Please use this identifier to cite or link to this item: https://rima.ufrrj.br/jspui/handle/20.500.14407/14565
Full metadata record
DC FieldValueLanguage
dc.contributor.authorRibeiro, Tatiana Santana
dc.date.accessioned2023-12-22T03:03:10Z-
dc.date.available2023-12-22T03:03:10Z-
dc.date.issued2004-06-29
dc.identifier.citationRibeiro, Tatiana Santana. Tranformações químicas no alcalóide natural piperina e avaliação tóxica sobre Trypanosoma cruzi. 2004. 139 f. Dissertação (Programa de Pós-Graduação em Química) - Universidade Federal Rural do Rio de Janeiro, Seropédica-RJ .por
dc.identifier.urihttps://rima.ufrrj.br/jspui/handle/20.500.14407/14565-
dc.description.abstractEste trabalho faz parte de uma linha de pesquisa que tem como principal objetivo a utilização de produtos naturais abundantes na síntese de moléculas com potencial aplicação como drogas antiparasitárias. Aqui encontram-se descritos os resultados obtidos na avaliação da atividade tripanocida do alcalóide natural piperina, isolada dos frutos secos de Piper nigrum, e outros 12 derivados sintéticos sobre formas epimastigotas e amastigotas do protozoário Trypanosoma cruzi, agente etiológico da grave e incurável doença de Chagas (Tripanossomíase Americana). A piperina foi testada freme a formas epimastigotas de T. cruzi, exibindo um efeito tóxico, dose-dependente, com valor de IC50 de 7,36 mM. Este resultado nos estimulou a preparar uma série de derivados, visando determinar os fatores presentes na estrutura da piperina, responsáveis pela atividade tripanocida exibida. Os resultados obtidos demonstram que o produto natural e seus derivados podem ser considerados como promissores compostos-protótipo para o desenvolvimento de uma nova família de drogas, fiteis na quimioterapia da doença de Chagas.por
dc.description.sponsorshipCoordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESpor
dc.formatapplication/pdf*
dc.languageporpor
dc.publisherUniversidade Federal Rural do Rio de Janeiropor
dc.rightsAcesso Abertopor
dc.subjectsíntese orgânicapor
dc.subjectPiperaceapor
dc.subjectdoença de chagaspor
dc.titleTranformações químicas no alcalóide natural piperina e avaliação tóxica sobre Trypanosoma cruzipor
dc.typeDissertaçãopor
dc.description.abstractOtherThis work is part of a research program aiming at the use of abundant natural products in the synthesis of new molecules with potential application as antiparasitic drugs. We describe herein an evaluation of trypanocida effects of the natural alkaloid piperine (isolated from Piper nigrum) and twelve synthetic derivatives against epimastigote and amastigote forms of the protozoan parasite Trypanosoma cruzi, the causative agent of the incurable human disease, Chagas' disease. Piperine was tested against T. cruzi epimastigotes showing a dose-dependent toxicity, with IC50 of 7.36 mM This preliminary result encouraged us to prepare a series of derivatives in order to determine the chemical features present in piperine responsible for the trypanocidal activity. The results obtained point to piperine and its derivatives as a suitable templates for the development of a new family of drugs with trypanocida activity.eng
dc.contributor.advisor1Lima, Marco Edilson Freire de
dc.contributor.advisor1Latteshttp://lattes.cnpq.br/8392420706762318por
dc.contributor.referee1Lima, Marco Edilson Freire de
