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> (R)-Sulforaphane [142825-10-3]

(R)-Sulforaphane [142825-10-3]

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(R)-Sulforaphane (L-Sulforaphane) is a orally active, potent inducer of the Keap1/Nrf2/ARE pathway, exhibiting antioxidant and anticancer activities. (R)-Sulforaphane primarily functions by upregulating phase II detoxifying enzymes in cells, aiding in the removal of carcinogens and combating oxidative stress. (R)-Sulforaphane is capable of modulating gene expression, influencing various signaling pathways, including Nrf2, NF-κB, and AP-1. (R)-Sulforaphane can be used in studies of tumor biology, antioxidant defense mechanisms, as well as inflammation and immune responses.

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(R)-Sulforaphane Chemical Structure

(R)-Sulforaphane Chemical Structure

CAS No. : 142825-10-3

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Based on 1 publication(s) in Google Scholar

Other Forms of (R)-Sulforaphane:

  • Sulforaphane In-stock

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Description

(R)-Sulforaphane (L-Sulforaphane) is a orally active, potent inducer of the Keap1/Nrf2/ARE pathway, exhibiting antioxidant and anticancer activities. (R)-Sulforaphane primarily functions by upregulating phase II detoxifying enzymes in cells, aiding in the removal of carcinogens and combating oxidative stress. (R)-Sulforaphane is capable of modulating gene expression, influencing various signaling pathways, including Nrf2, NF-κB, and AP-1. (R)-Sulforaphane can be used in studies of tumor biology, antioxidant defense mechanisms, as well as inflammation and immune responses[1][2][3][4][5][6][7].

IC50 & Target

Bax

 

Procaspase-3

 

NF-κB

 

In Vitro

(R)-Sulforaphane (10 μM, 24 hours) pre-treatment of H9c2 cells reduces the number of apoptotic cells, decreases the expression of pro-apoptotic proteins (Bax, caspase-3, cytochrome c), and counteracts the increase in mitochondrial membrane potential induced by Doxorubicin (HY-15142A) (1 μM, 2 hours)[4].
(R)-Sulforaphane (10 μM, 2 or 24 hours) pre-treatment enhances the expression of HO-1 in H9c2 cells and reduces the levels of ROS within the mitochondria (measured using MitoSOX Red reagent) induced by Doxorubicin (1 μM, 2 or 24 hours)[4].

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

(R)-Sulforaphane Related Antibodies

Western Blot Analysis[5]

Cell Line: MCF7 cells
Concentration: 20 μM
Incubation Time: 72h
Result: Increased the most the NQO1 transcript and protein levels in MCF7 cells.
Increased of Nrf2 transcript was observed in MCF7 cells.
Reduced transcription and protein of AhR gene in MCF7 cells.

Apoptosis Analysis[4]

Cell Line: H9c2 cells
Concentration: L-sulforaphane or D,L-sulforaphane: 10 μM; Doxorubicin: 1 μM
Incubation Time: L-sulforaphane or D,L-sulforaphane: 2h; Doxorubicin: 2, 24h
Result: Protected the H9c2 cells against doxorubicin-induced cell death.
Increased cell viability in a dose-dependent manner.
Significantly reduced the number of apoptotic cells treated with Doxorubicin.

RT-PCR[4]

Cell Line: H9c2 cells
Concentration: L-sulforaphane or D,L-sulforaphane: 10 μM; Doxorubicin: 1 μM
Incubation Time: L-sulforaphane or D,L-sulforaphane: 2h, 24h; Doxorubicin: 2h, 24h
Result: Induced heme oxygenase-1 (HO-1) mRNA expression in a dose-dependent manner.

Western Blot Analysis[4]

Cell Line: H9c2 cells
Concentration: L-sulforaphane or D,L-sulforaphane: 10 μM; Doxorubicin: 1 μM
Incubation Time: L-sulforaphane or D,L-sulforaphane: 2h; Doxorubicin: 2, 24h
Result: Prevented the release of cytochrome c into the cytosol.
Prevented the translocation of Bax into the cytosol.
Attenuated the doxorubicin-induced increase in the levels of cleaved caspase-3.
Induced a significant increase in HO-1 protein expression.
Induced a significantly higher level of Nrf2 expression in the nucleus compared to the cytoplasm.
Masse moléculaire

177.29

Formule

C6H11NOS2
CAS No.

142825-10-3
Appearance

Liquid

Color

Colorless to light yellow

SMILES

O=[S@@](CCCCN=C=S)C
Structure Classification
  • Others
Initial Source
  • Plants
  • other families
Livraison

Room temperature in continental US; may vary elsewhere.
Stockage

-20°C, protect from light

*In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Solvant et solubilité
In Vitro: 

DMSO : 100 mg/mL (564.05 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 5.6405 mL 28.2024 mL 56.4048 mL
5 mM 1.1281 mL 5.6405 mL 11.2810 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 (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

  • Calculateur de molarité

  • Calculateur de dilution

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

Mass
=
Concentration
×
Volume
×
Molecular Weight *

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

This equation is commonly abbreviated as: C1V1 = C2V2

Concentration (start)

C1

×
Volume (start)

V1

=
Concentration (final)

C2

×
Volume (final)

V2

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 (14.10 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% (20% SBE-β-CD in Saline)

    Solubility: ≥ 2.5 mg/mL (14.10 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 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

Animal weight
(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).

