2. Metabolic Enzyme/Protease Immunology/Inflammation
  3. Endogenous Metabolite Aryl Hydrocarbon Receptor
  4. 2-Mercaptobenzothiazole

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.

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2-Mercaptobenzothiazole Chemical Structure

2-Mercaptobenzothiazole Chemical Structure

CAS No. : 149-30-4

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Based on 1 publication(s) in Google Scholar

Other Forms of 2-Mercaptobenzothiazole:

2-Mercaptobenzothiazole Related Antibodies

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  • Biological Activity

  • Purity & Documentation

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Description

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].

IC50 & Target

Human Endogenous Metabolite

 

Cellular Effect
Cell Line Type Value Description References
MCF7 GI50
> 100 μM
Compound: 1a
Cytotoxicity against human MCF7 cells assessed as reduction in cell viability measured after 72 hrs by MTT assay
Cytotoxicity against human MCF7 cells assessed as reduction in cell viability measured after 72 hrs by MTT assay
[PMID: 27487570]
PC-3 GI50
84.9 μM
Compound: 1a
Cytotoxicity against human PC3 cells assessed as reduction in cell viability measured after 72 hrs by MTT assay
Cytotoxicity against human PC3 cells assessed as reduction in cell viability measured after 72 hrs by MTT assay
[PMID: 27487570]
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].

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

2-Mercaptobenzothiazole Related Antibodies

Cell Invasion Assay[1]

Cell Line: T24
Concentration: 1, 5, 25 μM; 1 μM AhR antagonist (SR1) co-incubation as MMP1 control
Incubation Time: 24 h
Result: Increased the cell invasion rate, which was decreased after co-incubation with SR1.

Western Blot Analysis[1]

Cell Line: T24
Concentration: 1, 5, 25 μM; 1 μM SR1 co-incubation as MMP1 control
Incubation Time: 24 h
Result: Increased protein expression of AhR, CYP1A1, CYP1B1 and cell metastasis marker MMP1.

Real Time qPCR[1]

Cell Line: T24
Concentration: 1, 5, 25 μM
Incubation Time: 24 h
Result: Increased mRNA expression of AhR, CYP1A1, CYP1B1 and cell metastasis marker MMP1
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].

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

Animal Model: NF51, NF54 (Xenopus laevis larvae)[2]
Dosage: 500, 250, 125, 62.5, and 31 g/L,continuously exposed, 21days for NF51; 500, 250, 125, 62.5, and 31 g/L, continuously exposed, 7 days for NF54
Administration: Exposure
Result: Delayed the development of the 21-day group but did not affect the 7-day group.
Caused thyroid histological changes, including hypertrophy, proliferation, and colloid depletion of follicular cells in a concentration-dependent manner; increased thyroid iodine levels; and increased NIS gene expression in thyroid tissue in a concentration-dependent manner.
Animal Model: F344/N rats and B6C3F1 mice[3]
Dosage: 750 and 1,500 mg/kg, 13 weeks; 0,375 and 750 mg/kg for mice and male rats, 0, 188 or 375 mg/kg for female rats, 5 days a week, 103 weeks
Administration: i.g.
Result: Caused cancer in rats, and even low doses caused cancer in male mice.
Animal Model: CF-1 male mice, Upjohn Sprague-Dawley male rats[4]
Dosage: 300 mg/kg
Administration: Intraperitoneal injection (i.p.)
Result: Caused the mice to have a depression state after 1 and 2 hours, when norepinephrine levels dropped to about 60% of the control group.
Blocked the conversion of dopamine to newly synthesized noradrenaline and physical activity decreased in rats.
Molecular Weight

167.25

Formula

C7H5NS2
CAS No.
Appearance

Solid

Color

White to yellow

SMILES

S=C1SC2=CC=CC=C2N1
Structure Classification
Initial Source
Shipping

Room temperature in continental US; may vary elsewhere.
Storage
Powder -20°C 3 years
4°C 2 years
In solvent -80°C 6 months
-20°C 1 month
Solvent & Solubility
In Vitro: 

DMSO : 100 mg/mL (597.91 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 5.9791 mL 29.8954 mL 59.7907 mL
5 mM 1.1958 mL 5.9791 mL 11.9581 mL
View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

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In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for in vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

  • Protocol 1

    Add each solvent one by one:  10% DMSO    40% PEG300    5% Tween-80    45% Saline

    Solubility: ≥ 2.5 mg/mL (14.95 mM); Clear solution

    This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

    Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
  • Protocol 2

    Add each solvent one by one:  10% DMSO    90% Corn Oil

    Solubility: ≥ 2.5 mg/mL (14.95 mM); Clear solution

    This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:

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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Calculation results:
Working solution concentration: mg/mL
Method for preparing stock solution: mg drug dissolved in μL  DMSO (Stock solution concentration: mg/mL).
The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only. If necessary, please contact MedChemExpress (MCE).
Method for preparing in vivo working solution for animal experiments: Take μL DMSO stock solution, add μL . μL , mix evenly, next add μL Tween 80, mix evenly, then add μL Saline.
 If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Purity & Documentation

Purity: 99.85%

SDS (597 KB)

COA (250 KB) HNMR (117 KB) RP-HPLC (69 KB)

Handling Instructions (2659 KB)
References

Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent Concentration Solvent Mass 1 mg 5 mg 10 mg 25 mg
DMSO 1 mM 5.9791 mL 29.8954 mL 59.7907 mL 149.4768 mL
5 mM 1.1958 mL 5.9791 mL 11.9581 mL 29.8954 mL
10 mM 0.5979 mL 2.9895 mL 5.9791 mL 14.9477 mL
15 mM 0.3986 mL 1.9930 mL 3.9860 mL 9.9651 mL
20 mM 0.2990 mL 1.4948 mL 2.9895 mL 7.4738 mL
25 mM 0.2392 mL 1.1958 mL 2.3916 mL 5.9791 mL
30 mM 0.1993 mL 0.9965 mL 1.9930 mL 4.9826 mL
40 mM 0.1495 mL 0.7474 mL 1.4948 mL 3.7369 mL
50 mM 0.1196 mL 0.5979 mL 1.1958 mL 2.9895 mL
60 mM 0.0997 mL 0.4983 mL 0.9965 mL 2.4913 mL
80 mM 0.0747 mL 0.3737 mL 0.7474 mL 1.8685 mL
100 mM 0.0598 mL 0.2990 mL 0.5979 mL 1.4948 mL
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2-Mercaptobenzothiazole Related Classifications

Help & FAQs
  • Do most proteins show cross-species activity?

    Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

2-Mercaptobenzothiazole149-30-4Endogenous MetaboliteAryl Hydrocarbon ReceptorAhRCYP1A1CYP1B1TPODopamine β-hydroxylaseInhibitorinhibitorinhibit

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