Abstract
The aim of this literature review is to compile data of heterocyclic antigiardial agents. The importance is to analyze the structural requirements for improved antigiardial activity, to overcome resistance and enhance the bioavailability of the compounds under study. Though, nitroimidazoles/ imidazoles and benzimidazoles are major classes, other heterocyclic scaffolds viz. oxoindolinylidene, dioxodihydroisobenzofuran-5-carboxamide, fluoroquinolone, thieno[2,3-b]pyridine- 5-carbonitrile, α-amino-phosphonate analogs of polyoxins, nitazoxanide benzologue, thiazole and triazolyl- quinolone chalcone also possess activity against Giardia species. Heterocyclic phytoconstituents are also included to have a deep idea of antigiardial activity of herbs possessing heterocyclic constituents.
Keywords: Antigiardial, heterocyclic constituents, nitroimidazole, benzimidazole, phytoconstituents, giardiasis.
Graphical Abstract
[1]
Erlandsen, S.L.; Meyer, E.A. Giardia and Giardiasis: Biology, Pathogenesis, and Epidemiology, 1st ed; Springer Science & Business Media: New York, 1984.
[2]
Thompson, R.C. Giardiasis as a re-emerging infectious disease and its zoonotic potential. Int. J. Parasitol., 2000, 30(12-13), 1259-1267.
[4]
Savioli, L.; Smith, H.; Thompson, A. Giardia and Cryptosporidium join the ‘Neglected Diseases Initiative’. Trends Parasitol., 2006, 22(5), 203-208.
[5]
Merck manual, Veterinary Manual: Overview of Giardiasis (Giardosis,
Lambliasis, Lambliosis) By Sharon Patton http://www.merckvetmanual.com/digestive-system/giardiasis-giardia/overview-of-giardiasis (Accessed August 07, 2017).
[6]
Buret, A.; denHollander, N.; Wallis, P.M.; Befus, D.; Olson, M.E. Zoonotic potential of giardiasis in domestic ruminants. J. Infect. Dis., 1990, 162(1), 231-237.
[7]
Erlandsen, S.L.; Sherlock, L.A.; Januschka, M.; Schupp, D.G.; Schaefer, F.W., III; Jakubowski, W.; Bemrick, W.J. Cross-species transmission of Giardia spp.: Inoculation of beavers and muskrats with cysts of human, beaver, mouse, and muskrat origin. Appl. Environ. Microbiol., 1988, 54(11), 2777-2785.
[8]
Ey, P.L.; Bruderer, T.; Wehrli, C.; Köhler, P. Comparison of genetic groups determined by molecular and immunological analyses of Giardia isolated from animals and humans in Switzerland and Australia. Parasitol. Res., 1996, 82(1), 52-60.
[9]
Rendtorff, R.C. The experimental transmission of human intestinal protozoan parasites. II. Giardia lamblia cysts given in capsules. Am. J. Hyg., 1954, 59(2), 209-220.
[11]
Bean, N.H.; Goulding, J.S.; Lao, C.; Angulo, F.J. Surveillance for
foodborne-disease outbreaks—United States 1988–1992 Morb
Mortal Wkly Rep. CDC Surveillance Summaries, October 25. 1996. 45(NSS-5), 1-66.
[12]
Levine, W.C.; Smart, J.F.; Archer, D.L.; Bean, N.H.; Tauxe, R.V. Foodborne disease outbreaks in nursing homes, 1975 through 1987. JAMA, 1991, 266(15), 2105-2109.
[13]
Osterholm, M.T.; Forfang, J.C.; Ristinen, T.L.; Dean, A.G.; Washburn, J.W.; Godes, J.R.; Rude, R.A.; McCullough, J.G. An outbreak of foodborne giardiasis. N. Engl. J. Med., 1981, 304(1), 24-28.
[14]
Black, R.E.; Dykes, A.C.; Sinclair, S.P.; Wells, J.G. Giardiasis in day-care centers: evidence of person-to-person transmission. Pediatrics, 1977, 60(4), 486-491.
