Diosgenin-based thio(seleno)ureas and triazolyl glycoconjugates as hybrid drugs. Antioxidant and antiproliferative profile

European Journal of Medicinal Chemistry

Volumn 99, Issue , 2015, Pages 67-81

  Romero Hernández, Laura L ^a   Merino Montiel, Penélope ^a   Montiel Smith, Sara ^a   Meza Reyes, Socorro ^a   Vega Báez, José Luis ^a   Abasolo, Ibane ^b,c   Schwartz, Simó ^b,c   López, Óscar ^d   Fernández Bolaños, José G ^d  

^a BENEMÉRITA UNIVERSIDAD AUTÓNOMA DE PUEBLA   (Mexico)

^b HOSPITAL UNIVERSITARI VALL D HEBRON   (Spain)

^c BIOMATERIALES Y NANOMEDICINA CIBER BBN   (Spain)

^d UNIVERSITY OF SEVILLE   (Spain)

Author keywords

Antioxidant; Antiproliferative agent; Diosgenin; ROS scavenger; Selenoureas; Thioureas

Indexed keywords

(25")[2 [3' (16"BETA ACETOXY 26" HYDROXY 22" OXOCHOLEST 5" EN 3"ALPHA YL)THIOUREIDO]ETHYL]AMINE; (25) 22 OXO 3BETA(PROP 2' INYL)OXY CHOLEST 5 ENE 16BETA,26 DIYL ACETATE; (25) 26 HYDROXY 22 OXO 3BETA(PROP 2' INYL)OXY CHOLEST 5 EN 16BETA YL ACETATE; (25) 26 HYDROXY 3ALPHA(3' N OCTYLTHIOUREIDO) 22 OXOCHOLEST 5 EN 16BETA YL ACETATE; (25) 3ALPHA 22 OXO(3' PHENYLSELENOUREIDO)CHOLEST 5 ENE 16BETA,26 DIYL DIACETATE; (25) 3ALPHA AMINO 22 OXOCHOLEST 5 ENE 16BETA,26 DIYL DIACETATE; (25) 3ALPHA AZIDO 22 OXOCHOLEST 5 ENE 16BETA,26 DIYL DIACETATE; (25) 3ALPHA(3' BENZYLTHIOUREIDO) 26 HYDROXY 22 OXOCHOLEST 5 EN 16BETA YL ACETATE; (25) 3ALPHA[4' [(2",3",4",6" TETRA O BENZYL ALPHA DEXTRO GLUCOPYRANOSYLOXY)METHYL] 1'H 1',2',3' TRIAZOL 1' YL] 22 OXOCHOLEST 5 ENE 16BETA,26 DIYL DIACETATE; (25) 3ALPHA[4' [(ALPHA DEXTRO GLUCOPYRANOSYLOXY)METHYL] 1'H 1',2',3' TRIAZOL 1' YL] 22 OXOCHOLEST 5 ENE 16BETA,26 DIYL DIACETATE; (25) 3BETA[1' (2",3",4",6" TETRA O BENZYL BETA DEXTRO GLUCOPYRANOSYL) 1'H 1,'2,'3' TRIAZOL 4' YL]METHYLOXY 22 OXOCHOLEST 5 ENE 16BETA,26 DIYL DIACETATE; (25) 3BETA[1' (2",3",6",2"',3"',4"',6"' HEPTA O BENZYL BETA LACTOSYL) 1'H 1',2',3' TRIAZOL 4' YL]METHYLOXY 22 OXOCHOLEST 5 ENE 16BETA,26 DIYL DIACETATE; (25) 3BETA[1' (BETA DEXTRO GLYCOPYRANOSYL) 1'H 1',2',3' TRIAZOL 4' YL]METHYLOXY 22 OXO 5ALPHA CHOLESTANE 16BETA,26 DIYL DIACETATE; 6A O [1' [(25") 16"BETA,26" DIACETOXY 22" OXOCHOLESTAN 3"ALPHA YL](1'H 1',2',3' TRIAZOL 4' YL)METHYL]ALPHA CYCLODEXTRIN; ANTIOXIDANT; DIOSGENIN; GLYCOCONJUGATE; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG; 2,2-DIPHENYL-1-PICRYLHYDRAZYL; ANTINEOPLASTIC AGENT; BIOMIMETIC MATERIAL; BIPHENYL DERIVATIVE; GLUTATHIONE PEROXIDASE; ORGANOSELENIUM DERIVATIVE; PICRIC ACID; REACTIVE OXYGEN METABOLITE; SCAVENGER; SELENOUREA; TRIAZOLE DERIVATIVE; UREA;

