Benzophenone-containing cholesterol surrogates: Synthesis and biological evaluation

Journal of Lipid Research

Volumn 45, Issue 8, 2004, Pages 1510-1518

  Spencer, Thomas A ^a   Wang, Pingzhen ^a   Li, Dansu ^a   Russel, Jonathon S ^a   Blank, David H ^a   Huuskonen, Jarkko ^c   Fielding, Phoebe E ^b   Fielding, Christopher J ^c  

^a Dartmouth College   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Apolipoprotein A I; Cellular sterol efflux; Cholesterol; Photoactivable sterols; Photoaffinity labeling

Indexed keywords

APOLIPOPROTEIN A1; BENZOPHENONE; CHOLESTEROL DERIVATIVE; HIGH DENSITY LIPOPROTEIN; TRITIUM;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CHOLESTEROL SYNTHESIS; CHOLESTEROL TRANSPORT; CONTROLLED STUDY; DILUTION; FIBROBLAST; HUMAN; HUMAN CELL; LIPID COMPOSITION; LIPID HYDROLYSIS; MONOLAYER CULTURE; PHOTOAFFINITY LABELING; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

ATP-BINDING CASSETTE TRANSPORTERS; BENZOPHENONES; CHOLESTEROL; FIBROBLASTS; HUMANS; RNA, MESSENGER; TRITIUM;

EID: 3442875823     PISSN: 00222275     EISSN: None     Source Type: Journal    
DOI: 10.1194/jlr.M400081-JLR200     Document Type: Article

References (63)