[15]
Gilman, R.H.; Marquis, G.S.; Miranda, E.; Vestegui, M.; Martinez, H. Rapid reinfection by Giardia lamblia after treatment in a hyperendemic Third World community. Lancet, 1988, 1(8581), 343-345.
[16]
Meyers, J.D.; Kuharic, H.A.; Holmes, K.K. Giardia lamblia infection in homosexual men. Br. J. Vener. Dis., 1977, 53(1), 54-55.
[17]
Hill, D.R. Giardiasis. Issues in diagnosis and management. Infect. Dis. Clin. North Am., 1993, 7(3), 503-525.
[18]
Bingham, A.K.; Meyer, E.A. Giardia excystation can be induced in vitro in acidic solutions. Nature, 1979, 277(5694), 301-302.
[19]
Hetsko, M.L.; McCaffery, J.M.; Svärd, S.G.; Meng, T.C.; Que, X.; Gillin, F.D. Cellular and transcriptional changes during excystation of Giardia lamblia in vitro. Exp. Parasitol., 1998, 88(3), 172-183.
[20]
Heyworth, M.F. Immunology of Giardia and Cryptosporidium infections. J. Infect. Dis., 1992, 166(3), 465-472.
[21]
Buret, A.; Gall, D.G.; Nation, P.N.; Olson, M.E. Intestinal protozoa
and epithelial cell kinetics, structure and function. Parasitol. Today
(Regul. Ed.), 1990, 6(12), 375-380.
[22]
Moore, G.T.; Cross, W.M.; McGuire, D.; Mollohan, C.S.; Gleason, N.N.; Healy, G.R.; Newton, L.H. Epidemic giardiasis at a ski resort. N. Engl. J. Med., 1969, 281(8), 402-407.
[23]
Farthing, M.J.G.; Mata, L.; Urrutia, J.J.; Kronmal, R.A. Natural history of Giardia infection of infants and children in rural Guatemala and its impact on physical growth. Am. J. Clin. Nutr., 1986, 43(3), 395-405.
[24]
Anderson, K.A.; Brooks, A.S.; Morrison, A.L.; Reid-Smith, R.J.; Martin, S.W.; Benn, D.M.; Peregrine, A.S. Impact of Giardia vaccination on asymptomatic Giardia infections in dogs at a research facility. Can. Vet. J., 2004, 45(11), 924-930.
[25]
Tracy, J.W.; Webster, L.T. Drugs used in the chemotherapy of protozoal infections. In:The pharmacological basis of therapeutics; Hardman, J.G.; Limbird, L.E., Eds.; New York, N.Y: McGraw-Hill Book Co., 1996, pp. 987-1008.
[26]
Darbon, A.; Portal, A.; Girier, L.; Pantin, J.; Leclaire, C. Traitement de la giardiase (lambliase) par le métronidazole. Presse Med., 1962, 70, 15-16.
[27]
Upcroft, P.; Upcroft, J.A. Drug targets and mechanisms of resistance in the anaerobic protozoa. Clin. Microbiol. Rev., 2001, 14(1), 150-164.
[29]
Cuckler, A.C.; Malanga, C.M.; Conroy, J. Therapeutic efficacy of new nitroimidazoles for experimental trichomoniasis, amebiasis, and trypanosomiasis. Am. J. Trop. Med. Hyg., 1970, 19(6), 916-925.
[30]
Giraldi, P.N.; Mariotti, V.; Nannini, G.; Tosolini, G.P.; Dradi, E.; Logemann, W.; De Carneri, I.; Monti, G. Studies on antiprotozoans. II. Synthesis and biological activity of some N-alkylamino-nitroimidazoles. Arzneimittelforschung, 1970, 20(1), 52-55.
[31]
Lemée, V.; Zaharia, I.; Nevez, G.; Rabodonirina, M.; Brasseur, P.; Ballet, J.J.; Favennec, L. Metronidazole and albendazole susceptibility of 11 clinical isolates of Giardia duodenalis from France. J. Antimicrob. Chemother., 2000, 46(5), 819-821.
