In vitro antileishmanial activity of trans-stilbene and terphenyl compounds

Experimental Parasitology

Volumn 166, Issue , 2016, Pages 1-9

  Castelli, Germano ^a   Bruno, Federica ^a   Vitale, Fabrizio ^a   Roberti, Marinella ^b   Colomba, Claudia ^d   Giacomini, Elisa ^c   Guidotti, Laura ^b   Cascio, Antonio ^d   Tolomeo, Manlio ^d  

^a ISTITUTO ZOOPROFILATTICO SPERIMENTALE DELLA SICILIA A MIRRI   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

^c ISTITUTO ITALIANO DI TECNOLOGIA   (Italy)

^d UNIVERSITY OF PALERMO   (Italy)

Author keywords

Leishmaniasis; Programmed cell death; Stilbenes; Terphenyls

Indexed keywords

3,4',5 TRIMETHOXY 3' AMINO STILBENE; RESVERATROL; STIBOGLUCONATE SODIUM; STILBENE 2; STILBENE 3; STILBENE 4; STILBENE 5; STILBENE DERIVATIVE; TERPHENYL 10; TERPHENYL 11; TERPHENYL 12; TERPHENYL 6; TERPHENYL 7; TERPHENYL 8; TERPHENYL 9; TERPHENYL DERIVATIVE; UNCLASSIFIED DRUG; ANTIPROTOZOAL AGENT;

AMASTIGOTE; ANTIMICROBIAL ACTIVITY; APOPTOSIS; ARTICLE; CELL ADHESION; CELL CYCLE REGULATION; CELL DEATH; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG DETERMINATION; EPITHELIUM CELL; HUMAN; HUMAN CELL; IN VITRO STUDY; INCUBATION TIME; LEISHMANIA INFANTUM; MACROPHAGE; MTT ASSAY; NONHUMAN; PRIORITY JOURNAL; PROMASTIGOTE; STRUCTURE ACTIVITY RELATION; ANIMAL; CELL CYCLE; CERCOPITHECUS; CHEMISTRY; CYTOLOGY; DRUG EFFECTS; FLOW CYTOMETRY; FLUORESCENCE MICROSCOPY; GROWTH, DEVELOPMENT AND AGING; IC50; PARASITOLOGY; U-937 CELL LINE;

ANIMALS; ANTIPROTOZOAL AGENTS; APOPTOSIS; CELL CYCLE; CERCOPITHECUS; EPITHELIAL CELLS; FLOW CYTOMETRY; HUMANS; INHIBITORY CONCENTRATION 50; LEISHMANIA INFANTUM; MACROPHAGES; MICROSCOPY, FLUORESCENCE; STILBENES; STRUCTURE-ACTIVITY RELATIONSHIP; TERPHENYL COMPOUNDS; U937 CELLS;

EID: 85018250688     PISSN: 00144894     EISSN: 10902449     Source Type: Journal    
DOI: 10.1016/j.exppara.2016.03.007     Document Type: Article

References (45)