dc.contributor.referee2Villar, José Daniel Figueroa
dc.contributor.referee3Echevarria, Áurea
dc.contributor.referee4Santa´Anna, Carlos Maurício Rabello
dc.creator.Latteshttp://lattes.cnpq.br/7952918513827867por
dc.publisher.countryBrasilpor
dc.publisher.departmentInstituto de Ciências Exataspor
dc.publisher.initialsUFRRJpor
dc.publisher.programPrograma de Pós-Graduação em Químicapor
dc.relation.referencesAGOSTA, W. C. Medicines and drugs from plants. J. Chem. Ed. 74: 857-860, 1997. AHN, J. W., AHN M. J., ZEE, O. P., KIM, E. J., LEE, S. G., KIM, H. J., KUBO, I. Piperidine alkaloids from Piper-retrofractum fruits. Phytochemistry 31(10): 3609- 12, 1992. ATAL, C. K., DUBEY, R.K., SINGH, J. Biochemical basis of enhanced drug bioavailability by piperine-evidence that piperine is a potent inhibitor of drugmetabolism. The J. Pharm. Exp. Therap. 232(1): 258-62, 1985. ATAL, C. K., ZUTSHI, U., RAO, P. G. Scientific evidence on the role of ayurvedic herbals on bioavailability of drugs. J. Ethnopharm. 4 (2): 229-232, 1981. ATAL, C. K., DHAR, K. L., SINGH, J. Chemistry of Indian Piper species. Loydia- the J. Nat. Prod. 38(3): 256-264, 1975. BANERJI, A & NANDI, G. Investigation of Piper-argyrophyllum miq-structure and synthesis of N-isobutyl-octadeca-2E, 4E-dienamide. Indian J. Chem. 27 (2): 163- 165, 1988. BANO, G., RAINA, R. K., ZUTSHI, U., BEDI, K. L., JOHRI, R. K., SHARMA, S. C. Effect of piperine on bioavailability and pharmacokinetics of propranolol and theophylline in healthy-volunteers. Eur. J. Clin. Pharm. 41 (6): 615-7, 1991. BARREIRO, E. J., FRAGA, C. A. M., ARAÚJO Jr., J. X. O uso de matérias-primas vegetais para a síntese de fármacos. In: Simões, C.M.O. (Ed.) et al., Farmacognosia: da planta ao medicamento, Florianópolis: Ed. Universidade/ Ed. da UFSC, p.123-142, 1999. BARRETO, L. M. & CARMO, E. H. Determinantes das condições de saúde e problemas prioritários no país. In: 11a Conferência Nacional de Saúde. Disponível no endereço: http:\\www.datasus.gov.br. BARRETO JÚNIOR, C. B. Estudos da síntese de dienamidas análogas à piperina e avaliação da atividade antiparasitária sobre Trypanosoma brucei. Monografia, UFRuralRJ, 2003. BHAT, B.G. & CHANDRASEKHARA, N. Interaction of piperina with rat-liver microsomes. Toxicology 44 (1): 91-8, 1987. BHAT, B.G. & CHANDRASEKHARA, N. Effect of black pepper and piperine on bile secretion and composition in rats. Toxicology 31 (9): 913-16, 1987. 132 BRENER, Z., & ANDRADE, Z. A. Trypanosoma cruzi e doença de Chagas. Guanabara Koogan, Rio de Janeiro , 1979. CHATAING, B., CONCEPCION, J. L., LOBATON, R., USUBILLAGA, A. Inhibition of Trypanosoma cruzi growth in vitro by Solanum alkaloids: a comparison with Ketoconazole. Planta Medica 64: 31-36, 1998. COUCEIRO, J. N. S. S., MARTINS-DA-SILVA, P., SANTOS, M. G. M., RIBEIRO, T. S., LIMA, M. E. F. Natural piperine as a new prototype of alternative antivirals against influenza. Vírus: Review & Research (trabalho submetido, 2004). COREY, E. J. & SCHMIDT, G. Useful procedures for the oxidation of alcohols involving pyridinium dichromate in aprotic media. Tetrahedron Lett. 5: 399-402, 1979. CORRÊA, A. G. Taxol: da descoberta ao uso terapêutico. Química Nova, 18: 460-67, 1995. COURA, J. R. & DE CASTRO, S. L. A Critical review on Chagas disease chemotherapy. Mem. Inst. Oswaldo Cruz, 97(1): 3-24, 2002. CRAGG, G. M., NEWMAN, D. J., SNADER, K. M. Natural