An in vitro and in vivo evaluation of new potential trans-sialidase inhibitors of Trypanosoma cruzi predicted by a computational drug repositioning method
Chagas disease is one of the most important neglected parasitic diseases afflicting developed and undeveloped countries. There are currently limited options for inexpensive and secure pharmacological treatment. In this study, we employed a structure-based virtual screening protocol for 3180 FDA-appr...
Guardado en:
| Autor principal: | |
|---|---|
| Otros Autores: | , , , , , , , |
| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
| Publicado: |
Elsevier Masson SAS
2017
|
| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
| Aporte de: | Registro referencial: Solicitar el recurso aquí |
| LEADER | 16780caa a22017297a 4500 | ||
|---|---|---|---|
| 001 | PAPER-14990 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518204536.0 | ||
| 008 | 190410s2017 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-85016308619 | |
| 024 | 7 | |2 cas |a azlocillin, 37091-65-9, 37091-66-0; cefonicid, 61270-58-4, 61270-78-8; cefoperazone, 62893-19-0, 62893-20-3; cefsulodin, 52152-93-9; cromoglycate disodium, 15826-37-6, 16110-51-3, 93356-79-7, 93356-84-4; dicoumarol, 66-76-2; doxazosin mesylate, 77883-43-3; flubendazole, 31430-15-6; ketanserin, 74050-98-9; raloxifene, 82640-04-8, 84449-90-1; salazosulfapyridine, 599-79-1; telmisartan, 144701-48-4; terfenadine, 50679-08-8; troglitazone, 97322-87-7; ziprasidone, 118289-78-4, 122883-93-6, 138982-67-9, 199191-69-0; sialidase, 9001-67-6; Anti-Inflammatory Agents; Antiprotozoal Agents; Glycoproteins; Neuraminidase; Sulfasalazine; trans-sialidase | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a EJMCA | ||
| 100 | 1 | |a Lara-Ramirez, E.E. | |
| 245 | 1 | 3 | |a An in vitro and in vivo evaluation of new potential trans-sialidase inhibitors of Trypanosoma cruzi predicted by a computational drug repositioning method |
| 260 | |b Elsevier Masson SAS |c 2017 | ||
| 270 | 1 | 0 | |m Rivera, G.; Centro de Biotecnología Genómica, Instituto Politécnico Nacional, Boulevard del Maestro, s/n, Esq. Elías Piña, Mexico; email: gildardors@hotmail.com |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Bern, C., Kjos, S., Yabsley, M.J., Montgomery, S.P., Trypanosoma cruzi and chagas' disease in the United States (2011) Clin. Microbiol. Rev., 24, pp. 655-681 | ||
| 504 | |a Strasen, J., Williams, T., Ertl, G., Zoller, T., Stich, A., Ritter, O., Epidemiology of Chagas disease in Europe: many calculations, little knowledge (2014) Clin. Res. Cardiol. Off. J. Ger. Card. Soc., 103, pp. 1-10 | ||
| 504 | |a WHO, Chagas Disease (American Trypanosomiasis) (2016), http://www.who.int/mediacentre/factsheets/fs340/en/, World Health Organization; Morillo, C.A., Marin-Neto, J.A., Avezum, A., Sosa-Estani, S., Rassi, A.J., Rosas, F., Villena, E., Yusuf, S., Randomized trial of benznidazole for chronic chagas' cardiomyopathy (2015) N. Engl. J. Med., 373, pp. 1295-1306 | ||