[32]
Tejman-Yarden, N.; Millman, M.; Lauwaet, T.; Davids, B.J.; Gillin, F.D.; Dunn, L.; Upcroft, J.A.; Miyamoto, Y.; Eckmann, L. Impaired parasite attachment as fitness cost of metronidazole resistance in Giardia lamblia. Antimicrob. Agents Chemother., 2011, 55(10), 4643-4651.
[33]
Melloni, P.; Dradi, E.; Logemann, W.; De Carneri, I.; Trane, F. Synthesis and antiprotozoal activity of methylnitro derivatives of 2,2′-biimidazole. J. Med. Chem., 1972, 15(9), 926-930.
[34]
Upcroft, J.A.; Campbell, R.W.; Benakli, K.; Upcroft, P.; Vanelle, P. Efficacy of new 5-nitroimidazoles against metronidazole-susceptible and -resistant Giardia, Trichomonas, and Entamoeba spp. Antimicrob. Agents Chemother., 1999, 43(1), 73-76.
[35]
Lo´ pez Nigroa, M.M., Palermob, A.M., Mudryc, M.D., Carballo, M.A. Cytogenetic evaluation of two nitroimidazole derivatives. Toxicol. In Vitro, 2003, 17, 35-40.
[36]
Upcroft, J.A.; Dunn, L.A.; Wright, J.M.; Benakli, K.; Upcroft, P.; Vanelle, P. 5-Nitroimidazole drugs effective against metronidazole-resistant Trichomonas vaginalis and Giardia duodenalis. Antimicrob. Agents Chemother., 2006, 50(1), 344-347.
[37]
Khabnadideh, S.; Rezaei, Z. Khalafi, Nezhad, A., Motazedian, M.H., Eskandari, M. Synthesis of metronidazole derivatives as antigiardiasis agents. Daru, 2007, 15(1), 17-20.
[38]
Valdez, C.A.; Tripp, J.C.; Miyamoto, Y.; Kalisiak, J.; Hruz, P.; Andersen, Y.S.; Brown, S.E.; Kangas, K.; Arzu, L.V.; Davids, B.J.; Gillin, F.D.; Upcroft, J.A.; Upcroft, P.; Fokin, V.V.; Smith, D.K.; Sharpless, K.B.; Eckmann, L. Synthesis and electrochemistry of 2-ethenyl and 2-ethanyl derivatives of 5-nitroimidazole and antimicrobial activity against Giardia lamblia. J. Med. Chem., 2009, 52(13), 4038-4053.
[39]
Dunn, L.A.; Burgess, A.G.; Krauer, K.G.; Eckmann, L.; Vanelle, P.; Crozet, M.D.; Gillin, F.D.; Upcroft, P.; Upcroft, J.A. A new-generation 5-nitroimidazole can induce highly metronidazole-resistant Giardia lamblia in vitro. Int. J. Antimicrob. Agents, 2010, 36(1), 37-42.
[40]
Khabnadideh, S.; Rezaei, Z.; Motazedian, M.H.; Kohpeyma, J. Antigiardiais Effects of New Metronidazole Derivatives on Trophozoites in TYI-S-33. Indian J. Pharm. Sci., 2011, 7(3), 181-184.
[41]
Miyamoto, Y.; Kalisiak, J.; Korthals, K.; Lauwaet, T.; Cheung, D.Y.; Lozano, R.; Cobo, E.R.; Upcroft, P.; Upcroft, J.A.; Berg, D.E.; Gillin, F.D.; Fokin, V.V.; Sharpless, K.B.; Eckmann, L. Expanded therapeutic potential in activity space of next-generation 5-nitroimidazole antimicrobials with broad structural diversity. Proc. Natl. Acad. Sci. USA, 2013, 110(43), 17564-17569.
[42]
Jarrad, A.M.; Karoli, T.; Debnath, A.; Tay, C.Y.; Huang, J.X.; Kaeslin, G.; Elliott, A.G.; Miyamoto, Y.; Ramu, S.; Kavanagh, A.M.; Zuegg, J.; Eckmann, L.; Blaskovich, M.A.; Cooper, M.A. Metronidazole-triazole conjugates: activity against Clostridium difficile and parasites. Eur. J. Med. Chem., 2015, 101, 96-102.
