NB598 hydrochloride

Modify Date: 2024-01-20 11:21:35

NB598 hydrochloride Structure
NB598 hydrochloride structure
Common Name NB598 hydrochloride
CAS Number 136719-25-0 Molecular Weight 486.132
Density N/A Boiling Point N/A
Molecular Formula C27H32ClNOS2 Melting Point N/A
MSDS N/A Flash Point N/A

 Use of NB598 hydrochloride


NB-598 hydrochloride is a potent and competitive inhibitor of squalene epoxidase (SE), and suppresses triglyceride biosynthesis through the farnesol pathway.

 Names

Name (E)-N-ethyl-6,6-dimethyl-N-[[3-[(4-thiophen-3-ylthiophen-2-yl)methoxy]phenyl]methyl]hept-2-en-4-yn-1-amine,hydrochloride
Synonym More Synonyms

 NB598 hydrochloride Biological Activity

Description NB-598 hydrochloride is a potent and competitive inhibitor of squalene epoxidase (SE), and suppresses triglyceride biosynthesis through the farnesol pathway.
Related Catalog
Target

squalene epoxidase

In Vitro NB598 (10 μM) causes a 36±7% reduction in total cholesterol level of MIN6 cells. NB598 causes a significant decrease in cholesterol by 49±2%, 46±7%, and 48±2% from PM, ER, and SG, respectively. NB598 dose-dependently inhibits insulin secretion under both basal (1 mM glucose) and glucose-stimulated (16.7 mM glucose) conditions. NB598 at concentrations up to 10 μM does not affect peak outward KV currents or the voltage dependence of activation but increases current inactivation[1]. NB-598 (10 μM) inhibits the synthesis of sterol and sterol ester from [14C]acetate without affecting the synthesis of other lipids such as phospholipids (PL), free fatty acids (FFA) and triacylglycerol (TG). In the absence of exogenous liposomal cholesterol, NB-598 reduces ACAT activity by 31%. NB-598 reduces ACAT activity by 22% even in the presence of a 600 PM concentration of liposomal cholesterol[2]. NB-598 suppresses the secretion of cholesterol and triacylglycerol from HepG2 cells into the medium[3].
Kinase Assay Caco-2 cells are grown in a 58 cm2 plastic dish with medium A for 13 days. The cells are washed with medium B, and then cultured with medium B including cholesterol-micelle and each compound. The compound is dissolved in Me2SO, and the final concentration of Me2SO is 0.1%(v/v). After 18 hr of incubation, the cells are washed extensively with phosphate-buffered saline (PBS) to remove the compound. Microsomes are prepared as described above. The reaction mixture (0.2 mL) consisted of 0.1 mg microsomes, 0.25% BSA and 40 PM [14C]oleoyl CoA in buffer A. To avoid the effects of endogenous cholesterol, liposome (2 mol of cholesterol: 1 mol of phosphatidylcholine) [15] is added to the reaction mixture. The microsomes are preincubated for 1 hr with or without exogenous cholesterol, and ACAT activity is determined as described above.
References

[1]. Xia F, et al. Inhibition of cholesterol biosynthesis impairs insulin secretion and voltage-gated calcium channel function in pancreatic beta-cells. Endocrinology. 2008 Oct;149(10):5136-45.

[2]. Horie M, et al. Effects of NB-598, a potent squalene epoxidase inhibitor, on the apical membrane uptake of cholesterol and basolateral membrane secretion of lipids in Caco-2 cells. Biochem Pharmacol. 1993 Jul 20;46(2):297-305.

[3]. Horie M, et al. An inhibitor of squalene epoxidase, NB-598, suppresses the secretion of cholesterol and triacylglycerol and simultaneously reduces apolipoprotein B in HepG2 cells. Biochim Biophys Acta. 1993 May 20;1168(1):45-51.

 Chemical & Physical Properties

Molecular Formula C27H32ClNOS2
Molecular Weight 486.132
Exact Mass 485.161377
PSA 68.95000
LogP 8.28520
Storage condition 2-8℃

 Synthetic Route

~%

NB598 hydrochloride Structure

NB598 hydrochloride

CAS#:136719-25-0

Literature: Banyu Pharmaceutical Co., Ltd. Patent: US5234946 A1, 1993 ;

 Synonyms

(E)-N-(6-6-dimethyl-2-hepten-4-ynyl)-N-ethyl-3-[4-(3-thienyl)-2-thienyl-methyloxy]benzylamine hydrochloride
(E)-N-ethyl-N-(6,6-dimethyl-2-heptyn-4-ynyl)-3-[(3,3'-bithiophen-5-yl)methoxy]benzenemethanamine hydrochloride
Benzenemethanamine, 3-([3,3'-bithiophen]-5-ylmethoxy)-N-[(2E)-6,6-dimethyl-2-hepten-4-yn-1-yl]-N-ethyl-, hydrochloride (1:1)
NB598 hydrochloride
(2E)-N-[3-(3,3'-Bithiophen-5-ylmethoxy)benzyl]-N-ethyl-6,6-dimethyl-2-hepten-4-yn-1-amine hydrochloride (1:1)
CS-1275
NB-598 hydrochloride||NB598 hydrochloride
(E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-ethyl-3-[4-(thien-3-yl)-thien-2-yl-methyloxy]benzylamine hydrochloride
NB-598 (hydrochloride)
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