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Synthesis, characterization and biological evaluation of bile acid-aromatic/heteroaromatic amides linked via amino acids as anti-cancer agents

Agarwal, Devesh S., Anantaraju, Hasitha Shilpa, Sriram, Dharmarajan, Yogeeswari, Perumal, Nanjegowda, Shankara H., Mallu, P., Sakhuja, Rajeev·2016·Steroids
DOI 10.1016/j.steroids.2015.12.022
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Abstract

A series of bile acid (Cholic acid and Deoxycholic acid) aryl/heteroaryl amides linked via α-amino acid were synthesized and tested against 3 human cancer cell-lines (HT29, MDAMB231, U87MG) and 1 human normal cell line (HEK293T). Some of the conjugates showed promising results to be new anticancer agents with good in vitro results. More specifically, Cholic acid derivatives 6a (1.35 μM), 6c (1.41 μM) and 6m (4.52 μM) possessing phenyl, benzothiazole and 4-methylphenyl groups showed fairly good activity against the breast cancer cell line with respect to Cisplatin (7.21 μM) and comparable with respect to Doxorubicin (1 μM), while 6e (2.49μM), 6i (2.46 μM) and 6m (1.62 μM) showed better activity against glioblastoma cancer cell line with respect to both Cisplatin (2.60 μM) and Doxorubicin (3.78 μM) drugs used as standards. Greater than 65% of the compounds were found to be safer on human normal cell line.

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Research works printed but not linked: 49

