Submitted by Sandra Pereira (srpereira@ufrrj.br) on 2016-08-01T17:07:57Z
No. of bitstreams: 1
2011 - Juliana Mariano Torres.pdf: 1156662 bytes, checksum: 6ae713d0002e13c804fc2eba73bd8f5b (MD5) / Made available in DSpace on 2016-08-01T17:07:57Z (GMT). No. of bitstreams: 1
2011 - Juliana Mariano Torres.pdf: 1156662 bytes, checksum: 6ae713d0002e13c804fc2eba73bd8f5b (MD5)
Previous issue date: 2011-07-22 / Conselho Nacional de Desenvolvimento Cient?fico e Tecnol?gico, CNPq. / The increase in life expectancy is a worldwide occurrence that shows the relative
success of public health politics, and Brazil is among the countries where people are
living longer and in better physical health. But the increase in life expectancy has a
negative effect: the appearance of degenerative diseases typical of old age, including
several forms of dementia, like Alzheimer?s Disease (AD) that is certainly the most
important. It is an irreversible and progressive disease characterized by neuronal
deterioration that results in loss of cognitive functions such as memory, communication
skills, judgment and reasoning. Donepezil, rivastigmine and galantamine are medicines
used for the treatment of AD and act reversibly inhibiting the acetylcholinesterase
(AChE). Evidences suggest that the enzyme butyrylcholinesterase (BChE), closely
related to AChE, plays a significant role in AD because it is involved in neural
functions such as cholinergic co-regulation and non-cholinergic neurotransmission. The
aim of this research is to provide new substances with anticholinesterase action by using
?-carboline derivatives from the natural product harmane and carry out a kinetic study
to determine the inhibition profile of the enzymes AChE e BChE, which could help in
the discovery of new compounds which could be useful in the treatment of AD. Firstly,
a screening was carried out with seven ?-carboline derivatives. In a second stage, a
kinetic investigation, employing Ellman?s method, was run with these compounds and
all of them presented high anticholinesterase action for both AChE and BChE. All
seven derivatives presented a non-competitive reversible inhibition. / Torres, Juliana Mariano. ESTUDO CIN?TICO DA ATIVIDADE
ANTICOLINESTER?SICA DE DERIVADOS -CARBOL?NICOS DO
PRODUTO NATURAL HARMANA. 2011. Disserta??o (mestrado em Qu?mica
Org?nica). Instituto de Ci?ncias Exatas, Departamento de Qu?mica, Universidade
Federal Rural do Rio de Janeiro, Serop?dica, RJ, 2011.
O aumento da expectativa de vida ? um fen?meno mundial que mostra o relativo
sucesso de pol?ticas de sa?de p?blica, e o Brasil se inclui entre os pa?ses em que as
pessoas est?o vivendo por mais tempo e em condi??es melhores de sa?de. No entanto, o
aumento da expectativa de vida tem como efeito negativo o aparecimento de doen?as
degenerativas, t?picas de idades mais avan?adas, incluindo-se as v?rias formas de
dem?ncia e entre estas, a mais importante ?, sem d?vida, a Doen?a de Alzheimer (DA),
patologia irrevers?vel e progressiva caracterizada pela deteriora??o neuronal que resulta
em perda de fun??es cognitivas, tais como mem?ria, capacidade de comunica??o,
julgamento e racioc?nio. Para o tratamento da DA s?o utilizados f?rmacos como o
donepezil, galantamina e rivastigmina, os quais agem inibindo revers?velmente a
acetilcolinesterase (AChE). Evid?ncias sugerem que a enzima butirilcolinesterase
(BChE), intimamente relacionada com a AChE, tem um papel significante na DA, uma
vez que est? envolvida em fun??es neurais tais como a corregula??o da
neurotransmiss?o colin?rgica e n?o-colin?rgica. Esta pesquisa pretendeu estudar novas
subst?ncias com a??o anticolinester?sica utilizando derivados -carbol?nicos do produto
natural harmana, bem como fazer um estudo cin?tico a fim de descobrir qual o perfil de
inibi??o das enzimas AChE e BChE, a fim de buscar novos compostos que poderiam ser
?teis no tratamento dos sintomas da DA. Desta forma, foi efetuada preliminarmente
uma triagem com 7 derivados -carbol?nicos e posteriormente foi realizada uma
investiga??o cin?tica com estes compostos, uma vez que, todos apresentaram alta a??o
anticolinester?sica tanto para AChE quanto para BChE. A cin?tica enzim?tica foi
estudada segundo o m?todo de Ellman. Contudo, observou-se que todos os 7 derivados
apresentaram uma inibi??o revers?vel n?o competitiva.
