The C19 position of 25-hydroxyvitamin D3 faces outward in the vitamin D sterol-binding pocket of vitamin D-binding protein

被引：10

作者：

Addo, JK ^{[1
]}

Swamy, N ^{[1
]}

Ray, R ^{[1
]}

机构：

[1] Boston Univ, Sch Med, Dept Med, Sect Endocrinol Diabet & Metab, Boston, MA 02118 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2002年 / 12卷 / 03期

关键词：

D O I：

10.1016/S0960-894X(01)00738-7

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The radiolabeled affinity and photoaffinity analogues of 25-hydroxyvitamin D-3 (25-OH-D-3) with probes at the C-19 position failed to specifically label the 25-OH-D-3-binding pocket of vitamin D-binding protein (DBP). However, a hybrid analogue, with a bromoacetate affinity probe and a photoaffinity probe at C-3-OH and C-19 positions, respectively, specifically labeled the ligand-binding pocket, suggesting that C-3-OH points towards the 'inside' of the binding cavity while the C-19 position faces away from it. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：279 / 281

页数：3

共 28 条

[1] Synthesis and binding-analysis of 5E-[19-(2-bromoacetoxy)methyl]25-hydroxyvitamin D3 and 5E-25-hydroxyvitamin D3-19-methyl[(4-azido-2-nitro)phenyl]glycinate:: Novel C19-modified affinity and photoaffinity analogs of 25-hydroxyvitamin D3 [J].

Addo, JK ;

Ray, R .

STEROIDS, 1998, 63 (04) :218-223

[2] C-6 functionalized analogs of 25-hydroxyvitamin D3 and 1α,25-dihydroxyvitamin D3:: Synthesis and binding analysis with vitamin D-binding protein and vitamin D receptor [J].

Addo, JK ;

Swamy, N ;

Ray, R .

STEROIDS, 1999, 64 (04) :273-282

[3]

ALIAU S, 1997, BIOCHEMISTRY-US, V36, P36

[4] IDENTIFICATION OF THE STEROL-BINDING AND ACTIN-BINDING DOMAINS OF PLASMA VITAMIN-D BINDING-PROTEIN (GC-GLOBULIN) [J].

HADDAD, JG ;

HU, YZ ;

KOWALSKI, MA ;

LARAMORE, C ;

RAY, K ;

ROBZYK, P ;

COOKE, NE .

BIOCHEMISTRY, 1992, 31 (31) :7174-7181

[5] PLASMA VITAMIN-D-BINDING PROTEIN (GC-GLOBULIN) - MULTIPLE TASKS [J].

HADDAD, JG .

JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, 1995, 53 (1-6) :579-582

[6] Why do we need a three-dimensional architecture of the ligand-binding domain of the nuclear 1α,25-dihydroxyvitamin D3 receptor? [J].

Mohr, SC ;

Swamy, N ;

Xu, WR ;

Ray, R .

STEROIDS, 2001, 66 (3-5) :189-201

[7]

MURDOCK GL, 1998, BIOCHEMISTRY-US, V27, P4452

[8]

RAY R, 1988, Steroids, V51, P623, DOI 10.1016/0039-128X(88)90057-8

[9] SYNTHESIS OF 25-HYDROXYVITAMIN-D3 3-BETA-3'-[N-(4-AZIDO-2-NITROPHENYL)AMINO]PROPYL ETHER, A 2ND-GENERATION PHOTOAFFINITY ANALOG OF 25-HYDROXYVITAMIN-D3 - PHOTOAFFINITY-LABELING OF RAT SERUM VITAMIN-D BINDING-PROTEIN [J].

RAY, R ;

BOUILLON, R ;

VANBAELEN, H ;

HOLICK, MF .

BIOCHEMISTRY, 1991, 30 (19) :4809-4813

[10] SYNTHESIS OF A PHOTOAFFINITY-LABELED ANALOG OF 1,25-DIHYDROXYVITAMIN-D3 [J].

RAY, R ;

HOLICK, SA ;

HOLICK, MF .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (11) :702-703

← 1 2 3 →