Sulforaphane
Sulforaphane is an inducer of chemopreventative enzymes via Keap1-Nrf2 signaling [1]. Sulforaphane is present naturally in widely consumed vegetables and has a particularly high concentration in broc-coli [1].
The Keap1-Nrf2 pathway is the major regulator of cytoprotective responses to oxidative and electrophilic stress. Nrf2 triggers the signaling pathways to prevent cancer initiation and progression in normal and premalignant tissues. In fully malignant cells, Nrf2 activity provides growth advantage by increasing cancer chemoresistance and enhancing tumor cell growth [2].
In human colon carcinoma cells (HT29) cells, sulforaphane at 15 μM inhibited cell growth and induced cell death. Sulforaphane induced a cell cycle arrest in a dose-dependent manner, followed by cell death. Sulforaphane induced cell cycle arrested in G2 -M Phase, which was correlated with increased expression of cyclins A and B1. Sulforaphane increased expression of the proapoptotic protein bax, the release of cytochrome c from the mitochondria to the cytosol, and the proteolytic cleavage of poly(ADP-ribose) polymerase [1].
References:
[1] Gamet-Payrastre L, Li P, Lumeau S, et al. Sulforaphane, a naturally occurring isothiocyanate, induces cell cycle arrest and apoptosis in HT29 human colon cancer cells[J]. Cancer research, 2000, 60(5): 1426-1433.
[2] Kansanen E, Kuosmanen S M, Leinonen H, et al. The Keap1-Nrf2 pathway: mechanisms of activation and dysregulation in cancer[J]. Redox biology, 2013, 1(1): 45-49.
- 1. Zhongcheng Xie, Jiamin Guo, et al. "The suppression of FSP1 expression via NRF2 promotes ferroptosis induced by reactive oxygen species in vascular smooth muscle cells." Process Biochemistry. August 2024.
- 2. Fabian Szepanowski, Jaqueline Zipfel, et al. "Enhancement of Heme-Oxygenase 1 in the Injured Peripheral Nerve Following Sulforaphane Administration Fosters Regeneration via Proliferation and Maintenance of Repair Schwann Cells" Antioxidants 2024, 13(9), 1038
- 3. Folbergrová J, Ješina P, et al. "Protective Effect of Sulforaphane on Oxidative Stress and Mitochondrial Dysfunction Associated with Status Epilepticus in Immature Rats." Mol Neurobiol 2023 Jan 04 PMID: 36598650
- 4. Pandi Peng, Dong Wang, et al. "Targeting clock-controlled gene Nrf2 ameliorates inflammation-induced intervertebral disc degeneration." Arthritis Res Ther. 2022 Aug 3;24(1):181. PMID: 35922862
- 5. Zheng K, Ma J, et al. "Sulforaphane Inhibits Autophagy and Induces Exosome-Mediated Paracrine Senescence via Regulating mTOR/TFE3." Mol Nutr Food Res. 2020;e1901231. PMID: 32476238
- 6. Junjun Yang, Xiongbo Song, et al. "Natural ingredients-derived antioxidants attenuate H2O2-induced oxidative stress and have chondroprotective effects on human osteoarthritic chondrocytes via Keap1/Nrf2 pathway." Free Radical Biology and Medicine. 28 January 2020. PII: S0891-5849(19)32431-1.
| Storage | Store at -20°C, Light exposure should be avoided |
| M.Wt | 177.3 |
| Cas No. | 4478-93-7 |
| Formula | C6H11NOS2 |
| Synonyms | SFN |
| Solubility | ≥51.6 mg/mL in H2O; ≥58.2 mg/mL in EtOH; ≥67.6 mg/mL in DMSO |
| Chemical Name | 1-isothiocyanato-4-(methylsulfinyl)-butane |
| SDF | Download SDF |
| Canonical SMILES | CS(CCCCN=C=S)=O |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |
| Cell experiment:[1] | |
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Cell lines |
HT29 human colon cancer cells |
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Reaction Conditions |
0 ~ 30 μM sulforaphane for 48 h incubation |
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Applications |
Sulforaphane resulted in a net decrease in the total number of cells and an accumulation of cells floating in the culture medium. The inhibition of growth and the effect on the adherence were already important at 15 μM. Sulforaphane at 15 μM was able to inhibit cell growth and induce cell death. Cell mortality was already 75% at 24 h and almost total at 96 h. |
| Animal experiment:[2] | |
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Animal models |
Female Sprague-Dawley rats, 40 days of age |
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Dosage form |
75 or 150 μmol Once daily by gavage for 5 days |
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Applications |
When sulforaphane was administered by gavage (75 or 150 μmol per day for 5 days) around the time of exposure to the 9,10-dimethyl-1,2-benzanthracene carcinogen, the incidence, multiplicity, and weight of mammary tumors were significantly reduced, and their development was delayed. Sulforaphane was able to protect against carcinogenesis. |
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Note |
The technical data provided above is for reference only. |
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References: 1. Gamet-Payrastre L, Li P, Lumeau S, et al. Sulforaphane, a naturally occurring isothiocyanate, induces cell cycle arrest and apoptosis in HT29 human colon cancer cells. Cancer Research, 2000, 60(5): 1426-1433. 2. Zhang Y, Kensler TW, Cho CG, et al. Anticarcinogenic activities of sulforaphane and structurally related synthetic norbornyl isothiocyanates. Proceedings of the National Academy of Sciences of the United States of America, 1994, 91(8): 3147-3150. |
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