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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Review Article

Hybrid Compounds in the Search for Alternative Chemotherapeutic Agents against Neglected Tropical Diseases

Author(s): Chonny Herrera Acevedo, Luciana Scotti*, Mateus F. Alves, Margareth de F.F.M. Diniz and Marcus Tullius Scotti

Volume 16, Issue 2, 2019

Page: [81 - 92] Pages: 12

DOI: 10.2174/1570178615666180402123057

Price: $65

Abstract

Neglected tropical diseases (NTDs) affect more than a billion people worldwide, mainly populations living in poverty conditions. More than 56% of annual NTD deaths are caused by Leishmaniasis, Sleeping sickness, and Chagas disease. For these three diseases, many problems have been observed with the chemotherapeutic drugs commonly used, these being mainly resistance, high toxicity, and low efficacy. In the search for alternative treatments, hybridization is an interesting approach, which generates new molecules by merging two pharmacophores and then looking for improvements in biological activity or reduced compound toxicity. Here, we review various studies that present such hybrid molecules with promising in vitro and in vivo activities against Leishmania and Trypanosoma parasites.

Keywords: Antiprotozoal activity, chagas disease, hybrid compounds, leishmaniasis, neglected tropical diseases, sleeping sickness.

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[1]
Khare, S.; Nagle, A.S.; Biggart, A.; Lai, Y.H.; Liang, F.; Davis, L.C.; Barnes, S.W.; Mathison, C.J.; Myburgh, E.; Gao, M.Y.; Gillespie, J.R.; Liu, X.; Tan, J.L.; Stinson, M.; Rivera, I.C.; Ballard, J.; Yeh, V.; Groessl, T.; Federe, G.; Koh, H.X.; Venable, J.D.; Bursulaya, B.; Shapiro, M.; Mishra, P.K.; Spraggon, G.; Brock, A.; Mottram, J.C.; Buckner, F.S.; Rao, S.P.; Wen, B.G.; Walker, J.R.; Tuntland, T.; Molteni, V.; Glynne, R.J.; Supek, F. Nature, 2016, 537(7619), 229-233.
[2]
Pearson, R.D.; Sousa, A.Q. Clin. Infect. Dis., 1996, 22(1), 1-13.
[3]
Herrera, A.C.; Scotti, L.; Feitosa, A.M.; Formiga, M.D.M.D.F.; Scotti, M.T. Molecules, 2017, 22(1), 79.
[4]
Burrows, J.N.; Elliott, R.L.; Kaneko, T.; Mowbray, C.E.; Waterson, D. MedChemComm, 2014, 5(6), 688-700.
[5]
Clementi, A.; Battaglia, G.; Floris, M.; Castellino, P.; Ronco, C.; Cruz, D.N. NDT Plus, 2011, 4(3), 147-152.
[6]
Shaw, C.D.; Lonchamp, J.; Downing, T.; Imamura, H.; Freeman, T.M.; Cotton, J.A.; Sanders, M.; Blackburn, G.; Dujardin, J.C.; Rijal, S.; Khanal, B.; Illingworth, C.J.; Coombs, G.H.; Carter, K.C. Mol. Microbiol., 2016, 99(6), 1134-1148.
[7]
Perez-Victoria, F.J.; Castanys, S.; Gamarro, F. Antimicrob. Agents Chemother., 2003, 47(8), 2397-2403.
[8]
