Synthesis of cholesterol analogs having varying length alkyl side chains including cholesterol-23, 23, 24, 24, 25, 26, 26, 26, 27, 27, 27-d11 as probes of cholesterol's functions and properties

Chemistry and Physics of Lipids

Volumn 175-176, Issue , 2013, Pages 99-104

  Baek, Dong Jae ^a   Bittman, Robert ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

Cholesterol synthesis; Cyano containing sterol intermediates; Decyanation; Deuterium labeling

Indexed keywords

BROMIDE; CHOLESTEROL; CHOLESTEROL DERIVATIVE; MEMBRANE LIPID; POTASSIUM;

ALKYLATION; ARTICLE; PRIORITY JOURNAL; SYNTHESIS;

CHOLESTEROL SYNTHESIS; CYANO-CONTAINING STEROL INTERMEDIATES; DECYANATION; DEUTERIUM LABELING;

ALKYLATION; CHEMISTRY TECHNIQUES, SYNTHETIC; CHOLESTEROL; MEMBRANE LIPIDS; MOLECULAR PROBES; STEROLS;

EID: 84884378369     PISSN: 00093084     EISSN: 18732941     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2013.08.003     Document Type: Article

References (27)

1. R. Bittman Has nature designed the cholesterol side chain for optimal interaction with phospholipids? Subcell. Biochem. 28 1997 145 171
2. H.-S. Byun, and R. Bittman Practical multigram-scale synthesis of 4,6- and 4,8-sphingadienes, chemopreventive sphingoid bases Chem. Phys. Lipids 165 2012 794 801
3. 2 wagging progression intensities J. Am. Chem. Soc. 115 1993 12050 12055 (Pubitemid 24028554)
4. 7]-cholesterol J. Labelled Compd. Radiopharm. 43 2000 773 779 (Pubitemid 30389096)
5. P. Ciuffreda, S. Casati, L. Alessandrini, G. Terraneo, and E. Santaniello Synthesis of deuterated isotopomers of 7α- and (25RS)-26- hydroxycholesterol, internal standards for in vivo determination of the two biosynthetic pathways of bile acids Steroids 68 2003 733 738 (Pubitemid 37414812)
6. T. Holm, and I. Crossland A simple preparation of hexadeuteriocholesterol J. Labelled Compd. Radiopharm. 38 1996 803 808 (Pubitemid 26290357)
7. S. Jaikishan, and J.P. Slotte Effect of hydrophobic mismatch and interdigitation on sterol/sphingomyelin interaction in ternary bilayer membranes Biochim. Biophys. Acta 1808 2011 1940 1945
8. D.N. Kirk, M.J. Varley, H.L.J. Makin, and D.J.H. Trafford Synthesis of cholesterol-26,27-d6 and derivatives substituted in the side chain J. Chem. Soc. Perkin Trans. 1 1983 2563 2567
9. L. Li, H. Wang, and J.X. Cheng Quantitative coherent anti-Stokes scattering imaging of lipid distribution in coexisting domains Biophys. J. 89 2005 3480 3490 (Pubitemid 41636102)
10. Z. Li, E. Mintzer, and R. Bittman First synthesis of free cholesterol-BODIPY conjugates J. Org. Chem. 71 2006 1718 1721
11. D. Lütjohann, C.O. Meese, J.R. Crouse 3rd, and K. von Bergmann Evaluation of deuterated cholesterol and deuterated sitostanol for measurement of cholesterol absorption in humans J. Lipid Res. 34 1993 1039 1046 (Pubitemid 23182701)
12. J.-M. Mattalia, C. Marchi-Delapierre, H. Hazimah, and M. Chanon The reductive decyanation reaction: chemical methods and synthetic applications ARKIVOC 2006 90 118
13. C. Matthaus, C. Krafft, B. Dietzek, B.R. Brehm, S. Lorkowski, and J. Popp Noninvasive imaging of intracellular lipid metabolism in macrophages by Raman microscopy in combination with stable isotopic labeling Anal. Chem. 84 2012 8549 8556
14. P. Mattjus, R. Bittman, C. Vilchèze, and J.P. Slotte Lateral domain formation in cholesterol/phospholipid monolayers as affected by the sterol side chain conformation Biochim. Biophys. Acta 1240 1995 237 247 (Pubitemid 26004748)
15. T.P. McMullen, C. Vilchèze, R.N. McElhaney, and R. Bittman Differential scanning calorimetric study of the effect of sterol side chain length and structure on dipalmitoylphosphatidylcholine thermotropic phase behavior Biophys. J. 69 1995 169 176
16. M. Mihailescu, O. Soubias, D. Worcester, S.H. White, and K. Gawrisch Structure and dynamics of cholesterol-containing polyunsaturated lipid membranes studied by neutron diffraction and NMR J. Membr. Biol. 239 2011 63 71
17. M. Morisaki, M. Shibata, C. Duque, N. Imamura, and N. Ikekawa Studies on steroids LXIII. Synthesis of cholesterol analogs with a modified side chain Chem. Pharm. Bull. 28 1980 606 611 (Pubitemid 11236582)
18. T. Ohsawa, T. Kobayashi, Y. Mizuguchi, T. Saitoh, and T. Oishi Dissolving metal reduction with crown ether-reductive decyanation Tetrahedron Lett. 26 1985 6103 6106
19. T. Patra, S. Agasti, and Mati D. Akanksha Nickel-catalyzed decyanation of inert carbon-cyano bonds Chem. Commun. 49 2013 69 71
20. J.P. Pezacki, J.A. Blake, D.C. Danielson, D.C. Kennedy, R.K. Lyn, and R. Singaravelu Chemical contrast for imaging living systems: molecular vibrations drive CARS microscopy Nat. Chem. Biol. 7 2011 137 145
21. G. Rojas, T.W. Baughman, and K.B. Wagener Quantitative α-alkylation of primary nitriles Synth. Commun. 37 2007 3923 3931
22. S.D. Rychnovsky, and D.E. Mickus Synthesis of ent-cholesterol, the unnatural enantiomer J. Org. Chem. 57 1992 2732 2736
23. D. Savoia, E. Tagliavini, C. Trombini, and A. Umani-Ronchi Potassium on alumina as a reagent for reductive decyanation of alkyl nitriles J. Org. Chem. 45 1980 3227 3229
24. Scheidt, H.A., Meyer, T., Nikolaus, J., Baek, D.J., Haralampiev, I., Thomas, L., Bittman, R., Müller, P., Herrmann, A., Huster, D., 2013. Cholesterol's aliphatic side chain structure modulates membrane properties. Angew. Chem., Int. Ed., in press, http://dx.doi.org/10.1002/anie.201306753.
25. J.P. Slotte, M. Junger, C. Vilchèze, and R. Bittman Effect of sterol side-chain structure on sterol-phosphatidylcholine interactions in monolayers and small unilamellar vesicles Biochim. Biophys. Acta 1190 1994 435 443 (Pubitemid 24098509)
26. C. Vilchèze, T.P. McMullen, R.N. McElhaney, and R. Bittman The effect of side-chain analogues of cholesterol on the thermotropic phase behavior of 1-stearoyl-2-oleoylphosphatidylcholine bilayers: a differential scanning calorimetric study Biochim. Biophys. Acta 1279 1996 235 242 (Pubitemid 26080855)
27. T.J. Weeks, and T.R. Huser Differential imaging of biological structures with doubly-resonant coherent anti-Stokes Raman scattering (CARS) J. Vis. Exp. 44 2010 2085 2090