[43]
Jarrad, A.M.; Debnath, A.; Miyamoto, Y.; Hansford, K.A.; Pelingon, R.; Butler, M.S.; Bains, T.; Karoli, T.; Blaskovich, M.A.; Eckmann, L.; Cooper, M.A. Nitroimidazole carboxamides as antiparasitic agents targeting Giardia lamblia, Entamoeba histolytica and Trichomonas vaginalis. Eur. J. Med. Chem., 2016, 120, 353-362.
[44]
Zhong, H.L.; Cao, W.J.; Rossignol, J.F.; Feng, M.L.; Hu, R.Y.; Gan, S.B.; Tan, W. Albendazole in nematode, cestode, trematode and protozoan (Giardia) infections. Chin. Med. J. (Engl.), 1986, 99(11), 912-915.
[45]
AI-Waili, N.S., Al-Waili, B.H., Saloom, K.Y. Therapeutic use of mebendazole in giardial infections. Trans. R. Soc. Trop. Moo. Hyg., 1988, 82, 438.
[46]
Edlind, T.D.; Hang, T.L.; Chakraborty, P.R. Activity of the anthelmintic benzimidazoles against Giardia lamblia in vitro. J. Infect. Dis., 1990, 162(6), 1408-1411.
[47]
Bell, C.A.; Dykstra, C.C.; Naiman, N.A.; Cory, M.; Fairley, T.A.; Tidwell, R.R. Structure-activity studies of dicationically substituted bis-benzimidazoles against Giardia lamblia: correlation of antigiardial activity with DNA binding affinity and giardial topoisomerase II inhibition. Antimicrob. Agents Chemother., 1993, 37(12), 2668-2673.
[48]
Xiao, L.; Saeed, K.; Herd, R.P. Efficacy of albendazole and fenbendazole against Giardia infection in cattle. Vet. Parasitol., 1996, 61(1-2), 165-170.
[49]
Valdez, J.; Cedillo, R.; Hernández-Campos, A.; Yépez, L.; Hernández-Luis, F.; Navarrete-Vázquez, G.; Tapia, A.; Cortés, R.; Hernández, M.; Castillo, R. Synthesis and antiparasitic activity of 1H-benzimidazole derivatives. Bioorg. Med. Chem. Lett., 2002, 12(16), 2221-2224.
[50]
Kazimierczuk, Z.; Upcroft, J.A.; Upcroft, P.; Górska, A.; Starościak, B.; Laudy, A. Synthesis, antiprotozoal and antibacterial activity of nitro- and halogeno-substituted benzimidazole derivatives. Acta Biochim. Pol., 2002, 49(1), 185-195.
[51]
Torres-Gómez, H.; Hernández-Núñez, E.; León-Rivera, I.; Guerrero-Alvarez, J.; Cedillo-Rivera, R.; Moo-Puc, R.; Argotte-Ramos, R. Rodríguez-Gutiérrez, Mdel.C.; Chan-Bacab, M.J.; Navarrete-Vázquez, G. Design, synthesis and in vitro antiprotozoal activity of benzimidazole-pentamidine hybrids. Bioorg. Med. Chem. Lett., 2008, 18(11), 3147-3151.
[52]
Valdez-Padilla, D.; Rodríguez-Morales, S.; Hernández-Campos, A.; Hernández-Luis, F.; Yépez-Mulia, L.; Tapia-Contreras, A.; Castillo, R. Synthesis and antiprotozoal activity of novel 1-methylbenzimidazole derivatives. Bioorg. Med. Chem., 2009, 17(4), 1724-1730.
[53]
Hernández-Luis, F.; Hernández-Campos, A.; Castillo, R.; Navarrete-Vázquez, G.; Soria-Arteche, O.; Hernández-Hernández, M.; Yépez-Mulia, L. Synthesis and biological activity of 2-(trifluoromethyl)-1H-benzimidazole derivatives against some protozoa and Trichinella spiralis. Eur. J. Med. Chem., 2010, 45(7), 3135-3141.