Hendrickx, S.; Inocêncio da Luz, R.A.; Bhandari, V.; Kuypers, K.; Shaw, C.D.; Lonchamp, J.; Salotra, P.; Carter, K.; Sundar, S.; Rijal, S.; Dujardin, J-C.; Cos, P.; Maes, L. PLoS Negl. Trop. Dis., 2012, 6(5), e1664.
[9]
Singh, N.; Kumar, M.; Singh, R.K. Asian Pac. J. Trop. Med., 2012, 5(6), 485-497.
[10]
McGwire, B.S.; Satoskar, A.R. QJM, 2014, 107(1), 7-14.
[11]
Apt, W. Drug Des. Devel. Ther., 2010, 4, 243-253.
[12]
Viotti, R.; Vigliano, C.; Lococo, B.; Alvarez, M.G.; Petti, M.; Bertocchi, G.; Armenti, A. Expert Rev. Anti Infect. Ther., 2009, 7(2), 157-163.
[13]
Nok, A.J. Parasitol. Res., 2003, 90(1), 71-79.
[14]
Babokhov, P.; Sanyaolu, A.O.; Oyibo, W.A.; Fagbenro-Beyioku, A.F.; Iriemenam, N.C. Pathog. Glob. Health, 2013, 107(5), 242-252.
[15]
Barrett, M.P.; Boykin, D.W.; Brun, R.; Tidwell, R.R. Br. J. Pharmacol., 2007, 152(8), 1155-1171.
[16]
GBD 2013 Mortality and Causes of Death Collaborators. Lancet, 2015, 385(9963), 117-171.
[17]
Strub-Wourgaft, N. BMJ Glob. Health, 2017, 2(Suppl. 2), A4-A4.
[18]
Müller-Schiffmann, A.; Sticht, H.; Korth, C. BioDrugs, 2012, 26(1), 21-31.
[19]
de Oliveira Pedrosa, M.; Duarte da Cruz, R.M.; de Oliveira Viana, J.; de Moura, R.O.; Ishiki, H.M.; Barbosa, F.J.M.; Diniz, M.F.; Scotti, M.T.; Scotti, L.; Bezerra Mendonca, F.J. Curr. Top. Med. Chem., 2017, 17(9), 1044-1079.
[20]
Decker, M. Curr. Med. Chem., 2011, 18(10), 1464-1475.
[21]
Muregi, F.W.; Ishih, A. Drug Dev. Res., 2010, 71(1), 20-32.
[22]
Walsh, J.; Bell, A. Curr. Pharm. Des., 2009, 15(25), 2970-2985.
[23]
Sashidhara, K.V.; Kumar, A.; Kumar, M.; Sarkar, J.; Sinha, S. Bioorg. Med. Chem. Lett., 2010, 20(24), 7205-7211.
[24]
Belluti, F.; Fontana, G.; Dal Bo, L.; Carenini, N.; Giommarelli, C.; Zunino, F. Bioorg. Med. Chem., 2010, 18(10), 3543-3550.
[25]
Dechy‐Cabaret, O.; Benoit‐Vical, F.; Robert, A.; Meunier, B. ChemBioChem, 2000, 1(4), 281-283.
[26]
Walsh, J.J.; Coughlan, D.; Heneghan, N.; Gaynor, C.; Bell, A. Bioorg. Med. Chem. Lett., 2007, 17(13), 3599-3602.
[27]
Wang, Y.; Damu, G.L.; Lv, J-S.; Geng, R-X.; Yang, D-C.; Zhou, C-H. Bioorg. Med. Chem. Lett., 2012, 22(17), 5363-5366.
[28]
Michalska, P. Curr. Top. Med. Chem., 2016, 16, 1-17.
[29]
Dodd, R.H.; Ouannes, C.; Robert-Gero, M.; Potier, P. J. Med. Chem., 1989, 32(6), 1272-1276.
[30]
Bell, C.A.; Hall, J.E.; Kyle, D.E.; Grogl, M.; Ohemeng, K.A.; Allen, M.A.; Tidwell, R.R. Antimicrob. Agents Chemother., 1990, 34(7), 1381-1386.
[31]
Sundar, S.; Singh, A. Ther. Adv. Infect. Dis., 2016, 3(3-4), 98-109.
[32]
Bialonska, D.; Zjawiony, J.K. Mar. Drugs, 2009, 7(2), 166-183.
[33]
Porwal, S.; Chauhan, S.S.; Chauhan, P.M.S.; Shakya, N.; Verma, A.; Gupta, S. J. Med. Chem., 2009, 52(19), 5793-5802.
[34]
