2-Mercaptobenzothiazole

2-Mercaptobenzothiazole is an activator of the aryl hydrocarbon receptor (AhR) [1], inhibiting thyroid hormone synthesis and dopamine beta-hydroxylase activity[2][4]. 2-Mercaptobenzothiazole promotes bladder cancer cell invasion by altering the conformation of the AhR ligand binding domain (LBD), activating AhR transcription, and upregulating the mRNA and protein expression of target genes CYP1A1 and CYP1B1[1]. 2-Mercaptobenzothiazole inhibits thyroid peroxidase (TPO) with an IC50 value of 11.5 μM, induces histological changes such as follicular cell hypertrophy in Xenopus laevis tadpoles, delaying metamorphosis[2]. 2-Mercaptobenzothiazole increases chromosomal aberrations and sister chromatid exchanges (SCEs) in Chinese hamster ovary (CHO) cells, and enhances carcinogenicity in F344/N rats[3]. 2-Mercaptobenzothiazole inhibits norepinephrine synthesis in mice and completely blocks the conversion of exogenous dopamine to norepinephrine in rat cardiomyocytes[4].

Product Specifications

CAS Number

[149-30-4]

UNSPSC

12352005

Hazard Statement

H317, H350, H410

Target

Aryl Hydrocarbon Receptor; Endogenous Metabolite

Type

Natural Products

Related Pathways

Immunology/Inflammation; Metabolic Enzyme/Protease

Applications

Metabolism-protein/nucleotide metabolism

Field of Research

Metabolic Disease

Assay Protocol

https://www.medchemexpress.com/2-mercaptobenzothiazole.html

Purity

99.85

Solubility

DMSO : 100 mg/mL (ultrasonic)

Smiles

S=C1SC2=CC=CC=C2N1

Molecular Formula

C7H5NS2

Molecular Weight

167.26

Precautions

H317, H350, H410

References & Citations

[1]Jiachen Zhang, et al. Promotion of Bladder Cancer Cell Metastasis by 2-Mercaptobenzothiazole via Its Activation of Aryl Hydrocarbon Receptor Transcription: Molecular Dynamics Simulations, Cell-Based Assays, and Machine Learning-Driven Prediction. Environ Sci Technol. 2022 Sep 20;56 (18) :13254-13263.|[2]Joseph E Tietge, et al. Inhibition of the thyroid hormone pathway in Xenopus laevis by 2-mercaptobenzothiazole. Aquat Toxicol. 2013 Jan 15:126:128-36. |[3]National Toxicology Program . “NTP Toxicology and Carcinogenesis Studies of 2-Mercaptobenzothiazole (CAS No. 149-30-4) in F344/N Rats and B6C3F1 Mice (Gavage Studies) .” National Toxicology Program technical report series vol. 332 (1988) : 1-172.|[4]G A Johnson, et al. 2-mercaptobenzothiazole, an inhibitor of dopamine beta-hydroxylase. Aquat Toxicol. 1970 Sep;22 (9) :710-2.