Synthesis, molecular docking and biological evaluation of novel phthaloyl derivatives of 3-amino-3-aryl propionic acids as inhibitors of Trypanosoma cruzi trans-sialidase

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In the last two decades, trans-sialidase of Trypanosoma cruzi (TcTS) has been an important pharmacological target for developing new anti-Chagas agents. In a continuous effort to discover new potential TcTS inhibitors, 3-amino-3-arylpropionic acid derivatives (series A) and novel phthaloyl derivativ...

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Autor principal: Kashif, M.
Otros Autores: Chacón-Vargas, K.F, López-Cedillo, J.C, Nogueda-Torres, B., Paz-González, A.D, Ramírez-Moreno, E., Agusti, R., Uhrig, M.L, Reyes-Arellano, A., Peralta-Cruz, J., Ashfaq, M., Rivera, G.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: Elsevier Masson SAS 2018
Acceso en línea:Registro en Scopus
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024 7 |2 scopus  |a 2-s2.0-85049568232 
024 7 |2 cas  |a benznidazole, 22994-85-0; nifurtimox, 23256-30-6; sialidase, 9001-67-6; Glycoproteins; Neuraminidase; Propionates; trans-sialidase; Trypanocidal Agents 
040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
030 |a EJMCA 
100 1 |a Kashif, M. 
245 1 0 |a Synthesis, molecular docking and biological evaluation of novel phthaloyl derivatives of 3-amino-3-aryl propionic acids as inhibitors of Trypanosoma cruzi trans-sialidase 
260 |b Elsevier Masson SAS  |c 2018 
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 
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504 |a Alanazi, A.M., El-Azab, A.S., Al-Suwaidan, I.A., ElTahir, K.E., Asiri, Y.A., Abdel-Aziz, N.I., Alaa, A.M., Structure-based design of phthalimide derivatives as potential cyclooxygenase-2 (COX-2) inhibitors: anti-inflammatory and analgesic activities (2015) Eur. J. Med. Chem., 92, pp. 115-123 
504 |a Abdel-Aziz, A.A.M., El-Azab, A.S., Attia, S.M., Al-Obaid, A.M., Al-Omar, M.A., El-Subbagh, H.I., Synthesis and biological evaluation of some novel cyclicimides as hypoglycaemic, anti-hyperlipidemic agents (2011) Eur. J. Med. Chem., 46, pp. 4324-4329 
504 |a Alanazi, A.M., El-Azab, A.S., Al-Suwaidan, I.A., ElTahir, K.E.H., Asiri, Y.A., Abdel-Aziz, N.I., Structure-based design of phthalimide derivatives as potential cyclooxygenase-2 (COX-2) inhibitors: anti-inflammatory and analgesic activities (2015) Eur. J. Med. Chem., 92, pp. 115-123 
504 |a Abdel-Aziz, A.A.M., El-Azab, A.S., Attia, S.M., Al-Obaid, A.M., Al-Omar, M.A., El-Subbagh, H.I., Synthesis and biological evaluation of some novel cyclicimides as hypoglycaemic, anti-hyperlipidemic agents (2011) Eur. J. Med. Chem., 46, pp. 4324-4329 
504 |a Kamiński, K., Obniska, J., Wiklik, B., Atamanyuk, D., Synthesis and anticonvulsant properties of new acetamide derivatives of phthalimide, and its saturated cyclohexane and norbornene analogs (2011) Eur. J. Med. Chem., 46, pp. 4634-4641 
