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Volumn 1828, Issue 8, 2013, Pages 1926-1937

Deciphering the role of charge, hydration, and hydrophobicity for cytotoxic activities and membrane interactions of bile acid based facial amphiphiles

Author keywords

Bile acids; Cancer; Cytotoxicity; Facial amphiphiles; Model membranes

Indexed keywords

AMPHOPHILE; ANNEXIN; BILE ACID; CATION; CHENODEOXYCHOLIC ACID; CHOLIC ACID; DEOXYCHOLIC ACID; LITHOCHOLIC ACID; TRIMETHYLAMMONIUM SALT DERIVATIVE;

EID: 84877820693     PISSN: 00052736     EISSN: 18792642     Source Type: Journal    
DOI: 10.1016/j.bbamem.2013.04.003     Document Type: Article
Times cited : (38)

References (34)
  • 1
    • 0033611305 scopus 로고    scopus 로고
    • The continuing importance of bile acids in liver and intestinal disease
    • A.F. Hofmann The continuing importance of bile acids in liver and intestinal disease Arch. Intern. Med. 159 1999 2647 2658
    • (1999) Arch. Intern. Med. , vol.159 , pp. 2647-2658
    • Hofmann, A.F.1
  • 2
    • 22644439708 scopus 로고    scopus 로고
    • Chemistry and biology of bile acids
    • S. Mukhopadhyay, and U. Maitra Chemistry and biology of bile acids: a review Curr. Sci. 87 2004 1666 1683 (Pubitemid 41024553)
    • (2004) Current Science , vol.87 , Issue.12 , pp. 1666-1683
    • Mukhopadhyay, S.1    Maitra, U.2
  • 3
    • 0035366705 scopus 로고    scopus 로고
    • Bile acid hydrophobicity is correlated with induction of apoptosis and/or growth arrest in HCT116 cells
    • DOI 10.1042/0264-6021:3560481
    • A.A. Powell, J.M. Larue, A.K. Batta, and J.D. Martinez Bile acid hydrophibicty is correlated with induction of apoptosis and/or growth arrest in HCT116 cells Biochem. J. 356 2001 481 486 (Pubitemid 32532359)
    • (2001) Biochemical Journal , vol.356 , Issue.2 , pp. 481-486
    • Powell, A.A.1    LaRue, J.M.2    Batta, A.K.3    Martinez, J.D.4
  • 4
    • 0037369402 scopus 로고    scopus 로고
    • Bile acid regulation of hepatic physiology III. Bile acids as nuclear receptors
    • J.Y.L. Chiang Bile acid regulation of hepatic physiology III. Bile acids as nuclear receptors Am. J. Physiol. Gastrointest. Liver Physiol. 284 2003 G349 G356
    • (2003) Am. J. Physiol. Gastrointest. Liver Physiol. , vol.284
    • Chiang, J.Y.L.1
  • 5
    • 12344253203 scopus 로고    scopus 로고
    • Diet, anaerobic bacterial metabolism, and colon cancer: A review of the literature
    • S.R. McGarr, J.M. Ridlon, and P.B. Hylemon Diet, anaerobicbacterial metabolism, and colon cancer: a review of the literature J. Clin. Gastroenterol. 39 2005 98 109 (Pubitemid 40130020)
    • (2005) Journal of Clinical Gastroenterology , vol.39 , Issue.2 , pp. 98-109
    • McGarr, S.E.1    Ridlon, J.M.2    Hylemon, P.B.3
  • 6
    • 70149089197 scopus 로고    scopus 로고
    • Diet, fecal water, and colon cancer development of a biomarker
    • J.R. Pearson, C.I. Gill, and I.R. Rowland Diet, fecal water, and colon cancer development of a biomarker Nutr. Rev. 67 2009 509 526
    • (2009) Nutr. Rev. , vol.67 , pp. 509-526
    • Pearson, J.R.1    Gill, C.I.2    Rowland, I.R.3
  • 7
    • 74249094907 scopus 로고    scopus 로고
    • Deoxycholic acid and selenium metabolite methylselenol exert common and distinct effects on cell cycle, apoptosis, and MAP kinase pathway in HCT116 human colon cancer cells
    • H. Zeng, J.H. Botnen, and M. Briske-Anderson Deoxycholic acid and selenium metabolite methylselenol exert common and distinct effects on cell cycle, apoptosis, and MAP kinase pathway in HCT116 human colon cancer cells Nutr. Cancer 62 2010 85 92
    • (2010) Nutr. Cancer , vol.62 , pp. 85-92
    • Zeng, H.1    Botnen, J.H.2    Briske-Anderson, M.3
  • 8
    • 25144462468 scopus 로고    scopus 로고
