Solid-state NMR study of fluorinated steroids

被引：5

作者：

Yang, Kai-Jay ^{[1
]}

Lin, Su-Ching ^{[1
]}

Huang, Shing-Jong ^{[2
]}

Ching, Wei-Min ^{[1
]}

Hung, Chen-Hsiung ^{[1
]}

Tzou, Der-Lii M. ^{[1
]}

机构：

[1] Acad Sinica, Inst Chem, Taipei 11529, Taiwan

[2] Natl Taiwan Univ, Instrumentat Ctr, Taipei 11617, Taiwan

来源：

STEROIDS | 2014年 / 80卷

关键词：

Solid-state NMR; Betamethasone; Fludrocortisone acetate; Steroidal ring conformation; Anisotropic chemical shift; MAGNETIC-RESONANCE SPECTRA; BETAMETHASONE; IDENTIFICATION; DRUGS;

D O I：

10.1016/j.steroids.2013.11.020

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Solid-state {H-1)C-13 cross-polarization/magic angle spinning (CP/MAS) NMR spectroscopy was performed to analyze two fluorinated steroids, i.e., betamethasone (BMS) and fludrocortisone acetate (FCA), that have fluorine attached to C9, as well as two non-fluorinated analogs, i.e., prednisolone (PRD) and hydrocortisone 21-acetate (HCA). The C-13 signals of BMS revealed multiplet patterns with splittings of 16-215 Hz, indicating multiple ring conformations, whereas the C-13 signals of FCA, HCA, and PRD exhibited only singlet patterns, implying a unique conformation. In addition, BMS and FCA exhibited substantial deviation (>3.5 ppm) in approximately half of the C-13 signals and significant deviation (>45 ppm) in the (13)C9 signal compared to PRD and HCA, respectively. In this study, we demonstrate that fluorinated steroids, such as BMS and FCA, have steroidal ring conformation(s) that are distinct from non-fluorinated analogs, such as PRD and HCA. (C) 2013 Elsevier Inc. All rights reserved.

引用

页码：64 / 70

页数：7

共 36 条

[1] MOLECULAR-DYNAMICS IN POLYCRYSTALLINE TESTOSTERONE STUDIED BY PROTON NMR [J].