| Identifer | oai:union.ndltd.org:IBICT/oai:localhost:jspui/1144 |
| Date | 22 July 2011 |
| Creators | Torres, Juliana Mariano |
| Contributors | Rumjanek, Victor marcos, Kummerle, Arthur Eugen |
| Publisher | Universidade Federal Rural do Rio de Janeiro, Programa de P?s-Gradua??o em Qu?mica, UFRRJ, Brasil, Instituto de Ci?ncias Exatas |
| Source Sets | IBICT Brazilian ETDs |
| Language | Portuguese |
| Detected Language | English |
| Type | info:eu-repo/semantics/publishedVersion, info:eu-repo/semantics/masterThesis |
| Format | application/pdf |
| Source | reponame:Biblioteca Digital de Teses e Dissertações da UFRRJ, instname:Universidade Federal Rural do Rio de Janeiro, instacron:UFRRJ |
| Rights | info:eu-repo/semantics/openAccess |
| Relation | 7 - REFER?NCIAS AIRAKSINEN, M. M.; KARI, I. Beta-carbolines, psychoactive compounds in the mammalian body 2 effects. Medical Biology. v. 59, pp. 190-211, 1981. AFSAH, E. M.; HAMMOUDA, M.; HAMAMA W. S. Pictet-Spengler reactions of Tryptamine and tryptophan with cycloalkanones and ketonicMannich bases. Monarshefte f?r Chemie. V. 116, pp. 851-855, 1985. BARBOSA-FILHO, J.M.; MEDEIROS, K. C. P.; DINIZ, M. F. F. M.; BATISTA, L. M.; ATHAYDE-FILHO, P. F.; SILVA, M. S.; DA CUNHA, E. V. L.; ALMEIDA, J. R. G. S.; QUINTANS-JUNIOR, L. J. Natural Protucts inhibitiors of the enzyme acetylcholinesterase. Revista Brasileira de Farmacognosia. v.16, n. 2, pp. 258-285, 2006. BAYNES, J. W. Bioqu?mica m?dica. Tradu??o da 2? Edi??o. Rio de Janeiro: Mosby Elesevier, 1991. ISBN: 978-85-352-2298-2. BECHER, P. G.; BEUCHAT, J.; GADEMANN, K.; J?TTNER, F. Nostocarboline: Isolation and Synthesis of a New Cholinesterase Inhibitor from Nostoc 78-12A. J. Nat. Prod. v. 68, pp. 1793-1795, 2005. BERG, J. M.; TYMOCZKO, J. L.; STRVER, L. Bioqu?mica. 6? Edi??o. Guanabara Koogan, 2008. ISBN: 8527713691. BIRKS, J.; HARVEY, R. J. Donepezil for dementia due to Alzheimer's disease. Cochrane Database of Systematic Reviews. (1), CD001190, 2006. BISSWANGER, H. Enzimes Kinetics. Principles and methods. 2?Edi??o; WILEYVCH; VERLAG GMBH & CO.KGA, 2008. ISBN: 978-3-527-31957-2 BONNET, U.; SCHERBAUM, N.; WIEMANN, M. The endogenous alkaloid harmane: Acidifying and activity-reducing effects on hippocampal neurons in vitro. Progress in neuro-Psychopharmacology & Biological Psychiatry. v. 32, pp. 362-367, 2008. 67 BOURNE, Y.; RADIC , Z.; KOLB, H. C.; SHARPLESS, K. B.; MARCHOT, P. Structural insights into conformational flexibility at the peripheral site and within the active center gorge of AChE. Chemico-Biological Interactions. v. 157, pp. 159-165, 2005. BUCKHOLTZ, N. S. Neurobiology of tetrahydro-beta-carbolines. Life Sciences. v. 27, pp. 893-903, 1980. BUTLER, M. S. The role of natural product chemistry in drug discovery. Journal of Natural Products. v. 67, pp. 2141-2153, 2004. CACABELOS, R.; TAKEDA, M.; WINBLAD, B. The glutamatergic system and neurodegeneration in dementia: preventive strategies in Alzheimers disease. International Journal of Geriatric Psychiatry. v. 14, pp. 3-47, 1999. CALLAWAY, J. C.; GYNTHER, J.; POSO, A.; VEPSALAINEM, J.; AIRALKSINEM, M. M. J. Journal of Heterocyclic Chmistry. v. 31, pp, 431-435, 1994. CAMPOS, L.S. Entender a Bioqu?mica. 2? Edi??o. Lisboa: Escolar Editora, 1999. ISBN: 972-592-108-9. CANEPA, F. G; PAULING, P.; SORUM, H. Structure