Histopathological, cytotoxicological, and genotoxic effects of the semi-synthetic compound dillapiole n-butyl ether in Balb/C mice

References

• Abramsson-Zetterberg, L., J. Wong, and N. G. Ilbäck. 2005. Distribuição do tecido de acrilamida e efeitos genotóxicos em uma infecção viral comum em camundongos. Toxicology 211:70–76. doi:10.1016/j.tox.2005.02.008.
   PubMedGoogle Scholar
• Aiub, C. A. F., E. C. A. Coelho, E. Sodré, L. F. R. Pinto, and I. Felzenszwalb. 2002. Genotoxic evaluation of the organophosphorus pesticide temephos. Genet. Mol. Res. 1:159–66.
   PubMedGoogle Scholar
• Alavanja, M. C. R., and M. R. Bonner. 2012. Occupational pesticide exposures and cancer risk: A review. J. Toxicol. Environ. Health B 15:238–63. doi:10.1080/10937404.2012.632358.
   PubMed Web of Science ®Google Scholar
• Araújo, V. E. M. D., J. M. T. Bezerra, F. F. Amâncio, V. M. D. A. Passos, and M. Carneiro. 2017. Increase in the burden of dengue in Brazil and federated units, 2000 and 2015: Analysis of the Global Burden of Disease Study 2015. Revista Brasileira De Epidemiologia 20:205–16. doi:10.1590/1980-5497201700050017.
   Google Scholar
• Associação Brasileira de Normas Técnicas (ABNT). 2009. Chemicals – Information about safety, health and environment Part 2: Hazard classification system. NBR 14725–4. Accessed December 15, 2018. https://www.abntcatalogo.com.br/pdfview/viewer.aspx?Q=2AF38AEA3FE5CBCA3173E904CA0329F6A77BCC39D565BCB315FE5D2B69B57C5F.
   Google Scholar
• Belzile, A. S., S. L. Majerus, C. Podeszfinski, G. Guillet, T. Durst, and J. T. Arnason. 2000. Dillapiol derivatives as synergists: Structure–activity relationship analysis. Pestic. Biochem. Physiol. 66:33–40. doi:10.1006/pest.1999.2453.
   Web of Science ®Google Scholar
• Benitez-Trinidad, A. B., J. F. Herrera-Moreno, G. Vázquez-Estrada, F. A. Verdín-Betancourt, M. Sordo, P. Ostrosky-Wegman, Y. Y. Bernal-Hernández, I. M. Medina-Díaz, B. S. Barrón-Vivanco, M. L. Robledo-Marenco, et al. 2015. Cytostatic and genotoxic effect of temephos in human lymphocytes and HepG2 cells. Toxicol. Vitro 29:779–86. doi:10.1016/j.tiv.2015.02.008.
   PubMed Web of Science ®Google Scholar
• Bhunya, S. P., and P. C. Pati. 1990. Effect of deltamethrin, a synthetic pyrethroid, on the induction of chromosome aberrations, micronuclei and sperm abnormalities in mice. Mutagenesis 5:229–32. doi:10.1093/mutage/5.3.229.
   PubMed Web of Science ®Google Scholar
• Bojarski, B., and M. Witeska. 2020. Blood biomarkers of herbicide, insecticide, and fungicide toxicity to fish—a review. Environ. Sci. Pollut. Res. Inst. 2020. doi:10.1007/s11356-020-08248-8.
   Google Scholar
• Braga, I. A., and D. Valle. 2007. Aedes aegypti: Inseticidas, mecanismos de ação e resistência. Epidemiologia E Serviços De Saúde 16:279–93.
   Google Scholar
• Cossolin, J. F. S., M. J. Pereira, L. C. Martínez, L. M. Turchen, M. Fiaz, H. Bozdoğan, and J. E. Serrão. 2019. Cytotoxicity of Piper aduncum (Piperaceae) essential oil in brown stink bug Euschistus heros (Heteroptera: Pentatomidae). Ecotoxicology 28:763–70. doi:10.1007/s10646-019-02072-8.
   PubMed Web of Science ®Google Scholar
• Cruz, D. L. V., A. K. L. Encarnação, A. C. S. Pinto, and M. S. Rafael. 2019. Toxicidade oral aguda do semissintético éter n-butil dilapiol em camundongos Balb/C. In Alicerces e Adversidades das Ciências da Saúde no Brasil 2, B. R. S. Neto. ed., Ponta Grossa (PR): Atena Editora. v. 2:206–214. doi:10.22533/at.ed.71319021021.