Costa, E.V.; Pinheiro, M.L.B.; Xavier, C.M.; Silva, J.R.; Amaral, A.C.F.; Souza, A.D.; Barison, A.; Campos, F.R.; Ferreira, A.G.; Machado, G.M. J. Nat. Prod., 2006, 69(2), 292-294.
[35]
Chen, M.; Christensen, S.B.; Blom, J.; Lemmich, E.; Nadelmann, L.; Fich, K.; Theander, T.G.; Kharazmi, A. Antimicrob. Agents Chemother., 1993, 37(12), 2550-2556.
[36]
Chen, M.; Christensen, S.B.; Theander, T.G.; Kharazmi, A. Antimicrob. Agents Chemother., 1994, 38(6), 1339-1344.
[37]
Junior, C.G.L.; de Assis, P.A.C.; Silva, F.P.L.; Sousa, S.C.O.; de Andrade, N.G.; Barbosa, T.P.; Nerís, P.L.N.; Segundo, L.V.G.; Anjos, Í.C.; Carvalho, G.A.U.; Rocha, G.B.; Oliveira, M.R.; Vasconcellos, M.L.A.A. Bioorg. Chem., 2010, 38(6), 279-284.
[38]
Barbosa, T.P.; Sousa, S.C.; Amorim, F.M.; Rodrigues, Y.K.; de Assis, P.A.; Caldas, J.P.; Oliveira, M.R.; Vasconcellos, M.L. Bioorg. Med. Chem., 2011, 19(14), 4250-4256.
[39]
Sharma, R.; Pandey, A.K.; Shivahare, R.; Srivastava, K.; Gupta, S.; Chauhan, P.M. Bioorg. Med. Chem. Lett., 2014, 24(1), 298-301.
[40]
Sunduru, N.; Agarwal, A.; Katiyar, S.B.; Goyal, N.; Gupta, S.; Chauhan, P.M.S. Bioorg. Med. Chem., 2006, 14(23), 7706-7715.
[41]
Gupta, L.; Sunduru, N.; Verma, A.; Srivastava, S.; Gupta, S.; Goyal, N.; Chauhan, P.M. Eur. J. Med. Chem., 2010, 45(6), 2359-2365.
[42]
Sharma, M.; Chauhan, K.; Shivahare, R.; Vishwakarma, P.; Suthar, M.K.; Sharma, A.; Gupta, S.; Saxena, J.K.; Lal, J.; Chandra, P.; Kumar, B.; Chauhan, P.M.S. J. Med. Chem., 2013, 56(11), 4374-4392.
[43]
Kumar, R.; Khan, S.; Verma, A.; Srivastava, S.; Viswakarma, P.; Gupta, S.; Meena, S.; Singh, N.; Sarkar, J.; Chauhan, P.M. Eur. J. Med. Chem., 2010, 45(8), 3274-3280.
[44]
Chauhan, S.S.; Gupta, L.; Mittal, M.; Vishwakarma, P.; Gupta, S.; Chauhan, P.M. Bioorg. Med. Chem. Lett., 2010, 20(21), 6191-6194.
[45]
Tovar, J.; Wilkinson, S.; Mottram, J.C.; Fairlamb, A.H. Mol. Microbiol., 1998, 29(2), 653-660.
[46]
Chauhan, S.S.; Pandey, S.; Shivahare, R.; Ramalingam, K.; Krishna, S.; Vishwakarma, P.; Siddiqi, M.I.; Gupta, S.; Goyal, N.; Chauhan, P.M.S. MedChemComm, 2015, 6(2), 351-356.
[47]
Kumar, S.; Bawa, S.; Gupta, H. Mini Rev. Med. Chem., 2009, 9(14), 1648-1654.
[48]
Michael, J.P. Nat. Prod. Rep., 2008, 25(1), 166-187.
[49]
Supong, K.; Thawai, C.; Supothina, S.; Auncharoen, P.; Pittayakhajonwut, P. Phytochem. Lett., 2016, 17, 100-106.
[50]
Faruk, K.M.O.; Levi, M.S.; Tekwani, B.L.; Wilson, N.H.; Borne, R.F. Bioorg. Med. Chem., 2007, 15(11), 3919-3925.
[51]
Nava-Zuazo, C.; Estrada-Soto, S.; Guerrero-Alvarez, J.; Leon-Rivera, I.; Molina-Salinas, G.M.; Said-Fernandez, S.; Chan-Bacab, M.J.; Cedillo-Rivera, R.; Moo-Puc, R.; Miron-Lopez, G.; Navarrete-Vazquez, G. Bioorg. Med. Chem. Lett., 2010, 18(17), 6398-6403.