ANTIOXIDANT ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; CLICK CHEMISTRY; CONTROLLED STUDY; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; EC50; FEMALE; HUMAN; HUMAN CELL; IC50; ANALOGS AND DERIVATIVES; ANIMAL; CELL PROLIFERATION; CHEMISTRY; DRUG DESIGN; DRUG EFFECTS; DRUG SCREENING; METABOLISM; MOUSE; TUMOR CELL LINE;

ANIMALS; ANTINEOPLASTIC AGENTS; BIOMIMETIC MATERIALS; BIPHENYL COMPOUNDS; CELL LINE, TUMOR; CELL PROLIFERATION; DIOSGENIN; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; FREE RADICAL SCAVENGERS; GLUTATHIONE PEROXIDASE; GLYCOCONJUGATES; HUMANS; MICE; ORGANOSELENIUM COMPOUNDS; PICRATES; REACTIVE OXYGEN SPECIES; TRIAZOLES; UREA;

EID: 84931271231     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2015.05.018     Document Type: Article

References (60)

1. A. Jemal, F. Bray, M.M. Center, J. Ferlay, E. Ward, D. Forman, Global cancer statistics, CA Cancer J. Clin. 61 (2011) 69-90.
2. a) R.J. Arroo, K. Beresford, A.S. Bhambra, M. Boarder, R. Budriesi, Z. Cheng, M. Micucci, K.C. Ruparelia, S. Surichan, V.P. Androutsopoulos, Phytoestrogens as natural prodrugs in cancer prevention: towards a mechanistic model, Phytochem. Rev. 13 (2014) 853-866;
3. b) O. Prakash, A. Kumar, K.W. Ajeet, Anticancer potential of plants and natural products: a review, Am. J. Pharm. Sci. 1 (2013) 104-115;
4. c) R. Ali, Z. Mirza, G.M.D. Ashraf, M.A. Kamal, S.A. Ansari, G.A. Damanhouri, A.M. Abuzenadah, A.G. Chaudhary, I.A. Sheikh, New anticancer agents: recent developments in tumor therapy, Anticancer Res. 32 (2012) 2999-3006.
5. a) P. Wang, X. Jin, J. Cai, J. Chen, M. Ji, Recent advances in small molecule prodrugs for cancer therapy, Anti-Cancer Agents Med. Chem. 14 (2014) 418-439;
6. b) J.J. Wilson, S.J. Lippard, Synthetic methods for the preparation of platinum anticancer complexes, Chem. Rev. 114 (2014) 4470-4495.
7. J. Szychowski, J.F. Truchon, Y.L. Bennani, Natural products in medicine: transformational outcome of synthetic chemistry, J. Med. Chem. 57 (2014) 9292-9308.
8. a) C. Nativi, O. Renaudet, Recent progress in antitumoral synthetic vaccines, ACS Med. Chem. Lett. 5 (2014) 1176-1178;
9. b) B. Fang, Development of synthetic lethality anticancer therapeutics, J. Med. Chem. 57 (2014) 7859-7873;
10. c) V. Sanna, N. Pala, M. Sechi, Targeted therapy using nanotechnology: focus on cancer, Int. J. Nanomed. 9 (2014) 467-483.
11. a) L.B. Travis, S.D. Fossa, H.D. Sesso, R.D. Frisina, D.N. Herrmann, C.J. Beard, D.R. Feldman, L.C. Pagliaro, R.C. Miller, D.J. Vaughn, L.H. Einhorn, N.J. Cox, M.E. Dolan, Chemotherapy-induced peripheral neurotoxicity and ototoxicity: new paradigms for translational genomics, J. Natl. Cancer Inst. 106 (2014) dju044;
12. b) N.C. Miltenburg, W. Boogerd, Chemotherapy-induced neuropathy: aA comprehensive survey, Cancer Treat. Rev. 40 (2014) 872-882.
13. S. Colak, J.P. Medema, Cancer stem cells - important players in tumor therapy resistance, FEBS J. 281 (2014) 4779-4791.
14. M. Dobbelstein, U. Moll, Targeting tumour-supportive cellular machineries in anticancer drug development, Nat. Rev. Drug Discov. 13 (2014) 179-196.