504 |a Akgün, H., Karamelekoğlu, I., Berk, B., Kurnaz, I., Sarıbıyık, G., Öktem, S., Synthesis and antimycobacterial activity of some phthalimide derivatives (2012) Bioorg. Med. Chem., 20, pp. 4149-4154 
504 |a Williams, R., Manka, J.T., Rodriguez, A.L., Vinson, P.N., Niswender, C.M., Weaver, C.D., Synthesis and SAR of centrally active mGlu5 positive allosteric modulators based on an aryl acetylenic bicyclic lactam scaffold (2011) Bioorg. Med. Chem. Lett, 21, pp. 1350-1353 
504 |a Cardoso, M.V.D.O., Moreira, D.R.M., Filho, G.B.O., Cavalcanti, S.M.T., Coelho, L.C.D., Espíndola, J.W.P., Design, synthesis and structure–activity relationship of phthalimides endowed with dual antiproliferative and immunomodulatory activities (2015) Eur. J. Med. Chem., 96, pp. 491-503 
504 |a Pessoa, C., Ferreira, P.M.P., Lotufo, L.V.C., de Moraes, M.O., Cavalcanti, S.M.T., Coêlho, L.C.D., Discovery of phthalimides as immunomodulatory and antitumor drug prototypes (2010) ChemMedChem, 5, pp. 523-528 
504 |a da Costa, P.M., da Costa, M.P., Carvalho, A.A., Cavalcanti, S.M.T., de Oliveira Cardoso, M.V., de Oliveira Filho, G.B., Improvement of in vivo anticancer and antiangiogenic potential of thalidomide derivatives (2015) Chem. Biol. Interact., 239. , 74–183 
504 |a de Santiago, E.F., de Oliveira, S.A., de Oliveira Filho, G.B., Moreira, D.R.M., Gomes, P.A.T., da Silva, A.C.L.A.C.L., Evaluation of the anti-schistosoma mansoni activity of thiosemicarbazones and thiazoles (2014) Antimicrob. Agents Chemother., 58, pp. 352-363 
504 |a de Moraes Gomes, P.A., Oliveira, A.R., de Oliveira Cardoso, M.V., de Farias Santiago, E., de Oliveira Barbosa, M., de Siqueira, L.R., Moreira, D.R., de Oliveira Mendes, A.P., Phthalimido-thiazoles as building blocks and their effects on the growth and morphology of Trypanosoma cruzi (2016) Eur. J. Med. Chem., 23. , 46–5 
504 |a Lebedev, A.V., Lebedeva, A.B., Sheludyakov, V.D., Kovaleva, E.A., Ustinova, O.L., Kozhevnikov, I.B., Competitive formation of β-amino acids, propenoic, and ylidenemalonic acids by the rodionov reaction from malonic acid, aldehydes, and ammonium acetate in alcoholic medium (2005) Russ. J. Gen. Chem., 75, pp. 1113-1124 
504 |a Ashfaq, M., Synthesis of novel bioactive phthalimido-4-methyl pentanoateorganotin (IV) esters with spectroscopic investigation (2006) J. Organomet. Chem., 691, pp. 1803-1808 
504 |a Watts, A.G., Damager, I., Amaya, M.L., Buschiazzo, A., Alzari, P., Frasch, A.C., Withers, S.G., Trypanosoma cruzi trans-sialidase operates through a covalent sialyl-enzyme intermediate: tyrosine is the catalytic nucleophile (2003) J. Am. Chem. Soc., 125, pp. 7532-7533 
504 |a Todeschini, A.R., Mendonça-Previato, L., Previato, J.O., Varki, A., Halbeek, H.V., Trans-sialidase from Trypanosoma cruzi catalyzes sialoside hydrolysis with retention of configuration (2000) Glycobiology, 10, pp. 213-221 