*In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

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.
Pureté et documentation
Références

  • [1]. De Nicola GR, et al. Novel gram-scale production of enantiopure R-sulforaphane from Tuscan black kale seeds. Molecules. 2014 May 27;19(6):6975-86.  [Content Brief]

    [2]. Abdull Razis AF, et al. The natural chemopreventive phytochemical R-sulforaphane is a far more potent inducer of the carcinogen-detoxifying enzyme systems in rat liver and lung than the S-isomer. Int J Cancer. 2011 Jun 15;128(12):2775-82.  [Content Brief]

    [3]. Gamet-Payrastre L, et al. Sulforaphane, a naturally occurring isothiocyanate, induces cell cycle arrest and apoptosis in HT29 human colon cancer cells. Cancer Res. 2000;60(5):1426-1433.  [Content Brief]

    [4]. Li B, et al. Sulforaphane prevents doxorubicin-induced oxidative stress and cell death in rat H9c2 cells. Int J Mol Med. 2015 Jul;36(1):53-64. doi: 10.3892/ijmm.2015.2199. Epub 2015 Apr 28.  [Content Brief]

    [5]. Licznerska B, et al. R-sulforaphane modulates the expression profile of AhR, ERα, Nrf2, NQO1, and GSTP in human breast cell lines. Mol Cell Biochem. 2021;476(2):525-533.  [Content Brief]

    [6]. Zhang Y, et al. Anticarcinogenic activities of sulforaphane and structurally related synthetic norbornylisothiocyanates. Proc Natl Acad Sci U S A. 1994 Apr 12;91(8):3147-50.  [Content Brief]

    [7]. Chen X, et al. Activation of Nrf2 by Sulforaphane Inhibits High Glucose-Induced Progression of PancreaticCancer via AMPK Dependent Signaling. ell Physiol Biochem. 2018;50(3):1201-1215.  [Content Brief]

  • [1]. De Nicola GR, et al. Novel gram-scale production of enantiopure R-sulforaphane from Tuscan black kale seeds. Molecules. 2014 May 27;19(6):6975-86.

    [2]. Abdull Razis AF, et al. The natural chemopreventive phytochemical R-sulforaphane is a far more potent inducer of the carcinogen-detoxifying enzyme systems in rat liver and lung than the S-isomer. Int J Cancer. 2011 Jun 15;128(12):2775-82.

    [3]. Gamet-Payrastre L, et al. Sulforaphane, a naturally occurring isothiocyanate, induces cell cycle arrest and apoptosis in HT29 human colon cancer cells. Cancer Res. 2000;60(5):1426-1433.

    [4]. Li B, et al. Sulforaphane prevents doxorubicin-induced oxidative stress and cell death in rat H9c2 cells. Int J Mol Med. 2015 Jul;36(1):53-64. doi: 10.3892/ijmm.2015.2199. Epub 2015 Apr 28.

    [5]. Licznerska B, et al. R-sulforaphane modulates the expression profile of AhR, ERα, Nrf2, NQO1, and GSTP in human breast cell lines. Mol Cell Biochem. 2021;476(2):525-533.

    [6]. Zhang Y, et al. Anticarcinogenic activities of sulforaphane and structurally related synthetic norbornylisothiocyanates. Proc Natl Acad Sci U S A. 1994 Apr 12;91(8):3147-50.

    [7]. Chen X, et al. Activation of Nrf2 by Sulforaphane Inhibits High Glucose-Induced Progression of PancreaticCancer via AMPK Dependent Signaling. ell Physiol Biochem. 2018;50(3):1201-1215.

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 (protect from light). 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 5.6405 mL 28.2024 mL 56.4048 mL 141.0119 mL
5 mM 1.1281 mL 5.6405 mL 11.2810 mL 28.2024 mL
10 mM 0.5640 mL 2.8202 mL 5.6405 mL 14.1012 mL
15 mM 0.3760 mL 1.8802 mL 3.7603 mL 9.4008 mL
20 mM 0.2820 mL 1.4101 mL 2.8202 mL 7.0506 mL
25 mM 0.2256 mL 1.1281 mL 2.2562 mL 5.6405 mL
30 mM 0.1880 mL 0.9401 mL 1.8802 mL 4.7004 mL
40 mM 0.1410 mL 0.7051 mL 1.4101 mL 3.5253 mL
50 mM 0.1128 mL 0.5640 mL 1.1281 mL 2.8202 mL
60 mM 0.0940 mL 0.4700 mL 0.9401 mL 2.3502 mL
80 mM 0.0705 mL 0.3525 mL 0.7051 mL 1.7626 mL
100 mM 0.0564 mL 0.2820 mL 0.5640 mL 1.4101 mL
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(R)-Sulforaphane Related Classifications

  • NF-κB Apoptosis Metabolic Enzyme/Protease Immunology/Inflammation
  • Keap1-Nrf2 Bcl-2 Family Caspase Reactive Oxygen Species NF-κB
Help & FAQs

Keywords:

(R)-Sulforaphane142825-10-3L-SulforaphaneKeap1-Nrf2Bcl-2 FamilyCaspaseReactive Oxygen SpeciesNF-κBNuclear factor-κBNuclear factor-kappaBApoptosisBaxCaspase-3Cytochrome cHT29DoxorubicinMitochondrial membrane potentialInhibitorinhibitorinhibit

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