메뉴 건너뛰기




Volumn 37, Issue 10, 2009, Pages 2069-2078

24-Hydroxycholesterol sulfation by human cytosolic sulfotransferases: Formation of monosulfates and disulfates, molecular modeling, sulfatase sensitivity, and inhibition of liver X receptor activation

Author keywords

[No Author keywords available]

Indexed keywords

24 HYDROXYCHOLESTEROL; APOLIPOPROTEIN E; BILE ACID; CHOLESTEROL DERIVATIVE; CYTOSOLIC SULFOTRANSFERASE; HOMODIMER; LIVER X RECEPTOR; LIVER X RECEPTOR AGONIST; N (2,2,2 TRIFLUOROETHYL) N [4 [2,2,2 TRIFLUORO 1 HYDROXY 1 (TRIFLUOROMETHOXY)ETHYL]PHENYL]BENZENESULFONAMIDE; OXYSTEROL; SULFATASE; SULFOTRANSFERASE; UNCLASSIFIED DRUG;

EID: 70349280717     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.108.025759     Document Type: Article
Times cited : (75)

References (42)
  • 3
    • 33751096969 scopus 로고    scopus 로고
    • Crossing the barrier: Oxysterols as cholesterol transporters and metabolic modulators in the brain
    • Björkhem I (2006) Crossing the barrier: oxysterols as cholesterol transporters and metabolic modulators in the brain. J Intern Med 260:493-508.
    • (2006) J Intern Med , vol.260 , pp. 493-508
    • Björkhem, I.1
  • 4
    • 33947706821 scopus 로고    scopus 로고
    • Rediscovery of cerebrosterol
    • Björkhem I (2007) Rediscovery of cerebrosterol. Lipids 42:5-14.
    • (2007) Lipids , vol.42 , pp. 5-14
    • Björkhem, I.1
  • 5
    • 0035813114 scopus 로고    scopus 로고
    • From brain to bile: Evidence that conjugation and omega-hydroxylation are important for elimination of 24S-hydroxycholesterol (cerebrosterol) in humans
    • DOI 10.1074/jbc.M103828200
    • Bjorkhem I, Andersson U, Ellis E, Alvelius G, Ellegard L, Diczfalusy U, Sjovall J, and Einarsson C (2001) From brain to bile. Evidence that conjugation and omega-hydroxylation are important for elimination of 24S-hydroxycholesterol (cerebrosterol) in humans. J Biol Chem 276:37004-37010. (Pubitemid 37390810)
    • (2001) Journal of Biological Chemistry , vol.276 , Issue.40 , pp. 37004-37010
    • Bjorkhem, I.1    Andersson, U.2    Ellis, E.3    Alvelius, G.4    Ellegard, L.5    Diczfalusy, U.6    Sjovall, J.7    Einarsson, C.8
  • 6
    • 0031848338 scopus 로고    scopus 로고
    • Cholesterol homeostasis in human brain: Turnover of 24S- Hydroxycholesterol and evidence for a cerebral origin of most of this oxysterol in the circulation
    • Björkhem I, Lütjohann D, Diczfalusy U, Ståhle L, Ahlborg G, and Wahren J (1998) Cholesterol homeostasis in human brain: turnover of 24S-hydroxycholesterol and evidence for a cerebral origin of most of this oxysterol in the circulation. J Lipid Res 39:1594-1600. (Pubitemid 28377923)
    • (1998) Journal of Lipid Research , vol.39 , Issue.8 , pp. 1594-1600
    • Bjorkhem, I.1    Lutjohann, D.2    Diczfalusy, U.3    Stahle, L.4    Ahlborg, G.5    Wahren, J.6
  • 7
    • 53149134712 scopus 로고    scopus 로고
    • Liver X receptor-mediated activation of reverse cholesterol transport from macrophages to feces in vivo requires ABCG5/G8
    • Calpe-Berdiel L, Rotllan N, Fiévet C, Roig R, Blanco-Vaca F, and Escolà-Gil JC (2008) Liver X receptor-mediated activation of reverse cholesterol transport from macrophages to feces in vivo requires ABCG5/G8. J Lipid Res 49:1904-1911.