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 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., 16, 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 Dassault Systèmes BIOVIA, Discovery Studio Modeling Environment, Release 2017 (2016), Dassault Systèmes San Diego; Mendoza-Martínez, C., Correa-Basurto, J., Nieto-Meneses, R., Márquez-Navarro, A., Aguilar-Suárez, R., Montero-Cortes, M.D., Nogueda-Torres, B., Rodriguez-Lezama, A., 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 Brener, Z., Therapeutic activity and criterion of cure on mice experimentally infected with Trypanosoma cruzi (1962) Rev. Inst. Med. Trop. Sao Paulo, 6, pp. 389-396 
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) J Parasitol Res., 113, pp. 2027-2035 
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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, p. 3073 
520 3 |a In the last two decades, trans-sialidase of Trypanosoma cruzi (TcTS) has been an important pharmacological target for developing new anti-Chagas agents. In a continuous effort to discover new potential TcTS inhibitors, 3-amino-3-arylpropionic acid derivatives (series A) and novel phthaloyl derivatives (series B, C and D) were synthesized and molecular docking, TcTS enzyme inhibition and determination of trypanocidal activity were carried out. From four series obtained, compound D-11 had the highest binding affinity value (−11.1 kcal/mol) compared to reference DANA (−7.8 kcal/mol), a natural ligand for TS enzyme. Furthermore, the 3D and 2D interactions analysis of compound D-11 showed a hydrogen bond, π-π stacking, π-anion, hydrophobic and Van der Waals forces with all important amino acid residues (Arg35, Arg245, Arg314, Tyr119, Trp312, Tyr342, Glu230 and Asp59) on the active site of TcTS. Additionally, D-11 showed the highest TcTS enzyme inhibition (86.9% ± 5) by high-performance ion exchange chromatography (HPAEC). Finally, D-11 showed better trypanocidal activity than the reference drugs nifurtimox and benznidazole with an equal % lysis (63 ± 4 and 65 ± 2 at 10 μg/mL) and LC50 value (52.70 ± 2.70 μM and 46.19 ± 2.36 μM) on NINOA and INC-5 strains, respectively. Therefore, D-11 is a small-molecule with potent TcTS inhibition and a strong trypanocidal effect that could help in the development of new anti-Chagas agents. © 2018 Elsevier Masson SAS  |l eng 
536 |a Detalles de la financiación: Consejo Nacional de Ciencia y Tecnología 
536 |a Detalles de la financiación: Secretaría de Investigación y Posgrado, Instituto Politécnico Nacional, SIP-20180306 
536 |a Detalles de la financiación: Fondo para la Investigación Científica y Tecnológica, CB-2014-01, 241615 
536 |a Detalles de la financiación: Consejo Nacional de Ciencia y Tecnología 
536 |a Detalles de la financiación: Comisión de Operación y Fomento de Actividades Académicas, Instituto Politécnico Nacional 
536 |a Detalles de la financiación: Universidad de Buenos Aires 
536 |a Detalles de la financiación: Agencia Nacional de Promoción Científica y Tecnológica 
536 |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas 
536 |a Detalles de la financiación: We wish to express our gratitude to the Consejo Nacional de Ciencia y Tecnología , Mexico ( Proyecto Apoyado por el Fondo Sectorial de Investigación para la Educación , CB-2014-01, 241615 ) and Secretaría de Investigación y Posgrado del Instituto Politécnico Nacional ( SIP-20180306 ) for their financial support. 
