Novel merosesquiterpene exerts a potent antitumor activity against breast cancer cells in vitro and in vivo

European Journal of Medicinal Chemistry - Tập 79 - Trang 1-12 - 2014
Esther Carrasco1,2, Pablo Juan Álvarez1, Consolación Melguizo1, José Prados1, Enrique Álvarez-Manzaneda3, Rachid Chahboun3, Ibtissam Messouri3, María Isabel Vázquez-Vázquez1, Antonia Aránega1, Fernando Rodríguez-Serrano1
1Institute of Biopathology and Regenerative Medicine (IBIMER), University of Granada, 18071 Granada, Spain
2PhD Program in Biomedicine, University of Granada, 18071 Granada, Spain
3Department of Organic Chemistry, Institute of Biotechnology, University of Granada, 18071 Granada, Spain

Tài liệu tham khảo

Ferlay, 2010, International Journal of Cancer, 127, 2893, 10.1002/ijc.25516 Jemal, 2011, CA: A Cancer Journal for Clinicians, 61, 69 Are, 2013, Journal of Surgical Oncology, 107, 221, 10.1002/jso.23248 Lü, 2011, Experimental and Therapeutic Medicine, 2, 821, 10.3892/etm.2011.279 Sheri, 2013, Clinical Oncology, 25, 117, 10.1016/j.clon.2012.10.007 Zhong, 2012, Cellular Physiology and Biochemistry, 30, 778, 10.1159/000341457 Robles-Fernández, 2013, Recent Patents on Anti-Cancer Drug Discovery, 8, 203, 10.2174/1574891X113089990034 Simpson, 1998, Topics in Current Chemistry, 195 Coval, 1995, Bioorganic & Medicinal Chemistry Letters, 5, 605, 10.1016/0960-894X(95)00081-4 Chackalamannil, 1995, Bioorganic & Medicinal Chemistry Letters, 5, 2005, 10.1016/0960-894X(95)00342-Q Tall, 1993, The Journal of Lipid Research, 34, 1255, 10.1016/S0022-2275(20)36957-1 Marotti, 1993, Nature, 364, 73, 10.1038/364073a0 Koizumi, 1991, Atherosclerosis, 90, 189, 10.1016/0021-9150(91)90114-I Barrero, 1997, Tetrahedron Letters, 38, 8101, 10.1016/S0040-4039(97)10119-8 Barrero, 1998, Tetrahedron, 54, 5635, 10.1016/S0040-4020(98)00235-X Alvarez-Manzaneda, 2005, Organic Letters, 7, 1477, 10.1021/ol047332j Bernet, 2006, Helvetica Chimica Acta, 89, 784, 10.1002/hlca.200690071 Arima, 2007, Tetrahedron Asymmetry, 18, 1701, 10.1016/j.tetasy.2007.07.010 Laube, 2009, Bioorganic & Medicinal Chemistry, 17, 1422, 10.1016/j.bmc.2009.01.028 Kawashima, 1964, Chemical & Pharmaceutical Bulletin, 12, 796, 10.1248/cpb.12.796 Wijeratue, 2008, Journal of Natural Products, 71, 218, 10.1021/np070600c Ishii, 2009, Chemical & Pharmaceutical Bulletin, 57, 1103, 10.1248/cpb.57.1103 Talpir, 1994, Tetrahedron, 50, 4179, 10.1016/S0040-4020(01)86712-0 Poigny, 1999, The Journal of Organic Chemistry, 64, 9318, 10.1021/jo9910886 Bernet, 2003, Helvetica Chimica Acta, 86, 2009, 10.1002/hlca.200390158 Laube, 2005, Tetrahedron, 61, 1141, 10.1016/j.tet.2004.11.059 Amano, 2005, Journal of Molecular Catalysis B: Enzymatic, 32, 141, 10.1016/j.molcatb.2004.11.007 Rubio, 2007, Journal of Natural Products, 70, 628, 10.1021/np060633c Yong, 2008, Tetrahedron, 64, 6341, 10.1016/j.tet.2008.04.091 Kono, 2000, The Journal of Antibiotics, 53, 459, 10.7164/antibiotics.53.459 Kono, 2002, The Journal of Antibiotics, 55, 99, 10.7164/antibiotics.55.99 Maezawa, 2007, Tetrahedron Letters, 48, 4865, 10.1016/j.tetlet.2007.05.043 Bonhoure, 2008, Leukemia, 22, 971, 10.1038/leu.2008.95 Murray, 1997, The Journal of Organic Chemistry, 62, 5638, 10.1021/jo970036i Cichewicz, 2004, Journal of the American Chemical Society, 126, 14910, 10.1021/ja046082z Robinson, 2009, Journal of Natural Products, 72, 1857, 10.1021/np900465e Gray, 2006, The Journal of Organic Chemistry, 71, 8685, 10.1021/jo060295k Wabo, 2007, Planta Medica, 73, 187, 10.1055/s-2007-967103 For some representative syntheses based on the two synthon