of acetylcholine and other substrates of cholinergic systems. Nature. v. 210, pp. 907- &, 1966. CARAMELLI, P.; CHAVES, M. L. F.; Engelhardt E, et al. Effects of galantamine on attention and memory in Alzheimers disease measured by computerized neuropsychological tests: results of the Brasilian Multi-Center galantamine study (GALBRA- 01). Arquivos de Neuro-Psiquiatria. v. 62, pp. 379-384, 2004. CASS, H. Herbs for the nervous system: Ginkgo, Kava, Valerian, Passionflower. Seminars in Integrative Medicine. v. 2, pp. 82-88, 2004. 68 CASTRO, A. T. Estudo por modelagem molecular da reativa??o da acetilcolinesterase inibida por agentes qu?micos neurol?gicos. 121 f. Disserta??o (mestrado em ?rea envolvida) ? IME, Rio de Janeiro, 2002. CHATONNET, A.; LOCKRIDGE, O. Comparison of butyrylcholinesterase and acetylcholinesterase. The Biochemical Journal. Londres, v.260, n.3, pp. 625-634, 1989. CHENG, Y. & PRUSOFF, W. H. Relationship between the inhibition constant (KI) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem. Pharmacol. v. 22, pp. 3099?3108, 1973. CRI - CENTO DE REFER?NCIA DO IDOSO DO HC/UFMG. Dados coletados com base nas informa??es do DATASUS (Sistema de Informa??es Ambulatoriais do SUS - (SAI/SUS), e pela Ger?ncia de Medicamentos Excepcionais (Superintend?ncia de Assist?ncia Farmac?utica/SES/MG), 2008. DALE, M. C.; LEBRETTO, S. E.; PATTERSON, C.; ANDERSON, J.; CHOUDHURY, T.; MCCAFFERTY, F.; MCWILLIAM, C.; RICHARDSON, M. Clinical experience of galantamine in dementia: A series of case reports. Current Medical Research and Opinion. v. 19, pp. 508-518, 2003. DESCARRIES, L.; LISIGER, V.; STERIADE M. Diffuse transmission by acetylcholine in the CNS. Progress in Neurobiology. v. 53, pp. 603-625, 1997. DEVLIN, M. T. Manual de Bioqu?mica com Correla??es Cl?nicas. Tradu??o da 6? Edi??o. Bl?cher, 2007. ISBN: 9788521204060. DEWICK, P. M. The biosynthesis of C-5-C-25 terpenoid compounds. Natural Product Reports. v. 19, pp. 181-122, 2002. DOWNEY, D. Pharmacologic management of Alzheimer Diseases. Journal of Neuroscience Nursing. v. 40, n.1, pp. 55-59, 2008. 69 EKHOLM, M. Predicting relative binding free energies of substrate and inhibitors of acetylcholin- and butyrylcholinesterases. Journal of Molucular Structure-Theochem. v. 572, pp. 25-34, 2001. ELHANANY, E.; ORDENTLICH, A.; DGANY, O.; KAPLAN, D.; SEGALL,Y.; BARAK, R.; VELLAN, B.; SHAFFERMAN, A. Resolving pathways of interaction of covalent inhibitors with the active site of acetylcholinesterases: MALDI-TOF/MS analysis of various nerve agent phosphyl adducts. Chemical Research in Toxicology. v. 14, pp. 912-918, 2001. ELISABETSKY, E.; COSTA-CAMPOS, L. The alkaloid alstonine: a review of its pharmacological properties. Evidence based complementary and alternative medicine. v. 3, pp. 39-48, 2006. ELLMAN. GL; COURTNEY. KD; ANDRES. V. JR; FEATHERSTONE. RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochemical Pharmacology. v.7, pp. 88-95, 1961. EVANS, F. J. Natural products as probes for new drug target identification. Journal of Ethnopharmacology. v. 32, PP. 91-101, 1991. FAN, P.; HAY, A.; MARSTON, A.; HOSTETTMANN, K., Acetycholinesterase- Inhibitory Acivity of Linarin from Buddleja davidii, Structure-Activity Relationships of Related Flavonoids, and Chemical Investigation of Buddeja nitida. Pharmaceutical Biology, v. 46, pp. 596-601, 2008. FARLOW, M. R. Effective pharmacologic management of Alzheimer?s disease. American Journal of Medicine. v. 120, pp. 388-397, 2007. FARZIN, D.; MANSOURI, N. Antidepressant-like effect of harmane and other - carbolines in the mouse forced swim test. European Neuropsychopharmalogy. v. 16, pp, 324-328, 2006. 