536 |a Detalles de la financiación: Muhammad Kashif is the recipient of a scholarship (No. 590887/715369) from Consejo Nacional de Ciencia y Tecnología, Mexico. Gildardo Rivera, Alicia Reyes-Arellano, Esther Ramírez-Moreno and Benjamín Nogueda-Torres hold a scholarship from the “Comisión de Operación y Fomento de Actividades Académicas” (COFAA-IPN) and the “Programa de Estímulos al Desempeño de los Investigadores” (EDI-IPN) . We thank Oscar Campetella and his group from the Universidad Nacional General San Martín (UNSAM) Argentina , for their kind gift of trans-sialidase from T. cruzi . Support for this work from the Universidad de Buenos Aires , the CONICET and the ANPCyT is gratefully acknowledged. RA and MLU are research members of the CONICET. Appendix A 
593 |a Laboratorio de Biotecnología Farmacéutica, Centro de Biotecnología Genómica, Instituto Politécnico Nacional, Reynosa, 88700, Mexico 
593 |a Departamento de Parasitología, Escuela Nacional de Ciencias Biológicas, Ciudad de México, 07320, Mexico 
593 |a Escuela Nacional de Medicina y Homeopatía, Instituto Politécnico Nacional, Ciudad de México, 07320, Mexico 
593 |a Universidad de Buenos Aires, Facultad de Ciencias Exactas y Naturales, Departamento de Química Orgánica, Ciudad Universitaria, Pabellón 2, Buenos Aires, C1428EG, Argentina 
593 |a Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET)-UBA, Centro de Investigaciones en Hidratos de Carbono (CIHIDECAR), Buenos Aires, Argentina 
593 |a Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Ciudad de México, 07320, Mexico 
593 |a Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur, Pakistan 
690 1 0 |a INHIBITORS 
690 1 0 |a MOLECULAR DOCKING 
690 1 0 |a PHTHALOYL 
690 1 0 |a PROPIONIC ACID 
690 1 0 |a TRANS-SIALIDASE 
690 1 0 |a TRYPANOSOMA CRUZI 
690 1 0 |a 2 [2 CARBOXY 1 (2 NITROPHENYL)ETHYL] 1,3 DIOXOISOINDOLINE 5 CARBOXYLIC ACID 
690 1 0 |a 2 [2 CARBOXY 1 (4 ETHYLPHENYL)ETHYL] 1,3 DIOXOISOINDOLINE 5 CARBOXYLIC ACID 
690 1 0 |a 2 [2 CARBOXY 1 (4 HYDROXYPHENYL)ETHYL] 1,3 DIOXOISOINDOLINE 5 CARBOXYLIC ACID 
690 1 0 |a 2 [2 CARBOXY 1 (4 METHOXYPHENYL)ETHYL] 1,3 DIOXOISOINDOLINE 5 CARBOXYLIC ACID 
690 1 0 |a 2 [2 CARBOXY 1 (4 NITROPHENYL)ETHYL] 1,3 DIOXOISOINDOLINE 5 CARBOXYLIC ACID 
690 1 0 |a 2 [2 CARBOXY 1 (4 TOLYL)ETHYL] 1,3 DIOXOISOINDOLINE 5 CARBOXYLIC ACID 
690 1 0 |a 3 (1,3 DIOXOISOINDOLIN 2 YL) 3 (4 ETHYLPHENYL)PROPANOIC ACID 
690 1 0 |a 3 (1,3 DIOXOISOINDOLIN 2 YL) 3 (4 HYDROXYPHENYL)PROPANOIC ACID 
690 1 0 |a 3 (1,3 DIOXOISOINDOLIN 2 YL) 3 (4 METHOXYPHENYL)PROPANOIC ACID 
690 1 0 |a 3 (1,3 DIOXOISOINDOLIN 2 YL) 3 (4 NITROPHENYL)PROPANOIC ACID 
690 1 0 |a 3 (1,3 DIOXOISOINDOLIN 2 YL) 3 (4 TOLYL)PROPANOIC ACID 
690 1 0 |a 3 (4 ETHYLPHENYL) 3 (5 METHYL 1,3 DIOXOISOINDOLIN 2 YL)PROPANOIC ACID 
690 1 0 |a 3 (4 HYDROXYPHENYL) 3 (5 METHYL 1,3 DIOXOISOINDOLIN 2 YL)PROPANOIC ACID 
