Design, synthesis, and biological evaluation of fluoroneplanocin A as the novel mechanism-based inhibitor of S-adenosylhomocysteine hydrolase

被引：61

作者：

Jeong, LS ^{[1
]}

Yoo, SJ

Lee, KM

Koo, MJ

Choi, WJ

Kim, HO

Moon, HR

Lee, MY

Park, JG

Lee, SK

Chun, MW

机构：

[1] Ewha Womans Univ, Coll Pharm, Med Chem Lab, Seoul 120750, South Korea

[2] Seoul Natl Univ, Div Chem & Mol Engn, Seoul 151742, South Korea

[3] Seoul Natl Univ, Coll Pharm, Seoul 151, South Korea

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 2003年 / 46卷 / 02期

关键词：

D O I：

10.1021/jm025557z

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Fluoroneplanocin A (12) was designed as a novel mechanism-based inhibitor of S-adenosylhomocysteine hydrolase (SAH) and efficiently synthesized via an electrophilic vinyl fluorination reaction (n-BuLi, N-fluorobenzenesulfonimide at -78 degreesC). Fluoroneplanocin A exhibited 2-fold more potent SAH inhibitory activity than the parent neplanocin A. A new mechanism of irreversible inhibition discovered in this work might provide new alternatives in the design of a different class of antiviral agents operating via SAH inhibition.

引用

页码：201 / 203

页数：3

共 50 条

[41] EVALUATION OF NAD(H) ANALOGUES AS SELECTIVE INHIBITORS FOR TRYPANOSOMA CRUZI S-ADENOSYLHOMOCYSTEINE HYDROLASE
Li, Qing-Shan
Cai, Sumin
Fang, Jianwen
Borchardt, Ronald T.
Kuczera, Krzysztof
Middaugh, C. Russell
Schowen, Richard L.
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2009, 28 (5-7): : 473 - 484
[42] Synthesis of apio analogues of neplanocin a and their inhibitory activity against S-adenosylhomocysteine hydrolase.
Lee, JA
Moon, HR
Lee, KM
Ko, YM
Kim, HJ
Yun, MY
Jeong, LS
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 227 : U36 - U36
[43] 3-DEAZAADENOSINE - S-ADENOSYLHOMOCYSTEINE HYDROLASE-INDEPENDENT MECHANISM OF ACTION IN MOUSE LYMPHOCYTES
ZIMMERMAN, TP
IANNONE, M
WOLBERG, G
JOURNAL OF BIOLOGICAL CHEMISTRY, 1984, 259 (02) : 1122 - 1126
[44] BASIS FOR RESISTANCE TO 3-DEAZAARISTEROMYCIN, AN INHIBITOR OF S-ADENOSYLHOMOCYSTEINE HYDROLASE, IN HUMAN B-LYMPHOBLASTS
GREENBERG, ML
CHAFFEE, S
HERSHFIELD, MS
JOURNAL OF BIOLOGICAL CHEMISTRY, 1989, 264 (02) : 795 - 803
[45] QUANTITATION OF S-ADENOSYLHOMOCYSTEINE HYDROLASE IN MOUSE L929-CELLS USING THE INHIBITOR NEPLANOCIN-A
BARTEL, RL
BORCHARDT, RT
ANALYTICAL BIOCHEMISTRY, 1985, 149 (01) : 191 - 196
[46] QUANTITATION OF S-ADENOSYLHOMOCYSTEINE HYDROLASE IN MOUSE L929 CELLS USING THE INHIBITOR NEPLANOCIN-A
BARTEL, RL
BORCHARDT, RT
FEDERATION PROCEEDINGS, 1985, 44 (03) : 865 - 865
[47] Thymine-based molecular beacon for sensing adenosine based on the inhibition of S-adenosylhomocysteine hydrolase activity
Nieh, Chih-Chun
Tseng, Wei-Lung
BIOSENSORS & BIOELECTRONICS, 2014, 61 : 404 - 409
[48] Design, synthesis, and evaluation of the first mechanism-based inhibitor of glucosamine 6-phosphate synthase
Massiere, F
BadetDenisot, MA
Rene, L
Badet, B
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (24) : 5748 - 5749
[49] INDUCTION OF ERYTHROID-DIFFERENTIATION IN LEUKEMIC K562 CELLS BY AN S-ADENOSYLHOMOCYSTEINE HYDROLASE INHIBITOR, ARISTEROMYCIN
MIZUTANI, Y
MASUOKA, S
IMOTO, M
KAWADA, M
UMEZAWA, K
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1995, 207 (01) : 69 - 74
[50] A method for fluorescence sensing of adenosine and alkaline phosphatase, based on the inhibition of S-adenosylhomocysteine hydrolase activity
Lin, Jia-Hui
Tseng, Wei-Lung
BIOSENSORS & BIOELECTRONICS, 2013, 41 : 379 - 385

← 1 2 3 4 5 →