70 FRAGA, A. S. Acetilcolinesterase, butirilcolinesterase, carboxilesterase e a resist?ncia de peixes neotropicais aos pesticiadas organofosforados. Rio de Janeiro, 2010. Tese (Doutorado em bioci?ncias). Universidade do Estado do Rio de Janeiro. Rio de Janeiro, 2010. FRANCIS, P. T.; PALMER, A. M.; SNAPE, M.; WILCOCK, G. K. J. The cholinergic hypothesis of Alzheimer's disease: a review of progress. Journal of Neurology Neurosurgery and Psychiatry. v. 66, pp. 137-147, 1999. FREITAS, E. V.; et al. Tratado de Geriatria e Gerontologia. Guanabara Koogan, 2002. GEISSLER, T.; BRANDT, W.; PORZEL, A.; SCHLESNZIG, D.; KEHLEN, A.; WESSJOHANN, L.; ARNOLD, N. Acetylcholinesterase inhibitors from the toadstool Cortinarius infractus. Bioorganic & Medicinal Chemistry. v. 18, pp. 2173-2177, 2010. GHOSAL, S.; BHATTACH, S. K.; MEHTA, R. Naturally occurring and synthetic betacarbolines as cholinesterase inhibitors. Journal of Pharmaceutical Sciences. v. 61, (5), pp. 808, 1972. GIACOBINE, E. In: Giacobin, E. (ed.), Cholinesterases and cholinesterase inhibitors. pp. 181-226, 2000. GLENNON, R. A.; DUKAT, M.; GRELLA, B. Binding of -carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug and alcohol dependence. v. 60, pp. 121-132, 2000. GOTTI, C.; CLEMENT, F. Neuronal nicotinic recptors: from estructure to pathology. Progress in Neurobiology. v. 74, pp. 363-396, 2004. GREIG, N. H.; UTSUKI, T.; INGRAM, D. K. Selective butyrylcholinesterase inhibition elevates brain acetylcholine, augments learning and lowers Alzheimer beta-amyloid 71 peptide in rodent. Proceedings of the national academy of sciences of the united states of America. v. 102, pp. 17413-17418, 2005. GRELLA, B.; DUKAT, M.; YOUNG, R.; TEITLER, M.; DEIVIS, K. H.; GAUTHIER, C. B.; GLENNON, R. A. Investigation of hallucinogenic and related -carbolines. Drug and Alcohol Dependence. v. 50, pp. 99-107, 1998. HAASS, C.; SCHLOSSMACHER, M. G.; HUNG, A. Y.; VIGO, C. P.; MELLON, A.; OSTASZEWSKI, B. L.; LIEBERBURG, I.; KOO, E. H.; SCHENK, D.; TEPLOW, D. B.; SELKOE, D. J. Amyloid -peptide is produced by cultured cells during normal metabolism. Nature. V. 359, pp. 322-325, 1992. HAMANN, J.; WERNICKE, C.; LEHMANN, J. 9-Methyl- -carboline up-regulates the appearance of differentiated dopaminergic neurones in primary mesencephalic culture. Neurochemistry International. v. 52, pp. 688-700, 2008. HARDIMAN, J.; CARREL, H. L.; ZACHARIAS, D. E.; GLUSKER, J. P. The structure of harman, a comutagen. Bioorganic Chemistry. v.15, pp. 127-132, 1987. HARDY, J.; ALLSOP, D. Amyloid deposition as the central event in the aetiology of Alzheimer's disease. Trends in Pharmacological Sciences, v.12, pp. 383-388, 1991. HARTMANN, J.; KIEWERT, C.; DUYSEN, E. G. Excessive hippocampal acetylcholine levels in acetylcholinesterase-deficient mice are moderated by butyrylcholinesterase activity. Journal of Neurochemistry. v. 100, pp. 1421-1429, 2007. HEMMATEENEJAD, B.; ABBASPOUR, A.; MAGHAMI, H. Partial least squaresbased multivariate spectral calibration method for simultaneous determination of betacarboline derivatives in Peganum harmala seed extracts. Analytica Chimica Acta. v. 575, pp. 290-299, 2006. HENRIQUES, A. T.; KERBER, V. A.; MORENO, P. R. H. Alcal?ides: Generalidades e aspectos b?sicos. In: Sim?es, C. M. O. et al., Farmacognosia. Da planta ao 72 medicamento. 