[52]
Rando, D.G.; Avery, M.A.; Tekwani, B.L.; Khan, S.I.; Ferreira, E.I. Bioorg. Med. Chem., 2008, 16(14), 6724-6731.
[53]
Khan, K.M.; Rasheed, M.; Ullah, Z.; Hayat, S.; Kaukab, F.; Choudhary, M.I.; Rahman, A.; Perveen, S. Bioorg. Med. Chem., 2003, 11(7), 1381-1387.
[54]
Bernardino, A.M.R.; Gomes, A.O.; Charret, K.S.; Freitas, A.C.C.; Machado, G.M.C.; Canto-Cavalheiro, M.M.; Leon, L.L.; Amaral, V.F. Eur. J. Med. Chem., 2006, 41(1), 80-87.
[55]
Coa, J.C.; Castrillon, W.; Cardona, W.; Carda, M.; Ospina, V.; Munoz, J.A.; Velez, I.D.; Robledo, S.M. Eur. J. Med. Chem., 2015, 101, 746-753.
[56]
Chan, M.M.; Grogl, M.; Chen, C.C.; Bienen, E.J.; Fong, D. Proc. Natl. Acad. Sci. USA, 1993, 90(12), 5657-5661.
[57]
Chan, M.M.; Grogl, M.; Callahan, H.; Fong, D. Antimicrob. Agents Chemother., 1995, 39(7), 1609-1611.
[58]
Sundar, S.; Olliaro, P.L. Ther. Clin. Risk Manag., 2007, 3(5), 733-740.
[59]
Godinho, J.L.; Georgikopoulou, K.; Calogeropoulou, T.; de Souza, W.; Rodrigues, J.C. Exp. Parasitol., 2013, 135(1), 153-165.
[60]
Tiwari, A.; Kumar, S.; Shivahare, R.; Kant, P.; Gupta, S.; Suryawanshi, S.N. Bioorg. Med. Chem. Lett., 2015, 25(2), 410-413.
[61]
Porcal, W.P.H.; Boiani, M.; Aguirre, G.; Boiani, L.; Chidichimo, A.; Cazzulo, J.J.; Campillo, N.E.; Paez, J.A.; Castro, A.; Krauth-Siegel, R.L.; Davies, C.; Basombrio, M.A.; Gonzalez, M.; Cerecetto, H. J. Med. Chem., 2007, 50(24), 6004-6015.
[62]
Porcal, W.; Hernandez, P.; Aguirre, G.; Boiani, L.; Boiani, M.; Merlino, A.; Ferreira, A.; Maio, R.D.; Castro, A.; Gonzalez, M.; Cerecetto, H. Bioorg. Med. Chem, 2007. 15(0968-0896(Print)), 7
[63]
Aguirre, G.; Boiani, L.; Boiani, M.; Cerecetto, H.; Di Maio, R.; González, M.; Porcal, W.; Denicola, A.; Piro, O.E.; Castellano, E.E. Bioorg. Med. Chem., 2005, 13(23), 6336-6346.
[64]
Porcal, W.; Hernández, P.; Boiani, L.; Boiani, M.; Ferreira, A.; Chidichimo, A.; Cazzulo, J.J.; Olea-Azar, C.; González, M.; Cerecetto, H. Bioorg. Med. Chem., 2008, 16(14), 6995-7004.
[65]
Castro, D.; Boiani, L.; Benitez, D.; Hernández, P.; Merlino, A.; Gil, C.; Olea-Azar, C.; González, M.; Cerecetto, H.; Porcal, W. Eur. J. Med. Chem., 2009, 44(12), 5055-5065.
[66]
da Silva Júnior, E.N.; de Souza, M.C.B.; Fernandes, M.C.; Menna-Barreto, R.F.; Maria do Carmo, F.; de Assis Lopes, F.; de Simone, C.A.; Andrade, C.K.Z.; Pinto, A.V.; Ferreira, V.F. Bioorg. Med. Chem., 2008, 16(9), 5030-5038.
[67]
da Silva, E.N.; Menna-Barreto, R.F.; Maria do Carmo, F.; Silva, R.S.; Teixeira, D.V.; de Souza, M.C.B.; De Simone, C.A.; De Castro, S.L.; Ferreira, V.F.; Pinto, A.V. Eur. J. Med. Chem., 2008, 43(8), 1774-1780.
[68]
