Development of new estradiol-cationic lipid hybrids: Ten-carbon twin chain cationic lipid is a more suitable partner for estradiol to elicit better anticancer activity

European Journal of Medicinal Chemistry

Volumn 86, Issue , 2014, Pages 653-663

  Sudhakar, Godeshala ^a   Bathula, Surendar Reddy ^a,b   Banerjee, Rajkumar ^a,b  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b ACADEMY OF SCIENTIFIC AND INNOVATIVE RESEARCH ACSIR   (India)

Author keywords

Anti cancer activity; Apoptosis; Cationic lipid derivatives; Estradiol; Hybrid molecules

Indexed keywords

17ALPHA [3 N,N DIDECYL (METHYL) AMINO PROPANE] 17BETA ESTRADIOL; 17ALPHA [3 N,N DIDODECYL (METHYL) AMINO PROPANE] 17BETA ESTRADIOL; 17ALPHA [3 N,N DIHEXYL (METHYL) AMINO PROPANE] 17BETA ESTRADIOL; 17ALPHA [3 N,N DITETRADECYL (METHYL) AMINO PROPANE] 17BETA ESTRADIOL; 3 TERT BUTYLDIMETHYLSILYLOXY 17ALPHA [3 N,N DIALKYL (AMINO) PROPANE 17BETA ESTRADIOL; 3 TERT BUTYLDIMETHYLSILYLOXY 17ALPHA [3 N,N DIDECYL (AMINO) PROPANE 17BETA ESTRADIOL; 3 TERT BUTYLDIMETHYLSILYLOXY 17ALPHA [3 N,N DIDECYL (METHYL) AMINOPROPANE] 17BETA ESTRADIOL; 3 TERT BUTYLDIMETHYLSILYLOXY 17ALPHA [3 N,N DIDODECYL (AMINO) PROPANE] 17BETA ESTRADIOL; 3 TERT BUTYLDIMETHYLSILYLOXY 17ALPHA [3 N,N DIDODECYL (METHYL) AMINOPROPANE] 17BETA ESTRADIOL; 3 TERT BUTYLDIMETHYLSILYLOXY 17ALPHA [3 N,N DIHEXYL (METHYL) AMINOPROPANE] 17BETA ESTRADIOL; 3 TERT BUTYLDIMETHYLSILYLOXY 17ALPHA [3 N,N DITETRADECYL (AMINO) PROPANE] 17BETA ESTRADIOL; 3 TERT BUTYLDIMETHYLSILYLOXY 17ALPHA [3 N,N DITETRADECYL (METHYL) AMINOPROPANE] 17BETA ESTRADIOL; ANTINEOPLASTIC AGENT; CARBON; CATIONIC LIPID MODIFIED ESTRADIOL DERIVATIVE; ESTRADIOL DERIVATIVE; UNCLASSIFIED DRUG; CATION; ESTRADIOL; LIPID;

ANIMAL CELL; ANIMAL CELL CULTURE; ANIMAL EXPERIMENT; ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHO CELL LINE; CYTOTOXICITY; DRUG CONJUGATION; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; IN VITRO STUDY; MCF 7 CELL LINE; MELANOMA; MOLECULAR HYBRIDIZATION; MOUSE; NONHUMAN; PHARMACOPHORE; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; 3T3 CELL LINE; ANIMAL; C57BL MOUSE; CELL CULTURE; CELL CYCLE; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; CRICETULUS; DOSE RESPONSE; DRUG DESIGN; DRUG EFFECTS; DRUG SCREENING; NEOPLASMS, EXPERIMENTAL; PATHOLOGY; SYNTHESIS;

ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; CATIONS; CELL CYCLE; CELL PROLIFERATION; CELLS, CULTURED; CHO CELLS; CRICETULUS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; ESTRADIOL; FEMALE; HUMANS; LIPIDS; MCF-7 CELLS; MICE; MICE, INBRED C57BL; MOLECULAR STRUCTURE; NEOPLASMS, EXPERIMENTAL; NIH 3T3 CELLS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84907818280     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.09.030     Document Type: Article

References (31)