products in drug discovery and development. J. Nat. Prod. 60 (1): 52-60, 1997. DAS, B. & MADHUSUDHAN Transformation of the conjugated dienamide system of some natural alkamides to the b,g-unsaturated amide function using Zn/HOAc. Tetrahedron Lett. 39: 9099-9100, 1998. DA CONCEIÇÃO, A. P. S. Piperina: Modificações Estruturais, Síntese de Análogos e Avaliação Citotóxica. Dissertação de Mestrado, UFRuralRJ, 1999. DA SILVA, E. F., CANTO-CAVALHEIRO, M. M., BRAZ, V. R., CYSNEFINKELSTEIN, L., LEON, L., ESCHEVARRIA, A. Synthesis, and biological evaluation of new 1,3,4-thiadiazolium-2-phenylamine derivatives against Leishmania amazonensis promastigotes and amastigotes. Eur. J. Med.Chem. 37: 979-984, 2002. DE ARAÚJO-JÚNIOR, J. X., DUARTE, C. M., CHAVES, M. C. O., PARENTE, J. P., FRAGA, C. A. M., BARREIRO, E. J. Synthesis of natural amide alkaloid piperdardine and a new bioactive analogue. Synth. Commun. 31 (1): 117-723, 2001. DE ARAÚJO-JÚNIOR, J. X., BARREIRO, E. J., PARENTE, J. P., FRAGA, C. A. M. Synthesis of piperamidas and new analogues from natural safrole. Synth. Commun. 29 (2): 263-273, 1999. 133 DE ARAÚJO-JÚNIOR, J. X., DA CUNHA, E. V. L., CHAVES, M. C. O., GRAY, A. I. Piperdardine, a piperidine alkaloid from Piper tuberculatum. Phytochemistry 44 (3): 559-561, 1997. DEMAIN, A. L. Pharmaceutically active secondary metabolites of microorganisms. Appl. Microb. Biotechn. 52 (4): 455-463, 1999. DENIS, J. N., GREENE, A. E., GUENARD, D., GUERITTEVOEGELEIN, F., MANGATAL, L., POTIER, P. A highly efficient, practical approach to natural Taxol. J. Am. Chem. Soc. 110 (17): 5917-5919, 1988. DE PAULA, V. F., BARBOSA, L. C. A., DEMUNER, A. J., VELOSO, D. P., PICANÇO, M. C. Synthesis and inseticidal activity of new amide derivatives of piperine. Pest Manag. Sci. 56 (2): 168-174, 2000. D’HOOGE, R., PEI, Y. Q., RAES, A., LEBRUM, P., VANBOGAERT, P. P., DE DEYN P. P. Anticonvulsant activity of piperine on seizures induced by excitatory amino acid receptor agonists. Arzneim. Forsch./Drug Res. 46 (6): 557-60, 1996. DIAS, J. C. P. Trypanosoma cruzi e Doença de Chagas. Epidemologia. In Z. Brener, Z. Andrade, M. Barral-Neto (eds), 2a ed., Guanabara Koogan, Rio de Janeiro, p.48- 74, 2000. DOGRA, R. K. S., KHANNA, S., SHANKER, R., Immunotoxicological effects of piperine in mice. Toxicology 196: 229-236, 2003. EPSTEIN, W., NETZ, D., SEIDEL, J. Isolation of piperine from black pepper. J. Chem. Educ. 70 (7): 598-99, 1993. FOURNET, A., INCHAUST, A., YALUFF, G., ROJAS, A. A., GUINADEAU, H., BRUNETON, J., BREIDENBACH, M. A., KARPLUS, P. A., FAERMAN, C. H. Trypanocidal bisbenzyllisoquinolina alkaloids are inhibitors of trypanothione reductase. J. Enzym. Inhib. 13: 1-9, 1998. GEISLER, J.G. & GROSS, G.G. The biosynthesis of piperine in Piper nigrum. Phytochemistry 29 (2): 489-92, 1990. GEISMAN ,T. A. & CROUT, D. H. G. Organic Chemistry of Secundary Plant Metabolism. Freenar Cooper, San Francisco, p.170, 1969. GHOSHAL, S., PRASAD, B. N. K., LAKSIMI, V. Antiamoebic activity of Piper longum fruits against Entamoeba histolytica in vitro and in vivo. J. Ethnopharm. 50 (3):167-70, 1996. 