1? Edi??o. Ed. Universidade/UFRGS. Ed. UFSC. Porto Alegre/ Florian?polis, 1999. HERRAIZ, T.; GALISTEO, O. J.; CHAPARRO, R. C. Preparation of beta-carboline compounds, useful as inhibitors of monoamino-oxidase for treating e.g. depression, comprises enzymatic oxidation of natural tetrahydro precursors. Consejo Superior Investigaciones Cientif. Patent: ES2278534-A1; WO2007085679-A1; ES2278534-B1, 2008. HERRAIZ, T.; CHAPARRO, R. C. Human monoamine oxidase enzyme inhibition by coffee and -carbolines norharman and harman isolated from coffee. Life Sciences. v. 78, pp. 795-802, 2006. HUSBANDS, S. M.; GLENNON, R. A.; GORGERAT, S.; GOUGH, R.; TYACKE, R.; CROSBY, J.; NUTT, D. J.; LEWIS, J. W.; HUDSON, A. L. Beta-carboline binding to imidazoline receptors. Drug Alcohol Dependence. v. 64, pp. 203-208, 2001. ISHIDA, J.; WANG, H. K.; OYAMA, M.; COSENTINO, M. L.; HU, C. Q.; LEE, K. H. Anti-AIDS agents. 46. Anti-HIV activity of harman, an anti-HIV principle from Symplocos setchuensis, and its derivatives. Journal of Natural Products. v. 64, pp. 958-960, 2001. KATALINIC, M.; KUSAK, G.; DOMACINOVIC, J.; SINKO, G.; JELIC, D.; ANTOLOVIC, R.; DOVARIK, Z. Strutuctural aspects of flavonoids as inhibitors of human butyrylcholinesterase. European Journal of Medicinal Chemistry, v. 45, pp. 186-192, 2010. KAWASHIMA, K.; FUJII, T. The lymphocytic cholinergic system and its contribution to the regulation of immune activity. Life Sciences. v. 74, pp. 675- 696, 2003. KUSURKAR, R. S.; GOSWAMI, S. K.; VYAS, S.M. Corrigendum to: Efficient one-pot synthesis of anti HIV and antitumor compounds: harman and substituted harmans. Tetrahedron Letters. v. 44, pp. 4761-4763, 2003. 73 KUSURKAR, R. S.; GOSWAMI, S. K. Efficient one-pot synthesis of anti-HIV and antitumour -carbolines. Tetrahedron. v. 60, pp. 5315-5318, 2004. LANCT?T, K. L., HERRMANN, N., YAU, K. K., KHAN, L. R.; LIU, B. A.; LOULOU, M. M.; EINARSON, T. R. Efficasy and safety of cholinesterase inhibitors in alzheimer?s diseases: a meta analysis. Canadian Medical Association or its Licensors. v. 169, pp. 557-564, 2003. LEVIN, E. D., SIMON, B. B. Nicotinic acetylcholine involvement in cognitive function in animals. Psychopharmacology. v. 138, pp. 217-230, 1998. LIEBERMAN, S. L. Morphine with pentothal anesthesia. Jama-Journal of the American Medical Association. v. 127, pp. 1147-1147, 1945. LINEWEAVER, H. BURK, D. The determination of enzyme dissociation constants. J. Amer. Chem. Soc. v. 56, pp. 658-666; 1934. LUTOMSK, J. Qualitative and quantitative chromatografhyc investigation of alkaloids of Passiflora incarnata. Biul. Inst. Roslin Leczniczych. v. 5, pp. 181-198, 1959. MARUM, R. J.V. Current and future theraphy in alzheimer?s disease. Fundamental & Clinical Pharmacology. v. 22, pp. 265-274, 2008. MASSOULI?, J.; PEZZEMENTE, L.; BON, S.; KREJCI, S.; VALLETTE, F. M. Molecular and cellular biology of cholinesterases. Progress in Neurobiology. v. 41, pp. 31-91, 1993. MESULAM, M.M.; GUILLOZET, A. ; SHAW, P. Acetylcholinesterase knockouts establish central cholinergic pathways and can use butyrylcholinesterase to hydrolyze acetylcholine. Neuroscience. v. 110, pp. 627-639, 2002. MICHAELIS. L.; MENTEN. M. L. Die Kinetik der Invertinwirkung. Biochemische Zeitschrift. v. 49, pp. 333-369, 1913. 