1. D. Lane, Designer combination therapy for cancer, Nat. Biotechnol. 24 (2006) 163e164.
2. P. Rougier, C. Lepere, Metastatic colorectal cancer: first-and second line treatment in 2005, Semin. Oncol. 32 (2005) 15e20.
3. S. Decker, E.A. Sausville, Preclinical modeling of combination treatments: fantasy or requirement? Ann. N. Y. Acad. Sci. 1059 (2005) 61e69.
4. E. Frei III, Combination cancer therapy, Cancer Res. 32 (1972) 2593e2607.
5. E. Frei III, Curative cancer chemotherapy, Cancer Res. 45 (1985) 6523e6537.
6. S.T. Nawrocki, J.S. Carew, M.S. Pino, R.A. Highshaw, K. Dunner Jr., P. Huang, J.L. Abbruzzese, D.J. McConkey, Bortezomib sensitizes pancreatic cancer cells to endoplasmic reticulum stress-mediated apoptosis, Cancer Res. 65 (2005) 11658e11666.
7. M. Koufaki, A. Detsi, C. Kiziridi, Multifunctional lipoic acid conjugates, Curr. Med. Chem. 16 (2009) 4728e4742.
8. (b) P. Catsoulacos, D. Catsoulacos, Hybrid anticancer compounds. Steroidal lactam esters of carboxylic derivatives of N, N-bis (2-chloroethyl) aniline, Anticancer Res. 11 (1991) 1773e1777.
9. B. Meunier, Hybrid molecules with a dual mode of action: dream or reality? Acc. Chem. Res. 41 (2008) 69e77.
10. P.P. Karmali, A. Chaudhuri, Cationic liposomes as non-viral carriers of gene medicines: resolved issues, open questions, and future promises, Med. Res. Rev. 27 (2007) 696e722.
11. C. Lonez, M. Vandenbranden, J.-M. Ruysschaert, Cationic lipids activate intracellular signaling pathways, Adv. Drug. Deliv. Rev. 64 (2012) 1749e1758.
12. Y. Aramaki, S. Takano, S. Tsuchiya, Induction of apoptosis in macrophages by cationic liposomes, FEBS Lett. 460 (1999) 472e476.
13. Y. Aramaki, S. Takano, H. Arima, S. Tsuchiya, Induction of apoptosis in WEHI 231 cells by cationic liposomes, Pharm. Res. 17 (2000) 515e520.
14. M. Ouali, J.M. Ruysschaert, C. Lonez, M. Vandenbranden, Cationic lipids involved in gene transfer mobilize intracellular calcium, Mol. Membr. Biol. 24 (2007) 225e232.
15. K. Kusumoto, T. Ishikawa, Didodecyl dimethyl ammonium bromide (DDAB) induces caspase-mediated apoptosis in human leukemia HL-60 cells, J. Control. Release 147 (2010) 246e252.
16. L. Kongkaneramit, N. Sarisuta, N. Azad, Y. Lu, A.K. Iyer, L. Wang, Y. Rojanasakul, Dependence of reactive oxygen species and FLICE inhibitory protein on lipofectamine-induced apoptosis in human lung epithelial cells, J. Pharmacol. Exp. Ther. 325 (2008) 969e977.
17. S. Iwaoka, T. Nakamura, S. Takano, S. Tsuchiya, Y. Aramaki, Cationic liposomes induce apoptosis through p38 MAP kinase-caspase-8-Bid pathway in macrophage like RAW264.7 cells, J. Leukoc. Biol. 79 (2006) 184e191.
18. P. Samadder, Y. Xu, F. Schweizer, G. Arthur, Cytotoxic properties of D-gluco-, D-galacto-and D-manno-configured 2-amino-2-deoxy-glycerolipids against epithelial cancer cell lines and BT-474 breast cancer stem cells, Eur. J. Med. Chem. 78 (2014) 225e235.
19. S. Sinha, S. Roy, S.R. Bathula, K. Pal, G. Sudhakar, S. Iyer, S. Dutta, E. Wang, P.K. Vohra, K.R. Roy, P. Reddanna, D. Mukhopadhyay, R. Banerjee, A lipidmodified estrogen derivative that treats breast cancer independent of estrogen receptor expression through simultaneous induction of autophagy and apoptosis, Mol. Cancer. Res. 9 (2011) 364e374.
20. K. Pal, S.K. Pore, S. Sinha, R. Janardhanan, D. Mukhopadhyay, R. Banerjee, Structure-activity study to develop cationic lipid-conjugated haloperidol derivatives as a new class of anticancer therapeutics, J. Med. Chem. 54 (2011) 2378e2390.
21. P.R. Muktapurama, R.K. Gara, K. Sharma, C. Rohit, K. Srinivas, D.P. Mishra, B.S. Reddy, Anticancer siRNA delivery by new anticancer molecule: a novel combination strategy for cancer cell killing, Eur. J. Med. Chem. 56 (2012) 400e408.
22. W. Wang, Z. Bai, F. Zhang, C. Wang, Y. Yuan, J. Shao, Synthesis and biological activity evaluation of emodin quaternary ammonium salt derivatives as potential anticancer agents, Eur. J. Med. Chem. 56 (2012) 320e331.
23. S. Chia, W. Gradishar, Fulvestrant: expanding the endocrine treatment options for patients with hormone receptor-positive advanced breast cancer, Breast 17 (2008) S16eS21.
24. J. Peng, S. Sengupta, V.C. Jordan, Potential of selective estrogen receptor modulators as treatments and preventives of breast cancer, Anticancer Agents Med. Chem. 9 (2009) 481e499.
25. W. Shelly, M.W. Draper, V. Krishnan, M. Wong, R.B. Jaffe, Selective estrogen receptor modulators: an update on recent clinical findings, Obstet. Gynecol. Surv. 63 (2008) 163e181.
26. W.L. Scott, W.L. Athena, Apoptosis in cancer, Carcinogenesis 21 (2000) 485e495.
27. R.P. Singh, R. Agarwal, Phytochemicals as cell cycle modulators-A less toxic approach in halting human cancers, Cell. Cycle 1 (2002) 156e161.
28. (b) R.P. Singh, R. Agarwal, Natural flavonoids targeting deregulated cell cycle progression in cancer cells, Curr. Drug. Targets 7 (2006) 345e354.
29. A. Tanemura, A.Q. van Hoesel, T. Mori, T. Yu, D.S. Hoon, The role of estrogen receptor in melanoma, Expert Opin. Ther. Targets 11 (2007) 1639e1648.
30. S. Roy, B.S. Reddy, G. Sudhakar, J.M. Kumar, R. Banerjee, 17b-Estradiol-Linked Nitro-L-arginine as simultaneous Iinducer of apoptosis in melanoma and tumor-angiogenic vascular endothelial cells, Mol. Pharm. 8 (2011) 350e359.
31. S. Konduri, R.E. Schwarz, Estrogen receptor beta/alpha ratio predicts response of pancreatic cancer cells to estrogens and phytoestrogens, J. Surg. Res. 140 (2007) 55e66.