Fluorescent dyes

• US 9,416,153 B2
• Filed: 10/11/2011
• Issued: 08/16/2016
• Est. Priority Date: 10/11/2011
• Status: Active Grant

• Current Assignee: Enzo Life Sciences Incorporated (Enzo Biochem Incorporated)
• Original Assignee: Enzo Life Sciences Incorporated (Enzo Biochem Incorporated)
• Inventors: Li, Zaiguo, Pande, Praveen
• Primary Examiner(s): Oh, T. Victor
• Application Number:
  US13/270,456
• Publication Number:
  US 20130089853A1
• Time in Patent Office: 1,771 Days
• Field of Search: 546/37, 546/48, 548/303.7, 548/525, 549/223, 549/227
• US Class Current: 1/1
• 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 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: C07H 19/04 Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
• CPC Class Codes: C07H 21/00 Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
• CPC Class Codes: C09B 11/02 derived from diarylmethanes
• CPC Class Codes: C09B 11/06 Hydroxy derivatives of triarylmethanes in which at least one OH group is bound to an aryl nucleus and their ethers or esters
• 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: C12Q 1/707 non-A, non-B Hepatitis, excluding hepatitis D

Abstract

Provided are various compounds comprising the formula

Also provided are fluorescent dyes comprising the above compound. Additionally, a fluorescence energy transfer system is provided that comprises the above-described fluorescent dye and a second dye, wherein the second dye is capable of energy transfer with the fluorescent dye. Further provided is a kit for labeling a target molecule, where the kit comprises the above-described fluorescent dye with additional reagents useful for labeling the target molecule. Additionally provided is a target molecule labeled with the above-described fluorescent dye. Methods of labeling a target molecule with the above-described fluorescent dye are also provided.

Claims

1. A compound having the formula

2. The compound of claim 1, wherein n is 1-4.

3. The compound of claim 1, wherein -A-B—

Z is

4. The compound of claim 1, wherein -A-B—

Z is

5. The compound of claim 1, having the structure:

6. The compound of claim 5, wherein R⁶ and R⁹ are both H or CH₃.

7. The compound of claim 5, wherein X and Y are

(a) OH and O, respectively;

(b) NHCH₂CH₃ and NCH₂CH₃, respectively;

or

(c) N(CH₃)₂ and N⁺(CH₃)₂, respectively.

10. The compound of claim 1, selected from the group consisting of:

11. The compound of claim 1, wherein the carbon length for said alkenyl, alkynyl, and alkyl groups is from 1-10.

8. A compound selected from the group consisting of:

9. A compound selected from the group consisting of: