Cargando…
The Hydractinia echinata Test-System. III: Structure-Toxicity Relationship Study of Some Azo-, Azo-Anilide, and Diazonium Salt Derivatives
Structure-toxicity relationships for a series of 75 azo and azo-anilide dyes and five diazonium salts were developed using Hydractinia echinata (H. echinata) as model species. In addition, based on these relationships, predictions for 58 other azo-dyes were made. The experimental results showed that...
Autores principales: | , , , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2014
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270994/ https://www.ncbi.nlm.nih.gov/pubmed/25006787 http://dx.doi.org/10.3390/molecules19079798 |
_version_ | 1783376826279657472 |
---|---|
author | Chicu, Sergiu Adrian Munteanu, Melania Cîtu, Ioana Şoica, Codruta Dehelean, Cristina Trandafirescu, Cristina Funar-Timofei, Simona Ionescu, Daniela Simu, Georgeta Maria |
author_facet | Chicu, Sergiu Adrian Munteanu, Melania Cîtu, Ioana Şoica, Codruta Dehelean, Cristina Trandafirescu, Cristina Funar-Timofei, Simona Ionescu, Daniela Simu, Georgeta Maria |
author_sort | Chicu, Sergiu Adrian |
collection | PubMed |
description | Structure-toxicity relationships for a series of 75 azo and azo-anilide dyes and five diazonium salts were developed using Hydractinia echinata (H. echinata) as model species. In addition, based on these relationships, predictions for 58 other azo-dyes were made. The experimental results showed that the measured effectiveness Mlog(1/MRC(50)) does not depend on the number of azo groups or the ones corresponding to metobolites, but it is influenced by the number of anilide groups, as well as by the substituents’ positions within molecules. The conformational analysis pointed out the intramolecular hydrogen bonds, especially the simple tautomerization of quinoidic (ST(OH)) or aminoidic (ST(NH2)) type. The effectiveness is strongly influenced by the “push-pull” electronic effect, specific to two hydroxy or amino groups separated by an azo moiety (double alternate tautomery, (DAT), to the –COOH or –SO(3)H groups which are located in ortho or para position with respect to the azo group. The levels of the lipophylic/hydrophilic, electronic and steric equilibriums, pointed out by the Mlog(1/MRC(50)) values, enabled the calculation of their average values Clog(1/MRC(50)) (“Köln model”), characteristic to one derivative class (class isotoxicity). The azo group reduction and the hydrolysis of the amido/peptidic group are two concurrent enzymatic reactions, which occur with different reaction rates and mechanisms. The products of the partial biodegradation are aromatic amines. No additive or synergic effects are noticed among them. |
format | Online Article Text |
id | pubmed-6270994 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-62709942018-12-21 The Hydractinia echinata Test-System. III: Structure-Toxicity Relationship Study of Some Azo-, Azo-Anilide, and Diazonium Salt Derivatives Chicu, Sergiu Adrian Munteanu, Melania Cîtu, Ioana Şoica, Codruta Dehelean, Cristina Trandafirescu, Cristina Funar-Timofei, Simona Ionescu, Daniela Simu, Georgeta Maria Molecules Article Structure-toxicity relationships for a series of 75 azo and azo-anilide dyes and five diazonium salts were developed using Hydractinia echinata (H. echinata) as model species. In addition, based on these relationships, predictions for 58 other azo-dyes were made. The experimental results showed that the measured effectiveness Mlog(1/MRC(50)) does not depend on the number of azo groups or the ones corresponding to metobolites, but it is influenced by the number of anilide groups, as well as by the substituents’ positions within molecules. The conformational analysis pointed out the intramolecular hydrogen bonds, especially the simple tautomerization of quinoidic (ST(OH)) or aminoidic (ST(NH2)) type. The effectiveness is strongly influenced by the “push-pull” electronic effect, specific to two hydroxy or amino groups separated by an azo moiety (double alternate tautomery, (DAT), to the –COOH or –SO(3)H groups which are located in ortho or para position with respect to the azo group. The levels of the lipophylic/hydrophilic, electronic and steric equilibriums, pointed out by the Mlog(1/MRC(50)) values, enabled the calculation of their average values Clog(1/MRC(50)) (“Köln