15. a) S.N. Sunassee, T. Ransom, C.J. Henrich, J.A. Beutler, D.G. Covell, J.B. McMahon, K.R. Gustafson, Steroidal alkaloids from the marine sponge Corticium niger that inhibit growth of human colon carcinoma cells, J. Nat. Prod. 77 (2014) 2475-2480;
16. b) A. Yokosuka, T. Suzuki, S. Tatsuno, Y. Mimaki, Steroidal glycosides from the underground parts of Yucca glauca and their cytotoxic activities, Phytochemistry 101 (2014) 109-115;
17. c) H. Kirmizibekmez, M. Masullo, M. Festa, A. Capasso, S. Piacente, Steroidal glycosides with antiproliferative activities from, Digit. Trojana. Phytother. Res. 28 (2014) 534-538.
18. a) R. Bansal, P.C. Acharya, Man-made cytotoxic steroids: exemplary agents for cancer therapy, Chem. Rev. 114 (2014) 6986-7005;
19. b) F. Le Bideau, S. Dagorne, Synthesis of transition-metal steroid derivatives, Chem. Rev. 113 (2013) 7793-7850;
20. c) N.-J. Fan, J.-J. Tang, H. Li, X.-J. Li, B. Luo, J.-M. Gao, Synthesis and cytotoxic activity of some novel steroidal C-17 pyrazolinyl derivatives, Eur. J. Med. Chem. 69 (2013) 182-190.
21. J.A.R. Salvador, J.F.S. Carvalho, M.A.C. Neves, S.M. Silvestre, A.J. Leitão, M.M.C. Silva, M.L. Sáe Melo, Anticancer steroids: linking natural and semi-synthetic compounds, Nat. Prod. Rep. 30 (2013) 324-374.
22. A. Gupta, B.S. Kumar, A.S. Negi, Current status on development of steroids as anticancer agents, J. Steroid Biochem. Mol. Biol. 137 (2013) 242-270.
23. a) W. Zhiyu, C. Yue, W. Neng, W.D. Mei, L.W. Wei, H. Feng, S.J. Gang, Y. De Po, G.X. Yuan, C. Jian-Ping, Dioscin induces cancer cell apoptosis through elevated oxidative stress mediated by downregulation of peroxiredoxins, Cancer Biol. Ther. 13 (2012) 138-147;
24. b) K. Patel, M. Gadewar, V. Tahilyani, D.K. Patel, A review on pharmacological and analytical aspects of diosgenin: a concise report, Nat. Prod. Bioprospect 2 (2012) 46-52;
25. c) J. Raju, R. Mehta, Cancer chemopreventive and therapeutic effects of diosgenin, a food saponin, Nutr. Cancer 61 (2009) 27-35.
26. E. Yakubov, M. Buchfelder, I.Y. Eyüpoglu, N.E. Savaskan, Selenium action in neuro-oncology, Biol. Trace Elem. Res. 161 (2014) 246-254.
27. M.V. Gil, M.J. Arévalo, Ó. López, Click chemistry - what's in a Name? Triazole synthesis and beyond, Synthesis (2007) 1589-1620.
28. A. Rana, J.M. Alex, M. Chauhan, G. Joshi, R. Kumar, A review on pharmacophoric designs of antiproliferative agents, Med Chem Res. 24 (2015) 903-920.
29. K. Nepali, S. Sharma, M. Sharma, P.M.S. Bedi, K.L. Dhar, Rational approaches, design strategies, structure activity relationship and mechanistic insights for anticancer hybrids, Eur. J. Med. Chem. 77 (2014) 422-487.
30. R. Kohen, A. Nyska, Oxidation of biological systems: oxidative stress phenomena, antioxidants, redox reactions, and methods for their quantification, Toxicol. Pathol. 30 (2002) 620-650.
31. S. Reuter, S.C. Gupta, M.M. Chaturvedi, B.B. Aggarwal, Oxidative stress, inflammation, and cancer: how are they linked? Free Radic. Biol. Med. 49 (2010) 1603-1616.