    • (2008) J Lipid Res , vol.49 , pp. 1904-1911
    • Calpe-Berdiel, L.1    Rotllan, N.2    Fiévet, C.3    Roig, R.4    Blanco-Vaca, F.5    Escolà-Gil, J.C.6
  • 9
    • 0037044830 scopus 로고    scopus 로고
    • Mice expressing the human CYP7A1 gene in the mouse CYP7A1 knock-out background lack induction of CYP7A1 expression by cholesterol feeding and have increased hypercholesterolemia when fed a high fat diet
    • DOI 10.1074/jbc.M205117200
    • Chen JY, Levy-Wilson B, Goodart S, and Cooper AD (2002) Mice expressing the human CYP7A1 gene in the mouse CYP7A1 knock-out background lack induction of CYP7A1 expression by cholesterol feeding and have increased hypercholesterolemia when fed a high fat diet. J Biol Chem 277:42588-42595. (Pubitemid 35285627)
    • (2002) Journal of Biological Chemistry , vol.277 , Issue.45 , pp. 42588-42595
    • Chen, J.Y.1    Levy-Wilson, B.2    Goodart, S.3    Cooper, A.D.4
  • 10
    • 33845587711 scopus 로고    scopus 로고
    • Enzymatic Reduction of Oxysterols Impairs LXR Signaling in Cultured Cells and the Livers of Mice
    • DOI 10.1016/j.cmet.2006.11.012, PII S1550413106003950
    • Chen W, Chen G, Head DL, Mangelsdorf DJ, and Russell DW (2007) Enzymatic reduction of oxysterols impairs LXR signaling in cultured cells and the livers of mice. Cell Metab 5:73-79. (Pubitemid 44933109)
    • (2007) Cell Metabolism , vol.5 , Issue.1 , pp. 73-79
    • Chen, W.1    Chen, G.2    Head, D.L.3    Mangelsdorf, D.J.4    Russell, D.W.5
  • 12
    • 49449115829 scopus 로고    scopus 로고
    • Sulfotransferase 2B1b in human breast: Differences in subcellular localization in African American and Caucasian women
    • Dumas NA, He D, Frost AR, and Falany CN (2008) Sulfotransferase 2B1b in human breast: differences in subcellular localization in African American and Caucasian women. J Steroid Biochem Mol Biol 111:171-177.
    • (2008) J Steroid Biochem Mol Biol , vol.111 , pp. 171-177
    • Dumas, N.A.1    He, D.2    Frost, A.R.3    Falany, C.N.4
  • 13
    • 0030996250 scopus 로고    scopus 로고
    • Enzymology of human cytosolic sulfotransferases
    • Falany CN (1997) Enzymology of human cytosolic sulfotransferases. FASEB J 11:206-216.
    • (1997) FASEB J , vol.11 , pp. 206-216
    • Falany, C.N.1
  • 14
    • 0029549968 scopus 로고
    • Human dehydroepiandrosterone sulfotransferase. Purification, molecular cloning, and characterization
    • DOI 10.1111/j.1749-6632.1995.tb17372.x
    • Falany CN, Comer KA, Dooley TP, and Glatt H (1995) Human dehydroepiandrosterone sulfotransferase. Purification, molecular cloning, and characterization. Ann N Y Acad Sci 774:59-72. (Pubitemid 26140360)
    • (1995) Annals of the New York Academy of Sciences , vol.774 , pp. 59-72
    • Falany, C.N.1    Comer, K.A.2    Dooley, T.P.3    Glatt, H.4
  • 15
    • 33751015135 scopus 로고    scopus 로고
    • Human cytosolic sulfotransferase 2B1: Isoform expression, tissue specificity and subcellular localization
    • DOI 10.1016/j.jsbmb.2006.09.011, PII S0960076006002524
    • Falany CN, He D, Dumas N, Frost AR, and Falany JL (2006) Human cytosolic sulfotransferase 2B1: isoform expression, tissue specificity and subcellular localization. J Steroid Biochem Mol Biol 102:214-221. (Pubitemid 44750635)
    • (2006) Journal of Steroid Biochemistry and Molecular Biology , vol.102 , Issue.1-5 SPEC. ISS , pp. 214-221
    • Falany, C.N.1    He, D.2    Dumas, N.3    Frost, A.R.4    Falany, J.L.5
  • 16
    • 0029053067 scopus 로고
    • Bacterial expression and characterization of a cDNA for human liver estrogen sulfotransferase
    • Falany CN, Krasnykh V, and Falany JL (1995) Bacterial expression and characterization of a cDNA for human liver estrogen sulfotransferase. J Steroid Biochem Mol Biol 52:529-539.