[54]
Laudy, A.E.; Moo-Puc, R.; Cedillo-Rivera, R.; Kazimierczuk, Z.; Orzeszko, A. Synthesis and Antimicrobial Activities of New Polyhalogenated Benzimidazoles. J. Heterocycl. Chem., 2012, 49(5), 1059-1065.
[55]
Wang, C.C.; Somoza, J.; Page, J.P.; Knegtel, R.M.A.; Kuntz, I.D.; Oshiro, C.M.; Skillman, A.G. Heterocyclic derivatives as inhibitors of purine salvage phosphoribosyltransferases US006075044A Jun
13, 2000.
[56]
Aronov, A.M.; Munagala, N.R.; Ortiz de Montellano, P.R.; Kuntz, I.D.; Wang, C.C. Substituted 4-phthalimidocarboxanilides as inhibitors
of purine salvage phosphoribosyltransferases US 6221877
B1, Apr 24, 2001.
[57]
Sousa, M.C.; Poiares-da-Silva, J. The cytotoxic effects of ciprofloxacin in Giardia lamblia trophozoites. Toxicol. In Vitro, 2001, 15(4-5), 297-301.
[58]
Bernardino, A.M.; da Silva Pinheiro, L.C.; Rodrigues, C.R.; Loureiro, N.I.; Castro, H.C.; Lanfredi-Rangel, A.; Sabatini-Lopes, J.; Borges, J.C.; Carvalho, J.M.; Romeiro, G.A.; Ferreira, V.F.; Frugulhetti, I.C.; Vannier-Santos, M.A. Design, synthesis, SAR, and biological evaluation of new 4-(phenylamino)thieno[2,3-b]pyridine derivatives. Bioorg. Med. Chem., 2006, 14(16), 5765-5770.
[59]
Cano, P.A.; Islas-Jácome, A.; González-Marrero, J.; Yépez-Mulia, L.; Calzada, F.; Gámez-Montaño, R. Synthesis of 3-tetrazolylmethyl-4H-chromen-4-ones via Ugi-azide and biological evaluation against Entamoeba histolytica, Giardia lamblia and Trichomona vaginalis. Bioorg. Med. Chem., 2014, 22(4), 1370-1376.
[60]
Staake, M.; Chauhan, J.; Zhou, D.; Shanker, A.; De Chatterjee, A.; Das, S.; Patterson, S.E. Phosphonoxins III: synthesis of α-aminophosphonate analogs of antifungal polyoxins with anti-Giardia activity. Org. Lett., 2010, 12(20), 4596-4599.
[61]
Chen, C.Z.; Kulakova, L.; Southall, N.; Marugan, J.J.; Galkin, A.; Austin, C.P.; Herzberg, O.; Zheng, W. High-throughput Giardia lamblia viability assay using bioluminescent ATP content measurements. Antimicrob. Agents Chemother., 2011, 55(2), 667-675.
[62]
Kulakova, L.; Galkin, A.; Chen, C.Z.; Southall, N.; Marugan, J.J.; Zheng, W.; Herzberg, O. Discovery of novel antigiardiasis drug candidates. Antimicrob. Agents Chemother., 2014, 58(12), 7303-7311.
[63]
Navarrete-Vazquez, G.; Chávez-Silva, F.; Argotte-Ramos, R. Rodríguez-Gutiérrez, Mdel.C.; Chan-Bacab, M.J.; Cedillo-Rivera, R.; Moo-Puc, R.; Hernández-Nuñez, E. Synthesis of benzologues of Nitazoxanide and Tizoxanide: a comparative study of their in vitro broad-spectrum antiprotozoal activity. Bioorg. Med. Chem. Lett., 2011, 21(10), 3168-3171.
[64]
Tejman-Yarden, N.; Miyamoto, Y.; Leitsch, D.; Santini, J.; Debnath, A.; Gut, J.; McKerrow, J.H.; Reed, S.L.; Eckmann, L. A reprofiled drug, auranofin, is effective against metronidazole-resistant Giardia lamblia. Antimicrob. Agents Chemother., 2013, 57(5), 2029-2035.
