Synthesis of New Water-Soluble Cholesterol Derivatives

REFERENCES

• Smith , L. L. Another cholesterol hypothesis: Cholesterol as antioxidant . Free Radic. Biol. Med. 1991 , 11 , 47 – 61 .
   PubMed Web of Science ®Google Scholar
• Hamlyn , J. M. ; Lu , Z. R. ; Manunta , P. ; Ludens , J. H. ; Kimura , K. ; Shah , J. R. ; Laredo , J. ; Hamilton , J. P. ; Hamilton , M. J. ; Hamilton , B. P. Observations on the nature, biosynthesis, secretion, and significance of endogenous ouabain . Clin. Exp. Hypertens. 1998 , 20 , 523 – 533 .
   PubMed Web of Science ®Google Scholar
• Komiyama , Y. ; Nishimura , N. ; Munakata , M. ; Mori , T. ; Okuda , K. ; Nishino , N. ; Hirose , S. ; Kosaka , C. ; Masuda , M. ; Takahashi , H. Identification of endogenous ouabain in culture supernatant of PC12 cells . J. Hypertens. 2001 , 19 , 229 – 236 .
   PubMed Web of Science ®Google Scholar
• Perrin , A. ; Brasmes , B. ; Chambaz , E. M. ; Defaye , G. Bovine adrenocortical cells in culture synthesize an ouabain-like compound . Mol. Cell. Endocrinol. 1997 , 126 , 7 – 15 .
   PubMed Web of Science ®Google Scholar
• Lichtstein , D. ; Steinitz , M. ; Gati , I. ; Samuelov , S. ; Deutsch , J. ; Orly , J. Biosynthesis of digitalis-like compounds in rat adrenal cells: Hydroxycholesterol as possible precursor . Life Sci. 1998 , 62 , 2109 – 2126 .
   PubMedGoogle Scholar
• Qazzaz , H. M. ; Cao , Z. ; Bolanowski , D. D. ; Clark , B. J. ; Valdes , Jr., R. De novo biosynthesis and radiolabeling of mammalian digitalis-like factors . Clin. Chem. 2004 , 50 , 612 – 620 .
   PubMedGoogle Scholar
• Dmitrieva , R. I. ; Bagrov , A. Y. ; Lalli , E. ; Sassone-Corsi , P. ; Stocco , D. M. ; Doris , P. A. Mammalian bufadienolide is synthesized from cholesterol in the adrenal cortex by a pathway that is independent of cholesterol side-chain cleavage . Hypertension 2000 , 36 , 442 – 448 .
   PubMed Web of Science ®Google Scholar
• Jing , Y. ; Ohizumi , H. ; Kawazoe , N. ; Hashimoto , S. ; Masuda , Y. ; Nakajo , S. ; Yoshida , T. ; Kuroiwa , Y. ; Nakaya , K. Selective inhibitory effect of bufalin on growth of human tumor cells in vitro: Association with the induction of apoptosis in leukemia HL-60 cells . Jpn. J. Cancer Res. 1994 , 85 , 645 – 651 .
   PubMedGoogle Scholar
• Kawazoe , N. ; Aiuchi , T. ; Masuda , Y. ; Nakajo , S. ; Nakaya , K. Induction of apoptosis by bufalin in human tumor cells is associated with a change of intracellular concentration of Na+ ions . J. Biochem. 1999 , 126 , 278 – 286 .
   PubMed Web of Science ®Google Scholar
• Masuda , Y. ; Kawazoe , N. ; Nakajo , S. ; Yoshida , T. ; Kuroiwa , Y. ; Nakaya , K. Bufalin induces apoptosis and influences the expression of apoptosis-related genes in human leukemia cells . Leuk. Res. 1995 , 19 , 549 – 556 .
   PubMed Web of Science ®Google Scholar
• Sreenivasan , Y. ; Raghavendra , P. B. ; Manna , S. K. Oleandrin-mediated expression of Fas potentiates apoptosis in tumor cells . J. Clin. Immunol. 2006 , 26 , 308 – 322 .