    • (1995) J Steroid Biochem Mol Biol , vol.52 , pp. 529-539
    • Falany, C.N.1    Krasnykh, V.2    Falany, J.L.3
  • 18
    • 34548506770 scopus 로고    scopus 로고
    • Interactions of the human cytosolic sulfotransferases and steroid sulfatase in the metabolism of tibolone and raloxifene
    • Falany JL and Falany CN (2007) Interactions of the human cytosolic sulfotransferases and steroid sulfatase in the metabolism of tibolone and raloxifene. J Steroid Biochem Mol Biol 107:202-210.
    • (2007) J Steroid Biochem Mol Biol , vol.107 , pp. 202-210
    • Falany, J.L.1    Falany, C.N.2
  • 19
    • 2442438167 scopus 로고    scopus 로고
    • Sulfation of tibolone and tibolone metabolites by expressed human cytosolic sulfotransferases
    • DOI 10.1016/j.jsbmb.2004.01.005, PII S0960076004000391
    • Falany JL, Macrina N, and Falany CN (2004) Sulfation of tibolone and tibolone metabolites by expressed human cytosolic sulfotransferases. J Steroid Biochem Mol Biol 88:383-391. (Pubitemid 38625603)
    • (2004) Journal of Steroid Biochemistry and Molecular Biology , vol.88 , Issue.4-5 , pp. 383-391
    • Falany, J.L.1    Macrina, N.2    Falany, C.N.3
  • 20
  • 21
    • 33846827336 scopus 로고    scopus 로고
    • 24S-hydroxycholesterol induces cholesterol release from choroid plexus epithelial cells in an apical- And apoE isoform-dependent manner concomitantly with the induction of ABCA1 and ABCG1 expression
    • DOI 10.1111/j.1471-4159.2006.04240.x
    • Fujiyoshi M, Ohtsuki S, Hori S, Tachikawa M, and Terasaki T (2007) 24S-Hydroxycholesterol induces cholesterol release from choroid plexus epithelial cells in an apical- and apoE isoform-dependent manner concomitantly with the induction of ABCA1 and ABCG1 expression. J Neurochem 100:968-978. (Pubitemid 46213922)
    • (2007) Journal of Neurochemistry , vol.100 , Issue.4 , pp. 968-978
    • Fujiyoshi, M.1    Ohtsuki, S.2    Hori, S.3    Tachikawa, M.4    Terasaki, T.5
  • 24
    • 0035660223 scopus 로고    scopus 로고
    • Purification, characterization and crystallization of human placental estrone/dehydroepiandrosterone sulfatase, a membrane-bound enzyme of the endoplasmic reticulum
    • DOI 10.1016/S0960-0760(01)00119-4, PII S0960076001001194
    • Hernandez-Guzman FG, Higashiyama T, Osawa Y, and Ghosh D (2001) Purification, characterization and crystallization of human placental estrone/dehydroepiandrosterone sulfatase, a membrane-bound enzyme of the endoplasmic reticulum. J Steroid Biochem Mol Biol 78:441-450. (Pubitemid 34019166)
    • (2001) Journal of Steroid Biochemistry and Molecular Biology , vol.78 , Issue.5 , pp. 441-450
    • Hernandez-Guzman, F.G.1    Higashiyama, T.2    Osawa, Y.3    Ghosh, D.4
  • 25
    • 33947716119 scopus 로고    scopus 로고
    • A semiempirical free energy force field with charge-based desolvation
    • Huey R, Morris GM, Olson AJ, and Goodsell DS (2007) A semiempirical free energy force field with charge-based desolvation. J Comput Chem 28:1145-1152.
    • (2007) J Comput Chem , vol.28 , pp. 1145-1152
    • Huey, R.1    Morris, G.M.2    Olson, A.J.3    Goodsell, D.S.4
  • 26
    • 30144445705 scopus 로고    scopus 로고
    • Estrogen sulfatase
    • Iwamori M (2005) Estrogen sulfatase. Methods Enzymol 400:293-302.