32. A. Mencalha, V.J. Victorino, R. Cecchini, C. Panis, Mapping oxidative changes in breast cancer: understanding the basic to reach the clinics, Anticancer Res. 34 (2014) 1127-1140.
33. M.A. Fernández-Herrera, J. Sandoval-Ramírez, S. Meza-Reyes, S. Montiel-Smith, Side-chain opening of steroidal sapogenins to form 22-oxocholestanic skeletons. An approach to analogues of the aglycone of the potent anticancer agent OSW-1, J. Mex. Chem. Soc. 53 (2009) 126-130.
34. S. Rincón, R.E. del Río, J. Sandoval-Ramírez, S. Meza-Reyes, S. Montiel-Smith, M.A. Fernández, N. Farfán, R. Santillán, A new route for the preparation of the 22,23-dioxocholestane side chain from diosgenin and its application to the stereocontrolled construction of the 22R,23S-diol function, Tetrahedron 62 (2006) 2594-2602.
35. Ó. López, I. Maya, J. Fuentes, J.G. Fernández-Bolaños, Simple and efficient synthesis of O-unprotected glycosyl thiourea and isourea derivatives from glycosylamines, Tetrahedron 60 (2004) 61-72.
36. J.G. Fernández-Bolaños, I. Maya, A. Oliete, Multivalent glycoconjugates in medicinal chemistry, in: A.P. Rauter, T.K. Lindhorst (Eds.), Carbohydrate Chemistry vol. 38, RSCPublishing, 2012, pp. 303-337.
37. B. Yu, X.-J. Shi, Y.-F. Zheng, Y. Fang, E. Zhang, D.-Q. Yu, H.-M. Liu, A novel [1,2,4] triazolo [1,5-a] pyrimidine-based phenyl-linked steroid dimer: synthesis and its cytotoxic activity, Eur. J. Med. Chem. 69 (2013) 323-330.
38. C.W. Nogueira, G. Zeni, J.B.T. Rocha, Organoselenium and organotellurium compounds: toxicology and pharmacology, Chem. Rev. 104 (2004) 6255-6285.
39. G.K. Azad, R.S. Tomar, Ebselen, a promising antioxidant drug: mechanisms of action and targets of biological pathways, Mol. Biol. Rep. 41 (2014) 4865-4879.
40. A.P. Fernandes, V. Gandin, Selenium compounds as therapeutic agents in cancer, Biochim. Biophys. Acta. 1850 (2015) 1642-1660.
41. a) M.A. Fernández-Herrera, J. Sandoval-Ramírez, L. Sánchez-Sánchez, H. López-Muñoz, M.L. Escobar-Sánchez, Probing the selective antitumor activity of 22-oxo-26-selenocyanocholestane derivatives, Eur. J. Med. Chem. 74 (2014) 451-460;
42. b) O.E.D. Rodrigues, D. de Souza, L.C. Soares, L. Dornelles, R.A. Burrow, J.R. Appelt, C.F. Alves, D. Alves, A.L. Braga, Stereoselective synthesis of selenosteroids, Tetrahedron Lett. 51 (2010) 2237-2240;
43. c) S.A. Sadek, S.M. Shaw, W.V. Kessler, G.C. Wolf, Selenosteroids as potential estrogen-receptor scanning agents, J. Org. Chem. 46 (1981) 3259-3262.
44. Ó. López, S. Maza, V. Ulgar, I. Maya, J.G. Fernández-Bolaños, Synthesis of sugar-derived isoselenocyanates, selenoureas, and selenazoles, Tetrahedron 65 (2009) 2556-2566.
45. a) D. Gonzaga, M.R. Senger, F. de Carvalho da Silva, V.F. Ferreira, F. Paes Silva Jr., 1-Phenyl-1H- and 2-phenyl-2H-1,2,3-triazol derivatives: design, synthesis and inhibitory effect on alpha-glycosidases, Eur. J. Med. Chem. 74 (2014) 461-476;
46. b) C.Y. Lee, R. Held, A. Sharma, R. Baral, C. Nanah, D. Dumas, S. Jenkins, S. Upadhaya, W. Du, Copper-granule-catalyzed microwave-assisted click synthesis of polyphenol dendrimers, J. Org. Chem. 78 (2013) 11221-11228.