1. Dorman, G., and G. D. Prestwich. 1994. Benzophenone photophores in biochemistry. Biochemistry. 33: 5661-5673.
2. Kym, P. R., K. E. Carlson, and J. A. Katzenellenbogen. 1993. Progestin 16α, 17α-dioxolane ketals as molecular probes for the progesterone receptor: synthesis, binding affinity, and photochemical evaluation. J. Med. Chem. 36: 1111-1119.
3. Fra, A. M., M. Masserini, P. Palestini, S. Sonnino, and K. Simons. 1995. A photoreactive derivative of ganglioside GM1 specifically crosslinks VIP21-caveolin on the cell surface. FEBS Lett. 375: 11-14.
4. Thiele, C., M. J. Hannah, F. Fahrenholz, and W. B. Huttner. 2000. Cholesterol binds to synaptophysin and is required for biogenesis of synaptic vesicles. Nat. Cell Biol. 2: 42-49.
5. Cruz, J. C., M. Thomas, E. Wong, N. Ohgami, S. Sugii, T. Curphey, C. C. Y. Chang, and T-Y. Chang. 2002. Synthesis and biochemical properties of a new photoactivatable cholesterol analog 7,7-azocholestanol and its linoleate ester in Chinese hamster ovary cell lines. J. Lipid Res. 43: 1341-1347.
6. Simons, M., E-M. Krämer, C. Thiele, W. Stoffel, and J. Trotter. 2000. Assembly of myelin by association of proteolipid protein with cholesterol- and galactosylceramide-rich membrane domains. J. Cell Biol. 151: 143-153.
7. Matyash, V., C. Geier, A. Henske, S. Mukherjee, D. Hirsh, C. Thiele, B. Grant, F. R. Maxfield, and T. V. Kurzchalia. 2001. Distribution and transport of cholesterol in Caenorhabditis elegans. Mol. Biol. Cell. 12: 1725-1736.
8. Wang, N., D. L. Silver, C. Thiele, and A. R. Tall. 2001. ATP-binding cassette transporter A1 (ABCA1) functions as a cholesterol efflux regulatory protein. J. Biol. Chem. 276: 23742-23747.
9. Mintzer, E. A., B-L. Waarts, J. Wilschut, and R. Bittman. 2002. Behavior of a photoactivable analog of cholesterol, 6-photocholesterol, in model membranes. FEBS Lett. 510: 181-184.
10. Prestwich, G. D., G. Dorman, J. T. Elliott, D. M. Marecak, and A. Chaudhary. 1997. Benzophenone photophores in biochemistry. Photochem. Photobiol. 65: 222-234.
11. Nakatani, Y., M. Yamamoto, Y. Diyizou, W. Warnock, V. Dolle, W. Hahn, A. Milon, and G. Ourisson. 1996. Studies on the topography of biomembranes: regioselective photolabeling in vesicles with the tandem use of cholesterol and a photoactivable phospholipidic probe. Chem. Eur. J. 2: 129-138.
12. Weber, P. J. A., and A. G. Beck-Sickinger. 1997. Comparison of the photochemical behavior of four different photoactivable probes. J. Pept. Res. 49: 375-383.
13. Fielding, P. E., J. S. Russel, T. A. Spencer, H. Hakamata, K. Nagao, and C. J. Fielding. 2002. Sterol efflux to apolipoprotein A-I originates from caveolin-rich microdomains and potentiates PDGF-dependent protein kinase activity. Biochemistry. 41: 4929-4937.
14. Johnson, W. J., F. H. Mahlberg, G. H. Rothblat, and M. C. Phillips. 1991. Cholesterol transport between cells and high-density lipoproteins. Biochim. Biophys. Acta. 1085: 273-298.
15. Marecak, D. M., Y. Horiuchi, H. Arai, M. Shimonaga, Y. Maki, T. Koyama, K. Ogura, and G. D. Prestwich. 1997. Benzoylphenoxy analogs of isoprenoid diphosphates as photoactivatable substrates for bacterial prenyltransferases. Bioorg. Med. Chem. Lett. 7: 1973-1978.
16. Mitsunobu, O. 1981. The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products. Synthesis. 1-28.
17. Partridge, J. J., S. Faber, and M. R. Uskokovic. 1974. Vitamin D3 metabolites I. Synthesis of 25-hydroxycholesterol. Helv. Chim. Acta. 57: 764-771.
18. Kim, H-S., W. K. Wilson, D. H. Needleman, F. D. Pinkerton, D. K. Wilson, F. A. Quiocho, and G. J. Schroepfer, Jr. 1989. Inhibitors of sterol synthesis. Chemical synthesis, structure, and biological activities of (25R)-3β-26- dihydroxy-5α-cholest-8(14)-en-15-one, a metabolite of 3β-hydroxy- 5α-cholest-8(14)-en-15-one. J. Lipid Res. 30: 247-261.
19. Takaku, H., K. Kamaike, and H. Tsuchiya. 1984. Synthesis of ribooligonucleotides using the 4-methoxybenzyl group as a new protecting group for the 2′-hydroxyl group. J. Org. Chem. 49: 51-56.
20. Rychnovsky, S. D., and D. E. Mickus. 1992. Synthesis of ent-cholesterol, the unnatural enantiomer. J. Org. Chem. 57: 2732-2736.