    • (2005) Methods Enzymol , vol.400 , pp. 293-302
    • Iwamori, M.1
  • 28
    • 0034991507 scopus 로고    scopus 로고
    • Cholesterol and hydroxycholesterol sulfotransferases: Identification, distinction from dehydroepiandrosterone sulfotransferase, and differential tissue expression
    • DOI 10.1210/en.142.7.2978
    • Javitt NB, Lee YC, Shimizu C, Fuda H, and Strott CA (2001) Cholesterol and hydroxycholesterol sulfotransferases: identification, distinction from dehydroepiandrosterone sulfotransferase, and differential tissue expression. Endocrinology 142:2978-2984. (Pubitemid 32575535)
    • (2001) Endocrinology , vol.142 , Issue.7 , pp. 2978-2984
    • Javitt, N.B.1    Lee, Y.C.2    Shimizu, C.3    Fuda, H.4    Strott, C.A.5
  • 29
    • 30844464332 scopus 로고    scopus 로고
    • LXR and PPAR activators stimulate cholesterol sulfotransferase type 2 isoform 1b in human keratinocytes
    • DOI 10.1194/jlr.M500235-JLR200
    • Jiang YJ, Kim P, Elias PM, and Feingold KR (2005) LXR and PPAR activators stimulate cholesterol sulfotransferase type 2 isoform 1b in human keratinocytes. J Lipid Res 46:2657-2666. (Pubitemid 43107477)
    • (2005) Journal of Lipid Research , vol.46 , Issue.12 , pp. 2657-2666
    • Jiang, Y.J.1    Kim, P.2    Elias, P.M.3    Feingold, K.R.4
  • 30
    • 0033051051 scopus 로고    scopus 로고
    • Regulation of estrogen activity by sulfation in human Ishikawa endometrial adenocarcinoma cells
    • DOI 10.1016/S0960-0760(99)00022-9, PII S0960076099000229
    • Kotov A, Falany JL, Wang J, and Falany CN (1999) Regulation of estrogen activity by sulfation in human Ishikawa endometrial adenocarcinoma cells. J Steroid Biochem Mol Biol 68:137-144. (Pubitemid 29242843)
    • (1999) Journal of Steroid Biochemistry and Molecular Biology , vol.68 , Issue.3-4 , pp. 137-144
    • Kotov, A.1    Falany, J.L.2    Wang, J.3    Falany, C.N.4
  • 31
    • 0037155952 scopus 로고    scopus 로고
    • Cholesterol's role in synapse formation
    • Koudinov AR and Koudinova NV (2002) Cholesterol's role in synapse formation. Science 295:2213.
    • (2002) Science , vol.295 , pp. 2213
    • Koudinov, A.R.1    Koudinova, N.V.2
  • 34
    • 0345492012 scopus 로고    scopus 로고
    • Broad Substrate Specificity of Human Cytochrome P450 46A1 Which Initiates Cholesterol Degradation in the Brain
    • DOI 10.1021/bi035512f
    • Mast N, Norcross R, Andersson U, Shou M, Nakayama K, Bjorkhem I, and Pikuleva IA (2003) Broad substrate specificity of human cytochrome P450 46A1 which initiates cholesterol degradation in the brain. Biochemistry 42:14284-14292. (Pubitemid 37499426)
    • (2003) Biochemistry , vol.42 , Issue.48 , pp. 14284-14292
    • Mast, N.1    Norcross, R.2    Andersson, U.3    Shou, M.4    Nakayama, K.5    Bjorkhem, I.6    Pikuleva, I.A.7
  • 35
    • 0034895787 scopus 로고    scopus 로고
    • Expression and characterization of the human 3 beta-hydroxysteroid sulfotransferases (SULT2B1a and SULT2B1b)
    • DOI 10.1016/S0960-0760(01)00064-4, PII S0960076001000644
    • Meloche CA and Falany CN (2001) Expression and characterization of the human 3 beta-hydroxysteroid sulfotransferases (SULT2B1a and SULT2B1b). J Steroid Biochem Mol Biol 77:261-269. (Pubitemid 32703624)
    • (2001) Journal of Steroid Biochemistry and Molecular Biology , vol.77 , Issue.4-5 , pp. 261-269
    • Meloche, C.A.1    Falany, C.N.2
  • 36
    • 33644865172 scopus 로고    scopus 로고