| 504 | |a Bern, C., Chagas' disease (2015) N. Engl. J. Med., 373, pp. 456-466 | ||
| 504 | |a Maguire, J.H., Treatment of Chagas' Disease — Time Is Running Out (2015), http://Dx.doi.org/10.1056/NEJMe1510170, (Accessed 22 November 2016) http://www.nejm.org/doi/full/10.1056/NEJMe1510170; Telleria, C.M., Drug repurposing for cancer therapy (2012) J. Cancer Sci. Ther., 4, pp. ix-xi | ||
| 504 | |a Kaiser, M., Mäser, P., Tadoori, L.P., Ioset, J.-R., Brun, R., Antiprotozoal activity profiling of approved drugs: a starting point toward drug repositioning (2015) PLoS One, 10, p. e0135556 | ||
| 504 | |a Chong, C.R., Sullivan, D.J., New uses for old drugs (2007) Nature, 448, pp. 645-646 | ||
| 504 | |a Meng, X.-Y., Zhang, H.-X., Mezei, M., Cui, M., Molecular Docking: a powerful approach for structure-based drug discovery (2011) Curr. Comput. Aided Drug Des., 7, pp. 146-157 | ||
| 504 | |a Bellera, C.L., Balcazar, D.E., Alberca, L., Labriola, C.A., Talevi, A., Carrillo, C., Application of computer-aided drug repurposing in the search of new cruzipain inhibitors: discovery of amiodarone and bromocriptine inhibitory effects (2013) J. Chem. Inf. Model, 53, pp. 2402-2408 | ||
| 504 | |a Bellera, C.L., Balcazar, D., Alberca, O.E.L., Labriola, C.A., Talevi, A., Carrillo, C., Bellera, C.L., Carrillo, C., Identification of levothyroxine antichagasic activity through computer-aided drug repurposing, identification of levothyroxine antichagasic activity through computer-aided drug repurposing (2014) Sci. World J. Sci. World J., 2014, p. e279618. , 2014 | ||
| 504 | |a Bellera, C.L., Balcazar, D.E., Vanrell, M.C., Casassa, A.F., Palestro, P.H., Gavernet, L., Labriola, C.A., Talevi, A., Computer-guided drug repurposing: identification of trypanocidal activity of clofazimine, benidipine and saquinavir (2015) Eur. J. Med. Chem., 93, pp. 338-348 | ||
| 504 | |a Sibley, L.D., Invasion and intracellular survival by Protozoan parasites (2011) Immunol. Rev., 240, pp. 72-91 | ||
| 504 | |a Buschiazzo, A., Amaya, M.F., Cremona, M.L., Frasch, A.C., Alzari, P.M., The crystal structure and mode of action of trans-sialidase, a key enzyme in Trypanosoma cruzi pathogenesis (2002) Mol. Cell., 10, pp. 757-768 | ||
| 504 | |a Miller, B.R., Roitberg, A.E., Trypanosoma cruzi trans-sialidase as a drug target against Chagas disease (American trypanosomiasis) (2013) Future Med. Chem., 5, pp. 1889-1900 | ||
| 504 | |a Silva, B.L., Filho, J.D.S., Andrade, P., Carvalho, I., Alves, R.J., Design, synthesis and enzymatic evaluation of 3-O-substituted aryl β-D-galactopyranosides as inhibitors of Trypanosoma cruzi trans-sialidase (2014) Bioorg. Med. Chem. Lett., 24, pp. 4529-4532 | ||
| 504 | |a Neres, J., Brewer, M.L., Ratier, L., Botti, H., Buschiazzo, A., Edwards, P.N., Mortenson, P.N., Douglas, K.T., Discovery of novel inhibitors of Trypanosoma cruzi trans-sialidase from in silico screening (2009) Bioorg. Med. Chem. Lett., 19, pp. 589-596 | ||