   PubMed Web of Science ®Google Scholar
• Fassbender , K. ; Simons , M. ; Bergmann , C. ; Stroick , M. ; Lutjohann , D. ; Keller , P. ; Runz , H. ; Kuhl , S. ; Bertsch , T. ; von Bergmann , K. ; Hennerici , M. ; Beyreuther , K. ; Hartmann , T. Simvastatin strongly reduces levels of Alzheimer's disease β-amyloid peptides Abeta 42 and Abeta 40 in vitro and in vivo . Proc. Natl. Acad. Sci. USA 2001 , 98 , 5856 – 5861 .
   PubMed Web of Science ®Google Scholar
• Haley , R. W. ; Dietschy , J. M. Is there a connection between the concentration of cholesterol circulating in plasma and the rate of neuritic plaque formation in Alzheimer disease? Arch. Neurol. 2000 , 57 , 1410 – 1412 .
   PubMedGoogle Scholar
• Refolo , L. M. ; Malester , B. ; LaFrancois , J. ; Bryant-Thomas , T. ; Wang , R. ; Tint , G. S. ; Sambamurti , K. ; Duff , K. ; Pappolla , M. A. Hypercholesterolemia accelerates the Alzheimer's amyloid pathology in a transgenic mouse model . Neurobiol. Dis. 2000 , 7 , 321 – 331 .
   PubMed Web of Science ®Google Scholar
• Simons , M. ; Keller , P. ; De Strooper , B. ; Beyreuther , K. ; Dotti , C. G. ; Simons , K. Cholesterol depletion inhibits the generation of β-amyloid in hippocampal neurons . Proc. Natl. Acad. Sci. USA 1998 , 95 , 6460 – 6464 .
   PubMed Web of Science ®Google Scholar
• Simons , M. ; Keller , P. ; Dichgans , J. ; Schulz , J. B. Cholesterol and Alzheimer's disease: Is there a link? Neurology 2001, 57, 1089–1093.
   PubMed Web of Science ®Google Scholar
• Chandrasekar , K. ; Baskar , G. Cholesterol mesogen containing water-soluble copolymers: Design and organization behavior at different interfaces . Biomacromolecules 2007 , 8 , 1665 – 1675 .
   PubMedGoogle Scholar
• Ioffe , D. V. ; Klimov , A. N. ; Mal'tseva , O. A. ; Nekrasova , V. B. Water-soluble sterol derivatives . Khim. Prir. Soedin. 1980 , 5 , 655 – 657 .
   Google Scholar
• Klein , B. ; Kleinman , N. B. ; Foreman , J. A. Preparation and evaluation of a water-soluble cholesterol standard . Clin. Chem. 1974 , 20 , 482 – 485 .
   PubMed Web of Science ®Google Scholar
• Proksch , G. J. ; Bonderman , D. P. A water-soluble cholesterol derivative for use in augmenting serum control materials . Clin. Chem. 1978 , 24 , 1924 – 1926 .
   PubMed Web of Science ®Google Scholar
• Wang , D. A. ; Narang , A. S. ; Kotb , M. ; Gaber , A. O. ; Miller , D. D. ; Kim , S. W. ; Mahato , R. I. Novel branched poly(ethylenimine)-cholesterol water-soluble lipopolymers for gene delivery . Biomacromolecules 2002 , 3 , 1197 – 1207 .
   PubMed Web of Science ®Google Scholar
• Lee , M. ; Rentz , J. ; Bikram , M. ; Han , S. ; Bull , D. A. ; Kim , S. W. Hypoxia-inducible VEGF gene delivery to ischemic myocardium using water-soluble lipopolymer . Gene Ther. 2003 , 10 , 1535 – 1542 .
   PubMed Web of Science ®Google Scholar
• Lee , M. ; Rentz , J. ; Han , S. O. ; Bull , D. A. ; Kim , S. W. Water-soluble lipopolymer as an efficient carrier for gene delivery to myocardium . Gene Ther. 2003 , 10 , 585 – 593 .
   PubMed Web of Science ®Google Scholar
• Roelen , H. C. P. F. ; Bijsterbosch , M. K. ; Bakkeren , H. F. ; Van Berkel , T. J. C. ; Kempen , H. J. M. ; Buytenhek , M. ; Van der Marel , G. A. ; Van Boom , J. H. Water-soluble cholesteryl-containing phosphorothioate monogalactosides: Synthesis, properties, and use in lowering blood cholesterol by directing plasma lipoproteins to the liver . J. Med. Chem. 1991 , 34 , 1036 – 1042 .
