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Master's Dissertation
DOI
10.11606/D.9.2007.tde-25102007-151610
Document
Author
Full name
Paula Carpes Victorio Carmazen
E-mail
Institute/School/College
Knowledge Area
Date of Defense
Published
São Paulo, 2007
Supervisor
Committee
Loureiro, Ana Paula de Melo (President)
Marcourakis, Tania
Onuki, Janice
Title in Portuguese
Investigação de lesões em DNA induzidas por produtos de redução do corante C. I. Disperse Blue 291
Keywords in Portuguese
Adutos de DNA
C.I. Disperse Blue 291
Corante dinitrobromoaminoazobenzeno
PBTAs
PBTAs não clorados
Abstract in Portuguese
CI Disperse Blue 291 (CI DB 291) é um corante dinitrobromoaminoazobenzeno com atividade mutagênica para S. typhimurium, aumentada na presença de nitrorredutase, o-acetiltransferase e enzimas microssomais (S9). Neste estudo foram isolados e caracterizados quatro produtos da redução de DB 291 com ditionito de sódio (in vitro), sendo denominados 2- fenilbenzotriazóis não clorados (não-ClPBTAs). Os espectros de absorbância não apresentam o pico correspondente à ligação azo (?λ=613 nm), indicando a redução dessa ligação. Espectros de massas e 1H RMN mostram que os produtos são dois pares de tautômeros com m/z 465 [M+H]+ e m/z 449 [M+H]+. Esses produtos foram acetilados com piridina/anidrido acético e espectros de massas desses produtos indicam adição de grupamento acetil na molécula e formação de produtos com m/z 507 [M+H]+ e m/z 491 [M+H]+. Esses compostos foram reagidos com dGuo e obtivemos dois produtos com m/z 632 [M+H]+ e m/z 683 [M+H]+, sendo os possíveis adutos. A partir do composto não clorado com m/z 449 obtido após redução com ditionito de sódio, sintetizamos o análogo clorado (PBTA) após reação de cloração. Espectros de massa confirmam a formação do composto clorado com m/z 483 [M+H]+. Também incubamos o corante CI DB 291 com nitrorredutase/NADH. Análises por HPLC/ESI/MS indicam a formação de não-ClPBTA (m/z 449). Uma vez que não-ClPBTAs são mais mutagênicos para linhagens de S. typhimurium (com fração S9) que seus dinitrofenilazo corantes precursores, a conversão enzimática do corante para não-ClPBTAs pode ser uma via importante para sua bioativação.
Title in English
Investigation of DNA damage induced by products of the C.I. Disperse Blue 291 reduction 2007
Keywords in English
Azo dye
Chlorinated phenylbenzotriazole
DNA adducts
Nitro compounds
Non- chlorinated phenylbenzotriazole
Abstract in English
C.I. Disperse Blue 291 (C.I. DB 291) is a dinitrobromoaminoazobenzene dye with mutagenic activity to S. typhimurium, that is increased in the presence of nitroreductase, o-acetyltransferase and microsomal enzymes (S9). In this study were isolated and characterized four products of the reduction of DB 291 with sodium dithionite (in vitro), named non- chlorinated 2- phenylbenzotriazoles (non-ClPBTAs). The absorbance spectra do not present the peak corresponding to the band of azo bond (λ= 613 nm), indicating that the reduction of this bond occured. Mass spectra and 1H NMR show that the products are two pairs of tautomers with m/z 465 [M+H]+ and m/z 449 [M+H]+. These compounds were acetylated with pyridine/acetic anhydride and their mass spectra indicate the addition of an acetyl group to the molecules and formation of products with m/z 507 [M+H]+ e m/z 491 [M+H]+. After reaction of these compounds with dGuo we have got two products with m/z 632 [M+H]+ and m/z 683 [M+H]+, which are possible adducts. Starting from the non chlorinated compound with m/z 449, obtained through the dye reduction with sodium dithionite, we have synthesized the chlorinated analogous (PBTA) after chlorination reaction. Mass spectrum confirms formation of the chlorinated product with m/z 483 [M+H]+. The DB 291 dye was also incubated with nitroreductase NADH. HPLC/ESI/MS analyses indicate the formation of a non chlorinated PBTA (m/z 449). Since non- chlorinated PBTAs are more mutagenic to S. typhimurium strains (with S9 mix) than the parent phenylbenzotriazole dye, enzymatic conversion of this type of dye non chlorinated PBTAs may be an important way for its bioactivation.
 
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PAULACARPES.pdf (4.40 Mbytes)
Publishing Date
2008-03-31
 
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