Some heterocyclic thione derivatives exhibit anticoccidial activity by inhibiting glycosidases

• Autorzy: Balbaa M. , El-Hady N. A. , Taha N. , El Ashry E. S. H.
• Języki publikacji: EN

Abstrakty

EN

 Coccidiosis is one of the most common parasitic diseases affecting many species of domestic animals. This disease has a major economic significance and the search for new compounds having anticoccidial activity is of great importance. In this article, different levels of protection from coccidian infection by Eimeria stiedae were developed in rabbits by treatment with compounds incorporating the skeleton of thiourea. These compounds include 4,5-diphenylimidazole-2-thione (1), 4,5-Diphenyl-1,2,4-triazole-3-thiol (2) and 5-(2-Hydroxyphenyl)-4-phenyl-1,2,4-triazole-3-thiol (3) compared to the anticoccidial drug toltrazuril as a reference compound. Compounds 1-3 inhibit coccidiosis-induced activity of α-glucosidase. The protection from coccidial infection by compound 1 was higher than that shown for compounds 2 and 3. These data suggest that diazole and triazole thione derivatives have a mimetic effect for anticoccidial drugs through their inhibition of glycosidases.

• Wydawca: -
• Czasopismo: Acta Biochimica Polonica
• Rocznik: 2012
• Tom: 59
• Numer: 4
• Opis fizyczny: p.575-580,fig.,ref.

Twórcy

autor

Balbaa M.

• Biochemistry Department, Faculty of Science, Alexandria University, Alexandria, Egypt

autor

El-Hady N. A.

• Biochemistry Department, Faculty of Science, Alexandria University, Alexandria, Egypt

autor

Taha N.

• Biochemistry Department, Edfina Faculty of Veterinary Medicine, Alexandria University, Alexandria, Egypt

autor

El Ashry E. S. H.

• Chemistry Department, Faculty of Science, Alexandria University, Alexandria, Egypt