74 MIKAMI, L. R. Variabiliadade dos Exons 2 e 4 do gene BChE e sua rela??o com a atividade da butirilcolinesterase. Curitiva, 2005. Tese (Doutorado em ci?ncias biol?gicas) ? ?rea de gen?tica. Universidade Federal do Paran?. Curitiba, 2005. MILLARD, C.B.; BROOMFIELD. C.A. A computer model of glycosylated human butyrylcholinesterase. Biochemical and Biophysical Research Communications. San Diego, v. 189, p. 1280-1286, 1992. M?LLER. E. E. A FAMILY WITH ALZHEIMER'S DISEASE. Acta Psychiatrica Scandinavica. v. 21, pp. 233-244, 1946. MOURA, D. J.; RORIG, C.; VIEIRA, D. L. Effects of beta-carboline alkaloids on the object recognition task in mice. Life Sciences. v. 79, pp. 2099-2014, 2006. M?US?, P.K.; MARTTILA, R. J.; RINNE, U. K. Survival and cause of death in Alzheimer's disease and multi-infarct dementia. Acta Neurologica Scandinavica. v. 74, n. 2, pp. 103-107, 1986. MUDHER, A.; LOVESTONE, S. Alzheimer?s disease ? do tauists and baptists finally shake hands? Trends in Neurosciences. v. 25, n. 1, pp. 22-25, 2002. NACHMANSOHN, D.; ROTHENBERG, M. A. Studies on cholinesterase .1. On the specificity of the enzyme in nerve tissue. Journal of Biological Chemistry. v. 158, pp. 653-666, 1945. NACHMANSOHN, D.; WILSON, I. B. The enzymic hydrolysis and synthesis of acetylcholine. Advances in Enzymology and Related Subjects of Biochemistry. v. 12, pp. 259-339, 1951. NELSON, N.L.; COX, M. M. Lehninger Princ?pios da Bioqu?mica. 3? Edi??o. Sarvier, 2002. ISBN: 85-7378-125-4. 75 NIKOLAEV, A.; MCLAUGHLIN, T.; O'LEARY, D.; TESSIER-LAVIGNE, M. APP binds DR6 to trigger axon pruning and neuron death via distinct caspases. Nature. v. 457, pp. 981-990, 2009. NODARI, R. O.; GUERRA, M. P. Biodiversidade: aspectos biol?gicos, geogr?ficos, legais e ?ticos. Em Farmacognosia: da planta ao medicamento, ed. por C. M. O. Sim?es, E. P. Schenkel, G. Gosmann, J. C. P. Mello, L. A. Mentz, e P. R. Petrovick, pp. 11-24, Editora UFSC/Editora UFRGS, Florian?polis/Porto Alegre, 2003. NOWACKI, E.; JURZYSTA M; GORSKI P. Study on origin and protective function of alkaloids in plants. 2. Efect of availability of nitrogen on alkaloid synthesis in Solanaceae. Bulletin del Academie Polonaise des Sciences-Serie des Sciences Biologiques. v. 23, pp. 219-225, 1975. ORHAN, I.; KARTAL, M.; TOSUN, F.; SENER, B. Screening of Various Phenolic Acids and Flavonoid Derivatives for Their Anticholinesterase Potential. Zeitschrift f?r Naturforschung, v. 62, pp. 829-832, 2007. PANG, Y. P.; KOLLMEYER, T. M. ; HONG, F. ; LEE, J-C.; MAMMOND, P. I.; HAUGALO, K. S.; BRIMJOIN, S. Rational design of alkylene-linked bispyridiniumalidoximes as improved acetylcholinesterase reactivators. Chemistry & Biology. v.10, pp. 491-502, 2003. PATOCKA, J.; KUCA, K.; JUN, D. Acetylcholinesterase and butyrylcholinesterase - important enzymes of human body. Acta Medica, Hradec Kr?lov?, v. 47, n.4, p.215- 228, 2004. PELLETIER, S. W.; The nature and definition of an alkaloid. In: Alkaloids and Biological Perspectives. John Wiley, New York, pp. 1-31, 1983. PENG, L. F. Acetylcholinesterase inhibition by territrem B derivatives. Journal Natural Products. v. 58, pp. 857-862, 1995. 