   Google Scholar
• de Paulis Carlis, M. S., A. Féboli, A. C. de Laurentiz, R. da Silva Filardi, A. H. P. de Oliveira, M. L. A. Silva, and R. D. S. de Laurentiz. 2019. In vitro anthelmintic activity of the crude hydroalcoholic extract of Piper cubeba fruits and isolated natural products against gastrointestinal nematodes in sheep. Vet. Prasitol. 275:108932. doi:10.1016/j.vetpar.2019.108932.
   PubMed Web of Science ®Google Scholar
• Domingos, P. R. C., A. C. S. Pinto, J. M. M. Santos, and M. S. Rafael. 2014. Insecticidal and genotoxic potential of two semi-synthetic derivatives of dillapiole for the control of Aedes (Stegomyia) aegypti (Diptera: Culicidae). Mutat. Res. Genet. Toxicol. Environ. Mutagen. 772:42–54. doi:10.1016/j.mrgentox.2014.07.008.
   PubMed Web of Science ®Google Scholar
• Domingos, P. R. C., M. S. Rafael, W. P. Tadei, and A. C. S. Pinto. 2019. Composições compreendendo derivados de dilapiol e uso das composições (Patente). Patente BR n.102012033337-6. Titular: Instituto Nacional de Pesquisas da Amazônia.
   Google Scholar
• Dulout, F. N., O. A. Olivero, H. Von Guradze, and M. C. Pastori. 1982. Cytogenetic effect of malathion assessed by the micronucleus test. Mutat. Res. Lett. 105:413–16. doi:10.1016/0165-7992(82)90186-5.
   PubMedGoogle Scholar
• Ebeye, O. A., E. Emore, B. U. Enaibe, and P. S. Igbigbi. 2007. Histopathological effect of Piper guineese extract on Wistar rats. J. Biol. Sci. 7:1484–87. doi:10.3923/jbs.2007.1484.1487.
   Google Scholar
• Estrela, J. L. V., M. Fazolin, V. Catani, M. R. Alécio, and M. S. D. Lima. 2006. Toxicity of essential oils of Piper aduncum and Piper hispidinervum against Sitophilus zeamais. Pesquisa Agropecuária Brasileira 41:217–22. doi:10.1590/S0100-204X2006000200005.
   Web of Science ®Google Scholar
• Fazolin, M., J. L. V. Estrela, V. Catani, and C. R. Costa. 2006. Potencialidades da pimenta-de-macaco (Piper aduncum L.): Características gerais e resultados de pesquisa. Rio Branco: Embrapa- CPAF/AC.
   Google Scholar
• Fazolin, M., J. L. V. Estrela, V. Catani, and M. R. Alécio. 2007. Propriedade inseticida dos óleos essenciais de Piper hispidinervum C. DC.; Piper aduncum L. e Tanaecium nocturnum (Barb. Rodr.) Bur. and K. Shum sobre Tenebrio molitor L., 1758. Ciência E Agrotecnologia 31:113–20. doi:10.1590/S1413-70542007000100017.
   Google Scholar
• Gandhi, G., J. B. Chowdhury, P. K. Sareen, and V. P. S. Dhillon. 1995. Genotoxic effects of deltamethrin in the mouse bone marrow micronucleus assay. Mutat. Res. Lett. 346:203–06. doi:10.1016/0165-7992(95)90036-5.
   PubMed Web of Science ®Google Scholar
• Gratz, N. G. 2004. Critical review of the vector status of Aedes albopictus. Med. Vet. Entomol. 18:215–27. doi:10.1111/j.0269-283X.2004.00513.x.
   PubMed Web of Science ®Google Scholar
• Koul, O., S. Walia, and G. S. Dhaliwal. 2008. Essential oils as green pesticides: Potential and and constraints. Biopestic. Int. 4:63–84.
   Google Scholar
• Lima, J. B. P., M. P. Da-Cunha, R. C. D. S. Júnior, A. K. R. Galardo, S. D. S. Soares, I. A. Braga, and D. Valle. 2003. Resistance of Aedes aegypti to organophosphates in several municipalities in the state of Rio de Janeiro and Espirito Santo, Brazil. Am. J. Trop. Med. Hyg. 68:329–33. doi:10.4269/ajtmh.2003.68.329.