21. Zhao, H., N. Neamati, Y. Pommier, and T. R. Burke, Jr. 1997. Design and synthesis of photoactivatable coumarin-containing HIV-1 integrase inhibitors. Heterocycles. 45: 2277-2282.
22. Barton, D. H. R., and L. R. Morgan, Jr. 1962. Photochemical transformations. XII. Photolysis of azides. J. Chem. Soc. 622-631.
23. Jarreau, F. X., Q. Khung-Huu, and R. Goutarel. 1963. Steroid alkaloids. XIX. New method of synthesis of 3β-amino-Δ-5-steroids. Bull. Soc. Chim. Fr. 8-9: 1861-1865.
24. Wolff, H. 1946. Schmidt reaction. Org. React. III: 307-336.
25. Barnett, J., B. E. Ryman, and F. Smith. 1946. Aminosteroids. II. Preparation of 3,7-diketocholestene. J. Chem. Soc. 526-528.
26. Bose, A. K., J. F. Kistner, and L. Farber. 1962. Convenient synthesis of axial amines. J. Org. Chem. 27: 2925-2927.
27. Firestone, R. A., J. M. Pisano, J. R. Falck, M. M. McPhaul, and M. M. Krieger. 1984. Selective delivery of cytotoxic compounds to cells by the LDL pathway. J. Med. Chem. 27: 1037-1043.
28. Cope, A. C., and E. Ciganek. 1963. N,N-Dimethylcyclohexylmethylamine. Org. Synth. Coll. Vol. 4: 339-342.
29. Wertheim, E. 1933. Benzylbenzaldoxime. J. Am. Chem. Soc. 55: 2540-2543.
30. Blakey, W., W. I. Jones, and H. A. Scarborough. 1927. Substitution products of 4-hydroxybenzophenone and of its methyl ether. J. Chem. Soc. Abstracts. 2865-2872.
31. Dorman, G., J. D. Olszewski, G. D. Prestwich, Y. Hong, and D. G. Ahern. 1995. Synthesis of highly tritiated 4-benzoyl-L-phenylalanine, a photoactivatable amino acid. J. Org. Chem. 60: 2292-2297.
32. Brewer, H. B., Jr., R. Ronan, and C. Bishop. 1986. Isolation and characterization of apolipoproteins A-I, A-II, and A-IV. Methods Enzymol. 128: 223-246.
33. Fielding, C. J. 1985. Lecithin-cholesterol acyltransferase and cholesterol transport. MethodsEnzymol. 111: 267-274.
34. Huuskonen, J., M. Vishnu, C. R. Pullinger, P. E. Fielding, and C. J. Fielding. 2004. Regulation of ATP-binding cassette transporter A1 transcription by thyroid hormone receptor. Biochemistry. 43: 1626-1632.
35. Tomkinson, N. C. O., T. M. Willson, J. S. Russel, and T. A. Spencer. 1998. Efficient stereoselective synthesis of 24(S),25-epoxycholesterol. J. Org. Chem. 63: 9919-9923.
36. Spencer, T. A., D. Li, J. S. Russel, N. C. O. Tomkinson, and T. M. Willson. 2000. Further studies on the synthesis of 24(S),25-epoxy-cholesterol. A new efficient synthesis of desmosterol. J. Org. Chem. 65: 1919-1923.
37. Lawn, R. M., D. P. Wade, M. R. Garvin, X. Wang, K. Schwartz, J. G. Porter, J. J. Seilhamer, A. M. Vaughan, and J. F. Oram. 1999. The Tangier disease gene product ABC1 controls the cellular apolipoprotein-mediated lipid removal pathway. J. Clin. Invest. 104: R25-R31.
38. Huuskonen, J., M. Abedin, M. Vishnu, C. R. Pullinger, S. E. Baranzini, J. P. Kane, P. E. Fielding, and C. J. Fielding. 2003. Dynamic regulation of alternative ATP-binding cassette transporter A1 transcripts. Biochem. Biophys. Res. Commun. 306: 463-468.
39. Yeagle, P. L. 1991. Modulation of membrane function by cholesterol. Biochimie. 73: 1303-1310.
40. McConnell, H. M., and A. Radhakrishnan. 2003. Condensed complexes of cholesterol and phospholipids. Biochim. Biophys. Acta. 1610: 159-173.
41. Cao, H., N. Tokutake, and S. L. Regen. 2003. Unraveling the mystery surrounding cholesterol's condensing effect. J. Am. Chem. Soc. 125: 16182-16183.
42. Wang, J., Megha, and E. London. 2004. Relationship between sterol/steroid structure and participation in ordered lipid domains (lipid rafts): implications for lipid raft structure and function. Biochemistry. 43: 1010-1018.
43. Friedland, N., H-L. Liou, P. Lobel, and A. M. Stock. 2003. Structure of a cholesterol-binding protein deficient in Niemann-Pick type C2 disease. Proc. Natl. Acad. Sci. USA. 100: 2512-2517.
44. Mathieu, A. P., P. Lavigne, and J-G. LeHoux. 2002. Molecular modeling and structure-based thermodynamic analyses of the StAR protein. Endocr. Res. 28: 419-423.
