Labeling reagents and methods of their use

• US 8,586,743 B2
• Filed: 01/30/2008
• Issued: 11/19/2013
• Est. Priority Date: 01/30/2007
• Status: Active Grant

• Current Assignee: Life Technologies Corporation (Thermo Fisher Scientific Incorporated)
• Original Assignee: Life Technologies Corporation (Thermo Fisher Scientific Incorporated)
• Inventors: Gee, Kyle, Rukavishnikov, Aleksey, Antoulinakis, Evan
• Primary Examiner(s): Kosar, Andrew D
• Assistant Examiner(s): COVINGTON, RAYMOND K
• Application Number:
  US12/023,019
• Publication Number:
  US 20090004753A1
• Time in Patent Office: 2,120 Days
• Field of Search: 546/13, 546/22, 546/58, 548/110, 548/156, 548/157, 549/226, 549/302, 549/303, 549/304, 549/307, 549/466, 549/467, 549/470, 549/471
• US Class Current: 546/13
• CPC Class Codes: C07D 209/14 Radicals substituted by nitrogen atoms, not forming part of a nitro radical
• CPC Class Codes: C07D 209/18 Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
• CPC Class Codes: C07D 311/18 substituted otherwise than in position 3 or 7
• CPC Class Codes: C07D 311/82 Xanthenes
• CPC Class Codes: C07D 401/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 493/14 Ortho-condensed systems
• CPC Class Codes: C07D 495/22 in which the condensed system contains four or more hetero rings
• CPC Class Codes: C07F 5/022 without C-boron linkages
• 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: C09B 11/26 Triarylmethane dyes in which at least one of the aromatic nuclei is heterocyclic phthaleins C09B11/24
• CPC Class Codes: C09B 23/04 one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
• CPC Class Codes: C09B 23/08 more than three >CH- groups, e.g. polycarbocyanines
• CPC Class Codes: C09B 45/00 Complex metal compounds of azo dyes
• CPC Class Codes: C09B 56/16 Methine- or polymethine-azo dyes
• CPC Class Codes: G01N 33/532 Production of labelled immunochemicals
• CPC Class Codes: G01N 33/58 involving labelled substances G01N33/53 takes precedence
• CPC Class Codes: G01N 33/582 with fluorescent label

Abstract

The present disclosure is directed to a reactive ester agent capable of conjugating a reporter molecule to a carrier molecule or solid support. The reactive ester agent has the general formula:

wherein the variables are described throughout the application.

Claims

1. A compound having the following structure or a tautomer or salt thereof:

2. The compound of claim 1, wherein R¹ and R² are chloro.

3. The compound of claim 1, wherein R³ is —

SO₃<sup>′

.</sup>

4. The compound of claim 1, wherein R¹ and R² are chloro and wherein R³ is —

SO₃<sup>−

.</sup>

5. The compound of claim 1 wherein the water solubilizing group comprises a polar substituent.

6. The compound of claim 1 wherein the water solubilizing group comprises a charged substituent that increases water solubility of a base molecule.

7. The compound of claim 6 wherein the water solubilizing group comprises an anionic substituent.

8. The compound of claim 6 wherein the water solubilizing group is appended directly to the base molecule.

9. The compound of claim 6 wherein the water solubilizing group is appended through a linker to the base molecule.

10. The compound of claim 1 wherein the water solubilizing group comprises a carboxyl group, sulphonic acid, hydroxyl group, substituted azenyl group, a polyoxyalkylene, phosphate group, or a bisphosphonate group.

11. The compound of claim 10 wherein the water solubilizing group comprises a polyoxyalkylene and the polyoxyalkylene is poly (ethylene glycol).

12. The compound of claim 1 wherein the water solubilizing group comprises a substituent that introduces an additional net charge into the molecule.