   PubMed Web of Science ®Google Scholar
• Lima, V. S., A. C. Pinto, and M. S. Rafael. 2015. Effect of isodillapiole on the expression of the insecticide resistance genes GSTE7 and CYP6N12 in Aedes aegypti from central Amazonia. Genet. Mol. Res. 14:16728–35. doi:10.4238/2015.December.11.20.
   PubMed Web of Science ®Google Scholar
• Macedo, A. L., D. P. da Silva, D. L. Moreira, L. N. de Queiroz, T. R. Vasconcelos, G. F. Araujo, and B. K. Robbs. 2019. Cytotoxicity and selectiveness of Brazilian Piper species towards oral carcinoma cells. Biomed. Pharmacother. 110:342–52. doi:10.1016/j.biopha.2018.11.129.
   PubMed Web of Science ®Google Scholar
• Maciel-de-Freitas, R., and D. Valle. 2014. Challenges encountered using standard vector control measures for dengue in Boa Vista, Brazil. Bulletin of the World Health Organization, 92:685–689. doi:10.2471/BLT.13.119081
   PubMed Web of Science ®Google Scholar
• Maroni, M., C. Colosio, A. Ferioli, and A. Fait. 2000. Biological monitoring of pesticide exposure: A review. Introduction. Toxicology 143:1–118. doi:10.1016/S0300-483X.(99).00152-3.
   PubMed Web of Science ®Google Scholar
• Meireles, S. F., P. R. C. Domingos, A. C. S. Pinto, and M. S. Rafael. 2016. Toxic effect and genotoxicity of the semisynthetic derivatives dillapiole ethyl ether and dillapiole n-butyl ether for control of Aedes albopictus (Diptera: Culicidae). Mutat. Res. Genet. Toxicol. Environ. Mutagen. 807:1–7. doi:10.1016/j.mrgentox.2016.07.003.
   PubMed Web of Science ®Google Scholar
• Mélo, M. E. B. D., K. D. C. Merlo, R. R. D. C. Fernandes, C. F. Luna, G. T. N. Diniz, M. T. J. D. A. Catanho, and L. Regis. 2008. Mutagenic effects of the organophosphate insecticide temephos on mice bone marrow cells. Revista Do Instituto Adolfo Lutz 67:196–201.
   Google Scholar
• Moyes, C. L., J. Vontas, A. J. Martins, L. C. Ng, S. Y. Koou, I. Dusfour, K. Raghavendra, J. Pinto, V. Corbel, J.-P. David, et al. 2017. Contemporary status of insecticide resistance in the major Aedes vectors of arboviruses infecting humans. PLoS Negl. Trop. Dis. 11. doi:10.1371/journal.pntd.0005625.
   PubMed Web of Science ®Google Scholar
• Mughal, A., A. Vikram, P. Ramarao, and G. B. Jena. 2010. Micronucleus and comet assay in the peripheral blood of juvenile rat: Establishment of assay feasibility, time of sampling and the induction of DNA damage. Mutat. Res. Genet. Toxicol. Environ. Mutagen. 700:86–94. doi:10.1016/j.mrgentox.2010.05.014.
   PubMed Web of Science ®Google Scholar
• Naik, B. R., G. S. Gowreeswari, Y. Singh, R. Satyavathi, S. S. Daravath, and P. R. Reddy. 2014. Bio-synthesis of silver nanoparticles from leaf extract of Pongamia pinnata as an effective larvicide on dengue vector Aedes albopictus (Skuse) (Diptera: Culicidae). Adv. Entomol. 2:93. doi:10.4236/ae.2014.22016.
   Google Scholar
• Niwa, A. M., N. A. de Paula, D. C. Vesenick, D. Sartori, E. L. Maistro, L. R. Ribeiro, and M. S. Mantovani. 2016. Evaluation of lignan (–)-cubebin extracted from Piper cubeba on human colon adenocarcinoma cells (HT29). J. Toxicol. Environ. Health A 79:92–100. doi:10.1080/15287394.2015.1110067.
   PubMed Web of Science ®Google Scholar
• Nobre, A. 1998. Instruções para o pessoal de Combate ao Vetor: Manual de Normas Técnicas. 2ª ed. Brasília, DF, Brasil: Ministério da Saúde. Secretaria Executiva. Plano Diretor de Erradicação do Aedes aegypti do Brasil, FUNASA.