| 504 | |a Baber, J.C., Shirley, W.A., Gao, Y., Feher, M., The use of consensus scoring in ligand-based virtual screening (2006) J. Chem. Inf. Model, 46, pp. 277-288 | ||
| 504 | |a Laskowski, R.A., Swindells, M.B., LigPlot+: multiple ligand-protein interaction diagrams for drug discovery (2011) J. Chem. Inf. Model, 51, pp. 2778-2786 | ||
| 504 | |a Agustí, R., París, G., Ratier, L., Frasch, A.C.C., de Lederkremer, R.M., Lactose derivatives are inhibitors of Trypanosoma cruzi trans-sialidase activity toward conventional substrates in vitro and in vivo (2004) Glycobiology, 14, pp. 659-670 | ||
| 504 | |a De Pablos, L.M., Osuna, A., Multigene families in Trypanosoma cruzi and their role in infectivity (2012) Infect. Immun., 80, pp. 2258-2264 | ||
| 504 | |a Amin, A., Chitsazan, M., Navid, H., Left ventricular systolic dysfunction in two patients with ankylosing spondylitis: what is the role of corticosteroids? (2016) Eur. J. Rheumatol., 3, pp. 179-181 | ||
| 504 | |a Lui, N.L., Thumboo, J., Inman, R., Cardiomyopathy in ankylosing spondylitis (2011) Arthritis Care Res., 63, pp. 564-569 | ||
| 504 | |a Irwin, J.J., Sterling, T., Mysinger, M.M., Bolstad, E.S., Coleman, R.G., ZINC: a free tool to discover chemistry for biology (2012) J. Chem. Inf. Model, 52, pp. 1757-1768 | ||
| 504 | |a Morris, G.M., Huey, R., Lindstrom, W., Sanner, M.F., Belew, R.K., Goodsell, D.S., Olson, A.J., AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility (2009) J. Comput. Chem., 30, pp. 2785-2791 | ||
| 504 | |a Trott, O., Olson, A.J., AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading (2010) J. Comput. Chem., 31, pp. 455-461 | ||
| 504 | |a Velec, H.F.G., Gohlke, H., Klebe, G., DrugScore(CSD)-knowledge-based scoring function derived from small molecule crystal data with superior recognition rate of near-native ligand poses and better affinity prediction (2005) J. Med. Chem., 48, pp. 6296-6303 | ||
| 504 | |a Wang, R., Lai, L., Wang, S., Further development and validation of empirical scoring functions for structure-based binding affinity prediction (2002) J. Comput. Aided Mol. Des., 16, pp. 11-26 | ||
| 504 | |a Liu, S., Fu, R., Zhou, L.-H., Chen, S.-P., Application of consensus scoring and principal component analysis for virtual screening against β-secretase (BACE-1) (2012) PLoS One, 7 | ||
| 504 | |a Development Core Team, R., R: a Language and Environment for Statistical Computing (2016), https://www.R-project.org, R Found. Stat. Comput Vienna Austria https://www.R-project.org/; Sülsen, V.P., Cazorla, S.I., Frank, F.M., Redko, F.C., Anesini, C.A., Coussio, J.D., Malchiodi, E.L., Muschietti, L.V., Trypanocidal and leishmanicidal activities of flavonoids from Argentine medicinal plants (2007) Am. J. Trop. Med. Hyg., 77, pp. 654-659 | ||
