1. Apoptosis Anti-infection
  2. Apoptosis Bacterial Fungal
  3. Dipyrithione

Dipyrithione is a potent antimicrobial agent. Dipyrithione shows antifungal activity and antiproliferative activity. Dipyrithione induces apoptosis and cycle arrest at G1 phase. Dipyrithione shows anti-inflammatory activity in vivo. Dipyrithione shows anti-tumor activity. Dipyrithione has the potential for the research of dermatophytosis.

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Dipyrithione Chemical Structure

Dipyrithione Chemical Structure

CAS No. : 3696-28-4

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Based on 1 publication(s) in Google Scholar

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Description

Dipyrithione is a potent antimicrobial agent. Dipyrithione shows antifungal activity and antiproliferative activity. Dipyrithione induces apoptosis and cycle arrest at G1 phase. Dipyrithione shows anti-inflammatory activity in vivo. Dipyrithione shows anti-tumor activity. Dipyrithione has the potential for the research of dermatophytosis[1][2][3].

In Vitro

Dipyrithione (20?μg/mL) shows antifungal activity with MIC values of 6.03 μM for Trichophyton rubrum[1].
Dipyrithione (72 h) shows cytotoxic activity against 293?T cells with an IC50 value of 0.22 μM[1].
Dipyrithione (1-5 μM; 8.5 h) inhibits LPS (100 ng/ml)-induced up-regulation of iNOS and COX-2 in RAW264.7 cells in a dose-dependent manner[2].
Dipyrithione (1 μM; 8.5 h) suppresses LPS-induced increase of iNOS but not COX-2 mRNA level, inhibits LPS-increased NO production[2].
Dipyrithione (3 μM; 2, 5 h) decreases phosphorylation of STAT1 induced by LPS and does not influence LPS-induced MAPK and NF-κB activation in RAW 246.7 cells[2].
Dipyrithione (0-5 μg/mL; 48 h) shows antiproliferative activity for KB, 231, U937 and K562 cells in a dose dependent manner[3].
Dipyrithione (2.5 μg/ml) induces apoptosis and cycle arrest at G1 phase[3].

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

Western Blot Analysis[2]

Cell Line: RAW264.7 cells
Concentration: 1-5 µM
Incubation Time: 8.5 h
Result: Inhibited the expression of LPS (100 ng/ml)-induced up-regulation of iNOS and COX-2 in a dose-dependent manner.

Cell Proliferation Assay[2]

Cell Line: KB, 231, U937, K562 cells
Concentration: 2.5 μg/ml
Incubation Time: 24 h
Result: Induced cell cycle arrest at G1 phase with induced p21 accumulation, CyclinD1 and CyclinE1 expressions were downregulated.

Apoptosis Analysis[3]

Cell Line: KB, 231, U937, K562 cells
Concentration: 2.5 μg/ml
Incubation Time: 36 h
Result: Induced apoptosis by induced cleavage of caspase-9, caspase-3 and PARP.

Western Blot Analysis[3]

Cell Line: RAW264.7 cells
Concentration: 1-5 µM
Incubation Time: 8.5 h
Result: Inhibited the expression of LPS (100 ng/ml)-induced up-regulation of iNOS and COX-2 in a dose-dependent manner.
In Vivo

Dipyrithione (0.2 mg/cm2; externally once daily for 10 days) shows great anti-dermatophyte activity effects in guinea pig[1].
Dipyrithione (1, 2.5, 5 mg/kg; i.p.) shows anti-inflammatory activity in mouse[2]. Dipyrithione (5 mg/kg; i.p.; daily for 10 days) shows anti-tumor acyivity in mouse[3].

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

Animal Model: Guinea pig (infected with Trichophyton rubrum)[1]
Dosage: 0.2 mg/cm2
Administration: Externally once daily for 10 days
Result: Showed normal hair growth, with no scaly skin.
Animal Model: 18-22g male ICR mice2
Dosage: 1, 2.5, 5 mg/kg
Administration: I.p.
Result: Raised the survival rate from 10% to 30%, 60% and 90%, respectively.
Animal Model: 6 weeks, 18-20 g male ICR mice (hepatoma 22 (H22) cells)[3]
Dosage: 2.5 mg/kg
Administration: I.p.; daily for 10 days
Result: Inhibited the growth of tumor.
Molecular Weight

252.31

Formula

C10H8N2O2S2

CAS No.
Appearance

Solid

Color

White to off-white

SMILES

[O-][N+]1=CC=CC=C1SSC2=CC=CC=[N+]2[O-]

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 : 10 mg/mL (39.63 mM; ultrasonic and warming and heat to 60°C; 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 3.9634 mL 19.8169 mL 39.6338 mL
5 mM 0.7927 mL 3.9634 mL 7.9268 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.

  • Molarity Calculator

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Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

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Molecular Weight *

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

Concentration (start)

C1

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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: ≥ 1 mg/mL (3.96 mM); Clear solution

    This protocol yields a clear solution of ≥ 1 mg/mL (saturation unknown).

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (10.0 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% (20% SBE-β-CD in Saline)

    Solubility: ≥ 1 mg/mL (3.96 mM); Clear solution

    This protocol yields a clear solution of ≥ 1 mg/mL (saturation unknown).

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (10.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

    Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:

Dosage

mg/kg

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(per animal)

g

Dosing volume
(per animal)

μL

Number of animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
%
DMSO +
+
%
Tween-80 +
%
Saline
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
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 3.9634 mL 19.8169 mL 39.6338 mL 99.0845 mL
5 mM 0.7927 mL 3.9634 mL 7.9268 mL 19.8169 mL
10 mM 0.3963 mL 1.9817 mL 3.9634 mL 9.9084 mL
15 mM 0.2642 mL 1.3211 mL 2.6423 mL 6.6056 mL
20 mM 0.1982 mL 0.9908 mL 1.9817 mL 4.9542 mL
25 mM 0.1585 mL 0.7927 mL 1.5854 mL 3.9634 mL
30 mM 0.1321 mL 0.6606 mL 1.3211 mL 3.3028 mL
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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.

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Dipyrithione
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