134 GOMES, D. C. F., ALEGRIO, L. V., FREIRE DE LIMA, M. E., LEON, L. L., ARAÚJO, C. A. C Synthetic derivatives of curcumin and their activity against Leishmania amazonensis. Arzneim. Forsch./Drug Res. 52 (2): 120-124, 2002a. GOMES, D. C. F., ALEGRIO, L. V., LEON, L. L., FREIRE DE LIMA, M. E. Total Synthesis and Anti-leishmanial activity of some curcumin analogues. Arzneim. Forsch./Drug Res. 52 (9): 695-698, 2002b. HARVEY, C. A. Colonization of agricultural windbreaks by forest trees: Effects of connectivity and remmant trees. Ecolog. Applic.10 (6): 1762-1773, 2000. HOLTON, R. A., KIM, H. B., SOMOZA, C., LIANG, F., BIEDIGER, R. J., BOATMAN, P. D., SHINDO, M., SMITH, C. C., KIM, S. C., NADIZADEH, H., SUZUKI, Y., TAO, C. L., VU, P., TANG, S. H., ZHANG, P. S., MURTHI, K. K., GENTILE, L. N., LIU, J. H. First total synthesis of Taxol .2. completion of the Cring and D-ring. J. Am. Chem. Soc. 116 (4): 1597-1598, 1994a. HOLTON, R. A., KIM, H. B., SOMOZA, C., LIANG, F., BIEDIGER, R. J., BOATMAN, P. D., SHINDO, M., SMITH, C. C., KIM, S. C., NADIZADEH, H., SUZUKI, Y., TAO, C. L., VU, P., TANG, S. H., ZHANG, P. S., MURTHI, K. K., GENTILE, L. N., LIU, J. H. First total synthesis of Taxol .1. functionalization of the B-ring. J. Am. Chem. Soc. 116 (4): 1599-1600, 1994b. HUDLICKÝ, M. Reductions in Organic Chemistry. John Wiley & Sons, New York, pp. 1-3, 1986. IKAN, R. In: Natural Products: A Laboratory Guide. Academic Press, 2nd Edition, pp. 233-238, 1991. JOHRI, R. K., THUSU, N., KHAJURIA, A., ZUTSHI, U. Piperine-mediated changes in the permeability of rat intestinal epithelial-cells-the status of gamma-glutamyl transpeptidase activity, uptake of amino-acids and lipid-peroxidation. Biochem. Pharmacol. 43 (7): 1401-7, 1992. KAPIL, A. Piperine: A potent inhibition of Leishmania donovani promastigotes in vitro. Planta Medica 59: 474, 1993. KOUL, S., KOUL, J. L., TANEJA, S. C., DHAR, K. L., JAMWAL, D. S., SINGH, K., RENN, R. R., SINGH, J. Struture-Activity relationship of piperine and its synthetic analogues for their inhibitory potentials of rat hepatic microsomal constitutive and inducible cytochrome P450 activities. J. Bioorg. Med. Chem. 8(1): 251-268, 2000. 135 KUSAMA, H., HARA, R., KAWAHARA, S., NISHIMORI, T., KASHIMA, H., NAKAMURA, N., MORIHIRA, K., KUWAJIMA, I. Enationselective total synthesis of (-)-taxol. J. Am. Chem. Soc. 122: 3811-3820, 2000. LEE, S. E., PARK, B. S., KIM, M. K., CHOI, W.S., KIM, H. T., CHO, K. Y., LEE, S. G., LEE, H. S. Fungicidal activity of pipernonaline, a piperidine alkaloid derived from long pepper, Piper longum L., against phytopathogenic fungi. Crop. Protec. 20: 523-528, 2001. LIN, Z. X., HOULT, J. R. S., BENNET, D. C., RAMAN, A. Stimulation of mouse melanocyte proliferation by Piper nigrum fruit extract and its main alkaloid, piperine. Planta medica 65: 600, 1999. LIU, L & SIMON A. S. Similarities and differences in the currentes activated by capsaicin, piperine, and zingerone in rat trigeminal ganglion cells. J. Neuroph. 76 (3): 1858-69, 1996. LIU, G. Q., ALGERI, S., CECI, A., GARATTINI, S., GOBBI, M., MURAI, S. Stimulation of serotonin synthesis in rat-brain after antiepilepsirine, na antiepileptic piperine derivative. Biochem. Pharmacol. 33 (23): 3883-86, 1984. MCLAFFERT, F. W. & TURECEK, F. Interpretation of Mass Spectra, 4thed., University Science Books, Mill Valley, CA, 1993. MADHYASTHA, M. S. & BHAT, R. V. Aspergillus-parasiticus growth and aflatoxin production on black and white pepper and the inhibitory-action of their chemicalconstituents. Appl. Environm. Microbiol. 