Abstract:
:Several antibacterial halogenated salicylanilides, including 3,3',4',5-tetrachlorosalicylanilide (TCSA) and 3,4',5-tribromosalicylanilide (TBSA) are known to cause photoallergy. We have carried out photochemical and spin trapping studies to determine whether free radicals may be involved in the photoallergic response. Irradiation (lambda greater than 300 nm) of TCSA in buffered (pH 7.4) 50% ethanol resulted in the rapid loss of the 3-chloro atom, followed by the much slower release of 5- and then the 4'-chloro atoms to give 3'-chlorosalicylanilide as a stable photoproduct. Under the same conditions TBSA successively lost the 3-, 5- and 4'-bromine atoms to give salicylanilide. When TCSA or TBSA were irradiated (lambda = 356 nm) in buffered (pH 7.4) 50% ethanol containing 2-methyl-2-nitrosopropane (MNP) only solvent-derived free radicals were detected. However, irradiation (lambda = 356 nm) of TCSA and MNP in 0.1 N NaOH generated an ESR spectrum consisting of a broad triplet (aN = 15.6 G). This spectrum was attributed to the adduct formed by the reaction of MNP with the aryl radical generated by the loss of a chlorine atom from the sterically hindered 3-(or 4'-)-position. Under the same conditions TBSA initially generated a broad triplet (aN = 15.5 G) similar to that observed for TCSA. However, upon further irradiation a 21-line spectrum (aN = 14.4 G, a2H = 2.0 G and a2H = 0.9 G) appeared.(ABSTRACT TRUNCATED AT 250 WORDS)
journal_name
Photochem Photobioljournal_title
Photochemistry and photobiologyauthors
Chignell CF,Sik RHdoi
10.1111/j.1751-1097.1989.tb04162.xsubject
Has Abstractpub_date
1989-09-01 00:00:00pages
287-95issue
3eissn
0031-8655issn
1751-1097journal_volume
50pub_type
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pub_type: 杂志文章
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pub_type: 杂志文章
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更新日期:1995-03-01 00:00:00
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journal_title:Photochemistry and photobiology
pub_type: 杂志文章,评审
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pub_type: 杂志文章,评审
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更新日期:2017-03-01 00:00:00
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