pH sensors

Patent metadata

Field	Value
Publication number	US-9702824-B2
Application number	US-201314384081-A
Country	US
Kind code	B2
Filing date	Mar 8, 2013
Priority date	Mar 9, 2012
Publication date	Jul 11, 2017
Grant date	Jul 11, 2017

Abstract

Provided herein are fluorescent sensor agents, and methods of use and manufacture thereof. In particular, sensor agents are provided that exhibit a detectable change in fluorescence (e.g., fluorescence intensity) upon alteration of the pH of the surrounding environment (e.g., upon moving from one pH environment to another).

First claim

We claim:

1. A pH sensor agent comprising:

wherein R1 and R2 are independently alkyl sulfonic acids, and wherein R3-R6 are independently: H, F, Cl, Br, I, OH, an alkoxide group, an alkyl group, a heteroalkyl group, an aryl group, CO 2 H, SO 3 H, L-CO 2 H, L-SO 3 H, L-W, or L-CS; wherein L is a linear, branched, and/or cyclic covalent linkage comprising 0-16 non-hydrogen atoms and comprising any suitable combination of: ester, acid, sulphonic acid, sulfamide, amine, amide, alcohol, ether, thioether, halide, single bonds, double bonds, triple bonds, and aromatic bonds; wherein W is a reactive group; wherein X is: O, CR 17 , MR 17 ; wherein R 17 is: H, F, Cl, Br, I, OH, an alkoxide group, an alkyl group, an aryl group, CO 2 H, SO 3 H, L-CO 2 H, L-SO 3 H, L-Y, or L-CS; and wherein M is selected from C, N, O, Si, P, S, Ge, As, Se, Sn, Sb, Te, Pb, Bi, and Po.

2. The pH sensor agent of claim 1 , wherein R1 and R2 are CH 2 (CH 2 ) n SO 3 − , wherein n=0-25.

3. A composition comprising an entity of interest tethered to a pH sensor agent of claim 1 .

4. A method of detecting the pH of an environment comprising:
a) contacting a pH sensor agent of claim 1 to said environment;
b) detecting fluorescence from said pH sensor agent; and
c) correlating said fluorescence to said pH.

5. A method of monitoring changes in the pH of an environment comprising:
a) contacting a pH sensor agent of claim 1 with said environment;
b) detecting fluorescence from said pH sensor agent over time; and
c) correlating changes in fluorescence to changes in pH.

6. A method of detecting movement of an entity of interest from a first pH environment to a second pH environment comprising:
a) contacting a pH sensor agent of claim 1 to said first pH environment;
b) detecting fluorescence of said pH sensor agent in said first pH environment;
c) monitoring said fluorescence of said pH sensor agent, wherein a change in said fluorescence indicates movement of said pH sensor agent to a second pH environment.

7. The pH sensor agent of claim 2 , wherein n=1-6.

8. The pH sensor of claim 7 , wherein R1 and R2 are alkyl sulfonic acids of the same length.

9. The pH sensor of claim 7 , wherein R1 and R2 are butyl sulphonic acid sulfonic acid.

10. The pH sensor of claim 7 , wherein R3, R5, and R6 are hydrogen.

11. The pH sensor of claim 10 , comprising a compound of:

12. The pH sensor of claim 10 , comprising a compound of:

Assignees

• Promega Corp

Inventors

• Cong Mei
• Corona Cesear
• Mcdougall Mark G
• Zimprich Chad

Classifications

• G01N2021/7786

  Fluorescence · CPC title

• C09B11/28

  Pyronines {; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes} · CPC title

• G01N21/80 Primary

  Indicating pH value · CPC title

• C09B11/24

  Phthaleins containing amino groups {; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes} · CPC title

• G01N31/221 Primary

  for investigating pH value · CPC title