   PubMed Web of Science ®Google Scholar
• Xie , W. ; Peng , H. R. ; Kim , D. I. ; Kunkel , M. ; Powis , G. ; Zalkow , L. H. Structure–activity relationship of aza-steroids as PI-PLC inhibitors . Bioorg. Med. Chem. 2001 , 9 , 1073 – 1083 .
   PubMedGoogle Scholar
• Ashton , P. R. ; Huff , J. ; Menzer , S. ; Parsons , I. W. ; Preece , J. A. ; Stoddart , J. F. ; Tolley , M. S. ; White , A. J. P. ; Williams , D. J. Bis[2]catenanes and a bis[2]rotaxane: Model compounds for polymers with mechanically interlocked components . Chem. Eur. J. 1996 , 2 , 31 – 44 .
   Web of Science ®Google Scholar
• Dekker , F. J. ; de Mol , N. J. ; van Ameijde , J. ; Fischer , M. J. E. ; Ruijtenbeek , R. ; Redegeld , F. A. M. ; Liskamp , R. M. J. Replacement of the intervening amino acid sequence of a Syk-binding diphosphopeptide by a nonpeptide spacer with preservation of high affinity . Chem. Bio. Chem. 2002 , 3 , 238 – 242 .
   Google Scholar
• Goncalves , M. ; Estieu-Gionnet , K. ; Berthelot , T. ; Lain , G. ; Bayle , M. ; Canron , X. ; Betz , N. ; Bikfalvi , A. ; Deleris , G. Design, synthesis, and evaluation of original carriers for targeting vascular endothelial growth factor receptor interactions . Pharm. Res. 2005 , 22 , 1411 – 1421 .
   PubMedGoogle Scholar
• Katritzky , A. R. ; Singh , S. K. ; Meher , N. K. ; Doskocz , J. ; Suzuki , K. ; Jiang , R. ; Sommen , G. L. ; Ciaramitaro , D. A. ; Steel , P. J. Triazole-oligomers by 1,3-dipolar cycloaddition . Arkivoc 2006 , 43 – 62 .
   Google Scholar
• Yaniç , C. ; Bredenkamp , M. W. ; Jacobs , E. P. ; Swart , P. Adsorbed surfactants for affinity chromatography: End-group modification of ethylene glycol polymers . Bioorg. Med. Chem. Lett. 2003 , 13 , 1381 – 1384 .
   PubMedGoogle Scholar
• Barragan-Montero , V. ; Winum , J. Y. ; Moles , J. P. ; Emmanuelle , J. ; Clavel , C. ; Montero , J. L. Synthesis and properties of isocannabinoid and cholesterol derivatized rhamnosurfactants: Application to liposomal targeting of keratinocytes and skin . Eur. J. Med. Chem. 2005 , 40 , 1022 – 1029 .
   PubMedGoogle Scholar
• Loiseau , F. A. ; Hii , K. K. ; Hill , A. M. Multigram synthesis of well-defined extended bifunctional polyethylene glycol (PEG) chains . J. Org. Chem. 2004 , 69 , 639 – 647 .
   PubMed Web of Science ®Google Scholar
• Barluenga , J. ; de Prado , A. ; Santamaria , J. ; Tomas , M. Polymer-bound fischer tungsten carbene complexes: Synthesis and reactivity. Organometallics 2005, 24, 3614–3617.
   Google Scholar
• Saad , H. Y. ; Higuchi , W. I. Water solubility of cholesterol . J. Pharm. Sci. 1965 , 54 , 1205 – 1206 .
   PubMed Web of Science ®Google Scholar
• Liu , M. L. ; Mao , X. A. ; Ye , C. H. ; Huang , H. ; Nicholson , J. K. ; Lindon , J. C. Improved watergate pulse sequences for solvent suppression in NMR spectroscopy . J. Magn. Reson. 1998 , 132 , 125 – 129 .
   Web of Science ®Google Scholar