    • Ursodeoxycholic acid inhibits translocation of protein kinase C in human colonic cancer cell lines
    • DOI 10.1016/j.ejca.2005.06.015, PII S0959804905005551
    • S.A. Shah, E. Looby, Y. Volkov, A. Long, and D. Kelleher Ursodeoxycholic acid inhibits translocation of protein kinase C in human colonic cancer cell lines Eur. J. Cancer 41 2005 2160 2169 (Pubitemid 41337959)
    • (2005) European Journal of Cancer , vol.41 , Issue.14 , pp. 2160-2169
    • Shah, S.A.1    Looby, E.2    Volkov, Y.3    Long, A.4    Kelleher, D.5
  • 9
    • 48049086570 scopus 로고    scopus 로고
    • Bile acids and derivatives, their nuclear receptors FXR, PXR and ligands: Role in health and disease and their therapeutic potential
    • A. Zimber, and C. Gespach Bile acids and derivatives, their nuclear receptors FXR, PXR and ligands: Role in health and disease and their therapeutic potential Anticancer Agents Med. Chem. 8 2008 540 563
    • (2008) Anticancer Agents Med. Chem. , vol.8 , pp. 540-563
    • Zimber, A.1    Gespach, C.2
  • 11
    • 80052771111 scopus 로고    scopus 로고
    • Bile acids and colon cancer: Solving the puzzle with nuclear receptors
    • C. Degirolamo, S. Modica, G. Palasciano, and A. Moschetta Bile acids and colon cancer: solving the puzzle with nuclear receptors Trends Mol. Med. 17 2011 564 572
    • (2011) Trends Mol. Med. , vol.17 , pp. 564-572
    • Degirolamo, C.1    Modica, S.2    Palasciano, G.3    Moschetta, A.4
  • 13
    • 24344482024 scopus 로고    scopus 로고
    • Synthetic bile acid derivatives induce apoptosis through a c-Jun N-terminal kinase and NF-kB-dependent processing human cervical carcinoma cells
    • E. Ima, S. Choia, H. Suhb, Y. Hyun, C.Y.H. Yood, and N.D. Kim Synthetic bile acid derivatives induce apoptosis through a c-Jun N-terminal kinase and NF-kB-dependent processing human cervical carcinoma cells Cancer Lett. 229 2005 49 57
    • (2005) Cancer Lett. , vol.229 , pp. 49-57
    • Ima, E.1    Choia, S.2    Suhb, H.3    Hyun, Y.4    Yood, C.Y.H.5    Kim, N.D.6
  • 15
    • 77956342528 scopus 로고    scopus 로고
    • Bile acid toxicity structure-activity relationships: Correlations between cell viability and lipophilicity in a panel of new and known bile acids using an oesophageal cell line (HET-1A)
    • R. Sharma, F. Majer, V.K. Peta, J. Wang, R. Keaveney, D. Kelleher, A. Long, and J.F. Gilmer Bile acid toxicity structure-activity relationships: correlations between cell viability and lipophilicity in a panel of new and known bile acids using an oesophageal cell line (HET-1A) Bioorg. Med. Chem. 18 2010 6886 6895
    • (2010) Bioorg. Med. Chem. , vol.18 , pp. 6886-6895
    • Sharma, R.1    Majer, F.2    Peta, V.K.3    Wang, J.4    Keaveney, R.5    Kelleher, D.6    Long, A.7    Gilmer, J.F.8
  • 16
    • 51649084472 scopus 로고    scopus 로고
    • New lithocholic and chenodeoxycholic piperazinylcarboxamides with antiproliferative and pro-apoptotic effects on human cancer cell lines
    • L.E. Kihel, M. Clement, M. Bazin, G. Descamps, M. Khalid, and S. Rault New lithocholic and chenodeoxycholic piperazinylcarboxamides with antiproliferative and pro-apoptotic effects on human cancer cell lines Bioorg. Med. Chem. 16 2008 8737 8744
    • (2008) Bioorg. Med. Chem. , vol.16 , pp. 8737-8744
    • Kihel, L.E.1    Clement, M.2    Bazin, M.3    Descamps, G.4    Khalid, M.5    Rault, S.6
  • 17
    • 0035835492 scopus 로고    scopus 로고
    • Novel bile acid derivatives induce apoptosis via a p53-independent pathway in human breast carcinoma cells
    • DOI 10.1016/S0304-3835(00)00671-6, PII S0304383500006716
