Inhibition of sterol biosynthesis in animal cells by 14 alpha-hydroxymethyl sterols.

Kandutsch, 1973, Inhibition of sterol synthesis in cultured mouse cells by 7α-hydroxycholesterol, 7β-hydroxycholesterol, and 7-ketocholesterol, J. Biol. Chem., 248, 8408, 10.1016/S0021-9258(19)43148-7

Kandutsch, 1974, Inhibition of sterol synthesis in cultured mouse cells by cholesterol derivatives oxygenated in the side chain, J. Biol. Chemin, 6057, 10.1016/S0021-9258(19)42218-7

Kandutsch, 1975, Regulation of sterol synthesis in cultured cells by oxygenated derivatives of cholesterol, J. Cell. Physiol., 85, 415, 10.1002/jcp.1040850408

Kandutsch, 1978, Biological activity of some oxygenated sterols, Science., 201, 498, 10.1126/science.663671

Bloch, 1965, The biological synthesis of cholesterol, Science., 150, 19, 10.1126/science.150.3692.19

Frantz, 1967, Sterol biosynthesis, Ann. Rev. Biochem., 36, 691, 10.1146/annurev.bi.36.070167.003355

Schroepfer, 1972, Recent investigations on the nature of sterol intermediates in the biosynthesis of cholesterol, Proc. Royal Soc. (London) B., 180, 125

Gaylor, 1973, Investigation of the multienzymic system of microsomal cholesterol biosynthesis, Ann. New York Acad. Sci., 212, 122, 10.1111/j.1749-6632.1973.tb47591.x

Fried, 1968, Enzymatic conversion of 32-oxygenated Δ7-lanosterol derivatives and of Δ8(14)-4,4-dimethyl-cholestenol to cholesterol, Biochem. Biophys. Res. Commun., 32, 568, 10.1016/0006-291X(68)90701-8

Trowbridge, 1975, The enzymatic removal of carbon atom 32 of cholesterol precursors, Federation Proc., 34, 495

Gibbons, 1976, Lanosterol 14α-demethylase. The metabolism of some potential intermediates by cell-free systems from rat liver, Biochem. Biophys. Res. Commun., 69, 781, 10.1016/0006-291X(76)90943-8

Akhtar, 1977, The pathway for the removal of the 15α-methyl group of lanosterol. The role of lanost-8-en-3β,32-diol in cholesterol biosynthesis, Bioorg. Chem., 6, 473, 10.1016/0045-2068(77)90046-3

Schroepfer, 1978, Inhibition of sterol biosynthesis by 14α-hydroxymethyl sterols, Biochem. Biophys. Res. Commun., 83, 1024, 10.1016/0006-291X(78)91498-5

Knapp, 1975, Chemical synthesis, spectral properties, and chromatography of 4α-methyl and 4β-methyl isomers of (24R)-24 - ethyl - 5α - cholestan -3ß-ol and (245) - 24 - ethyl-cholesta-5,22-dien-3β-ol, Steroids., 26, 339, 10.1016/0039-128X(75)90079-3

Knapp, 1976, Mass spectra fragmentation of 5α-hydroxysteroids, Chem. Phys. Lipids., 16, 31, 10.1016/0009-3084(76)90013-X

Martin, 1970, Enzymatic conversion of 14α-methyl-cholest-7-en-3β,15ξ-diol to cholesterol, Biochem. Biophys. Res. Commun., 39, 1170, 10.1016/0006-291X(70)90683-2

Spike, 1978, Sterol synthesis. Chemical syntheses, structure determination, and metabolism of 14α-methyl-5α-cholest-7-en-3β,15β-diol and 14α-methyl-5α-cholest-7-en-3β,15α-diol, Chem. Phys. Lipids., 21, 31, 10.1016/0009-3084(78)90053-1

Pascal, 1979, Chemical synthesis of three 14α-hydroxymethyl cholestenols, J. Lipid Res., 20, 570, 10.1016/S0022-2275(20)40578-4

Schroepfer, G. J., Jr. 1974. Recent studies on the biosynthesis of cholesterol. Abstracts, 17th International Conference on the Biochemistry of Lipids. Milan, Italy. p. 28.

Schroepfer, 1974, Studies in sterol synthesis, J. Amer. Oil. Chem. Soc., 51, A516

Schroepfer, G. J., Jr. 1974. Metabolism of sterols and sphingolipids: major constituents of the membranes of eukaryotes. Abstracts, Southwest Regional A.C.S. Meeting Houston, Texas. A23.