   Google Scholar
• OECD. 2016a. Guidelines for the testing of chemicals – In vivo mammalian alkaline comet assay. Updated Test Guideline 489. Organization for Economic Co-operation and Development. Paris France.
   Google Scholar
• OECD. 2016b. Guidelines for the testing of chemicals – mammalian erythrocyte micronucleus test. Updated Test Guideline 474. Organization for Economic Co-operation and Development. Paris France.
   Google Scholar
• Omorodion, N. T., and W. O. Ajanwachuku. 2018. Investigation of histopathological effect of Piper nigrum consumption on selected organ of male Wistar rats. Acta Sci. Nutr. Health 2:03–07.
   Google Scholar
• Pavela, R. 2014. Limitação de biopesticidas vegetais. In Advances in biopesticides plant, D. Singh. ed., 347–59. Nova Deli: Springer.
   Google Scholar
• Pereira, B. B., E. S. Caixeta, P. C. Freitas, V. S. V. Santos, J. E. Limongi, E. O. De Campos Júnior, C. F. Campos, H. N. Souto, T. S. Rodrigues, and S. Morelli. 2016. Toxicological assessment of spinosad: Implications for integrated control of Aedes aegypti using larvicides and larvivorous fish. J. Toxicol. Environ. Health A 79:477–81. doi:10.1080/15287394.2016.1176974.
   PubMed Web of Science ®Google Scholar
• Pinto, A. C. S., K. L. Nogueira, F. C. M. Chaves, L. V. S. Silva, W. P. Tadei, and A. M. Pohlit. 2012. Adulticidal activity of dillapiol and semi-synthetic derivatives of dillapiol against Aedes aegypti (L.) (Culicidae). J. Mosq. Res. 2:1–7. doi:10.5376/jmr.2012.01.0001.
   Google Scholar
• Pohlit, A. M., A. C. S. Pinto, B. C. Cavalcanti, C. O. Pessoa, E. C. C. Silva, F. C. M. Chaves, K. L. Nogueira, L. V. C. Lotufo, L. F. R. Silva, M. R. S. Melo, et al. 2008. Adulticidal activity of dillapiol and semi-synthetic derivatives of dillapiol against Aedes aegypti. In Biopharmaceuticals synthesis, A. C. L. Guimarães. ed., 347–72. Edições UFC: Carioca JOB, organizer, Brazilian Network on Green Chemistry-Awareness, Responsability and Action, Fortaleza-CE.
   Google Scholar
• Rafael, M. S., W. J. Hereira-Rojas, J. J. Roper, S. M. Nunomura, and W. P. Tadei. 2008. Potential control of Aedes aegypti (Diptera: Culicidae) with Piper aduncum L. (Piperaceae) extracts demonstrated by chromosomal biomarkers and toxic effects on interphase nuclei. Genet. Mol. Res. 7:772–81. doi:10.4238/vol7-3gmr481.
   PubMed Web of Science ®Google Scholar
• Salvadori, D. M. F., L. R. Ribeiro, C. A. B. Pereira, and W. Beçak. 1988. Cytogenetic effects of malathion insecticide on somatic and germ cells of mice. Mutat. Res. Genet. Toxicol. 204:283–87. doi:10.1016/0165-1218(88)90101-2.
   PubMedGoogle Scholar
• Santana, H. T., F. T. T. Trindade, S. RG, A. A. E. Silva, J. S. T. L. Militão, and V. A. Facundo. 2015. Essential oils of leaves of Piper species display larvicidal activity against the dengue vector, Aedes aegypti (Diptera: Culicidae). Revista Brasileira De Plantas Medicinais 17:105–11. doi:10.1590/1983-084X/13_052.
   Google Scholar
• Scopel, W., E. L. Scopel, V. W. Botteon, and M. F. Roza-Gomes. 2018. Bioatividade de macerados de Anthemis sp., Coriandrum sativum e Piper nigrum contra Sitophilus zeamais (Coleoptera: Curculionidae). Evidência-Ciência E Biotecnologia 18:95–109. doi:10.18593/eba.v18i1.16872.
   Google Scholar
• Silva, M. 2020. Effects of low dose chlorpyrifos on neurobehavior and potential mechanisms: A review of studies in rodents, zebrafish, and Caenorhabditis elegans. Birth Defects Res. 112:445–79. doi:10.1002/bdr2.1661.
