Water-soluble triazabutadienes

Patent metadata

Field	Value
Publication number	US-10047061-B2
Application number	US-201515317894-A
Country	US
Kind code	B2
Filing date	Jun 10, 2015
Priority date	Jun 11, 2014
Publication date	Aug 14, 2018
Grant date	Aug 14, 2018

Abstract

Water-soluble triazabutadiene molecules and methods for producing and using such compounds. The triazabutadiene molecules may be more labile at pH levels below physiological pH, such as pH 7, pH 6, pH 5, etc. The triazabutadiene molecules and compounds may be used for depositing diazonium salt and/or cargo in a pH-sensitive manner. The triazabutadiene molecules may alternatively be cleaved in reducing conditions or as a light-catalyzed reaction. The compounds herein may be used for delivery of drugs, as part of detection systems, or for other applications such as underwater adhesive applications.

First claim

What is claimed is:

1. A water-soluble triazabutadiene molecule having a structure of any one of the following:

wherein Me is methyl, Mes is 2, 4, 6-trimethylbenzene, and t-Bu is tert-butyl.

2. The triazabutadiene molecule of claim 1 , wherein the molecule has half-life of at least 12 hours in a pH 7.4 buffer.

3. The triazabutadiene molecule of claim 1 , wherein the triazabutadiene molecule breaks down to a diazonium species and a cyclic guanidine species.

4. The triazabutadiene molecule of claim 3 , wherein breaking down of the triazabutadiene occurs in a pH of 7.0 or less, a pH of 6.0 or less, or a pH of 5.0 or less.

5. The water-soluble triazabutadiene molecule of claim 1 , wherein the triazabutadiene molecule breaks down in reducing conditions yielding an aniline and a hydrazine, or a urea functionality and a terminal aryl triazene.

6. The triazabutadiene molecule of claim 3 , wherein breaking down of the triazabutadiene occurs when the triazabutadiene molecule is subjected to light.

7. The triazabutadiene molecule of claim 6 , wherein the light has a wavelength from 340 nm to 420 nm.

8. The triazabutadiene molecule of claim 3 , wherein the diazonium species reacts with an electron rich aromatic to produce a product species.

9. The triazabutadiene molecule of claim 8 , wherein the electron rich aromatic comprises a resorcinol species or a phenol species.

10. The triazabutadiene molecule of claim 9 , wherein the phenol species is that of a tyrosine molecule.

11. The triazabutadiene molecule of claim 1 , wherein the molecule is conjugated to a protein.

12. The triazabutadiene molecule of claim 8 , wherein the product species comprises an aryl azo dye.

13. The triazabutadiene molecule of claim 1 , wherein the molecule is conjugated to a surface.

Assignees

• Univ Arizona

Inventors

• Jewett John C
• Kimani Flora W

Classifications

• C07D405/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D277/50

  Nitrogen atoms bound to hetero atoms · CPC title

• C07D233/88

  Nitrogen atoms, e.g. allantoin · CPC title

• C07C245/06

  with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings · CPC title

• C07D235/30

  Nitrogen atoms not forming part of a nitro radical · CPC title