45. Li, H., Z. Yao, B. Degenhardt, G. Teper, and V. Papadopoulos. 2001. Cholesterol binding and the cholesterol recognition/interaction amino acid consensus (CRAC) of the peripheral-type benzodiazepine receptor and inhibition of steroidogenesis by an HIV TAT-CRAC peptide. Proc. Natl. Acad. Sci. USA. 98: 1267-1272.
46. Li, H., and V. Papadopoulos. 1998. Peripheral-type benzodiazepine receptor function in cholesterol transport. Identification of a putative cholesterol recognition/interaction amino acid sequence and consensus pattern. Endocrinology. 139: 4991-4997.
47. Fielding, C. J., A. Bist, and P. E. Fielding. 1998. Intracellular cholesterol transport in synchronized human skin fibroblasts. In Intracellular Cholesterol Trafficking. T-Y. Chang, and D. A. Freeman, editors. Kluwer Academic Publishing, Boston, MA. 273-288.
48. Forre, T. M., J. J. Bell-Quint, and F. Cheng. 1981. Lipoproteins of fetal and newborn calves and adult steer: a study of developmental changes. Lipids. 16: 240-245.
49. Fielding, P. E., and C. J. Fielding. 1996. Intracellular transport of low density lipoprotein derived free cholesterol begins at clathrin coated-pits and terminates at cell surface caveolae. Biochemistry. 35: 14932-14938.
50. Subtil, A., I. Gaidarov, K. Kobylarz, M. A. Lampson, J. H. Keen, and T. E. McGraw. 1999. Acute cholesterol depletion inhibits clathrin-coated pit budding. Proc. Natl. Acad. Sci. USA. 96: 6775-6780.
51. Gagescu, R., N. Demaurex, R. G. Parton, W. Hunziker, L. A. Huber, and J. Gruenberg. 2000. The recycling endosome of Madin-Darby canine kidney cells is a mildly acidic compartment rich in raft components. Mol. Biol. Cell. 11: 2775-2791.
52. Wilson, M. D., and L. L. Rudel. 1994. Review of cholesterol absorption with emphasis on dietary and biliary cholesterol. J. Lipid Res. 35: 943-955.
53. Salen, G., S. Shefer, L. Nguyen, G. C. Ness, G. S. Tint, and V. Shore. 1992. Sitosterolemia. J. Lipid Res. 33: 945-955.
54. Lee, M-H., K. Lu, S. Hazard, H. Yu, S. Shulenin, H. Hidaka, H. Kojima, R. Allikmets, N. Sakuma, R. Pegoraro, A. K. Srivastava, G. Salen, M. Dean, and S. B. Patel. 2001. Identification of a gene, ABCG5, important in the regulation of dietary cholesterol absorption. Nat. Genet. 27: 79-83.
55. Lu, K., M. H. Lee, S. Hazard, A. Brooks-Wilson, H. Hidaka, H. Kojima, L. Ose, A. F. H. Stalenhoef, T. Mietennen, I. Bjorkhem, E. Bruckert, A. Pandya, H. B. Brewer, Jr., G. Salen, M. Dean, A. Srivastava, and S. B. Patel. 2001. Two genes that map to the STSL locus cause sitosterolemia: genomic structure and spectrum of mutations involving sterolin-1 and sterolin-2, encoded by ABCG5 and ABCG8, respectively. Am. J. Hum. Genet. 69: 278-290.
56. Schroeder, F., G. Nemecz, E. Gratton, Y. Barenholtz, and T. E. Thompson. 1988. Fluorescence properties of cholestatrienol in phosphatidylcholine bilayer vesicles. Biophys. Chem. 32: 57-72.
57. Mukherjee, S., X. Zha, I. Tabas, and F. R. Maxfield. 1998. Cholesterol distribution in living cells: fluorescence imaging using dehydroergosterol as a fluorescent cholesterol analog. Biophys. J. 75: 1915-1925.
58. Xu, X., R. Bittman, G. Duportail, D. Heissler, C. Vilcheze, and E. London. 2001. Effect of the structure of natural sterols and sphingolipids on the formation of ordered sphingolipid/sterol domains (rafts). J. Biol. Chem. 276: 33540-33546.
59. Scheidt, H. A., P. Müller, A. Herrmann, and D. Huster. 2003. The potential of fluorescent and spin-labeled steroid analogs to mimic natural cholesterol. J. Biol. Chem. 278: 45563-45569.
60. Wenz, J. J., and F. J. Barrantes. 2003. Steroid structural requirements for stabilizing or disrupting lipid domains. Biochemistry. 42: 14267-14276.
61. Forslind, E., and R. Kjellander. 1975. Structure model for the lecithin-cholesterol-water membrane. J. Theor. Biol. 51: 97-109.
62. Thurnhofer, H., and H. Hauser. 1990. Uptake of cholesterol by small intestinal brush border membrane is protein-mediated. Biochemistry. 29: 2142-2148.
63. Zheng, Y-H., A. Plemenitas, C. J. Fielding, B. Peterlin, and B. Matija. 2003. Nef increases the synthesis of and transports cholesterol to lipid rafts and HIV-1 progeny virions. Proc. Natl. Acad. Sci. USA. 100: 8460-8465.