Anti-viral azide containing compounds

Patent metadata

Field	Value
Publication number	US-10179143-B2
Application number	US-201715671360-A
Country	US
Kind code	B2
Filing date	Aug 8, 2017
Priority date	Jul 28, 2010
Publication date	Jan 15, 2019
Grant date	Jan 15, 2019

Abstract

Methods of using azide-modified biomolecules, such as fatty acids, carbohydrates and lipids, to treat a plant, an insect or an animal infected with a virus or to inhibit infectivity of a virus, such as the human immunodeficiency virus, are provided. Also provided are methods of labeling a virus, such as human immunodeficiency virus, with an azide-modified biomolecule, such as a fatty acid, a carbohydrate, or an isoprenoid lipid. Also, provided are methods of tracking a virus in vivo, with an azide-modified biomolecule, such as a fatty acid, a carbohydrate, or an isoprenoid lipid. The azide-modified biomolecules may be combined with a pharmaceutically acceptable excipient to produce a pharmaceutical composition, optionally containing another anti-viral agent and/or a delivery agent, such as a liposome.

First claim

What is claimed:

1. A method of tracking a virus in vivo comprising the steps of
contacting cultured cells or a subject with an azide-modified carbohydrate, azide-modified fatty acid, azide-modified isoprenoid lipid, or a pharmaceutically acceptable salt thereof;
contacting the cultured cells or the subject with an alkyne labeled reporter molecule to result in a reporter-labeled virus; and
tracking the reporter-labeled virus in the cultured cells or the subject,

wherein the azide-modified fatty acid or pharmaceutically acceptable salt thereof, has the formula:
Y—CH 2 —X—CO 2 H

wherein,
Y is H or an azido group; and
when Y is an azido group, X is a linear or branched carbon chain comprising 12 to 28 carbons, wherein one or more of said carbons may be independently replaced by an oxygen, selenium, silicon, sulfur, SO, SO 2 or NR 1 , or wherein one or more pairs of said carbons adjacent to one another may be attached to one another by a double or triple bond; or
when Y is H, X is a linear or branched carbon chain comprising 6 to 28 carbons, wherein one hydrogen on one of said carbons is replaced with an azido group and wherein one or more of said carbons not having an the azido group attached thereto may be independently replaced by an oxygen, selenium, silicon, sulfur, SO, SO 2 or NR 1 , or wherein one or more pairs of said carbons adjacent to one another and not having an azido group may be attached to one another by a double or triple bond;

wherein, R 1 is H or an alkyl comprising 1 to 6 carbons.

2. The method of claim 1 , wherein the cultured cells or the subject is contacted with the azide-modified fatty acid or pharmaceutically acceptable salt thereof.

3. The method of claim 1 , wherein Y is an azido group.

4. The method of claim 3 , wherein X is a linear carbon chain.

5. The method of claim 4 , wherein the carbon chain comprises 12 to 15 carbons.

6. The method of claim 1 , wherein the azide-modified fatty acid is 15-azidopentadecanoic acid or pharmaceutically acceptable salt thereof.

7. The method of claim 1 , wherein the azide-modified fatty acid is 14-azidomyristic acid or 16-azidopalmitic acid or pharmaceutically acceptable salt thereof.

Assignees

• Life Technologies Corp

Inventors

• Agnew Brian
• Singh Upinder
• Grecian Scott

Classifications

• C12N7/00 Primary

  Viruses; Bacteriophages; Compositions thereof; Preparation or purification thereof (preparing medicinal viral antigen or antibody compositions, e.g. virus vaccines, A61K39/00) · CPC title

• C12N2740/16051

  Methods of production or purification of viral material · CPC title

• C12N2740/16063

  by chemical treatment · CPC title

• C12N2710/14163

  by chemical treatment · CPC title

• A61K31/655 Primary

  Azo (—N=N—), diazo (=N2), azoxy (>N—O—N< or N(=O)—N<), azido (—N3) or diazoamino (—N=N—N<) compounds · CPC title