    • Pharmacological activation of liver X receptors promotes reverse cholesterol transport in vivo
    • DOI 10.1161/CIRCULATIONAHA.105.560177, PII 0000301720060103000015
    • Naik SU, Wang X, Da Silva JS, Jaye M, Macphee CH, Reilly MP, Billheimer JT, Rothblat GH, and Rader DJ (2006) Pharmacological activation of liver X receptors promotes reverse cholesterol transport in vivo. Circulation 113:90-97. (Pubitemid 43958493)
    • (2006) Circulation , vol.113 , Issue.1 , pp. 90-97
    • Naik, S.U.1    Wang, X.2    Da Silva, J.S.3    Jaye, M.4    Macphee, C.H.5    Reilly, M.P.6    Billheimer, J.T.7    Rothblat, G.H.8    Rader, D.J.9
  • 37
    • 0034625464 scopus 로고    scopus 로고
    • Crystal structure of SULT2A3, human hydroxysteroid sulfotransferase
    • DOI 10.1016/S0014-5793(00)01479-4, PII S0014579300014794
    • Pedersen LC, Petrotchenko EV, and Negishi M (2000) Crystal structure of SULT2A3, human hydroxysteroid sulfotransferase. FEBS Lett 475:61-64. (Pubitemid 30331079)
    • (2000) FEBS Letters , vol.475 , Issue.1 , pp. 61-64
    • Pedersen, L.C.1    Petrotchenko, E.V.2    Negishi, M.3
  • 39
    • 0037093546 scopus 로고    scopus 로고
    • Crystal structure of human dehydroepiandrosterone sulphotransferase in complex with substrate
    • Rehse PH, Zhou M, and Lin SX (2002) Crystal structure of human dehydroepiandrosterone sulphotransferase in complex with substrate. Biochem J 364:165-171. (Pubitemid 34538959)
    • (2002) Biochemical Journal , vol.364 , Issue.1 , pp. 165-171
    • Rehse, P.H.1    Zhou, M.2    Lin, S.-X.3
  • 40
    • 0035372651 scopus 로고    scopus 로고
    • Auto-oxidized cholesterol sulfates are antagonistic ligands of liver X receptors: Implications for the development and treatment of atherosclerosis
    • DOI 10.1016/S0039-128X(00)00239-7, PII S0039128X00002397
    • Song C, Hiipakka RA, and Liao S (2001) Auto-oxidized cholesterol sulfates are antagonistic ligands of liver X receptors: implications for the development and treatment of atherosclerosis. Steroids 66:473-479. (Pubitemid 32140924)
    • (2001) Steroids , vol.66 , Issue.6 , pp. 473-479
    • Song, C.1    Hiipakka, R.A.2    Liao, S.3
  • 41
    • 0032080151 scopus 로고    scopus 로고
    • Sulfuryl transfer: The catalytic mechanism of human estrogen sulfotransferase
    • DOI 10.1074/jbc.273.18.10888
    • Zhang H, Varlamova O, Vargas FM, Falany CN, Leyh TS, and Varmalova O (1998) Sulfuryl transfer: the catalytic mechanism of human estrogen sulfotransferase. J Biol Chem 273:10888-10892. (Pubitemid 28204925)
    • (1998) Journal of Biological Chemistry , vol.273 , Issue.18 , pp. 10888-10892
    • Zhang, H.1    Varmalova, O.2    Vargas, F.M.3    Falany, C.N.4    Leyh, T.S.5
  • 42
    • 0034761899 scopus 로고    scopus 로고
    • Crystallization and preliminary crystallographic results of apo and complex forms of human dehydroepiandrosterone sulfotransferase
    • DOI 10.1107/S0907444901010964
    • Zhou M, Rehse P, Chang HJ, Luu-The V, and Lin SX (2001) Crystallization and preliminary crystallographic results of apo and complex forms of human dehydroepiandrosterone sulfotransferase. Acta Crystallogr D Biol Crystallogr 57:1630-1633. (Pubitemid 33037727)
    • (2001) Acta Crystallographica Section D: Biological Crystallography , vol.57 , Issue.11 , pp. 1630-1633
    • Zhou, M.1    Rehse, P.2    Chang, H.-J.3    Luu-The, V.4    Lin, S.-X.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.