[65]
Nava-Zuazo, C.; Chávez-Silva, F.; Moo-Puc, R.; Chan-Bacab, M.J.; Ortega-Morales, B.O.; Moreno-Díaz, H.; Díaz-Coutiño, D.; Hernández-Núñez, E.; Navarrete-Vázquez, G. 2-acylamino-5-nitro-1,3-thiazoles: preparation and in vitro bioevaluation against four neglected protozoan parasites. Bioorg. Med. Chem., 2014, 22(5), 1626-1633.
[66]
Mocelo-Castell, R.; Villanueva-Novelo, C.; Cáceres-Castillo, D.; Carballo, R.M.; Quijano-Quiñones, R.F.; Quesadas-Rojas, M.; Cantillo-Ciau, Z.; Cedillo-Rivera, R.; Moo-Puc, R.E.; Moujir, L.M.; Mena-Rejón, G.J. 2-Amino-4-arylthiazole Derivatives as Anti-giardial Agents: Synthesis, Biological Evaluation and QSAR Studies. De Gruyter open. Open Chem., 2015, 13, 1127-1136.
[67]
Bahadur, V.; Mastronicola, D.; Singh, A.K.; Tiwari, H.K.; Pucillo, L.P.; Sarti, P.; Singh, B.K.; Giuffrè, A. Antigiardial activity of novel triazolyl-quinolone-based chalcone derivatives: when oxygen makes the difference. Front. Microbiol., 2015, 6, 256.
[68]
Santos, M.F.C.; Harper, P.M.; Williams, D.E.; Mesquita, J.T.; Pinto, É.G.; da Costa-Silva, T.A.; Hajdu, E.; Ferreira, A.G.; Santos, R.A.; Murphy, P.J.; Andersen, R.J.; Tempone, A.G.; Berlinck, R.G.S. Anti-parasitic Guanidine and Pyrimidine Alkaloids from the Marine Sponge Monanchora arbuscula. J. Nat. Prod., 2015, 78(5), 1101-1112.
[69]
Wright, C.W.; Anderson, M.M.; Allen, D.; Phillipson, J.D.; Kirby, G.C.; Warhurst, D.C.; Chang, H.R. Quassinoids exhibit greater selectivity against Plasmodium falciparum than against Entamoeba histolytica, Giardia intestinalis or Toxoplasma gondii in vitro. J. Eukaryot. Microbiol., 1993, 40(3), 244-246.
[70]
Gillin, F.D.; Reiner, D.S.; Suffness, M. Bruceantin, a potent amoebicide from a plant, Brucea antidysenterica. Antimicrob. Agents Chemother., 1982, 22(2), 342-345.
[71]
Calzada, F.; Alanis, A.D.; Meckes, M.; Tapia-Contreras, A.; Cedillo-Rivera, R. In vitro susceptibility of Entamoeba histolytica and Giardia lamblia to some medicinal plants used by the people of southern Mexico. Phytother. Res., 1998, 12, 70-72.
[72]
Calzada, F.; Cerda-García-Rojas, C.M.; Meckes, M.; Cedillo-Rivera, R.; Bye, R.; Mata, R. Geranins A and B, new antiprotozoal A-type proanthocyanidins from Geranium niveum. J. Nat. Prod., 1999, 62(5), 705-709.
[73]
Calzada, F.; Cedillo-Rivera, R.; Bye, R.; Mata, R. Geranins C and D, additional new antiprotozoal A-type proanthocyanidins from Geranium niveum. Planta Med., 2001, 67(7), 677-680.
[74]
Calzada, F.; Meckes, M.; Cedillo-Rivera, R.; Tapia-Contreras, A.; Mata, R. Screening of Mexican medicinal plants for antiprotozoal activity. Pharm. Biol., 1998, 36, 305-309.
[75]
Calzada, F.; Meckes, M.; Cedillo-Rivera, R. Antiamoebic and antigiardial activity of plant flavonoids. Planta Med., 1999, 65(1), 78-80.
[76]
Calzada, F.; Cedillo-Rivera, R.; Mata, R. Antiprotozoal activity of the constituents of Conyza filaginoides. J. Nat. Prod., 2001, 64(5), 671-673.