    • E. Im, Y.H. Choi, K. Paik, H. Suh, Y. Jin, K. Kim, Y.H. Yoo, and N.D. Kim Novel bile acid derivatives induce apoptosis via a p53-independent pathway in human breast carcinoma cells Cancer Lett. 163 2001 83 93 (Pubitemid 32121833)
    • (2001) Cancer Letters , vol.163 , Issue.1 , pp. 83-93
    • Im, E.-O.1    Choi, Y.H.2    Paik, K.-J.3    Suh, H.4    Jin, Y.5    Kim, K.-W.6    Yoo, Y.H.7    Kim, N.D.8
  • 18
    • 59149096566 scopus 로고    scopus 로고
    • Characterization of enantiomeric bile acid-induced apoptosis in colon cancer cell lines
    • B.W. Katona, S. Anant, D.F. Covey, and W.F. Stenson Characterization of enantiomeric bile acid-induced apoptosis in colon cancer cell lines J. Biol. Chem. 284 2009 3354 3364
    • (2009) J. Biol. Chem. , vol.284 , pp. 3354-3364
    • Katona, B.W.1    Anant, S.2    Covey, D.F.3    Stenson, W.F.4
  • 19
    • 50249155880 scopus 로고    scopus 로고
    • Synthesis and gene transfection properties of PEI cholesterol based lipopolymers
    • A. Bajaj, P. Kondaiah, and S. Bhattacharya Synthesis and gene transfection properties of PEI cholesterol based lipopolymers Bioconjug. Chem. 19 2008 1640 1651
    • (2008) Bioconjug. Chem. , vol.19 , pp. 1640-1651
    • Bajaj, A.1    Kondaiah, P.2    Bhattacharya, S.3
  • 20
    • 28544443984 scopus 로고    scopus 로고
    • Promoting apoptosis as a strategy for cancer drug discovery
    • DOI 10.1038/nrc1736
    • S.W. Fesik Promoting apoptosis as a strategy for cancer drug discovery Nat. Rev. Cancer 5 2005 876 885 (Pubitemid 41746032)
    • (2005) Nature Reviews Cancer , vol.5 , Issue.11 , pp. 876-885
    • Fesik, S.W.1
  • 21
    • 34047272300 scopus 로고    scopus 로고
    • Membrane-forming properties of pseudoglyceryl backbone based gemini lipids possessing oxyethylene spacers
    • DOI 10.1021/jp068383w
    • S. Bhattacharya, and A. Bajaj Membrane-forming properties of pseudoglyceryl backbone based gemini lipids possessing oxyethylene spacers J. Phys. Chem. B 111 2007 2463 2472 (Pubitemid 46548727)
    • (2007) Journal of Physical Chemistry B , vol.111 , Issue.10 , pp. 2463-2472
    • Bhattacharya, S.1    Bajaj, A.2
  • 23
    • 84874161797 scopus 로고    scopus 로고
    • Fluorescence (fluidity/hydration) and calorimetric studies of interactions of bile acid-drug conjugates with model membranes
    • V. Sreekanth, and A. Bajaj Fluorescence (fluidity/hydration) and calorimetric studies of interactions of bile acid-drug conjugates with model membranes J. Phys. Chem. B 117 2013 2123 2133
    • (2013) J. Phys. Chem. B , vol.117 , pp. 2123-2133
    • Sreekanth, V.1    Bajaj, A.2
  • 24
    • 50249133322 scopus 로고    scopus 로고
    • Fluorescence and thermotropic studies of the interactions of PEI-cholesterol based PEI-chol lipopolymers with dipalmitoyl phosphatidylcholine membranes
    • S. Bhattacharya, and A. Bajaj Fluorescence and thermotropic studies of the interactions of PEI-cholesterol based PEI-chol lipopolymers with dipalmitoyl phosphatidylcholine membranes Biochim. Biophys. Acta 1778 2008 2225 2233
    • (2008) Biochim. Biophys. Acta , vol.1778 , pp. 2225-2233
    • Bhattacharya, S.1    Bajaj, A.2
  • 25
    • 0020161197 scopus 로고
    • A scanning calorimetric study of small molecule-lipid bilayer mixtures
    • J.M. Sturtevant A scanning calorimetric study of small molecule-lipid bilayer mixtures Proc. Natl. Acad. Sci. U. S. A. 79 1982 3963 3967
    • (1982) Proc. Natl. Acad. Sci. U. S. A. , vol.79 , pp. 3963-3967
    • Sturtevant, J.M.1
  • 26
    • 0015501763 scopus 로고
    • Calorimetric studies of dilute aqueous suspensions of bilayers formed from synthetic L-α-lecithins
    • H.J. Hinz, and J.M. Sturtevant Calorimetric studies of dilute aqueous suspensions of bilayers formed from synthetic L-α-lecithins J. Biol. Chem. 247 1972 6071 6075
    • (1972) J. Biol. Chem. , vol.247 , pp. 6071-6075