Bibliografia

• Abdel Megeed KN, Abuel Ezz NM, Abdel-Rahman EH (2005) Protective effect of Eimeria stiedae coproantigen against hepatic coccidiosis in rabbits. J Egypt Soc Parasitol 35: 581-595. 
• Adams C, Vahl HA, Veldman A (1996) Interaction between nutrition and Eimeria acervulina infection in broiler chickens: diet compositions that improve fat digestion during Eimeria acervulina infection. Br J Nutr 75: 867-873. 
• Baghdadi HB, Al-Mathal EM (2010) Anti-coccidial effect of Commiphora molmol in the domestic rabbit (Oryctolagus cuniculus domesticus L.). J Egypt Soc Parasitol 40: 653-668. 
• Balba M, El-Hady NA, Taha N, Rezki N, El Ashry el SH (2011) Inhibition of α-glucosidase and α-amylase by diaryl derivatives of imidazole-thione and 1,2,4-triazole-thiol. Eur J Med Chem 46: 2596-2601. 
• Balbaa M, Mansour H, El-Sawy H, El-Ashry el-SH (2002) Inhibition of some hepatic glycosidases by the diseco nucleoside, 4-amino-3-(d-glucopentitol-1-yl)-5-mercapto-1,2,4-triazole and its 3-methyl analog. Nucleosides Nucleotides Nucleic Acids 21: 695-708. 
• Bernfeld P (1995) Amylases, alpha and beta. Methods Enzymol 1: 149-158.
• Biftu T, Feng D, Ponpipom M, Girotra N, Liang GB, Qian X, Bugianesi R, Simeone J, Chang L, Gurnett A, Liberator P, Dulski P, Leavitt PS, Crumley T, Misura A, Murphy T, Rattray S, Samaras S, Tamas T, Mathew J, Brown C, Thompson D, Schmatz D, Fisher M, Wyvratt M (2005) Synthesis and SAR of 2,3-diarylpyrrole inhibitors of parasite cGMP-dependent protein kinase as novel anticoccidial agents. Bioorg Med Chem Lett 15: 3296-3301. 
• Cam Y, Atasever A, Eraslan G, Kibar M, Atalay O, Beyaz L, Inci A, Liman BC (2008) Eimeria stiedae: experimental infection in rabbits and the effect of treatment with toltrazuril and ivermectin. Exp Parasitol 119: 164-172. 
• Dahlqvist A (1970) Assay of intestinal disaccharidases. Enzymol Biol Clin 11: 52-56. 
• Drouet-Viard F, Coudert P, Licois D, Boivin M (1997) Vaccination against Eimeria magna coccidiosis using spray dispersion of precocious line oocysts in the nest box. Vet Parasitol 70: 61-66. 
• El-Ashry ESH, Rashed N, Awad LF, Ramadan E, Abdel-Maggeed SM, Rezki N (2008) Synthesis of 5-aryl-3-glycosylthio-4-phenyl-4h-1,2,4-triazoles and their acyclic analogs under conventional and microwave conditions. J Carbohydr Chem 27: 70-85.
• El-Ashry ESH, Rashed N, Awad LF, Ramadan E, Abdel-Maggeed SM, Rezki N (2007) MAOS versus conventional synthesis of 4,5-di- and 3,4,5-triphenylimidazole-2-thione and their derivatives. ARKIVOC vii: 30-40.
• Fischer EA, Stein EA (1961) α-Amylase from human saliva. Biochem Prep 8: 27-32.
• Goffard A, Callens N, Bartosch B, Wychowski C, Cosset FL, Montpellier C, Dubuisson J (2005) Role of N-linked glycans in the functions of hepatitis C virus envelope glycoproteins. J Virol 79: 8400-8409. 
• Haberkorn A, Mundt HC (1999) Investigation with a broad spectrum anticoccidial agent. Prakt Tierarzt 69: 49-51.
• Hauptman K, Tichy F, Knotek Z (2001) Clinical diagnostics of hepatopathies in small mammals: evaluation of importance of individual methods. Acta Vet Brno 70: 297-311.
• Helenius A, Aebi M (2001) Intracellular functions of N-linked glycans. Science 291: 2364-2369. 
• Jenkins MC, Seferian PG, Augustine PC, Danforth HD (1993) Protective immunity against coccidiosis elicited by radiation attenuated Eimeria maxima, sporozoites that are incapable a sexual development. Avian Dis 37: 74-82. 
• Kudweis M , Lojda Z, Julis I (1991) Beta-d-glucosidase in the microvillous zone of small intestine enterocytes in experimental coccidiosis in suckling piglets. Vet Med (Praha) 36: 225-234. 
• Long G, Westenberg M, Wang H, Vlak JM, Hu Z (2006) Function, oligomerization and N-linked glycosylation of the helicoverpa armigera single nucleopolyhedrovirus envelope fusion protein. J Gen Virol 87: 839-846. 
• Major JR Jr, Ruff MD (1978) Disaccharidase activity in the intestinal tissue of broilers infected with coccidia. J Parasitol 64: 706-711. 
• Mathis GF, Froyman R, Kennedy T (2004) Coccidiosis control by administering toltrazuril in the drinking water for 2-day period. Vet Parasitol 121: 1-9. 
• Horton-Smith C (1947) The treatment of hepatic coccidiosis in rabbits. Br Vet J 103: 207-213. 
• Nadanaka S, Yoshida H, Kano F, Murata M, Mori K (2004) Activation of mammalian unfolded protein response is compatible with the quality control system operating in the endoplasmic reticulum. Mol Biol Cell 15: 2537-2548. 
• Pakes SP, Gerrity LW (1994) Protozoal diseases. In The Biology of the Laboratory Rabbit, 2nd edn, pp 205-30, Academic Press, London.
• Pommier P, Keita A, Wessel-Robert S, Dellac B, Mundt HC (2003) Efficacy of toltrazuril in the prevention and the treatment of suckling piglets coccidiosis: Results of two field trials. Rev Med Vet 154: 41-46.
• Sabrina M, Shoaa Abdul R (2001) Novel compounds, specifically aromatic and heteroaromatic ureas and thioureas, useful against parasites and especially against coccidiosis. PCT Int Appl 12: 72-77.
• Scribner A, Meitz S, Fisher M, Wyvratt M, Leavitt P, Liberator P, Gurnett A, Brown C, Mathew J, Thompson D, Schmatz D, Biftu T (2008) Synthesis and biological activity of anticoccidial agents: 5,6-Diarylimidazo[2,1-b][1,3]thiazoles. Bioorg Med Chem Lett 18: 5263-5267. 
• Scribner A, Moore JA 3rd, Ouvry G, Fisher M, Wyvratt M, Leavitt P, Liberator P, Gurnett A, Brown C, Mathew J, Thompson D, Schmatz D, Biftu T (2009) Synthesis and biological activity of anticoccidial agents: 2,3-diarylindoles. Bioorg Med Chem Lett 19: 1517-1521. 
• Singla LD, Juyal PD, Sandhu BS (2000) Pathology and therapy in naturally Eimeria stiedae - infected rabbits. J Protozoal Res 10: 185-191.
• Tinder P (1969) Determination of blood glucose using an oxidase-peroxidase system with non carcinogenic chromogen. Ann Clin Biochem 6: 24-29.
• Talebi A, Mulcahy G (1995) Cross-reactivity among antisera raised against five avian Eimera species in the natural host and in rabbits. Avian Pathol 24: 533-544. 
• Torrelles JB, Azad AK, Schlesinger LS (2006) Fine discrimination in the recognition of individual species of phosphatidylmyo-inositol mannosides from mycobacterium tuberculosis by C-type lectin pattern recognition receptors. J Immunol 177: 1805-1816. 
• Tsuyosh Ohnishi S, James K. Barr (1978) A simplified method of quantitating protein using the biuret and phenol reagent. Anal Biochem 86: 193-200. 
• Wang YY, Yan CR, Weng YB, Jin H, Chen H (2009) Synthesis and anticoccidial activities of novel ethyl 6-aryloxy-7-bromo-4-hydroxy-3-quinolinecarboxylate against Eimeria tenella. Pest Biochem Physiol 93: 85-90.
• Yusa A, Kitajima K, Habuchi O (2006) N-Linked oligosaccharides on chondroitin 6-sulfotransferase-1 are required for production of the active anzyme, Golgi localization, and sulfotransferase activity toward keratan sulfate. J Biol Chem 281: 20393-20403. 
• Zhao W, Li T, Woodward R, Xia C, Wang PG, Guan W (2010) Enzymatic synthesis of complex carbohydrates. In Comprehensive natural products chemistry II: Carbohydrates, nucleosides & nucleic acids. Mander L, Liu HW eds, pp. 5-54. Elsevier, Oxford.

Uwagi

rekord w opracowaniu