Alvarez, G.; Gerpe, A.; Benitez, D.; Garibotto, F.; Zacchino, S.; Graebin, C.S.; Rosa, R.G.D.; Eifler-Lima, V.L.; Gonzalez, M.; Cerecetto, H. Lett. Drug Des. Discov., 2010, 7(6), 452-460.
[69]
Romeiro, N.C.; Aguirre, G.; Hernandez, P.; Gonzalez, M.; Cerecetto, H.; Aldana, I.; Perez-Silanes, S.; Monge, A.; Barreiro, E.J.; Lima, L.M. Bioorg. Med. Chem., 2009, 17(2), 641-652.
[70]
Hernández, P.; Rojas, R.; Gilman, R.H.; Sauvain, M.; Lima, L.M.; Barreiro, E.J.; González, M.; Cerecetto, H. Eur. J. Med. Chem., 2013, 59, 64-74.
[71]
Massarico, S.R.A.; Gonçalves, J.E.; de Souza, F.P.; de Melo Loureiro, A.P.; Storpirtis, S.; Krogh, R.; Andricopulo, A.D.; Dias, L.C.; Ferreira, E.I. Eur. J. Med. Chem., 2014, 82, 418-425.
[72]
Marella, A.; Tanwar, O.P.; Saha, R.; Ali, M.R.; Srivastava, S.; Akhter, M.; Shaquiquzzaman, M.; Alam, M.M. Saudi Pharm. J., 2013, 21(1), 1-12.
[73]
Cretton, S.; Breant, L.; Pourrez, L.; Ambuehl, C.; Marcourt, L.; Ebrahimi, S.N.; Hamburger, M.; Perozzo, R.; Karimou, S.; Kaiser, M.; Cuendet, M.; Christen, P. J. Nat. Prod., 2014, 77(10), 2304-2311.
[74]
Lechuga, G.C.; Borges, J.C.; Calvet, C.M.; de Araújo, H.P.; Zuma, A.A.; do Nascimento, S.B.; Motta, M.C.M.; Bernardino, A.M.R.; Pereira, M.C.D.S.; Bourguignon, S.C. Int. J. Parasitol. Drug Resist, 2016, 6(3), 154-164.
[75]
Vazquez-Rodriguez, S.; Figueroa-Guinez, R.; Matos, M.J.; Santana, L.; Uriarte, E.; Lapier, M.; Maya, J.D.; Olea-Azar, C. MedChemComm, 2013, 4(6), 993-1000.
[76]
Vazquez-Rodriguez, S.; Guinez, R.F.; Matos, M.; Olea-Azar, C.; Maya, J.; Uriarte, E.; Santana, L.; Borges, F. Med. Chem., 2015, 5, 173-177.
[77]
Qiao, Z.; Wang, Q.; Zhang, F.; Wang, Z.; Bowling, T.; Nare, B.; Jacobs, R.T.; Zhang, J.; Ding, D.; Liu, Y.; Zhou, H. J. Med. Chem., 2012, 55(7), 3553-3557.
[78]
Audisio, D.; Messaoudi, S.; Cojean, S.; Peyrat, J-F.; Brion, J-D.; Bories, C.; Huteau, F.; Loiseau, P.M.; Alami, M. Eur. J. Med. Chem., 2012, 52, 44-50.
[79]
Roussaki, M.; Hall, B.; Lima, S.C.; da Silva, A.C.; Wilkinson, S.; Detsi, A. Bioorg. Med. Chem. Lett., 2013, 23(23), 6436-6441.
[80]
Havrylyuk, D.; Zimenkovsky, B.; Karpenko, O.; Grellier, P.; Lesyk, R. Eur. J. Med. Chem., 2014, 85, 245-254.
[81]
Tolle, N.; Kunick, C. Curr. Top. Med. Chem., 2011, 11(11), 1320-1332.
[82]
Reichwald, C.; Shimony, O.; Dunkel, U.; Sacerdoti-Sierra, N.; Jaffe, C.L.; Kunick, C. J. Med. Chem., 2008, 51(3), 659-665.
[83]
Ryczak, J.; Papini, M.A.; Lader, A.; Nasereddin, A.; Kopelyanskiy, D.; Preu, L.; Jaffe, C.L.; Kunick, C. Eur. J. Med. Chem., 2013, 64, 396-400.
[84]
Belluti, F.; Uliassi, E.; Veronesi, G.; Bergamini, C.; Kaiser, M.; Brun, R.; Viola, A.; Fato, R.; Michels, P.A.; Krauth‐Siegel, R.L. ChemMedChem, 2014, 9(2), 371-382.

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