  1. Salvador, 2013, Anticancer steroids: linking natural and semi-synthetic compounds, Nat. Prod. Rep., 30, 324, 10.1039/C2NP20082A · DOI
  2. Hanson, 1976, Formation of bile acids in man: metabolism of 7α-hydroxy-4-cholesten-3-one in normal subjects with an intact enterohepatic circulation, Biochim. Biophys. Acta Lipids Lipid Metabol., 431, 335, 10.1016/0005-2760(76)90154-5 · DOI
  3. Yamanaka, 1976, Gastroenterol. Jpn, 11, 285, 10.1007/BF02777368 · DOI
  4. Axelson, 2000, Bile acid synthesis in cultured human hepatocytes: support for an alternative biosynthetic pathway to cholic acid, Hepatology, 31, 1305, 10.1053/jhep.2000.7877 · DOI
  5. Anwer, 1975, Bile acids secretion and synthesis by isolated rat hepatocytes, Biochem. Biophys. Res. Commun., 64, 603, 10.1016/0006-291X(75)90364-2 · DOI
  6. Hofmann, 1977, Clin. Gastroenterol., 6, 3, 10.1016/S0300-5089(21)00383-7 · DOI
  7. Mahmoud, 1999, Administration of an unconjugated bile acid increases duodenal tumors in a murine model of familial adenomatous polyposis, Carcinogenesis, 20, 299, 10.1093/carcin/20.2.299 · DOI
  8. Galle, 1990, Ursodeoxycholate reduces hepatotoxicity of bile salts in primary human hepatocytes, Hepatology, 12, 486, 10.1002/hep.1840120307 · DOI
  9. Rodrigues, 1999, Ursodeoxycholic acid prevents cytochrome c release in apoptosis by inhibiting mitochondrial membrane depolarization and channel formation, Cell Death Differ., 6, 842, 10.1038/sj.cdd.4400560 · DOI
  10. Carubbi, 2002, Comparative cytotoxic and cytoprotective effects of taurohyodeoxycholic acid (THDCA) and taurohyodeoxycholic acid (TUDCA) in HepG2 cell line, Biochim. Biophys. Acta Mol. Cell Biol. Lipids, 1580, 31, 10.1016/S1388-1981(01)00184-6 · DOI
  11. Araki, 2003, The cytotoxicity of hydrophobic bile acids is ameliorated by more hydrophilic bile acids in intestinal cell lines IEC-6 and Caco-2, Oncol. Rep., 10, 1931
  12. Im, 2005, Ursodeoxycholic acid can suppress deoxycholic acid-induced apoptosis by stimulating Akt/PKB-dependent survival signaling, Nutr. Cancer, 51, 110, 10.1207/s15327914nc5101_15 · DOI
  13. Kotb, 2012, Molecular mechanisms of ursodeoxycholic acid toxicity & side effects: ursodeoxycholic acid freezes regeneration & induces hibernation mode, Int. J. Mol. Sci., 13, 8882, 10.3390/ijms13078882 · DOI
  14. Carey, 2012, Chemoprevention of colorectal cancer with ursodeoxycholic acid: cons, Clin. Res. Hepatol. Gastroenterol., 36, 1, 10.1016/S2210-7401(12)70023-2 · DOI
  15. Serfaty, 2010, Ursodeoxycholic acid and chemoprevention of colorectal cancer, Gastroenterol. Clin. Biol., 34, 516, 10.1016/j.gcb.2010.05.005 · DOI
  16. Serfaty, 2012, Chemoprevention of colorectal cancer with ursodeoxycholic acid: pro, Clin. Res. Hepatol. Gastroenterol., 36, 53, 10.1016/S2210-7401(12)70022-0 · DOI
  17. Tatsumura, 1981, Jpn. J. Surg., 11, 84, 10.1007/BF02468874 · DOI
  18. Mikov, 2006, Eur. J. Drug Metab. Pharmacokinet., 31, 237, 10.1007/BF03190714 · DOI
  19. Festi, 2007, Curr. Clin. Pharmacol., 2, 155, 10.2174/157488407780598171 · DOI
  20. Marshall, 2005, J. Natl. Cancer Inst., 97, 805, 10.1093/jnci/dji140 · DOI
  21. Pang, 2015, Anticancer effect of ursodeoxycholic acid in human oral squamous carcinoma HSC-3 cells through the caspases, Nutrients, 7, 200, 10.3390/nu7053200 · DOI
  22. Dyakova, 2014, Metal Zn(II), Cu(II), Ni (II) complexes of ursodeoxycholic acid as putative anticancer agents, Biotechnol. Biotechnol. Equip., 28, 543, 10.1080/13102818.2014.927973 · DOI
  23. Komori, 2014, Eur. J. Pharmacol., 724, 161, 10.1016/j.ejphar.2013.12.023 · DOI
  24. Powell, 2001, Bile acid hydrophobicity is correlated with induction of apoptosis and/or growth arrest in HCT116 cells, Biochem. J., 356, 481, 10.1042/bj3560481 · DOI
  25. Kim, 2006, Modulation of the cell cycle and induction of apoptosis in human cancer cells by synthetic bile acids, Curr. Cancer Drug Targets, 6, 681, 10.2174/156800906779010236 · DOI
  26. Choi, 2003, Apoptosis and modulation of cell cycle control by synthetic derivatives of ursodeoxycholic acid and chenodeoxycholic acid in human prostate cancer cells, Cancer Lett., 199, 157, 10.1016/S0304-3835(03)00351-3 · DOI
  27. Choi, 2001, Apoptotic activity of novel bile acid derivatives in human leukemic T cells through the activation of caspases, Int. J. Oncol., 18, 979
  28. Baek, 1997, Induction of apoptosis by bile acids in HepG2 human hepatocellular carcinoma cells, Korean J. Physiol. Pharmacol., 107