Schroepfer, 1977, Inhibition of sterol biosynthesis in L cells and in mouse liver cells by 15-oxygenated sterols, J. Biol. Chem., 252, 8975, 10.1016/S0021-9258(17)38334-5

Saucier, 1979, Inactive 3-hydroxy-3-methylglutaryl-CoA reductase in broken cell preparations of various mammalian tissues and cell cultures, Biochim. Biophys. Acta., 572, 541, 10.1016/0005-2760(79)90162-0

Spike, 1974, Structure of a potential intermediate in cholesterol biosynthesis, J. Chem. Soc, Chem. Commun., 477, 10.1039/c39740000477

Knight, 1966, The synthesis of tritium-labeled 14α-methyl-5α-cholest-7-en-3β-ol and its enzymatic demethylation, J. Biol. Chem., 241, 1502, 10.1016/S0021-9258(18)96740-2

Woodward, 1957, The synthesis of lanosterol (lanostadienol), J. Chem. Soc., 1131, 10.1039/jr9570001131

Chan, 1980, Sterol synthesis. Studies of the metabolism of 14α-methyl-5α-cholest-7-en-3β-ol, J. Lipid Res., 20, 1007, 10.1016/S0022-2275(20)40003-3

Knight, 1967, Steroids and related natural products. Part XLII. 14α-methyl cholestanes, J. Chem. Soc., 2427

Schroepfer, 1977, Inhibition of sterol synthesis in L cells by 14α-ethyl-5α-cholest-7-en-15α-ol-3-one at nanomolar concentrations, Biochem. Biophys. Res. Commun., 79, 406, 10.1016/0006-291X(77)90172-3

Schroepfer, 1979, Inhibition of sterol synthesis in animal cells by 15-oxygenated sterols with the unnatural cis-C-D ring junction-5α, 14β-cholest-7-en-15α-ol-3-one and 5α,14β-cholest-7-en-15β-ol-3-one, Biochem. Pharmacol., 28, 249, 10.1016/0006-2952(79)90511-2

Pascal, 1980, Sterol synthesis. Chemical synthesis of 5α-cholest-7-en-3β,14α,diol, J. Lipid Res., 21, 118, 10.1016/S0022-2275(20)39845-X

Parish, 1979, Chemical synthesis of 5α-cholest-6,8(14)-dien-3β-ol-15-one and related 15-oxygenated sterols, Chem. Phys. Lipids., 25, 381, 10.1016/0009-3084(79)90076-8

Schroepfer, 1979, Further studies on the inhibition of sterol biosynthesis in animal cells by 15-oxygenated sterols, Chem. Phys. Lipids., 25, 265, 10.1016/0009-3084(79)90111-7

Fried, 1965, 32-Oxygenated lanostane derivatives from 3β-acetoxy-Δ7-lanostene via 7α,8α-epoxides, Tetrahedron Lett., 2499, 10.1016/S0040-4039(01)84013-2

Bhacca, 1964, Applications of NMR Spectroscopy in Organic Chemistry, 13

Schroepfer, 1976, Inhibition of cholesterol biosynthesis in L cells and in primary cultures of liver cells by 15-oxygenated sterols, Federation Proc., 35, 1697

Schroepfer, 1977, 14α-Ethyl-5α-cholest-7-en-3β,15α-diol, an extraordinary potent inhibitor of sterol synthesis in animal cells.), Amer. Chem. Soc., 99, 5494, 10.1021/ja00458a051

Schroepfer, 1980, Inhibition of sterol biosynthesis in animal cells by 14α-alkyl substituted 15-oxygenated sterols, J. Lipid Res., 20, 994, 10.1016/S0022-2275(20)40001-X

Lee, 1968, Enzymatic conversion of Δ8(14)-cholesten-3β-ol to cholesterol, Biochem. Biophys. Res. Commun., 32, 635, 10.1016/0006-291X(68)90285-4

Lutsky, 1968, Enzymatic conversion of Δ8,14-cholestadien-3β-ol to cholesterol, Biochem. Biophys. Res. Commun., 33, 492, 10.1016/0006-291X(68)90602-5

Lee, 1969, 5α-Cholest-8(14)-en-3β-ol, a possible intermediate in the biosynthesis of cholesterol. Enzymatic conversion to cholesterol and isolation from rat skin, J. Biol. Chem., 244, 5440, 10.1016/S0021-9258(18)63585-9

Lutsky, 1970, Studies on the enzymatic conversion of 5α-cholesta-8,14-dien-Зβ-ol to cholesterol, J. Biol. Chem., 245, 6449, 10.1016/S0021-9258(18)62629-8

Lutsky, 1971, Studies of the metabolism of 5α-cholesta-8,14-dien-3β-ol and 5α-cholesta-7,14-dien-3β-ol in rat liver homogenate preparations, J. Biol. Chem., 246, 6737, 10.1016/S0021-9258(19)45907-3

Lutsky, 1971, Enzymatic conversion of cholest-8(14)-en-3β-ol to cholesta-8,14-dien-3β-ol, Lipids., 6, 957, 10.1007/BF02531180

