NB-598 hydrochloride

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NB-598 hydrochloride is a potent and competitive inhibitor of squalene epoxidase (SE), and suppresses triglyceride biosynthesis through the farnesol pathway. NB-598 (hydrochloride) is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.

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NB-598 hydrochloride Chemical Structure

CAS No. : 136719-25-0

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Other In-stock Forms of NB-598 hydrochloride:

NB-598 Maleate

Other Forms of NB-598 hydrochloride:

NB-598 Maleate In-stock
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12 Publications Citing Use of MCE NB-598 hydrochloride

Proliferation Assay

: NB-598 hydrochloride purchased from MedChemExpress. Usage Cited in: J Steroid Biochem Mol Biol. 2015 Aug;152:34-44. [Abstract]; GC/MS quantitation of squalene (A) and cholesterol (B) extracted from confluent 6-well plates cell layers from SEBO662 AR+ treated or not (Ctrl) with 10 nM DHT, in the presence or not of the squalene epoxidase inhibitor NB-598 (10 μM). Treatment time is 7 days. Squalene is only detected in NB-598-treated cell layers. DHT significantly increases squalene without significantly modifying cholesterol.

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Biological Activity
Protocol
Purity & Documentation
References
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Description	NB-598 hydrochloride is a potent and competitive inhibitor of squalene epoxidase (SE), and suppresses triglyceride biosynthesis through the farnesol pathway. NB-598 (hydrochloride) is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
IC₅₀ & 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]. MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only. NB-598 hydrochloride Related Antibodies
Molecular Weight	486.13
Formula	C₂₇H₃₂ClNOS₂
CAS No.	136719-25-0
SMILES	CCN(C/C=C/C#CC(C)(C)C)CC1=CC=CC(OCC2=CC(C3=CSC=C3)=CS2)=C1.[H]Cl
Shipping	Room temperature in continental US; may vary elsewhere.
Storage	Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation	Data Sheet (272 KB) Handling Instructions (2659 KB)
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. [Content Brief] [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. [Content Brief] [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. [Content Brief]

Kinase Assay
^[2]

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.

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

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. [Content Brief]

[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. [Content Brief]

[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. [Content Brief]