model”), characteristic to one derivative class (class isotoxicity). The azo group reduction and the hydrolysis of the amido/peptidic group are two concurrent enzymatic reactions, which occur with different reaction rates and mechanisms. The products of the partial biodegradation are aromatic amines. No additive or synergic effects are noticed among them. MDPI 2014-07-08 /pmc/articles/PMC6270994/ /pubmed/25006787 http://dx.doi.org/10.3390/molecules19079798 Text en © 2014 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Chicu, Sergiu Adrian Munteanu, Melania Cîtu, Ioana Şoica, Codruta Dehelean, Cristina Trandafirescu, Cristina Funar-Timofei, Simona Ionescu, Daniela Simu, Georgeta Maria The Hydractinia echinata Test-System. III: Structure-Toxicity Relationship Study of Some Azo-, Azo-Anilide, and Diazonium Salt Derivatives |
title | The Hydractinia echinata Test-System. III: Structure-Toxicity Relationship Study of Some Azo-, Azo-Anilide, and Diazonium Salt Derivatives |
title_full | The Hydractinia echinata Test-System. III: Structure-Toxicity Relationship Study of Some Azo-, Azo-Anilide, and Diazonium Salt Derivatives |
title_fullStr | The Hydractinia echinata Test-System. III: Structure-Toxicity Relationship Study of Some Azo-, Azo-Anilide, and Diazonium Salt Derivatives |
title_full_unstemmed | The Hydractinia echinata Test-System. III: Structure-Toxicity Relationship Study of Some Azo-, Azo-Anilide, and Diazonium Salt Derivatives |
title_short | The Hydractinia echinata Test-System. III: Structure-Toxicity Relationship Study of Some Azo-, Azo-Anilide, and Diazonium Salt Derivatives |
title_sort | hydractinia echinata test-system. iii: structure-toxicity relationship study of some azo-, azo-anilide, and diazonium salt derivatives |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270994/ https://www.ncbi.nlm.nih.gov/pubmed/25006787 http://dx.doi.org/10.3390/molecules19079798 |
work_keys_str_mv | AT chicusergiuadrian thehydractiniaechinatatestsystemiiistructuretoxicityrelationshipstudyofsomeazoazoanilideanddiazoniumsaltderivatives AT munteanumelania thehydractiniaechinatatestsystemiiistructuretoxicityrelationshipstudyofsomeazoazoanilideanddiazoniumsaltderivatives AT cituioana thehydractiniaechinatatestsystemiiistructuretoxicityrelationshipstudyofsomeazoazoanilideanddiazoniumsaltderivatives AT soicacodruta thehydractiniaechinatatestsystemiiistructuretoxicityrelationshipstudyofsomeazoazoanilideanddiazoniumsaltderivatives AT deheleancristina thehydractiniaechinatatestsystemiiistructuretoxicityrelationshipstudyofsomeazoazoanilideanddiazoniumsaltderivatives AT trandafirescucristina thehydractiniaechinatatestsystemiiistructuretoxicityrelationshipstudyofsomeazoazoanilideanddiazoniumsaltderivatives AT funartimofeisimona thehydractiniaechinatatestsystemiiistructuretoxicityrelationshipstudyofsomeazoazoanilideanddiazoniumsaltderivatives AT ionescudaniela thehydractiniaechinatatestsystemiiistructuretoxicityrelationshipstudyofsomeazoazoanilideanddiazoniumsaltderivatives AT simugeorgetamaria thehydractiniaechinatatestsystemiiistructuretoxicityrelationshipstudyofsomeazoazoanilideanddiazoniumsaltderivatives AT chicusergiuadrian hydractiniaechinatatestsystemiiistructuretoxicityrelationshipstudyofsomeazoazoanilideanddiazoniumsaltderivatives AT munteanumelania hydractiniaechinatatestsystemiiistructuretoxicityrelationshipstudyofsomeazoazoanilideanddiazoniumsaltderivatives AT cituioana hydractiniaechinatatestsystemiiistructuretoxicityrelationshipstudyofsomeazoazoanilideanddiazoniumsaltderivatives AT soicacodruta hydractiniaechinatatestsystemiiistructuretoxicityrelationshipstudyofsomeazoazoanilideanddiazoniumsaltderivatives AT deheleancristina hydractiniaechinatatestsystemiiistructuretoxicityrelationshipstudyofsomeazoazoanilideanddiazoniumsaltderivatives AT trandafirescucristina hydractiniaechinatatestsystemiiistructuretoxicityrelationshipstudyofsomeazoazoanilideanddiazoniumsaltderivatives AT funartimofeisimona hydractiniaechinatatestsystemiiistructuretoxicityrelationshipstudyofsomeazoazoanilideanddiazoniumsaltderivatives AT ionescudaniela hydractiniaechinatatestsystemiiistructuretoxicityrelationshipstudyofsomeazoazoanilideanddiazoniumsaltderivatives AT simugeorgetamaria hydractiniaechinatatestsystemiiistructuretoxicityrelationshipstudyofsomeazoazoanilideanddiazoniumsaltderivatives |