Hsiung, 1975, Enzymatic conversion of 5α-cholesta-7,14-dien-Зβ-ol to 5α-cholesta-8,14-dien-3β-ol, Lipids., 10, 623, 10.1007/BF02532727

Huntoon, 1978, Sterol synthesis. Chemical syntheses and metabolism of 5α-cholest-8(14)-en-3β,15β-diol and 5α-cholest-8(14)-en-3β,15α-diol, J. Biol. Chem., 253, 775, 10.1016/S0021-9258(17)38170-X

Chang, 1977, Sterol biosynthesis. Further studies of the metabolism of [3α-3H]-14α-hydroxymethyl-5α-cholest-7-en-3β-ol, Federation Proc., 36, 816

Akhtar, 1968, The removal of the 14-methyl group in cholesterol biosynthesis, Chem. Commun., 1406

Gibbons, 1968, The stereochemistry of hydrogen elimination from C-15 during cholesterol biosynthesis, Chem. Commun., 1458

Canonica, 1968, The fate of the 15β-hydrogen of lanosterol in cholesterol biosynthesis, J. Amer. Chem. Soc., 90, 3597, 10.1021/ja01015a074

Canonica, 1968, Evidence for the biological conversion of Δ8,14 sterol dienes into cholesterol, J. Amer. Chem. Soc., 90, 6532, 10.1021/ja01025a062

Watkinson, 1969, The formation of an 8,14-diene system during cholesterol biosynthesis, Chem. Commun., 206, 10.1039/c2969000206a

Akhtar, 1969, The status of C-6, C-7, C-15 and C-16 hydrogen atoms in cholesterol biosynthesis, Eur. J. Biochem., 9, 107, 10.1111/j.1432-1033.1969.tb00582.x

Akhtar, 1969, The role of a cholesta-8,14-dien-3β-ol in cholesterol biosynthesis, Biochem. J., 111, 757, 10.1042/bj1110757

Akhtar, 1969, The origin of the 14α-hydrogen in cholesterol biosynthesis, Chem. Commun., 149, 10.1039/C29690000149

Alexander, 1971, The pathway for the removal of C-32 in cholesterol biosynthesis, Chem. Commun., 1479, 10.1039/c29710001479

Watkinson, 1971, The formation and reduction of the 14,15-double bond in cholesterol biosynthesis, Biochem. J., 121, 131, 10.1042/bj1210131

Alexander, 1972, The removal of the 32-carbon atom as formic acid in cholesterol biosynthesis, Chem. Commun., 383, 10.1039/c39720000383

Akhtar, 1978, Chemical and enzymic studies on the characterization of intermediates during the removal of the 14α-methyl group in cholesterol biosynthesis, Biochem. J., 169, 449, 10.1042/bj1690449b

Gibbons, 1972, Inhibition of cholesterol biosynthesis by carbon monoxide: accumulation of lanosterol and 24,25-dihydrolano-sterol, Biochem. J., 127, 315, 10.1042/bj1270315

Gibbons, 1975, The effect of carbon monoxide on the nature of the accumulated 4,4-dimethyl sterol precursors of cholesterol during its biosynthesis from [2–14C] mevalonic acid in vitro, Biochem. J., 132, 439, 10.1042/bj1320439

Gibbons, 1974, The metabolic sequence by which some 4,4-dimethyl sterols are converted into cholesterol, Biochem. J., 144, 59, 10.1042/bj1440059

Mitropoulos, 1976, Lanosterol 14α-demethylase. Similarity of the enzyme system from yeast and rat liver, Steroids., 27, 821, 10.1016/0039-128X(76)90141-0

Aoyama, 1978, Interaction of lanosterol to cytochrome P-450 purified from yeast microsomes: evidence for contribution of cytochrome P-450 to lanosterol metabolism, Biochem. Biophys. Res. Commun., 82, 33, 10.1016/0006-291X(78)90572-7

Aoyama, 1978, The 14α-demethylation of lanosterol by a reconstituted cytochrome P-450 system from yeast microsomes, Biochem. Biophys. Res. Commun., 85, 28, 10.1016/S0006-291X(78)80006-0

Schroepfer, 1961, Conversion of zymosterol-14C and zymostenol-3H to cholesterol by rat liver homogenates and intact rats, J. Biol. Chem., 236, 1668, 10.1016/S0021-9258(19)63282-5

Schroepfer, 1961, Conversion of Δ7-cholesterol-4–14C and 7-dehydrocholesterol-4–14C to cholesterol, J. Biol. Chem., 236, 3137, 10.1016/S0021-9258(18)93984-0

Chen, 1975, Relationship between sterol synthesis and DNA synthesis in phytohemagglutinin-stimulated mouse lymphocytes, Proc. Nat. Acad. Sci., U.S.A., 72, 1950, 10.1073/pnas.72.5.1950