Photoreactions of 3,3',4',5-tetrachlorosalicylanilide with proteins.

Abstract

The photoreactions of 3,3',4',5-tetrachlorosalicylanilide anion (TCSA-) with two serum proteins were studied. TCSA- and anions of two similar compounds, N-ethyl-3,5-dichlorosalicylamide and salicylanilide, bind noncovalently to human serum albumin (HSA) without irradiation in aqueous pH 7.4 buffered solutions. TCSA- noncovalently bound to HSA yields three types of photoproducts when irradiated with ultraviolet light (lambda greater than 360 nm). A covalently bonded photoadduct between TCSA- and HSA is formed and histidines in HSA are chemically modified. In addition to these two types of photoproducts which involve HSA, two of the four TCSA- photoproducts which form when HSA is absent are also formed when the TCSA-/HSA complex is irradiated. The results presented indicate that not all proteins in the skin are capable of being the carrier protein in photoallergy of TCSA- and that cross reactivity to other halogenated salicylanilides can be explained by further photochemical reactions of TCSA- photoproducts.

• Authors: I E Kochevar, L C Harber
• Journal: The Journal of investigative dermatology (J Invest Dermatol) Vol. 68 Issue 3 Pg. 151-6 (Mar 1977) ISSN: 0022-202X [Print] United States
• PMID: 14216 (Publication Type: Journal Article, Research Support, U.S. Gov't, P.H.S.)

Chemical References

• Anions
• Blood Proteins
• Haptens
• Salicylamides
• Salicylanilides
• Serum Albumin
• Xenon
• Histidine

Topics

• Anions
• Blood Proteins (metabolism)
• Chemical Phenomena
• Chemistry
• Dermatitis, Contact (etiology, immunology)
• Fluorescence
• Haptens
• Histidine
• Humans
• Hydrogen-Ion Concentration
• Photolysis
• Salicylamides (metabolism)
• Salicylanilides (metabolism)
• Serum Albumin (metabolism)
• Ultraviolet Rays
• Xenon