Azobenzene derivatives as labeling agents and intermediates thereof

US6602987B1 · kind B1 · utility

Assignee

• YEDA RESEARCH AND DEVELOPMENT CO. LTD. · IL

Inventors

• Meir Wilchek · Rehovot, IL
• Edward A. Bayer · Hod HaSharon, IL
• Heike Hofstetter · DeKalb, US
• Margherita Morpurgo · Teolo, IT

Key dates

• Filing date: Aug 7, 2001
• Grant date: Aug 5, 2003
• Expiry date: Aug 7, 2021

Classification

• Technology area (CPC G): Physics
• CPC primary: G01N33/533
• WIPO field: Measurement
• WIPO sector: Instruments

Abstract

A compound of the formula I: wherein R is H or —N═N-2-carboxyphenyl; A is (CH2)n or —CH═CH—, wherein n is an integer from 0 to 10, or A may also be —CH(COOH)— when R is —N═N-2-carboxyphenyl; and X is a radical selected from the group consisting of: (i) Cl; (ii) COOR1, wherein R1 is p-nitrophenyl or N-succinimidyl; (iii) CONH—NHR2, wherein R2 is H, COO(t-butyl) or COObenzyl; (iv) CONH—[B]—NHR3, wherein R3 is H, COOR1, or CO—[B′]—maleimido, wherein R1 is t-butyl, p-nitrophenyl or N-succinimidyl, and B and B′, the same or different, are (CH2)n wherein n is an integer from 2 to 10; (v) CONH—[B]—COOR4, wherein R4 is H, C1-C8 alkyl, N-succinimidyl; (vi) CONH—[B]—OH; (vii) CONH—[B]—CONH—NHR2, wherein R2 is H, COO(t-butyl) or COObenzyl; and (viii) NHR2, wherein R2 is H, COO(t-butyl) or COObenzyl, when A is —CH(COOH)— and R is —N═N-2-carboxyphenyl. The 4′-hydroxyazobenzene-2-carboxylic acid (HABA) compounds are novel reagents for labeling, isolation and detection of biological molecules.