NB-598 free base - CAS# 131060-14-5

NB-598 free base, CAS No. 131060-14-5, is a potent competitive inhibitor of squalene epoxidase (SE). NB-598 suppresses triglyceride biosynthesis through the farnesol pathway. NB-598 suppresses the secretion of cholesterol and triacylglycerol and simultaneously reduces apolipoprotein B in HepG2 cells. NB-598 reduced basolaterally secreted radioactivity in cholesterol, cholesterol ester, PL and TG. Furthermore, NB-598 suppressed the basolateral secretion of apolipoprotein (apo) B. When microsomes prepared from control Caco-2 cells were incubated with 10 microM NB-598, acyl CoA:cholesterol acyltransferase (ACAT) activity was inhibited slightly.

Product information

CAS Number: 131060-14-5

Molecular Weight: 449.67

Formula: C27H31NOS2

Synonym:

NB-598 free base

NB 598

NB598

NB-598

Chemical 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

Smiles: CCN(C/C=C/C#CC(C)(C)C)CC1=CC(=CC=C1)OCC1=CC(=CS1)C1=CSC=C1

InChiKey: KIRGLCXNEVICOG-SOFGYWHQSA-N

InChi: InChI=1S/C27H31NOS2/c1-5-28(14-8-6-7-13-27(2,3)4)18-22-10-9-11-25(16-22)29-19-26-17-24(21-31-26)23-12-15-30-20-23/h6,8-12,15-17,20-21H,5,14,18-19H2,1-4H3/b8-6+

Technical Data

Appearance: Solid Power.

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined.

HS Tariff Code: 382200

How to use

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. 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. NB-598 suppresses the secretion of cholesterol and triacylglycerol from HepG2 cells into the medium.

References:

1. Horie M, Iwasawa Y, Satoh T, Shimizu A, Nagata Y, Kamei T. 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. doi: 10.1016/0006-2952(93)90418-v. PMID: 8347152.
2. Horie M, Hayashi M, Satoh T, Hotta H, Nagata Y, Ishida F, Kamei T. 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. PMID: 8504141.
3. Hidaka Y, Hotta H, Nagata Y, Iwasawa Y, Horie M, Kamei T. Effect of a novel squalene epoxidase inhibitor, NB-598, on the regulation of cholesterol metabolism in Hep G2 cells. J Biol Chem. 1991 Jul 15;266(20):13171-7. PMID: 1649182.

Products are for research use only. Not for human use.