₆ and R₁₇ are alkyl groups substituted with an SO₃⁻

group.

8. The compound of claim 1 wherein R₇ is OH.

9. The compound of claim 1 wherein q is 3.

10. The compound of claim 1 wherein R₁₃ is OH.

11. The compound of claim 1 wherein R₁₃ is NR₁₄R₁₅ where R₁₄ is H or alkyl and R₁₅ is alkyl or a substituted alkyl.

12. The compound of claim 11 wherein the compound is attached to a nucleotide or oligonucleotide via substituted alkyl group R₁₅.