76 PIAZZI, L.; CAVALLI, A.; BELLUTI, F.; BISI, A.; GOBBI, S.; BARTOLINI, M.; ANDRISANO, V.; RACANATINI, M.; RAMPA, A. Extensive SAR and Computational Studies of 3-{4-[(Benzylmethylamino)methyl]phenyl}-6,7-dimethoxy-2H-2-chromenone (AP2238) Derivatives. Journal of Medicinal Chemistry. v. 50, pp. 4250-4254, 2007. PRATT, C. W.; CORNELY, K. Bioqu?mica Essencial. 1? Edi??o. Guanabara Koogan, 2006. ISBN: 85-277-1128-1. RANG, H.P.; DALE, M.M.; RITTER, J.M. Farmacologia, 5? edi??o. Elsevier. pp. 920, 2004. ISBN: 8535213686. RATES, S. M. K. Plants as source of drugs. Toxicon: Official Journal of the International Society on Toxinology. v. 39, pp. 603-613, 2001. RIVAS, P.; BRUCE, K.; CASSELS.; MORELLO, A.; REPETTO, Y. Effects of some - carboline alkaloids on intact Trypanosoma cruzi epimastigotes. Comparative Biochemistry and Physiology C-Toxicology & Pharmacology. v. 122, pp. 27-31, 1999. RIZZO, S.; CAVALLI, A.; CECCARINI, L.; BARTOLINI, M.; BELLUTI, F.; BISI, A.; ANDRISANO, V.; RECANATINI, M.; RAMPA, A. Structure-Activity Relationships and Binding Mode in the Human Acetylcholinesterase Active Site of Pseudo-Irreversible Inhibitors Related to Xanthostigmine. Chemmedchem. v. 4, pp. 670-679, 2009. RIZZO, S.; BARTOLINI, M.; CECCARINI, L.; PIAZZI, L.; GOBBI, S.; CAVALLI, A.; RECANATINI, M.; RAMPA, A. Targeting Alzheimer?s disease: Novel indanone hybrids bearing a pharmacophoric fragment of AP2238. Bioorganic & Medicinal Chemistry. v. 18, pp. 1749-1760, 2010. ROBBERS, J. E.; SPEEDIE, M.; TYLER, V. E. Farmacognosia e Farmacobiotecnologia. S?o Paulo. Premier, 1997. ROBINSON, T. Metabolism and Function of Alkaloids in Plants. Science. v. 184, pp. 430-435, 1974. 77 ROGERS, S. L.; DOODY, R. S.; MOHS, R. C. Friedhoff LT and the Donepezil Study Group. Donepezil improves cognition and global function in Alzheimer disease: a 15- week, doubleblind doubleblind, placebo-controlled study. Archives of Internal Medicine. v. 158, pp. 1021-1031, 1998. ROGERS, S.L.; FARLOW M. R.; MOHS, R. A 24-week, double-blind, placebocontrolled trial of donepezil in patients with Alzheimer?s disease. Neurology. v. 50, pp.136-145, 1998. SCHUMACHER, M.; CAMP, S.; MAULET, Y.; NEWTON, M.; MACPHEEQUIGLEY, K.; TAYLOR, S.S.; FRIEDMAN, T.; TAYLOR, P. Primary structures of Torpedo-californica acetylcholinesterase deduced from its cDNA sequence. Nature. v. 319, pp. 407-409, 1986. SHI, C. C.; CHEN, S. Y.; WANG, G. J. Vasorelaxant effect of Harman. European Journal of Pharmacology. v. 390, pp. 319-325, 2000. SILMAN, I.; HAREL, M.; AXELSEN, P.; RAVES, M.; SUSSMAN, J. L. Threedimensional structure of acetycholinesterase and of its complexes with anticholinesterase agents. Biochemical Society transactions. v. 22, pp.745-749, 1994. SILVA FILHO, M. V.; OLIVEIRA, M. M.; SALLES, J. B.; CUNHA BASTOS, V. L. F.; CASSANO, V. P. F.; CUNHA BASTOS, J. Methyl-paraoxon inhibition kinectics for acetylcholinesterase from brain of neotropical fishes. Toxicology Letters. v. 153 pp. 247-254, 2004. SIM?ES, C. M. O.; SCHENKEL, E. P.; GOSMAN, G., MELLO, J. C. P.; MENTZ, L. A.; PETROVICK, P. R. Farmacognosia. Da planta ao medicamento. 