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2-Mercaptobenzothiazole

MCE China：2-Mercaptobenzothiazole

Brand：MedChemExpress (MCE)

Cat. No.HY-W017113

CAS：149-30-4

Purity：99.24%

Storage：Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month

Shipping：Room temperature in continental US; may vary elsewhere.

Description：2-Mercaptobenzothiazole is an activator of the aryl hydrocarbon receptor (AhR), inhibiting thyroid hormone synthesis and dopamine beta-hydroxylase activity. 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. 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-Mercaptobenzothiazole increases chromosomal aberrations and sister chromatid exchanges (SCEs) in Chinese hamster ovary (CHO) cells, and enhances carcinogenicity in F344/N rats. 2-Mercaptobenzothiazole inhibits norepinephrine synthesis in mice and completely blocks the conversion of exogenous dopamine to norepinephrine in rat cardiomyocytes.

In Vitro：2-Mercaptobenzothiazole (1, 5, 25 μM; 24 h) activated AhR, upregulated the mRNA and protein expressions of AhR, CYP1A1, CYP1B1 (qPCR; WB) and the cell metastasis marker MMP1, and promoted the invasion of T24 cells (cell invasion)[1]. 2-Mercaptobenzothiazole (10-5M; 5 x 10-6M) non-competitively inhibits dopamine β-hydroxylase by 72% and 47%[4].

In Vivo：2-Mercaptobenzothiazole (500, 250, 125, 62.5, 31 g/L) inhibits thyroid hormone synthesis in African clawed frog larvae, causing histological reactions such as hypertrophy, hyperplasia, and diffuse hypertrophy of thyroid follicular cells, delaying metamorphic development[2]. 2-Mercaptobenzothiazole (750 and 1,500 mg/kg; Five times a week; 103 weeks; i.g.) has carcinogenic activity in male F344/N rats, manifested by increased incidence of monocytic leukemia, pancreatic acinar cell adenoma, adrenal pheochromocytoma, and preputial gland adenoma or carcinoma. It has carcinogenic activity in female F344/N rats, manifested by increased incidence of adrenal pheochromocytoma and pituitary adenoma[3]. 2-Mercaptobenzothiazole (300 mg/kg, i.p.) effectively block the conversion of exogenous dopamine to norepinephrine in rat cardiomyocytes, thereby inhibiting its synthesis[4].

IC50 & Target：Human Endogenous Metabolite

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References：

[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.  [Content Brief]

[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.  [Content Brief]

[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.  [Content Brief]

[4]. G A Johnson, et al. 2-mercaptobenzothiazole, an inhibitor of dopamine beta-hydroxylase. Aquat Toxicol. 1970 Sep;22(9):710-2.  [Content Brief]