strategy, see: Trammel, 1978, Tetrahedron Letters, 1525, 10.1016/S0040-4039(01)94594-0 Barrero, 1997, Tetrahedron Letters, 38, 2325, 10.1016/S0040-4039(97)00305-5 Arjona, 1997, Tetrahedron Letters, 38, 7249, 10.1016/S0040-4039(97)01683-3 Barrero, 1999, Tetrahedron, 55, 15181, 10.1016/S0040-4020(99)00992-8 Takao, 2001, Organic Letters, 3, 4291, 10.1021/ol016960n Maiti, 2001, Tetrahedron Letters, 42, 2389, 10.1016/S0040-4039(01)00153-8 Quideau, 2002, Organic Letters, 22, 3975, 10.1021/ol026855t Armstrong, 2003, Journal of Natural Products, 66, 1382, 10.1021/np030029r Alvarez-Manzaneda, 2008, Synthesis, 4019, 10.1055/s-0028-1083238 2009 Aránega, 2010 Yousefi, 2012, Medicinal Chemistry Research, 21, 1921, 10.1007/s00044-011-9716-z Uluer, 2012, Acta Histochemica, 114, 641, 10.1016/j.acthis.2011.11.010 Saleh, 2013, Oncology Letters, 5, 321, 10.3892/ol.2012.965 Álvarez, 2012, Expert Opinion on Therapeutic Patents, 22, 107, 10.1517/13543776.2012.661413 Levenson, 1997, Cancer Research, 57, 3071 Beaver, 2013, Clinical Cancer Research, 19, 5413, 10.1158/1078-0432.CCR-13-0884 Vera-Ramirez, 2011, Critical Reviews in Oncology/Hematology, 80, 347, 10.1016/j.critrevonc.2011.01.004 Saeidnia, 2013, Toxicology and Applied Pharmacology, 271, 49, 10.1016/j.taap.2013.05.004 Yang, 2008, Molecular Cancer Therapeutics, 7, 2319, 10.1158/1535-7163.MCT-08-0298 Watson, 2013, Open Biology, 3, 120144, 10.1098/rsob.120144 Sainz, 2012, Cancers (Basel), 4, 442, 10.3390/cancers4020442 Constant Anatole, 2013, Environmental Toxicology and Pharmacology, 36, 865, 10.1016/j.etap.2013.07.015 Morales, 2013, European Journal of Medicinal Chemistry, 70, 111, 10.1016/j.ejmech.2013.09.043 Raza, 2011, European Journal of Pharmacology, 668, 15, 10.1016/j.ejphar.2011.06.016 Chang, 2009, Nutrition and Cancer, 61, 735, 10.1080/01635580902825571 Zhao, 2011, Oncology Reports, 25, 1289 Pfaff, 2013, PLoS One, 8, e59169, 10.1371/journal.pone.0059169 Masamha, 2009, Cancer Research, 69, 6565, 10.1158/0008-5472.CAN-09-0913 Munro, 2012, Oncogene, 31, 4343, 10.1038/onc.2011.603 Song, 2013, Biochemical Genetics, 51, 603, 10.1007/s10528-013-9590-0 Yoon, 2012, Biochemical Society Transactions, 40, 981, 10.1042/BST20120092 He, 2012, Cancer Biotherapy & Radiopharmaceuticals, 27, 399, 10.1089/cbr.2010.0802 Tang, 2013, Cell Cycle, 12, 2665, 10.4161/cc.25728 Wang, 2013, Molecular Medicine Reports, 8, 1279, 10.3892/mmr.2013.1650 Vousden, 2002, Nature Reviews Cancer, 2, 594, 10.1038/nrc864 Yoshida, 2010, Cancer Science, 101, 831, 10.1111/j.1349-7006.2009.01488.x Carvajal, 2013, EMBO Reports, 14, 414, 10.1038/embor.2013.25 Wong, 2013, PLoS One, 8, e78021, 10.1371/journal.pone.0078021 Kaufmann, 1993, Cancer Research, 53, 3976 Singh, 2013, European Journal of Medicinal Chemistry, 70, 864, 10.1016/j.ejmech.2013.10.039 Roberts, 2007, Oncogene, 26, 3291, 10.1038/sj.onc.1210422 Zhou, 2013, PLoS One, 8, e55730, 10.1371/journal.pone.0055730 Huang, 2013, World Journal of Surgical Oncology, 11, 307, 10.1186/1477-7819-11-307 Caligiuri1, 2013, Oncotarget, 4, 875, 10.18632/oncotarget.1036 Talbot, 2012, International Journal of Biochemistry and Molecular Biology, 3, 117 Choi, 2013, Human Pathology, 44, 2581, 10.1016/j.humpath.2013.07.003 Smit, 2010, Aging, 2, 735, 10.18632/aging.100209 Baranwal, 2009, Biochemical and Biophysical Research, 384, 6, 10.1016/j.bbrc.2009.04.051 Menezes, 2012, Biochemical Journal, 444, 573, 10.1042/BJ20120205 de Jong, 2010, Journal of Nuclear Medicine, 51, 501, 10.2967/jnumed.109.065706 Young, 2010, Cancer Biology & Therapy, 10, 703, 10.4161/cbt.10.7.12904