    • Hinz, H.J.1    Sturtevant, J.M.2
  • 27
    • 0028942597 scopus 로고
    • New aspects of the interaction of cholesterol with dipalmitoylphosphatidylcholine bilayers as revealed by high-sensitivity differential scanning calorimetry
    • T.P.W. McMullen, and R.N. McElhaney New aspects of the interaction of cholesterol with dipalmitoylphosphatidylcholine bilayers as revealed by high-sensitivity differential scanning calorimetry Biochim. Biophys. Acta 1234 1995 90 98
    • (1995) Biochim. Biophys. Acta , vol.1234 , pp. 90-98
    • McMullen, T.P.W.1    McElhaney, R.N.2
  • 28
    • 70350049076 scopus 로고    scopus 로고
    • Biophysical interactions with model lipid membranes: Applications in drug discovery and drug delivery
    • C. Peetla, A. Stine, and V. Labhasetwar Biophysical interactions with model lipid membranes: applications in drug discovery and drug delivery Mol. Pharm. 6 2009 1264 1276
    • (2009) Mol. Pharm. , vol.6 , pp. 1264-1276
    • Peetla, C.1    Stine, A.2    Labhasetwar, V.3
  • 29
    • 62649142888 scopus 로고    scopus 로고
    • Higher liposomal membrane fluidity enhances the in vitro antitumor activity of folate-targeted liposomal mitoxantrone
    • K. Kawano, E. Onose, Y. Hattori, and Y. Maitani Higher liposomal membrane fluidity enhances the in vitro antitumor activity of folate-targeted liposomal mitoxantrone Mol. Pharm. 6 2009 98 104
    • (2009) Mol. Pharm. , vol.6 , pp. 98-104
    • Kawano, K.1    Onose, E.2    Hattori, Y.3    Maitani, Y.4
  • 30
    • 80052212748 scopus 로고    scopus 로고
    • Mixed DPPC/DPTAP monolayers at the air/water interface: Influence of Indolilo-3-acetic Acid and Selenate Ions on the monolayer morphology
    • B. Gzyl-Malcher, M. Filek, and G. Brezesinski Mixed DPPC/DPTAP monolayers at the air/water interface: influence of Indolilo-3-acetic Acid and Selenate Ions on the monolayer morphology Langmuir 27 2011 10886 10893
    • (2011) Langmuir , vol.27 , pp. 10886-10893
    • Gzyl-Malcher, B.1    Filek, M.2    Brezesinski, G.3
  • 31
    • 33846131989 scopus 로고    scopus 로고
    • Characterization of lipophilic gemcitabine prodrug-liposomal membrane interaction by differential scanning calorimetry
    • F. Castelli, M. Grazia Sarpietro, M. Ceruti, F. Rocco, and L. Cattel Characterization of lipophilic gemcitabine prodrug-liposomal membrane interaction by differential scanning calorimetry Mol. Pharm. 3 2006 738 746
    • (2006) Mol. Pharm. , vol.3 , pp. 738-746
    • Castelli, F.1    Grazia Sarpietro, M.2    Ceruti, M.3    Rocco, F.4    Cattel, L.5
  • 33
    • 42449162322 scopus 로고    scopus 로고
    • Binding of nonsteroidal anti-inflammatory drugs to DPPC: Structure and thermodynamic aspects
    • DOI 10.1021/la703584s
    • M. Lucio, F. Bringezu, S. Reis, J.F.C. Lima, and G. Brezesinski Binding of non-steroidal anti-inflammatory drugs to DPPC: structure and thermodynamic actions Langmuir 24 2008 4132 4139 (Pubitemid 351569020)
    • (2008) Langmuir , vol.24 , Issue.8 , pp. 4132-4139
    • Lucio, M.1    Bringezu, F.2    Reis, S.3    Lima, J.L.F.C.4    Brezesinski, G.5
  • 34
    • 0028149585 scopus 로고
    • Drug membrane interaction and the importance for drug transport, distribution, accumulation, efficacy and resistance
    • DOI 10.1002/ardp.19943271002
    • J.K. Seydel, E.A. Coats, H.P. Cordes, and M. Wiese Drug membrane interaction and the importance for drug transport, distribution, accumulation, efficacy and resistance Arch. Pharm. (Weinheim) 327 1994 601 610 (Pubitemid 24323858)
    • (1994) Archiv der Pharmazie , vol.327 , Issue.10 , pp. 601-610
    • Seydel, J.K.1    Coats, E.A.2    Cordes, H.P.3    Wiese, M.4


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