  29. Park, 1997, Induction of apoptosis in HepG2 human hepatocellular carcinoma cells by a novel derivative of ursodeoxycholic acid (UDCA), Arch. Pharmacal Res., 20, 29, 10.1007/BF02974038 · DOI
  30. Park, 2004, Synthetic bile acid derivatives inhibit cell proliferation and induce apoptosis in HT-29 human colon cancer cells, Int. J. Oncol., 25, 231
  31. Im, 1999, A novel ursodeoxycholic acid derivative induces apoptosis in human MCF-7 breast cancer cells, Pharm. Pharmacol. Commun., 5, 293, 10.1211/146080899128734875 · DOI
  32. Kim, 2004, Synthetic bile acid derivative HS-1200-induced apoptosis of human osteosarcoma cells, Korean J. Anat., 37, 449
  33. Im, 2001, Novel bile acid derivatives induce apoptosis via a p53-independent pathway in human breast carcinoma cells, Cancer Lett., 163, 83, 10.1016/S0304-3835(00)00671-6 · DOI
  34. Goldberg, 2013, Bile acids induce apoptosis selectively inandrogen-dependent and -independentprostate cancer cells, PeerJ, 1, e122, 10.7717/peerj.122 · DOI
  35. ElKihel, 2008, New lithocholic and chenodeoxycholic piperazinylcarboxamides with antiproliferative and pro-apoptotic effects on human cancer cell lines, Bioorg. Med. Chem., 16, 8737, 10.1016/j.bmc.2008.07.046 · DOI
  36. Brossard, 2010, Synthesis of bile acid derivatives and in vitro cytotoxic activity with pro-apoptotic process on multiple myeloma (KMS-11), glioblastoma multiforme (GBM), and colonic carcinoma (HCT-116) human cell lines, Eur. J. Med. Chem., 45, 2912, 10.1016/j.ejmech.2010.03.016 · DOI
  37. Brossard, 2014, Synthesis and biological evaluation of bile carboxamide derivatives with pro-apoptotic effect on human colon adenocarcinoma cell lines, Eur. J. Med. Chem., 86, 279, 10.1016/j.ejmech.2014.07.080 · DOI
  38. Chong, 2009, Bile acid-based polyaminocarboxylate conjugates as targeted antitumor agents, Chem. Commun., 21, 3011, 10.1039/b823000e · DOI
  39. Ahonen, 2012, Structural studies of five novel bile acid-4-aminopyridine conjugates, Steroids, 77, 1141, 10.1016/j.steroids.2012.06.003 · DOI
  40. Koivukorpi, 2008, Design, synthesis and spectral studies of novel bile acid-arene conjugates: trans to cis isomerization of azobenzene core controlled by bile acid hydrophobicity, J. Mol. Struct., 875, 63, 10.1016/j.molstruc.2007.03.058 · DOI
  41. Koivukorpi, 2008, Synthesis and characterization of novel bile-acid–heteroaryl conjugates with N-(2-aminoethyl)amido linker, J. Mol. Struct., 892, 53, 10.1016/j.molstruc.2008.04.057 · DOI
  42. Zheng, 2010, Structural requirements of the ASBT by 3D-QSAR analysis using aminopyridine conjugates of chenodeoxycholic acid, Bioconjug. Chem., 21, 2038, 10.1021/bc100273w · DOI
  43. Johan van Meerloo, Gertjan J.L. Kaspers, Jacqueline Cloos. Cell sensitivity assays: the MTT assay, in: Ian A. Cree (Ed.), Cancer Cell Culture: Methods and Protocols, second ed., vol. 731, Methods in Molecular Biology, 2011, pp. 237–45. · DOI
  44. Roda, 1996, Synthesis and physicochemical, biological, and pharmacological properties of new bile acids amidated with cyclic amino acids, J. Med. Chem., 39, 2270, 10.1021/jm9508503 · DOI
  45. Swaan, 1997, Enhanced transepithelial transport of peptides by conjugation to cholic acid, Bioconjug. Chem., 8, 520, 10.1021/bc970076t · DOI
  46. Bavikar, 2008, Synthesis of chimeric tetrapeptide-linked cholic acid derivatives: impending synergistic agents, Bioorg. Med. Chem. Lett., 18, 5512, 10.1016/j.bmcl.2008.09.013 · DOI
  47. Verma, 2012, Molecular docking and in vitro antileishmanial evaluation of chromene-2-thione analogues, ACS Med. Chem. Lett., 3, 243, 10.1021/ml200280r · DOI
  48. Lim, 2010, Ursodeoxycholic acid switches oxaliplatin-induced necrosis to apoptosis by inhibiting reactive oxygen species production and activating p53-caspase 8 pathway in HepG2 hepatocellular carcinoma, Int. J. Cancer, 126, 1582, 10.1002/ijc.24853 · DOI
  49. Wu, 2007, Design, synthesis, and antitumor activity of bile acid–polyamine–nucleoside conjugates, Bioorg. Med. Chem. Lett., 17, 2983, 10.1016/j.bmcl.2007.03.067 · DOI

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Metadata

Authors
Agarwal, D. S., Anantaraju, H. S., Sriram, D., Yogeeswari, P., Nanjegowda, S. H., Mallu, P., & Sakhuja, R.
Venue
Steroids
Publisher
Elsevier BV
Published
2016-03
Volume
107
Pages
87-97
ISSN
0039-128X
DOI
10.1016/j.steroids.2015.12.022
Cited by
37
References
0
Language
en
Licence
www.elsevier.com/tdm/userlicense/1.0/ (tdm)

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