690 1 0 |a 3 (4 METHOXYPHENYL) 3 (5 METHYL 1,3 DIOXOISOINDOLIN 2 YL)PROPANOIC ACID 
690 1 0 |a 3 (5 METHYL 1,3 DIOXOISOINDOLIN 2 YL) 3 (4 NITROPHENYL)PROPANOIC ACID 
690 1 0 |a 3 (5 METHYL 1,3 DIOXOISOINDOLIN 2 YL) 3 (4 TOLYL)PROPANOIC ACID 
690 1 0 |a 3 (5 METHYL 1,3 DIOXOISOINDOLIN 2 YL) 3 (NAPHTHALEN 2 YL)PROPANOIC ACID 
690 1 0 |a 3 AMINO 3 (4 ETHYLPHENYL)PROPANOIC ACID 
690 1 0 |a 3 AMINO 3 (4 HYDROXYPHENYL)PROPANOIC ACID 
690 1 0 |a 3 AMINO 3 (4 METHOXYPHENYL)PROPANOIC ACID 
690 1 0 |a 3 AMINO 3 (4 NITROPHENYL)PROPANOIC ACID 
690 1 0 |a 3 AMINO 3 (4 TOLYL)PROPANOIC ACID 
690 1 0 |a 3 DEOXY 2,3 DIDEHYDRO N ACETYLNEURAMINIC ACID 
690 1 0 |a ANTITRYPANOSOMAL AGENT 
690 1 0 |a BENZNIDAZOLE 
690 1 0 |a NIFURTIMOX 
690 1 0 |a PHTHALOYL DERIVATIVE 
690 1 0 |a PROPIONIC ACID DERIVATIVE 
690 1 0 |a SIALIDASE INHIBITOR 
690 1 0 |a UNCLASSIFIED DRUG 
690 1 0 |a UNINDEXED DRUG 
690 1 0 |a ANTITRYPANOSOMAL AGENT 
690 1 0 |a GLYCOPROTEIN 
690 1 0 |a PROPIONIC ACID DERIVATIVE 
690 1 0 |a SIALIDASE 
690 1 0 |a TRANS-SIALIDASE 
690 1 0 |a ARTICLE 
690 1 0 |a BIOLOGICAL ACTIVITY 
690 1 0 |a CONTROLLED STUDY 
690 1 0 |a CRYSTAL STRUCTURE 
690 1 0 |a DRUG STRUCTURE 
690 1 0 |a DRUG SYNTHESIS 
690 1 0 |a ENZYME INHIBITION 
690 1 0 |a HYDROGEN BOND 
690 1 0 |a ION EXCHANGE CHROMATOGRAPHY 
690 1 0 |a LC50 
690 1 0 |a LYSIS 
690 1 0 |a MOLECULAR DOCKING 
690 1 0 |a NONHUMAN 
690 1 0 |a SIALYLATION 
690 1 0 |a TRYPANOSOMA CRUZI 
690 1 0 |a AMINATION 
690 1 0 |a ANTAGONISTS AND INHIBITORS 
690 1 0 |a CHAGAS DISEASE 
690 1 0 |a CHEMISTRY 
690 1 0 |a DRUG DESIGN 
690 1 0 |a DRUG EFFECT 
690 1 0 |a ENZYMOLOGY 
690 1 0 |a HUMAN 
690 1 0 |a METABOLISM 
690 1 0 |a MOLECULAR DOCKING 
690 1 0 |a PARASITOLOGY 
690 1 0 |a STRUCTURE ACTIVITY RELATION 
690 1 0 |a TRYPANOSOMA CRUZI 
690 1 0 |a AMINATION 
690 1 0 |a CHAGAS DISEASE 
690 1 0 |a DRUG DESIGN 
690 1 0 |a GLYCOPROTEINS 
690 1 0 |a HUMANS 
690 1 0 |a MOLECULAR DOCKING SIMULATION 
690 1 0 |a NEURAMINIDASE 
690 1 0 |a PROPIONATES 
690 1 0 |a STRUCTURE-ACTIVITY RELATIONSHIP 
690 1 0 |a TRYPANOCIDAL AGENTS 
690 1 0 |a TRYPANOSOMA CRUZI 
700 1 |a Chacón-Vargas, K.F. 
700 1 |a López-Cedillo, J.C. 
700 1 |a Nogueda-Torres, B. 
700 1 |a Paz-González, A.D. 
700 1 |a Ramírez-Moreno, E. 
700 1 |a Agusti, R. 
700 1 |a Uhrig, M.L. 
700 1 |a Reyes-Arellano, A. 
700 1 |a Peralta-Cruz, J. 
700 1 |a Ashfaq, M. 
700 1 |a Rivera, G. 
773 0 |d Elsevier Masson SAS, 2018  |g v. 156  |h pp. 252-268  |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-s2.0-85049568232&doi=10.1016%2fj.ejmech.2018.07.005&partnerID=40&md5=639ab5208f82cc4559930a36be7d3b0f  |y Registro en Scopus 
856 4 0 |u https://doi.org/10.1016/j.ejmech.2018.07.005  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_02235234_v156_n_p252_Kashif  |y Handle 
856 4 0 |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_02235234_v156_n_p252_Kashif  |y Registro en la Biblioteca Digital 
961 |a paper_02235234_v156_n_p252_Kashif  |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 86060 

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