| 504 | |a Díaz-Chiguer, D.L., Márquez-Navarro, A., Nogueda-Torres, B., de la Luz León-Ávila, G., Pérez-Villanueva, J., Hernández-Campos, A., Castillo, R., Hernández-Luis, F., In vitro and in vivo trypanocidal activity of some benzimidazole derivatives against two strains of Trypanosoma cruzi (2012) Acta Trop., 122, pp. 108-112 | ||
| 504 | |a Villalobos-Rocha, J.C., Sánchez-Torres, L., Nogueda-Torres, B., Segura-Cabrera, A., García-Pérez, C.A., Bocanegra-García, V., Palos, I., Rivera, G., Anti-Trypanosoma cruzi and anti-leishmanial activity by quinoxaline-7-carboxylate 1,4-di-N-oxide derivatives (2014) Parasitol. Res., 113, pp. 2027-2035 | ||
| 504 | |a Wong-Baeza, C., Nogueda-Torres, B., Serna, M., Meza-Toledo, S., Baeza, I., Wong, C., Trypanocidal effect of the benzyl ester of N-propyl oxamate: a bi-potential prodrug for the treatment of experimental Chagas disease (2015) BMC Pharmacol. Toxicol., 16 | ||
| 504 | |a Mendoza-Martínez, C., Correa-Basurto, J., Nieto-Meneses, R., Márquez-Navarro, A., Aguilar-Suárez, R., Montero-Cortes, M.D., Nogueda-Torres, B., Hernández-Luis, F., Design, synthesis and biological evaluation of quinazoline derivatives as anti-trypanosomatid and anti-plasmodial agents (2015) Eur. J. Med. Chem., 96, pp. 296-307 | ||
| 504 | |a Cuevas-Hernández, R.I., Correa-Basurto, J., Flores-Sandoval, C.A., Padilla-Martínez, I.I., Nogueda-Torres, B., Villa-Tanaca, M.D.L., Tamay-Cach, F., Trujillo-Ferrara, J.G., Fluorine-containing benzothiazole as a novel trypanocidal agent: design, in silico study, synthesis and activity evaluation (2016) Med. Chem. Res., 25, pp. 211-224 | ||
| 504 | |a Elizondo-Jimenez, S., Moreno-Herrera, A., Reyes-Olivares, R., Dorantes-Gonzalez, E., Nogueda-Torres, B., de Oliveira, E.A.G., Romeiro, N.C., Rivera, G., Synthesis, biological evaluation and molecular docking of new benzenesulfonylhydrazone as potential anti-trypanosoma cruzi agents (2016) Med. Chem., 13, pp. 149-158 | ||
| 504 | |a Brener, Z., Therapeutic activity and criterion of cure on mice experimentally infected with Trypanosoma cruzi (1962) Rev. Inst. Med. Trop. São Paulo, 4, pp. 389-396 | ||
| 504 | |a Buschiazzo, A., Frasch, A.C., Campetella, O., Medium scale production and purification to homogeneity of a recombinant trans-sialidase from Trypanosoma cruzi (1996) Cell. Mol. Biol. noisy–gd. Fr., 42, pp. 703-710 | ||
| 504 | |a Cano, M.E., Agusti, R., Cagnoni, A.J., Tesoriero, M.F., Kovensky, J., Uhrig, M.L., de Lederkremer, R.M., Synthesis of divalent ligands of β-thio- and β-N-galactopyranosides and related lactosides and their evaluation as substrates and inhibitors of Trypanosoma cruzi trans-sialidase (2014) Beilstein J. Org. Chem., 10, pp. 3073-3086 | ||
| 504 | |a Filardi, L.S., Brener, Z., A rapid method for testing in vivo the susceptibility of different strains of Trypanosoma cruzi to active chemotherapeutic agents (1984) Mem. Inst. Oswaldo Cruz, 79, pp. 221-225 | ||
| 504 | |a Romanha, A.J., de Castro, S.L., Soeiro, M.D.N.C., Lannes-Vieira, J., Ribeiro, I., Talvani, A., Bourdin, B., Andrade, Z.D.A., In vitro and in vivo experimental models for drug screening and development for Chagas disease (2010) Mem. Inst. Oswaldo Cruz, 105, pp. 233-238 | ||