1? Edi??o. Universidade/UFRGS. Ed. UFSC. Porto Alegre/ Florian?polis, 1999. SMITH, T. W. Should Digoxin be the drug of 1st choice after diuretics in chronic congestive heart-failure - protagonists viewpoint. Journal of the American College of Cardiology. v. 12, pp. 267-271, 1988. 78 SOARES, E.; S. ?cidos fen?licos como antioxidantes. Rev. Nutr., v. 15, pp. 71-81, 2002. SOARES, L. F. Intoxica??es Agudas por Carbamatos em Pediatria. Aspectos Epidemiol?gicos, Cl?nicos e Terap?uticos. Rio de Janeiro, 1998. (Monografia do Curso de Especializa??o em Pediatria) Universidade Federal Fluminense ? UFF. Rio de Janeiro, 1998. SOREQ, H.; BEN-AZIZ, R.; PRODY, C.A.; SEIDMAN, S.; GNATT, A.; NEVILLE, L.; LIEMAN-HURWITZ, J.; LEV-LEHMAN, E.; GINZBERG, D.; LIPIDOT-LIFSON, Y. Molecular cloning and construction of the coding region for human acetylcholineterase reveals a G + C-rich attenuating structure. Proceedings of the Nacional Academy of Science. v. 87, pp. 9688-9692, 1990. SRIVASTAVA, V.; NEGI, A. S.; KUMAR, J. K., GUPTA, M. M.; KHANUJA, S. P. S. Plant-based anticancer molecules: A chemical and biological profile of some important leads. Bioorganic & Medicinal Chemistry. v. 13 (21), pp. 5892-5908, 2005. SUSSMAN, J.L.; HAREL, M.; PROLOW. F.; OEFNER, C.; GOLDMAN, A.; TOKER, L.; SILMAN, I. Atomic structure of acetylcholinesterase from Torpedo-californica: a prototypic acetylcholine-binding protein. Science. v. 253, pp. 872-879, 1991. TAYLOR, P. Anticholinesterase Agents. In: Hardman, J. G.; Gilman, A. G.; Limbird, L. E. (Ed). The Pharmacology Basis of Therapeutics. McGraw-Hill, New York, USA, pp. 161-176, 1996. TAYLOR, P.; BROWN, J, H. Acetylcholine. In: Siegel, G. J., Agranoff, B. W., Albers, R. W., Molinoff, P. B. (Ed). Basic Neurochemistry: Molecular, Celullar, Medical Aspects. Lippnicott-Raven Publishers Philadelphia, USA, pp. 214-242, 1999. TURK, T.; MACEK, P.; SUPUT, D. Inhibition of acetylcholinesterase by a pseudozoanthoxanthin-like compounds isolated from the zoanthid parazoanthus-axinellae (o-schmidt). Toxicon. v. 33, pp. 133-142, 1995. 79 VAN DER ZEE, E. A.; LUITEN, P. G. M. Muscarine acetylcholine repectors in the hippocampus, neocortex and amygdala : a review of immunocytochemical localization in relation to learning and memory. Progress and Neurobiology. v. 58, pp. 409-471, 1999. VIEGAS, C. J.; DA SILVA, V. B.; FURLAN, M.; ALBERTO, C. M. F.; BARREIRO, E. J. Produtos Naturais como canditados a f?rmacos ?teis no tratamento do Mal de Alzheimer. Qu?mica Nova, v. 27, n. 4, pp. 655-660, 2004. WAGNER, H. Pesquisa Fitom?dica do novo mil?nio: Tend?ncias e mudan?as. In: CECHINEL-FILHO, V., YUNES, R. A. Qu?mica de Produtos Naturais, novos f?rmacos e a moderna farmacognosia. 2? Edi??o. Itaja?: UNIVALI, pp. 31-47, 2009. WALDEMAR, G.; DUBOIS, B.; EMER, M. The Category Cued Recall test in very mild Alzheimer's disease: discriminative validity and correlation with semantic memory functions. European Journal of Neurology. v. 14, n. 1, pp. 102-108, 2007. WANI, M. C.; WALL, P. C.; HAROLD, L. T.; MONROE, E.; ANDREW, T. M. Plant antitumor agents. VI. Isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J. Am. Chem. Soc. V. 93, pp. 2325?2327, 1971. ZIMMERMAN, G.; SOREQ, H. Termination and beyond: acetylcholinesterase as a modulator of synaptic transmission. Cell and Tissue Research. v. 326, pp. 655?669, 2006 |
Page generated in 0.0032 seconds