48 (2): 376-9, 1984. MANN, J. Chemical Aspects of Biosynthesis. Oxford Science Publications, Oxford, pp. 51-58, 1994. MARCH, J. Advanced Organic Chemistry- Reactions, Mechanism and Struture. John Willey & Sons, 3rded., p.388, 1095,1099,1100,1101, 1985. MARTÍNEZ-DÍAZ, R. A., ESCARIO, J. A., NOGAL-RUIZ, J. J., GÓMES-BARRIO, Biological characterization of Trypanosoma cruzi strains. Mem. Inst. Oswaldo Cruz 96: 53, 2001. MARYANOFF, B. E. & REITZ, A. B. The wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspects. Chem. Rev. 89: 863, 1989. MORELLO, A., LIPCHENCA, I., CASSELS, B. K., SPEISKY, H., ALDUNATE, J., REPETTO, Y. Trypanocidal effect of boldine and related alkaloids upon several strains of Trypanosoma cruzi. Comp. Biochem. Physiol. C. Pharmacol. Toxicol. Endocrinol.107: 367-371, 1994. NEAL, R. A. & BUEREN, J. Comparative studies of drug susceptibility of 5 strains of Trypanosoma cruzi in vivo and in vitro. J. Trans. R. Soc. Trop. Med. Hyg. 82: 709, 1988. NICOLAOU, K. C., YANG, Z., LIU, J. J., UENO, H., NANTERMET, P. G., GUY, R. K., CLALBORNE, C. F., RENAUD, J., COULADOUROS, E. A., PAULVANNAN, K., SORENSEN, E. Total síntesis of Taxol. Nature 367: 630- 34, 1994. Para maiores detalhes sobre a produção brasileira de pimenta-do-reino veja: [http :\\www.brazilblackpepper.adm.br] PARK, I. K., LEE, S. G., SHIN, C. S., PARK, J. D., AHN, Y. J. Larvicidal activity of isobutylamides identified in Piper nigrum fruits against three mosquito species. J. Agric. Food Chem. 50: 1866-1870, 2002. PARMAR, V. S., JAIN, S. C., BISHT, K. S., JAIN, R., TANEJA, P., JHA, A., TYAGI, O. D., PRASAD, A. K., WENGEL, J., OLSEN, C. E., BOLL, P. M. Phytochemistry of the genus Piper. Phytochemistry 46 (4): 597-673, 1997. PARMAR, V. S., JAIN, S. C., GUPTA, S., TALWAR, S., RAJWANSHI, V. K., KUMAR, R., AZIM, A., MALHOTRA, S., KUMAR, N., JAIN, R., SHARMA, N. K., TYAGI, O. D., LAWRIE, S. J., ERRINGTON, W., HOWART, O. W., OLSEN, C. E., SINGH, S. K., WENGEL, J. Polyphenols and alkaloids from Piper species. Phytochemistry 49(4): 1069-1078, 1998. PERRIN, D. D., ARMAREGO, W. L. F., PERRIN, D. R. Purification of laboratory chemicals. Pergamon Press, 1966. PETSKO, G. A. For medicinal purposes. Nature 384 (6604): 7-9, 1996. PIYACHATURAWAT, P., GINSUKON, T., TORKULKAS, C. Acute and sub ascute toxicity of piperine in mice, rats and hamsters. Toxicol. Lett. 16: 351-359, 1983. RAAY, B., MEDDA, S., MUKHOPADHYAY, S., BASU, M. K. Targetin of piperine intercalated in mannose-coated liposomes in experimental leishmaniasis. Indian J. Biochem. Bioph. 36 (4): 248-251, 1999. RAMAN, G. & GAIKAR, V. G. Microwave-assisted extraction of piperine from Piper nigrum. Ind. End. Chem. Res. 41: 2521-2528, 2002a. 137 RAMAN, G. & GAIKAR, V. G. Extraction of piperine from Piper nigrum (black pepper) by hydrotropic solubilization. Ind. End. Chem. Res. 41: 2966-2976, 2002b. RANU, B. C. & SAMANTA, S. Remarkably selective reduction of the a? b-carboncarbon double bond in highly activated a,b,g,d-unsaturated alkenes by the InCl 3- NaBH4 reagent system. J. Organic. Chem. 68: 7130-7132, 2003. REEN, R. K.,WIEBEL, F. J., SINGH, J. Piperine inhibits aflatoxin B-1-induced cytotoxity and genotoxicity in V79 Chinese hamster cells genetically engineered to express rat cytochrome P4502B1. J. Ethnopharm. 