| 520 | 3 | |a Chagas disease is one of the most important neglected parasitic diseases afflicting developed and undeveloped countries. There are currently limited options for inexpensive and secure pharmacological treatment. In this study, we employed a structure-based virtual screening protocol for 3180 FDA-approved drugs for repositioning of them as potential trans-sialidase inhibitors. In vitro and in vivo evaluations were performed for the selected drugs against trypomastigotes from the INC-5 and NINOA strains of T. cruzi. Also, inhibition of sialylation by the trans-sialidase enzyme reaction was evaluated using high-performance anion-exchange chromatography with pulse amperometric detection to confirm the mechanism of action. Results from the computational study showed 38 top drugs with the best binding-energies. Four compounds with antihistaminic, anti-hypertensive, and antibiotic properties showed better trypanocidal effects (LC50 range = 4.5–25.8 μg/mL) than the reference drugs, nifurtimox and benznidazole (LC50 range = 36.1–46.8 μg/mL) in both strains in the in vitro model. The anti-inflammatory, sulfasalazine showed moderate inhibition (37.6%) of sialylation in a trans-sialidase enzyme inhibition reaction. Sulfasalazine also showed the best trypanocidal effects in short-term in vivo experiments on infected mice. This study suggests for the first time that the anti-inflammatory sulfasalazine could be used as a lead compound to develop new trans-sialidase inhibitors. © 2017 |l eng | |
| 593 | |a Unidad de Investigación Biomédica de Zacatecas, Instituto Mexicano del Seguro Social (IMSS), Zacatecas, 98000, Mexico | ||
| 593 | |a Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Ciudad de México, 01130, Mexico | ||
| 593 | |a Centro de Biotecnología Genómica, Instituto Politécnico Nacional, Reynosa, 88710, Mexico | ||
| 593 | |a Universidad de Buenos Aires, Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET), Centro de Investigaciones en Hidratos de Carbono (CIHIDECAR), Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Pabellón 2, Buenos Aires, 1428, Argentina | ||
| 690 | 1 | 0 | |a DOCKING |
| 690 | 1 | 0 | |a DRUG REPOSITIONING |
| 690 | 1 | 0 | |a FDA-DRUGS |
| 690 | 1 | 0 | |a TRANS-SIALIDASE |
| 690 | 1 | 0 | |a TRYPANOSOMA CRUZI |
| 690 | 1 | 0 | |a ANABOLIC AGENT |
| 690 | 1 | 0 | |a ANTIBIOTIC AGENT |
| 690 | 1 | 0 | |a ANTIHISTAMINIC AGENT |
| 690 | 1 | 0 | |a ANTIHYPERTENSIVE AGENT |
| 690 | 1 | 0 | |a AZLOCILLIN |
| 690 | 1 | 0 | |a CARDIAC GLYCOSIDE |
| 690 | 1 | 0 | |a CEFONICID |
| 690 | 1 | 0 | |a CEFOPERAZONE |
| 690 | 1 | 0 | |a CEFSULODIN |
| 690 | 1 | 0 | |a CROMOGLYCATE DISODIUM |
| 690 | 1 | 0 | |a DICOUMAROL |
| 690 | 1 | 0 | |a DOXAZOSIN MESYLATE |
| 690 | 1 | 0 | |a FLUBENDAZOLE |
| 690 | 1 | 0 | |a KETANSERIN |
| 690 | 1 | 0 | |a RALOXIFENE |
