Publicou 4 edições por ano
ISSN Imprimir: 0731-8898
ISSN On-line: 2162-6537
Indexed in
Mechanisms of Carcinogenicity of Aryl Hydrazines, Aryl Hydrazides, and Arenediazonium Ions
RESUMO
Aryl hydrazines carcinogenesis has been studied for over 25 years and remains poorly understood, although most aryl hydrazines are toxic, tumorigenic, or carcinogenic. In this article, aryl hydrazine cardnogenesis is reviewed comprehensively. The relevant chemistry and biochemistry of aryl hydrazines are first addressed and provide the framework for understanding how aryl hydrazines are metabolized, the reactive intermediates that are produced, and the biological reactive intermediates and products that are formed. Issues of DNA damage, mutagenicity, and enzyme activation are next addressed followed by a brief review of aryl hydrazine tumorigenicity studies. Because several related substrates are metabolized to the same intermediates as are aryl hydrazines, they are briefly discussed. The review concludes with a short discussion of the possible mechanism of cardnogenesis by aryl hydrazines.
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Pazo-Llorente Roman, Maskill Howard, Bravo-Diaz Carlos, Gonzalez-Romero Elisa, Dediazoniation of 4-Nitrobenzenediazonium Ions in Acidic MeOH/H2O Mixtures: Role of Acidity and MeOH Concentration on the Formation of Transient Diazo Ethers that Initiate Homolytic Dediazoniation, European Journal of Organic Chemistry, 2006, 9, 2006. Crossref
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Fernández-Alonso Alejandra, Bravo-Díaz Carlos, Effects of Micellar Aggregates on the Kinetics and Mechanism of the Reaction between 4-Nitrobenzenediazonium Ions and Some Amino Acids, Helvetica Chimica Acta, 90, 6, 2007. Crossref
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Beda N. V., Nedospasov A. A., NO-dependent modifications of nucleic acids, Russian Journal of Bioorganic Chemistry, 33, 2, 2007. Crossref
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Barreiro Sonia Losada, Sánchez-Paz Verónica, Gallego Maria José Pastoriza, Bravo-Díaz Carlos, Micellar Effects on the Reaction between an Arenediazonium Ion and the Antioxidants Gallic Acid and Octyl Gallate, Helvetica Chimica Acta, 91, 1, 2008. Crossref
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Marinozzi Maura, Marcelli Gloria, Carotti Andrea, Natalini Benedetto, One-pot, telescoped synthesis of N-aryl-5-aminopyrazoles from anilines in environmentally benign conditions, RSC Advances, 4, 14, 2014. Crossref
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Abdullah M. F., Zakaria R., Zein S. H. S., Green tea polyphenol–reduced graphene oxide: derivatisation, reduction efficiency, reduction mechanism and cytotoxicity, RSC Adv., 4, 65, 2014. Crossref
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Bravo-Dı́az Carlos, González-Romero Elisa, Monitoring dediazoniation product formation by high-performance liquid chromatography after derivatization, Journal of Chromatography A, 989, 2, 2003. Crossref
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Ueberschaar Nico, Ndejouong Basile Le Sage Tchize, Ding Ling, Maier Armin, Fiebig Heinz-Herbert, Hertweck Christian, Hydrazidomycins, cytotoxic alkylhydrazides from Streptomyces atratus, Bioorganic & Medicinal Chemistry Letters, 21, 19, 2011. Crossref
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Zolla Lello, Timperio Anna Maria, Involvement of active oxygen species in protein and oligonucleotide degradation induced by nitrofurans, Biochemistry and Cell Biology, 83, 2, 2005. Crossref
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Malvezzi Alberto, Queiroz Raphael F, de Rezende Leandro, Augusto Ohara, Amaral Antonia T.-do, MPO Inhibitors Selected by Virtual Screening, Molecular Informatics, 30, 6-7, 2011. Crossref
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DeVito Stephen C., Structural and Toxic Mechanism-Based Approaches to Designing Safer Chemicals, in Handbook of Green Chemistry, 2012. Crossref
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Jaszczuk Katarzyna, Dudzik Anna, Losada-Barreiro Sonia, Szymula Marta, Narkiewicz-Michalek Jolanta, Bravo-Díaz Carlos, Kinetics and mechanism of the reaction between 3-methylbenzenediazonium ions and catechol, Journal of Physical Organic Chemistry, 29, 11, 2016. Crossref
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McGregor Douglas, Boobis Alan, Binaglia Marco, Botham Phil, Hoffstadt Laurence, Hubbard Sue, Petry Thomas, Riley Anthony, Schwartz Dirk, Hennes Christa, Guidance for the classification of carcinogens under the Globally Harmonised System of Classification and Labelling of Chemicals (GHS), Critical Reviews in Toxicology, 40, 3, 2010. Crossref
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Dudzik Anna, Jaszczuk Katarzyna, Losada-Barreiro Sonia, Bravo-Díaz Carlos, Kinetic evidence for the formation of diazo ethers in the course of reactions between arenediazonium ions and antioxidants, New Journal of Chemistry, 41, 7, 2017. Crossref
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Manderville Richard A., Wetmore Stacey D., Understanding the Mutagenicity of O-Linked and C-Linked Guanine DNA Adducts: A Combined Experimental and Computational Approach, Chemical Research in Toxicology, 30, 1, 2017. Crossref
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Costas-Costas U., Bravo-Diaz Carlos, Gonzalez-Romero Elisa, Kinetics and Mechanism of the Reaction between Ascorbic Acid Derivatives and an Arenediazonium Salt: Cationic Micellar Effects, Langmuir, 21, 24, 2005. Crossref
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Kazius Jeroen, McGuire Ross, Bursi Roberta, Derivation and Validation of Toxicophores for Mutagenicity Prediction, Journal of Medicinal Chemistry, 48, 1, 2005. Crossref
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Costas-Costas U., Bravo-Diaz Carlos, Gonzalez-Romero Elisa, Sodium Dodecyl Sulfate Micellar Effects on the Reaction between Arenediazonium Ions and Ascorbic Acid Derivatives, Langmuir, 19, 13, 2003. Crossref
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Costas-Costas U., Bravo-Díaz Carlos, González-Romero Elisa, Micellar Effects on the Reaction between an Arenediazonium Salt and 6-O-Octanoyl-l-ascorbic Acid. Kinetics and Mechanism of the Reaction, Langmuir, 20, 5, 2004. Crossref
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Western Elizabeth C., Daft Jonathan R., Johnson Edward M., Gannett Peter M., Shaughnessy Kevin H., Efficient One-Step Suzuki Arylation of Unprotected Halonucleosides, Using Water-Soluble Palladium Catalysts, The Journal of Organic Chemistry, 68, 17, 2003. Crossref
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Gannett Peter M., Heavner Sue, Daft Jonathan R., Shaughnessy Kevin H., Epperson Jon D., Greenbaum Nancy L., Synthesis, Properties, and NMR Studies of a C8-Phenylguanine Modified Oligonucleotide that Preferentially Adopts the Z DNA Conformation, Chemical Research in Toxicology, 16, 10, 2003. Crossref
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Rossi Renzo, Ciofalo Maurizio, Palladium-Catalysed Intermolecular Direct C–H Bond Arylation of Heteroarenes with Reagents Alternative to Aryl Halides: Current State of the Art, Current Organic Chemistry, 26, 3, 2022. Crossref