   PubMedGoogle Scholar
• Silva, W. C., J. D. Ribeiro, H. D. Souza, and R. D. S. Corrêa. 2007. Atividade inseticida de Piper aduncum L. (Piperaceae) sobre Aetalion sp. (Hemiptera: Aetalionidae), praga de importância econômica no Amazonas. Acta Amazonica 37:293–98. doi:10.1590/S0044-59672007000200017.
   Google Scholar
• Singh, N. P., M. T. McCoy, R. R. Tice, and E. L. Schneider. 1988. A simple technique for quantitation of low levels of DNA damage in individual cells. Exp. Cell Res. 175:184–91. doi:10.1016/0014-4827(88)90265-0.
   PubMed Web of Science ®Google Scholar
• Sousa, P. J. C., C. A. L. Barros, J. C. S. Rocha, D. S. Lira, G. M. Monteiro, and J. G. S. Maia. 2008. Avaliação toxicológica do óleo essencial de Piper aduncum L. Revista Brasileira De Farmacognosia 18:217–21. doi:10.1590/S0102-695X2008000200013.
   Google Scholar
• Sujatha, S. 2010. Essential oil and its insecticidal activity of medicinal aromatic plant Vetiveria zizanioides (L.) against the red flour beetle Tribolium castaneum (Herbst). Asian. J. Agr. Sci. 2:84–88.
   Google Scholar
• Tice, R. R., E. Agurell, D. Anderson, B. Burlinson, A. Hartmann, H. Kobayashi, Y. Miyamae, E. Rojas, J.-C. Ryu, and Y. F. Sasaki. 2000. Single cell gel/comet assay: Guidelines for in vitro and in vivo genetic toxicology testing. Environ. Mol. Mutagen. 35:206–21. doi:10.1002/(SICI)1098-2280(2000)35:3<206:AID-EM8>3.0.CO;2-J.
   PubMed Web of Science ®Google Scholar
• Tice, R. R., G. L. Erexson, C. J. Hilliard, J. L. Huston, R. M. Boehm, D. Gulati, and M. D. Shelby. 1990a. Effect of treatment protocol and sample time on the frequencies of micronucleated polychromatic erythrocytes in mouse bone marrow and peripheral blood. Mutagenesis 5:313–22. doi:10.1093/mutage/5.4.313.
   PubMed Web of Science ®Google Scholar
• Tice, R. R., G. L. Erexson, and M. D. Shelby. 1990b. The induction of micronucleated polychromatic erythrocytes in mice using single and multiple treatments. Mutat. Res. Environ. Mutagen. Relat. Subj. 234:187–93. doi:10.1016/0165-1161(90)90014-F.
   PubMed Web of Science ®Google Scholar
• Vieira Santos, V. S., E. S. Caixeta, E. O. D. Campos Júnior, and B. B. Pereira. 2017. Ecotoxicological effects of larvicide used in the control of Aedes aegypti on nontarget organisms: Redefining the use of pyriproxyfen. J. Toxicol. Environ. Health A 80:155–60. doi:10.1080/15287394.2016.1266721.
   PubMed Web of Science ®Google Scholar
• Vikram, A., D. N. Tripathi, A. A. Pawar, P. Ramarao, and G. B. Jena. 2008. Pre-bledyoung-rats in genotoxicity testing: A model for peripheral blood micronucleus assay. Regul. Toxicol. Pharmacol. 52:147–57. doi:10.1016/j.yrtph.2008.07.005.
   PubMed Web of Science ®Google Scholar
• Wang, J., G. Zhou, C. Chen, H. Yu, T. Wang, Y. Ma, and Y. Li. 2007. Toxicidade aguda e biodistribuição de partículas de dióxido de titânio de diferentes tamanhos em camundongos após administração oral. Cartas De Toxicologia 168:176–85.
   Google Scholar
• Wolansky, M. J., and R. Tornero-Velez. 2013. Critical consideration of the multiplicity of experimental and organismic determinants of pyrethroid neurotoxicity: A proof of concept. J. Toxicol. Environ. Health B 16:453–90. doi:10.1080/10937404.2013.853607.
   PubMed Web of Science ®Google Scholar
• Zámbó, V., L. Simon-Szabó, P. Szelényi, E. Kereszturi, G. Bánhegyi, and M. Csala. 2013. Lipotoxicidade no fígado. World J. Hepatol. 5:550. doi:10.4254/wjh.v5.i10.550.
   PubMedGoogle Scholar