Red-shifted fluorophores

Patent metadata

Field	Value
Publication number	US-12344594-B2
Application number	US-202017116987-A
Country	US
Kind code	B2
Filing date	Dec 9, 2020
Priority date	Dec 9, 2019
Publication date	Jul 1, 2025
Grant date	Jul 1, 2025

Abstract

A compound of the following structure is provided:

First claim

What is claimed is:

1. A compound of the following structure:

wherein
Q is selected from the group consisting of CH(alkyl), C(alkyl) 2 , NH, N(alkyl), O, S, SO 2 , Si(alkyl) 2 , P(O)(aryl), P(O)(alkyl), PO 2 H, PO 2 (alkyl), Se, and replaced with two H atoms;
L is independently selected from the group consisting of O, OH, NH 2 , NH(alkyl), NH(deuterated alkyl), N(alkyl) 2 , N(deuterated alkyl) 2 , NH(aryl), N(aryl) 2 , N(alkyl)(aryl), N(deuterated alkyl) (aryl), substituted or unsubstituted cyclic amines with a ring size of 3, 4, 5, 6, 7, 8, or 9 atoms, and substituted or unsubstituted deuterated cyclic amines with a ring size of 3, 4, 5, 6, 7, 8, or 9 atoms, so long as when Q is O then L is not O or OH;
R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of H, D, halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), N 3 , NH 2 , NH(alkyl), N(alkyl) 2 , NH(aryl), N(aryl) 2 , NO 2 , CHO, C(O)(alkyl), C(O)(aryl), COOH, COO(alkyl), COO(aryl), C(O)NH(alkyl), C(O)NH(aryl), PO 3 H 2 , SO 3 H, alkyl and substituted alkyl, aryl and substituted aryl, alkenyl and substituted alkenyl, alkynyl or substituted alkynyl, or where each adjacent R substituent and L substituent, taken together with the carbon atoms to which they are bonded, independently form a substituted or unsubstituted ring containing 3, 4, 5, 6, 7, 8, or 9 atoms;
X is selected from the group consisting of alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, CN, COOH, COO(alkyl), COO(aryl), C(O)NH(alkyl), C(O)N(alkyl) 2 , C(O)NH(aryl), and C(O)N(aryl) 2 ;
when W is not present in the structure, Z is selected from the group consisting of H, halogen, OH, O(alkyl), O(aryl), COO, COOH, COO(alkyl), COO(aryl), C(O)NH(alkyl), C(O)N(alkyl) 2 , C(O)NH(aryl), C(O)N(aryl) 2 , PO 3 H 2 , SO 3 H, alkyl, substituted alkyl, alkenyl, and substituted alkenyl; and
when W is present in the structure, Z is selected from the group consisting of C(O), SO 2 , PO 2 H, or CR 2 where each R is independently selected from the group consisting of H, alkyl, and substituted alkyl; and W is selected from the group consisting of O, S, C(O), C(N 2 ), NH, N(alkyl), N(aryl), N(SO 2 R) where R can be alkyl, substituted alkyl, or CN.

2. The compound of claim 1 , wherein X is selected from the group consisting of

3. The compound of claim 1 , wherein Q is selected from the group consisting of C(alkyl) 2 , O, S, SO 2 , Si(alkyl) 2 , P(O)(aryl), P(O)(alkyl), PO 2 H, and replaced with two H atoms.

4. The compound of claim 1 , wherein Q is selected from selected from the group consisting of

and replaced with two H atoms.

5. The compound of claim 1 , wherein one or both L substituents are independently selected from the group consisting of O and OH.

6. The compound of claim 1 , wherein one or both L substituents are independently selected from the group consisting of NH 2 , NCH 3 (phenyl), NH(tert-butoxycarbonyl), and N(CH 3 ) 2 .

7. The compound of claim 1 , wherein one or both L substituents are independently selected from the group consisting of substituted or unsubstituted cyclic amines with a ring size of 4, 5, 6, 7, or 8 atoms.

8. The compound of claim 7 , wherein the substituted or unsubstituted cyclic amine with a ring size of 4, 5, 6, or 7 atoms is selected from the group consisting of

9. The compound of claim 1 , wherein the R 2 substituents, or the R 3 substituents, and L substituents are taken together with the carbon atoms to which they are bonded to form a substituted or unsubstituted ring containing 5, 6, 7, 8, or 9 atoms.

10. The compound of claim 1 , having a structure chosen from:

wherein X is selected from the group consisting of alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, CN, COOH, COO(alkyl), COO(aryl), C(O)NH(alkyl), C(O)N(alkyl) 2 , C(O)NH(aryl), and C(O)N(aryl) 2 .

11. The compound of claim 10 , wherein X is selected from the group consisting of

12. A method for detecting a target substance, comprising:
contacting a sample with the compound of claim 1 ; and
detecting an emission light from the compound, the emission light indicating the presence of the target substance.

13. The method of claim 12 , wherein the target substance is selected from a protein, a carbohydrate, a polysaccharide, a glycoprotein, a hormone, a receptor, an antigen, an antibody, a virus, a substrate, a metabolite, an inhibitor, a drug, a nutrient, a growth factor, a liprotein, and a combination thereof.

14. The method of claim 12 , wherein the detecting step is performed with a microscope.

15. The method of claim 12 , wherein the contacting step and the detecting step are performed in a live cell.

16. The method of c

Assignees

• Hughes Howard Med Inst

Inventors

• Lavis Luke D
• Grimm Jonathan B

Classifications

• C07D409/14

  containing three or more hetero rings · CPC title

• G01N21/6428

  Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" (in vivo A61B5/00; immunoassay G01N33/53) · CPC title

• G01N21/6458

  Fluorescence microscopy (fluorescence microscopes per se G02B21/0076 and G02B21/16) · CPC title

• C07D491/147

  the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom · CPC title

• C07D405/14

  containing three or more hetero rings · CPC title