1. Azzouz, S., Maache, M., Garcia, R.G., Osuna, A., Leishmanicidal activity of edelfosine, miltefosine and ilmofosine. Basic Clin. Pharmacol. Toxicol. 96 (2005), 60–65.
2. Baur, J.A., Sinclair, D.A., Therapeutic potential of resveratrol: the in vivo evidence. Nat. Rev. Drug Discov. 5 (2006), 493–506.
3. Brotherton, M.C., Bourassa, S., Legare, D., Poirier, G.G., Droit, A., Ouellette, M., Quantitative proteomic analysis of amphotericin B resistance in Leishmania infantum. Int. J. Parasitol. Drugs Drug Resist. 4 (2014), 126–132.
4. Castelli, G., Galante, A., Lo Verde, V., Migliazzo, A., Reale, S., Lupo, T., Piazza, M., Vitale, F., Bruno, F., Evaluation of two modified culture media for Leishmania infantum cultivation versus different culture media. J. Parasitol. 100 (2014), 228–230.
5. Changtam, C., de Koning, H.P., Ibrahim, H., Sajid, M.S., Gould, M.K., Suksamrarn, A., Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species. Eur. J. Med. Chem. 45 (2010), 941–956.
6. Croft, S.L., Seifert, K., Yardley, V., Current scenario of drug development for leishmaniasis. Indian J. Med. Res. 123 (2006), 399–410.
7. de Almeida Machado, P., Zamprogno Mota, V., de Lima Cavalli, A.C., Gonçalves de Carvalho, G.S., Da Silva, A.D., Gameiro, J., Cuin, A., Soares Coimbra, E., High selective antileishmanial activity of vanadium complex with stilbene derivative. Acta Trop. 148 (2015), 120–127.
8. De Souza Leao, S., Lang, T., Prina, E., Hellio, R., Antoine, J.C., Intracellular Leishmania amazonensis amastigotes internalize and degrade MHC class II molecules of their host cells. J. Cell Sci. 108 (1995), 3219–3231.
9. del Olmo, E., Armas, M.G., Lopez-Perez, J.L., Munoz, V., Deharo, E., San Feliciano, A., Leishmanicidal activity of some stilbenoids and related heterocyclic compounds. Bioorg. Med. Chem. Lett. 11 (2001), 2123–2126.
10. del Rey, B., Ramos, A.C., Caballero, E., Inchaustti, A., Yaluff, G., Medarde, M., Rojas de Arias, A., San Feliciano, A., Leishmanicidal activity of combretastatin analogues and heteroanalogues. Bioorg. Med. Chem. Lett. 9 (1999), 2711–2714.
11. Duarte, N., Kayser, O., Abreu, P., Ferreira, M.J., Antileishmanial activity of piceatannol isolated from Euphorbia lagascae seeds. Phytother. Res. 22 (2008), 455–457.
12. Dutta, S., Ray, D., Kolli, B.K., Chang, K.P., Photodynamic sensitization of Leishmania amazonensis in both extracellular and intracellular stages with aluminum phthalocyanine chloride for photolysis in vitro. Antimicrob. Agents Chemother. 49 (2005), 4474–4484.
13. Ferreiraa, C., Soaresa, D.C., Cunha do Nascimentoa, M.T., Pinto-da-Silvab, L.H., Galvão Sarzedasc, C., Wanderley Tinococ, L., Elvira Maria Saraivaa, E.M., Resveratrol is active against Leishmania amazonensis: in vitro effect of its association with Amphotericin B. Antimicrob. Agents Chemother. 58 (2014), 6197–6208.
14. Fremont, L., Biological effects of resveratrol. Life Sci. 66 (2000), 663–673.
15. Fuchino, H., Kiuchi, F., Yamanaka, A., Obu, A., Wada, H., Mori-Yasumoto, K., Kawahara, N., Flores, D., Palacios, O., Sekita, S., Satake, M., New leishmanicidal stilbenes from a Peruvian folk medicine, Lonchocarpus nicou. Chem. Pharm. Bull. (Tokyo) 61 (2013), 979–982.
16. Getti, G.T., Aslam, S.N., Humber, D.P., Stevenson, P.C., Cheke, R.A., The effect of cicerfuran, an arylbenzofuran from Cicer bijugum, and related benzofurans and stilbenes on Leishmania aethiopica, L. tropica and L. major. Planta Med. 72 (2006), 907–911.
17. Hart, J.H., Roloe of phytostilbenes in decay and disease resistance. Ann. Rev. Phytopathol. 19 (1981), 437–458.
18. Herwaldt, B.L., Miltefosine–the long-awaited therapy for visceral leishmaniasis?. N. Engl. J. Med. 341 (1999), 1840–1842.
19. Hussain, H., Al-Harrasi, A., Al-Rawahi, A., Green, I.R., Gibbons, S., Fruitful decade for antileishmanial compounds from 2002 to late 2011. Chem. Rev. 114 (2014), 10369–10428.
20. Kedzierski, L., Curtis, J.M., Kaminska, M., Jodynis-Liebert, J., Murias, M., In vitro antileishmanial activity of resveratrol and its hydroxylated analogues against Leishmania major promastigotes and amastigotes. Parasitol. Res. 102 (2007), 91–97.
21. Kee, H.J., Park, S., Kang, W., Lim, K.S., Kim, J.H., Ahn, Y., Jeong, M.H., Piceatannol attenuates cardiac hypertrophy in an animal model through regulation of the expression and binding of the transcription factor GATA binding factor 6. FEBS Lett. 588 (2014), 1529–1536.
22. Kim, S., Ko, H., Park, J.E., Jung, S., Lee, S.K., Chun, Y.J., Design, synthesis, and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P450 1B1 inhibitors. J. Med. Chem. 45 (2002), 160–164.