| 690 | 1 | 0 | |a SALAZOSULFAPYRIDINE |
| 690 | 1 | 0 | |a SIALIDASE INHIBITOR |
| 690 | 1 | 0 | |a TELMISARTAN |
| 690 | 1 | 0 | |a TERFENADINE |
| 690 | 1 | 0 | |a TROGLITAZONE |
| 690 | 1 | 0 | |a ZIPRASIDONE |
| 690 | 1 | 0 | |a ANTIINFLAMMATORY AGENT |
| 690 | 1 | 0 | |a ANTIPROTOZOAL AGENT |
| 690 | 1 | 0 | |a GLYCOPROTEIN |
| 690 | 1 | 0 | |a SALAZOSULFAPYRIDINE |
| 690 | 1 | 0 | |a SIALIDASE |
| 690 | 1 | 0 | |a TRANS-SIALIDASE |
| 690 | 1 | 0 | |a ANION EXCHANGE CHROMATOGRAPHY |
| 690 | 1 | 0 | |a ANTIHYPERTENSIVE ACTIVITY |
| 690 | 1 | 0 | |a ANTIMICROBIAL ACTIVITY |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CHEMICAL STRUCTURE |
| 690 | 1 | 0 | |a CONTROLLED STUDY |
| 690 | 1 | 0 | |a DRUG REPOSITIONING |
| 690 | 1 | 0 | |a DRUG SCREENING |
| 690 | 1 | 0 | |a ENZYMATIC ASSAY |
| 690 | 1 | 0 | |a ENZYME INHIBITION |
| 690 | 1 | 0 | |a ENZYME MECHANISM |
| 690 | 1 | 0 | |a FOOD AND DRUG ADMINISTRATION |
| 690 | 1 | 0 | |a IN VITRO STUDY |
| 690 | 1 | 0 | |a IN VIVO STUDY |
| 690 | 1 | 0 | |a NONHUMAN |
| 690 | 1 | 0 | |a SIALYLATION |
| 690 | 1 | 0 | |a TRYPANOSOMA CRUZI |
| 690 | 1 | 0 | |a ANIMAL |
| 690 | 1 | 0 | |a ANTAGONISTS AND INHIBITORS |
| 690 | 1 | 0 | |a CHEMISTRY |
| 690 | 1 | 0 | |a DRUG EFFECTS |
| 690 | 1 | 0 | |a DRUG REPOSITIONING |
| 690 | 1 | 0 | |a MOUSE |
| 690 | 1 | 0 | |a PROCEDURES |
| 690 | 1 | 0 | |a STRUCTURE ACTIVITY RELATION |
| 690 | 1 | 0 | |a TRYPANOSOMA CRUZI |
| 690 | 1 | 0 | |a ANIMALS |
| 690 | 1 | 0 | |a ANTI-INFLAMMATORY AGENTS |
| 690 | 1 | 0 | |a ANTIPROTOZOAL AGENTS |
| 690 | 1 | 0 | |a DRUG REPOSITIONING |
| 690 | 1 | 0 | |a GLYCOPROTEINS |
| 690 | 1 | 0 | |a MICE |
| 690 | 1 | 0 | |a NEURAMINIDASE |
| 690 | 1 | 0 | |a STRUCTURE-ACTIVITY RELATIONSHIP |
| 690 | 1 | 0 | |a SULFASALAZINE |
| 690 | 1 | 0 | |a TRYPANOSOMA CRUZI |
| 700 | 1 | |a López-Cedillo, J.C. | |
| 700 | 1 | |a Nogueda-Torres, B. | |
| 700 | 1 | |a Kashif, M. | |
| 700 | 1 | |a Garcia-Perez, C. | |
| 700 | 1 | |a Bocanegra-Garcia, V. | |
| 700 | 1 | |a Agusti, R. | |
| 700 | 1 | |a Uhrig, M.L. | |
| 700 | 1 | |a Rivera, G. | |
| 773 | 0 | |d Elsevier Masson SAS, 2017 |g v. 132 |h pp. 249-261 |p Eur. J. Med. Chem. |x 02235234 |w (AR-BaUEN)CENRE-4668 |t European Journal of Medicinal Chemistry | |
| 856 | 4 | 1 | |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-85016308619&doi=10.1016%2fj.ejmech.2017.03.063&partnerID=40&md5=d95cb79805b6d6404e1fe6077003c860 |y Registro en Scopus |
| 856 | 4 | 0 | |u https://doi.org/10.1016/j.ejmech.2017.03.063 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_02235234_v132_n_p249_LaraRamirez |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_02235234_v132_n_p249_LaraRamirez |y Registro en la Biblioteca Digital |
| 961 | |a paper_02235234_v132_n_p249_LaraRamirez |b paper |c PE | ||
| 962 | |a info:eu-repo/semantics/article |a info:ar-repo/semantics/artículo |b info:eu-repo/semantics/publishedVersion | ||
| 999 | |c 75943 | ||