Isolation and identification of thiohomosildenafil and thiosildenafil in health supplements

被引：71

作者：

Zou, Peng ^{[1
,2
]}

Hou, Peiling ^{[1
]}

Oh, Sharon Sze-Yin ^{[2
]}

Chong, Y. M. ^{[1
]}

Bloodworth, Bosco Chen ^{[2
]}

Low, Min-Yong ^{[2
]}

Koh, Hwee-Ling ^{[1
]}

机构：

[1] Natl Univ Singapore, Fac Sci, Dept Pharm, Singapore 117543, Singapore

[2] Hlth Sci Author, Ctr Analyt Sci, Singapore 169078, Singapore

来源：

JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS | 2008年 / 47卷 / 02期

关键词：

thiohomosildenafil; thiosildenafil; PDE-5; inhibitor; adulterant; health supplement;

D O I：

10.1016/j.jpba.2008.01.016

中图分类号：

O65 [分析化学];

学科分类号：

070302 ; 081704 ;

摘要：

Two unknown compounds are detected and isolated from health supplements for the enhancement of sexual function. The structures of the unknown compounds are elucidated using high-resolution MS, ESI-MS/MS, NMR, UV and IR. One compound is identified as an analogue of sildenafil in which the oxygen atom is substituted with a sulfur atom in the pyrazolopyrimidine moiety, and an ethyl group instead of a methyl group is attached to the piperazinyl nitrogen. Hence, this compound is named thiohomosildenafil. Another compound is also a sildenafil analogue in which the oxygen atom is substituted with a sulfur atom in the pyrazolopyrimidine moiety. This compound is named thiosildenafil. Both the two compounds are first detected in health supplements. The UV, IR and completely assigned NMR data of thiohomosildenafil and thiosildenafil are first reported. (c) 2008 Elsevier B.V. All rights reserved.

引用

页码：279 / 284

页数：6

共 23 条

[1] Determination of sildenafil, tadalafil, and vardenafil in tablets and adulterated herbal products by ESI-MS-MS [J].

Abdel-Hamid, ME .

JOURNAL OF LIQUID CHROMATOGRAPHY & RELATED TECHNOLOGIES, 2006, 29 (04) :591-603

[2] Structure elucidation of sildenafil analogues in herbal products [J].

Blok-Tip, L ;

Zomer, B ;

Bakker, F ;

Hartog, KD ;

Hamzink, M ;

ten Hove, J ;

Vredenbregt, M ;

de Kaste, D .

FOOD ADDITIVES AND CONTAMINANTS PART A-CHEMISTRY ANALYSIS CONTROL EXPOSURE & RISK ASSESSMENT, 2004, 21 (08) :737-748

[3] Application of LC-ESI-MS-MS for detection of synthetic adulterants in herbal remedies [J].

Bogusz, MJ ;

Hassan, H ;

Ai-Enazi, E ;

Ibrahim, Z ;

Al-Tufail, M .

JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2006, 41 (02) :554-564

[4] Evidence for contamination of herbal erectile dysfunction products with phosphodiesterase type 5 inhibitors [J].

Fleshner, N ;

Harvey, M ;

Adomat, H ;

Wood, C ;

Eberding, A ;

Hersey, K ;

Guns, E .

JOURNAL OF UROLOGY, 2005, 174 (02) :636-641

[5] Accurate mass measurement using Fourier transform ion cyclotron resonance mass spectrometry for structure elucidation of designer drug analogs of tadalafil, vardenafil and sildenafil in herbal and pharmaceutical matrices [J].

Gratz, Samuel R. ;

Gamble, Bryan M. ;

Flurer, Rick A. .

RAPID COMMUNICATIONS IN MASS SPECTROMETRY, 2006, 20 (15) :2317-2327

[6] Analysis of undeclared synthetic phosphodiesterase-5 inhibitors in dietary supplements and herbal matrices by LC-ESI-MS and LC-UV [J].

Gratz, SR ;

Flurer, CL ;

Wolnik, KA .

JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2004, 36 (03) :525-533

[7] Structural identification of a new acetildenafil analogue from pre-mixed bulk powder intended as a dietary supplement [J].

Hou, Peiling ;

Zou, Peng ;

Low, Min-Yong ;

Chan, Eli ;

Koh, Hwee-Ling .

FOOD ADDITIVES AND CONTAMINANTS, 2006, 23 (09) :870-875

[8] SYNTHESIS AND PHOTOCHEMICAL STUDY OF CU(I) COMPLEXES WITH TRI-P-TOLYLPHOSPHINE AND HETEROCYCLIC THIONES - THE CRYSTAL-STRUCTURE OF [CUCL(PYMTH)(P-CH3C6H4)3P]2 [J].

KARAGIANNIDIS, P ;

HADJIKAKOU, SK ;

ASLANIDIS, P ;

HOUNTAS, A .

INORGANICA CHIMICA ACTA, 1990, 178 (01) :27-34

[9]

Lai KC, 2006, J FOOD DRUG ANAL, V14, P19

[10] Low-energy collision-induced dissociation of sildenafil thiono analogues: gas-phase intramolecular nucleophilic substitution through ion-neutral complexes between a cationic substrate and a thione-containing neutral nucleophile [J].

Lee, J ;

Yoo, HH ;

KAng, MY ;

Kim, DH .

RAPID COMMUNICATIONS IN MASS SPECTROMETRY, 2005, 19 (12) :1767-1770

← 1 2 3 →