[77]
Calzada, F.; Velázquez, C.; Cedillo-Rivera, R.; Esquivel, B. Antiprotozoal activity of the constituents of Teloxys graveolens. Phytother. Res., 2003, 17(7), 731-732.
[78]
Calzada, F. Additional antiprotozoal constituents from Cuphea pinetorum, a plant used in Mayan traditional medicine to treat diarrhoea. Phytother. Res., 2005, 19(8), 725-727.
[79]
Calzada, F.; Cervantes-Martínez, J.A.; Yépez-Mulia, L. In vitro antiprotozoal activity from the roots of Geranium mexicanum and its constituents on Entamoeba histolytica and Giardia lamblia. J. Ethnopharmacol., 2005, 98(1-2), 191-193.
[80]
Calzada, F.; Yépez-Mulia, L.; Aguilar, A. In vitro susceptibility of Entamoeba histolytica and Giardia lamblia to plants used in Mexican traditional medicine for the treatment of gastrointestinal disorders. J. Ethnopharmacol., 2006, 108(3), 367-370.
[81]
Alanís, A.D.; Calzada, F.; Cedillo-Rivera, R.; Meckes, M. Antiprotozoal activity of the constituents of Rubus coriifolius. Phytother. Res., 2003, 17(6), 681-682.
[82]
Arrieta, J.; Reyes, B.; Calzada, F.; Cedillo-Rivera, R.; Navarrete, A. Amoebicidal and giardicidal compounds from the leaves of Zanthoxylum liebmannianun. Fitoterapia, 2001, 72(3), 295-297.
[83]
Khan, I.A.; Avery, M.A.; Burandt, C.L.; Goins, D.K.; Mikell, J.R.; Nash, T.E.; Azadegan, A.; Walker, L.A. Antigiardial activity of isoflavones from Dalbergia frutescens bark. J. Nat. Prod., 2000, 63(10), 1414-1416.
[84]
Wright, C.W.; Allen, D.; Phillipson, J.D.; Kirby, G.C.; Warhurst, D.C.; Massiot, G.; Le Men-Olivier, L. Alstonia species: are they effective in malaria treatment? J. Ethnopharmacol., 1993, 40(1), 41-45.
[85]
Wright, C.W.; Allen, D.; Cai, Y.; Chen, Z.P.; Phillipson, J.D.; Kirby, G.C.; Warhurst, D.C.; Tits, M.; Angenot, L. Selective antiprotozoal activity of some Strychnos alkaloids. Parasitol. Res., 1994, 8, 149-152.
[86]
Kaneda, Y.; Tanaka, T.; Saw, T. Effects of berberine, a plant alkaloid, on the growth of anaerobic protozoa in axenic culture. Tokai J. Exp. Clin. Med., 1990, 15(6), 417-423.
[87]
Tripathi, D.M.; Gupta, N.; Lakshmi, V.; Saxena, K.C.; Agrawal, A.K. Antigiardial and immunostimulatory effect of Piper longum on giardiasis due to Giardia lamblia. Phytother. Res., 1999, 13(7), 561-565.
Related Journals
Anti-Cancer Agents in Medicinal Chemistry
Anti-Inflammatory & Anti-Allergy Agents in Medicinal Chemistry
Current Drug Safety
Current Drug Targets
Current Organic Chemistry
Current Organic Synthesis
Mini-Reviews in Organic Chemistry
Letters in Organic Chemistry
Letters in Drug Design & Discovery
Current Drug Discovery Technologies
Related Books
Advances in Organic Synthesis
Frontiers in Drug Design and Discovery
The Synthetic Methods, Structures, and Properties of the Ca-C σ Bond Organocalcium Containing Compounds
Advances in Organic Synthesis
Chemistry of Bipyrazoles: Synthesis and Applications
Frontiers in Cardiovascular Drug Discovery
Advances in Organic Synthesis
Advanced Nanocatalysis for Organic Synthesis and Electroanalysis
Frontiers in Drug Design and Discovery
Advances in Organic Synthesis
Article Metrics
70
2