58 (3): 165-73, 1997. REEN, R. K., JAMWAL, D. S., TANEJA, S. C., KOUL, J. L., DUBEY, R. K., WIEBEL, F. J., SINGH, J. Impairment of UDP-glucose dehydrogenase and glucuronidation activities in liver and small-intestine of rat and guinea-pig in vitro by piperine. Biochem. Pharmacol. 46 (2): 229-38, 1993. SCHENKEL, E. P., GOSMANN, G., PETROVICK, P. R. Farmacognosia: da planta ao medicamento. In: Simões, C.M.O. et al. (Ed.), Florianópolis: Ed. Universidade/Ed. Da UFSC, p.291, 1999. SCHMUNIS, G. A. A tripanosomíase americana e seu impacto na saúde pública das Américas. In: BRENER, Z., ANDRADE, Z. A., BARRAL-NETO, M. (eds). Trypanosoma cruzi e Doença de Chagas. Rio de Janeiro: Guanabara Koogan, 2a ed. Cap. 1, 2000. SCOTT, W. P. & MCKIBBEN, G. H. Toxicity of black pepper extract to boll weevils. J. Econ. Entomol. 71(2): 343-44, 1978. SEMLER, U. & GROSS, G. G. Distribution of piperine in vegetative parts of Piper nigrum. Phytochemistry 27 (5): 1566-1567, 1988. SMITH, M. B. Organic Synthesis. Mc Graw Hill, second edition, pp. 287, 2001. SHOBA, G., JOY, D., THANGAM, J. MAJEED, M., RAGENDRAN, R., SRINIVAS, P. S. S. R. Influence of piperine on the pharmacokinetics of curcumin in animals and human volunteers. Planta Medica 64 (4): 353-6, 1998. SU, H. C. F. & HORVAT, R. Isolation, identification, and inseticidal properties of Piper nigrum amides. J. Agric. Food Chem. 29 (1): 115-8, 1981. SU, H. C. F. Insecticidal properties of black pepper to rice weevils and cowpea weevils. J. Econom. Entomol. 70 (1): 18-21, 1977. SUNILA, E. S. & KUTTAN, G. Immunomodulatory and antitumor activity of Piper longum Linn. and piperine. J. Ethnopharm. 90: 339-346, 2004. 138 TAKAKI, M., JIN, J. G., LU, Y. F., NAKAYAMA, S. Effects of piperine on the motility of the isolated guinea-pig ileum-comparison with capsaicin. Europ. J. Pharmacol. 186: 71-7, 1990. TROUILLER, P., REY, J. L., BOUSCHARAIN, P. Pharmaceutical development concerning diseases predominating in tropical regions: The concept of indigent drugs. Ann. Pharm. Fr. 58: 43-46, 2000. VENKATASAMY, R., FAAS, L., YOUNG, A. R., RAMAN, A., HIDER, R. C. Effects of piperine analogues on stimulation of melanocyte proliferation and melanocyte differentiation. Bioorg. Med. Chem. 12: 1-16, 2004. VOGEL, A. I. TextBook of Proctical Organic Chemistry, fifth edition, editora Longman, p.445, 1989. WIECHERT, R. Routes to new drugs. L’actualité Chimique Mai-Jun: 221-226, 1992.por
dc.subject.cnpqQuímicapor
dc.thumbnail.urlhttps://tede.ufrrj.br/retrieve/63275/2004%20-%20Tatiana%20Santana%20Ribeiro.pdf.jpg*
dc.originais.urihttps://tede.ufrrj.br/jspui/handle/jspui/4217
dc.originais.provenanceSubmitted by Celso Magalhaes (celsomagalhaes@ufrrj.br) on 2020-11-27T16:35:05Z No. of bitstreams: 1 2004 - Tatiana Santana Ribeiro.pdf: 6269169 bytes, checksum: cd8d8ee0f8462373e3712bc08fe3ae42 (MD5)eng
dc.originais.provenanceMade available in DSpace on 2020-11-27T16:35:05Z (GMT). No. of bitstreams: 1 2004 - Tatiana Santana Ribeiro.pdf: 6269169 bytes, checksum: cd8d8ee0f8462373e3712bc08fe3ae42 (MD5) Previous issue date: 2004-06-29eng
Appears in Collections:Mestrado em Química

Se for cadastrado no RIMA, poderá receber informações por email.
Se ainda não tem uma conta, cadastre-se aqui!

Files in This Item:
File Description SizeFormat 
2004 - Tatiana Santana Ribeiro.pdfTatiana Santana Ribeiro6.12 MBAdobe PDFThumbnail
View/Open


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.