47. T. Lecourt, A.J. Herault, M. Pearce, M. Sollogoub, P. Sinaÿ, Triisobutylaluminium and diisobutylaluminium hydride as molecular scalpels: the regioselective stripping of perbenzylated sugars and cyclodextrins, Chem. Eur. J. 10 (2004) 2960-2971.
48. K. Pérez-Labrada, I. Brouard, C. Morera, F. Estévez, J. Bermejo, D.G. Rivera, 'Click' synthesis of triazole-based spirostan saponin analogs, Tetrahedron 67 (2011) 7713-7727.
49. R.L. Prior, X. Wu, K. Schaich, Standardized methods for the determination of antioxidant capacity and phenolics in foods and dietary supplements, J. Agric. Food Chem. 53 (2005) 4290-4302.
50. P. Merino-Montiel, S. Maza, S. Martos, Ó. López, I. Maya, J.G. Fernández-Bolaños, Synthesis and antioxidant activity of O-alkyl selenocarbamates, selenoureas and selenohydantoins, Eur. J. Pharm. Sci. 14 (48) (2013) 582-592.
51. J.R. Arthur, The glutathione peroxidases, Cell. Mol. Life Sci. 57 (2000) 1825-1835.
52. D. Milić, T. Kop, Z. Juranić, M.J. Gasić, B. Tinant, G. Pocsfalvi, B.A. Solaja, Synthesis and antiproliferative activity of A-ring aromatised and conduritol-like steroidal compounds, Steroids 70 (2005) 922-932.
53. M. Nazari, A. Minai-Tehrania, R. Emamzadeh, Comparison of different probes based on labeled annexin V for detection of apoptosis, RSC Adv. 4 (2014) 45128-45135.
54. R. Huo, Q.-l. Zhou, B.-x. Wang, S.-i. Tashiro, S. Onodera, T. Ikejima, Diosgenin induces apoptosis in HeLa cells via activation of caspase pathway, Acta Pharmacol. Sin. 25 (2004) 1077-1082.
55. Y. Li, X. Wang, S. Cheng, J. Du, Z. Deng, Y. Zhang, Q. Liu, J. Gao, B. Cheng, C. Ling, Diosgenin induces G2/M cell cycle arrest and apoptosis in human hepatocellular carcinoma cells, Oncol. Rep. 33 (2015) 693-698.
56. A., Glasauer, N.S. Chandel, Targeting antioxidants for cancer therapy, Biochem. Pharmacol. 92 (2014) 90-101.
57. I.S. Son, J.H. Kim, H.Y. Sohn, K.H. Son, J.-S. Kim, C.-S. Kwon, Antioxidative and hypolipidemic effects of diosgenin, a steroidal saponin of yam (Dioscorea spp.), on high-cholesterol fed rats, Biosci. Biotechnol. Biochem. 71 (2007) 3063-3071.
58. W. Zhiyu, C. Yue, W. Neng, W.D. Mei, L.Y. Wei, H. Feng, S.J. Gang, Y. De Po, G.X. Yuan, C. Jian-Ping, Dioscin induces cancer cell apoptosis through elevated oxidative stress mediated by downregulation of peroxiredoxins, Cancer Biol. Ther. 13 (2012) 138-147.
59. a) G. Rodríguez-Berna, M.J. Díaz Cabañas, V. Mangas-Sanjuán, M. González-Álvarez, I. González-Álvarez, I. Abasolo, S. Schwartz Jr., M. Bermejo, A. Corma, Semisynthesis, cytotoxic activity, and oral availability of new lipophilic 9-substituted camptothecin derivatives, ACS Med. Chem. Lett. 4 (2013) 651-655;
60. b) P. Botella, I. Abasolo, Y. Fernández, C. Muniesa, S. Miranda, M. Quesada, J. Ruiz, S. Schwartz Jr., A. Corma, Surface-modified silica nanoparticles for tumor-targeted delivery of camptothecin and its biological evaluation, J. Control. Release 156 (2011) 246-257.