Pyrenyloxysulfonic acid fluorescent agents

• US 8,614,294 B2
• Filed: 08/23/2012
• Issued: 12/24/2013
• Est. Priority Date: 12/09/2003
• Status: Active Grant

• Current Assignee: Life Technologies Corporation (Thermo Fisher Scientific Incorporated)
• Original Assignee: Life Technologies Corporation (Thermo Fisher Scientific Incorporated)
• Inventors: Haugland, Richard, Leung, Wai-Yee, Liu, Jixiang
• Primary Examiner(s): Wilson, James O
• Assistant Examiner(s): Sackey, Ebenezer O
• Application Number:
  US13/592,532
• Publication Number:
  US 20130079497A1
• Time in Patent Office: 488 Days
• Field of Search: 530/367, 530/391.5, 548/545, 546/195
• US Class Current: 530/367
• CPC Class Codes: C07C 309/38 formed by at least three rings
• CPC Class Codes: C07D 207/16 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 207/46 with hetero atoms directly attached to the ring nitrogen atom
• CPC Class Codes: C07D 211/56 Nitrogen atoms nitro radicals C07D211/38
• CPC Class Codes: C07D 211/60 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 211/62 attached in position 4
• CPC Class Codes: C07D 401/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07H 17/08 Hetero rings containing eight or more ring members, e.g. erythromycins
• CPC Class Codes: C07H 19/04 Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
• CPC Class Codes: C07K 14/77 Ovalbumin
• CPC Class Codes: C07K 16/18 against material from animals or humans
• CPC Class Codes: C09B 57/001 Pyrene dyes
• CPC Class Codes: G01N 33/536 with immune complex formed in liquid phase

Abstract

The invention provides a novel class of reactive fluorescent agents that are based on a pyrene sulfonic acid nucleus. The agents are readily incorporated into conjugates with other species by reacting the reactive group with a group of complementary reactivity on the other species of the conjugate. Also provided are methods of using the compounds of the invention to detect and/or quantify an analyte in a sample. In an exemplary embodiment, the invention provides multi-color assays incorporating the compounds of the invention.

Claims

1. A compound having structure VI:

2. The compound of claim 1 wherein s is 1 and t is 2.

3. The compound of claim 1 wherein the linker arm comprises a straight-chain, saturated chain of atoms and includes unsubstituted polyalkylene.

13. A kit for the detection of an analyte in a sample, wherein said kit comprises a compound of claim 1.

4. A compound having structure VI:

5. The compound of claim 4 wherein s is 1 and t is 2.

14. A kit for the detection of an analyte in a sample, wherein said kit comprises a compound of claim 4.

6. A conjugate having structure VI:

7. The conjugate of claim 6 wherein s is 1 and t is 2.

8. The conjugate of claim 6 wherein the linker arm comprises a straight-chain, saturated chain of atoms and includes unsubstituted polyalkylene.

15. A kit for the detection of an analyte in a sample, wherein said kit comprises a conjugate of claim 6.

9. A conjugate having structure VI:

10. The conjugate of claim 9, wherein the linker arm comprises a cleavable group.

11. The conjugate of claim 9, wherein the linker arm comprises —

C(O)NH—

, —

C(O)O—

, —

NH—

, —

S—

, or —

O—

.

12. The conjugate of claim 9, wherein s is 1, and t is 2.

16. A kit for the detection of an analyte in a sample, wherein said kit comprises a conjugate of claim 9.