23. Li, D.D., Zhao, L.X., Mylonakis, E., Hu, G.H., Zou, Y., Huang, T.K., Yan, L., Wang, Y., Jiang, Y.Y., In vitro and in vivo activities of pterostilbene against Candida albicans biofilms. Antimicrob. Agents Chemother. 58 (2014), 2344–2355.
24. Liegler, T.J., Hyun, W., Yen, T.S.B., Stites, D.P., Detection and quantification of live, apoptotic, and necrotic human peripheral lymphocytes by single-laser flow cytometry. Clin. Diagn. Lab. Immunol. 2 (1995), 369–376.
25. Lucas, I.K., Kolodziej, H., In vitro antileishmanial activity of resveratrol originates from its cytotoxic potential against host cells. Planta Med. 79 (2013), 20–26.
26. Maia, C., Rolão, N., Nunes, M., Gonçalves, L., Campino, L., Infectivity of five different types of macrophages by Leishmania infantum. Acta Trop. 103 (2007), 150–155.
27. Marin, C., Boutaleb-Charki, S., Diaz, J.G., Huertas, O., Rosales, M.J., Perez-Cordon, G., Guitierrez-Sanchez, R., Sanchez-Moreno, M., Antileishmaniasis activity of flavonoids from Consolida oliveriana. J. Nat. Prod. 72 (2009), 1069–1074.
28. Metzler, M., Metabolic activation of diethylstilbestrol. Indirect evidence for the formation of a stilbene oxide intermediate in hamster and rat. Biochem. Pharmacol. 24 (1975), 1449–1453.
29. Metzler, M., Neumann, H.G., Epoxidation of the stilbene double bond, a major pathway in aminostilbene metabolism. Xenobiotica 7 (1977), 117–132.
30. Mishra, B.B., Kale, R.R., Singh, R.K., Tiwari, V.K., Alkaloids: future prospective to combat leishmaniasis. Fitoterapia 80 (2009), 81–90.
31. Mishra, B.B., Singh, R.K., Srivastava, A., Tripathi, V.J., Tiwari, V.K., Fighting against Leishmaniasis: search of alkaloids as future true potential anti-Leishmanial agents. Mini Rev. Med. Chem. 9 (2009), 107–123.
32. Monzote, L., Current treatment of leishmaniasis: a review. Open Antimicrob. Agents J. 1 (2009), 9–19.
33. Pizzirani, D., Roberti, M., Cavalli, A., Grimaudo, S., Di Cristina, A., Pipitone, R.M., Gebbia, N., Tolomeo, M., Recanatini, M., Antiproliferative agents that interfere with the cell cycle at the G1–>S transition: further development and characterization of a small library of stilbene-derived compounds. ChemMedChem 3 (2008), 345–355.
34. Purkait, B., Kumar, A., Nandi, N., Sardar, A.H., Das, S., Kumar, S., Pandey, K., Ravidas, V., Kumar, M., De, T., Singh, D., Das, P., Mechanism of amphotericin B resistance in clinical isolates of Leishmania donovani. Antimicrob. Agents Chemother. 56 (2012), 1031–1041.
35. Ribble, D., Goldstein, N.B., Norris, D.A., Shellman, Y.G., A simple technique for quantifying apoptosis in 96-well plates. BMC Biotechnol., 5, 2005, 12.
36. Riviere, C., Pawlus, A.D., Merillon, J.M., Natural stilbenoids: distribution in the plant kingdom and chemotaxonomic interest in Vitaceae. Nat. Prod. Rep. 29 (2012), 1317–1333.
37. Roberti, M., Pizzirani, D., Simoni, D., Rondanin, R., Baruchello, R., Bonora, C., Buscemi, F., Grimaudo, S., Tolomeo, M., Synthesis and biological evaluation of resveratrol and analogues as apoptosis-inducing agents. J. Med. Chem. 46 (2003), 3546–3554.
38. Roberti, M., Pizzirani, D., Recanatini, M., Simoni, D., Grimaudo, S., Di Cristina, A., Abbadessa, V., Gebbia, N., Tolomeo, M., Identification of a terphenyl derivative that blocks the cell cycle in the G0-G1 phase and induces differentiation in leukemia cells. J. Med. Chem. 49 (2006), 3012–3018.
39. Sharma, U., Singh, D., Kumar, P., Dobhal, M.P., Sing, H.S., Antiparasitic activity of plumericin & isoplumericin isolated from Plumeria bicolor against Leishmania donovani. Indian J. Med. Res. 134 (2011), 709–716.
40. Shen, T., Wang, X.N., Lou, H.X., Natural stilbenes: an overview. Nat. Prod. Rep. 26 (2009), 916–935.
41. Singh, N., Mishra, B.B., Bajpai, S., Singh, R.K., Tiwari, V.K., Natural product based leads to fight against leishmaniasis. Bioorg. Med. Chem. 22 (2014), 18–45.
42. Sundar, S., Murray, H.W., Availability of miltefosine for the treatment of kala-azar in India. Bull. World Health Organ. 83 (2005), 394–395.
43. Tipparaju, S.K., Joyasawal, S., Pieroni, M., Kaiser, M., Brun, R., Kozikowski, A.P., In pursuit of natural product leads: synthesis and biological evaluation of 2-[3-hydroxy-2-[(3-hydroxypyridine-2-carbonyl)amino]phenyl]benzoxazole-4-c arboxylic acid (A-33853) and its analogues: discovery of N-(2-benzoxazol-2-ylphenyl)benzamides as novel antileishmanial chemotypes. J. Med. Chem. 51 (2008), 7344–7347.
44. Tolomeo, M., Roberti, M., Scapozza, L., Tarantelli, C., Giacomini, E., Titone, L., Saporito, L., Di Carlo, P., Colomba, C., TTAS a new stilbene derivative that induces apoptosis in Leishmania infantum. Exp. Parasitol. 133 (2013), 37–43.
45. Young, S.L., Chaplin, D.J., Combretastatin A4 phosphate: background and current clinical status. Expert Opin. Investig. Drugs 13 (2004), 1171–1182.