Fisetin (Fustel; CCRIS-9034; NSC-407010)

Alias:
Cat No.:V0435 Purity: ≥98%
Fisetin (Fustel; CCRIS9034; NSC40701; 3, 7, 3′, 4′-tetrahydroxyflavone) is a naturally occuring and dietary flavonoid isolated from/found in a variety of fruits and vegetables (i.
Fisetin (Fustel; CCRIS-9034; NSC-407010) Chemical Structure CAS No.: 528-48-3
Product category: Sirtuin
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Fisetin (Fustel; CCRIS9034; NSC40701; 3, 7, 3′, 4′-tetrahydroxyflavone) is a naturally occuring and dietary flavonoid isolated from/found in a variety of fruits and vegetables (i.e. strawberries, apples, persimmons, onions and cucumbers). It has many important biological activity including anti-inflammatory, anti-oxidant, anti-diabetic, anti-invasive, anti-tumorigenic, neuroprotective, anti-angiogenic, and cardioprotective effects in cell culture and in animal models relevant to human diseases. It is a potent sirtuin activating compound (STAC) and an agent that modulates sirtuins. It also acts as a tubulin inhibitor/stabilizer. Fisetin is a structurally distinct chemical belonging to the flavonoid class of polyphenols.

Biological Activity I Assay Protocols (From Reference)
ln Vitro
Fisetin reduces lipid accumulation and lowers PPARγ expression in 3T3-L1 cells. Fisetin suppresses early phases of preadipocyte development and stimulates Sirt1 expression. Fisetin stimulates Sirt1-mediated deacetylation of PPARγ and FoxO1, boosts the binding of Sirt1 to the PPARγ promoter, consequently decreasing PPARγ transcriptional activity, thereby inhibiting adipogenesis [1]. Fisetin binds tubulin and stabilizes microtubules, having binding properties substantially superior to those of paclitaxel. Fisetin treatment of human prostate cancer cells resulted in substantial overexpression of microtubule-associated proteins (MAP)-2 and -4. Fisetin strongly suppresses PCa cell growth, migration and invasion. Nudc, a protein linked with the microtubule motor dynein/dynamin complex that governs microtubule dynamics, is inhibited by Fisetin therapy [2].
ln Vivo
Treatment with fisetin decreased inflammatory cell infiltration and proliferation in mice exposed to UVB rays. Additionally, treating with fisetin lowers the levels of inflammatory mediators like COX-2, PGE2 and its receptors (EP1–EP4), and MPO activity. Moreover, fisetin lowers UVB-exposed skin's concentrations of the inflammatory cytokines TNFα, IL-1β, and IL-6. Increased expression of the proteins p53 and p21 indicates that fisetin treatment also reduces DNA damage and markers of cell proliferation [3].
Animal Protocol
topical treatment of Fisetin 250 nmol/0.2 mL acetone/mouse
Mice: The mice are divided into six groups of eight animals each. The mice in the first group are topically treated with 0.2 mL acetone and used as vehicle control. The mice in the second and third groups receive topical treatment of Fisetin 250 nmol/0.2 mL acetone/mouse and 500 nmol/0.2 mL acetone/mouse respectively on their dorsal skin and serves as agent controls. The mice in the fourth, fifth and sixth groups are exposed to UVB. The mice in the fourth group receive a topical application of 0.2 mL acetone after 15 min of UVB exposure designated as vehicle control. The mice in the fifth and sixth groups are treated with topical application of Fisetin 250 nmol/0.2 mL acetone/mouse and 500 nmol/0.2 mL acetone/mouse respectively on to their dorsal skin after 15 min of UVB exposure
References
[1]. Kim SC, et al. Fisetin induces Sirt1 expression while inhibiting early adipogenesis in 3T3-L1 cells. Biochem Biophys Res Commun. 2015 Nov 27;467(4):638-44.
[2]. Mukhtar E, et al. Dietary flavonoid fisetin binds to β-tubulin and disrupts microtubule dynamics in prostate cancer cells. Cancer Lett. 2015 Oct 28;367(2):173-83
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H10O6
Molecular Weight
286.24
CAS #
528-48-3
Related CAS #
Fisetin quarterhydrate;Fisetin (Standard);528-48-3
SMILES
O1C2C([H])=C(C([H])=C([H])C=2C(C(=C1C1C([H])=C([H])C(=C(C=1[H])O[H])O[H])O[H])=O)O[H]
InChi Key
XHEFDIBZLJXQHF-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H10O6/c16-8-2-3-9-12(6-8)21-15(14(20)13(9)19)7-1-4-10(17)11(18)5-7/h1-6,16-18,20H
Chemical Name
2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-4H-chromen-4-one
Synonyms

Fisetholz; Fisetin; CCRIS 9034; CCRIS9034; CCRIS-9034; NSC 407010; NSC407010; NSC-656275

Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 57 mg/mL (199.1 mM)
Water:<1 mg/mL
Ethanol: 3 mg/mL (10.5 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (7.27 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (7.27 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: 10 mg/mL (34.94 mM) in 45% PEG300 5% Tween-80 50% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.4936 mL 17.4679 mL 34.9357 mL
5 mM 0.6987 mL 3.4936 mL 6.9871 mL
10 mM 0.3494 mL 1.7468 mL 3.4936 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT06133634 Recruiting Dietary Supplement: Fisetin
Other: Placebo
Aging
Endothelial Dysfunction
University of Colorado, Boulder September 25, 2023 Phase 1
Phase 2
NCT05416515 Recruiting Drug: Fisetin Carpal Tunnel Syndrome Peter C. Amadio, M.D. October 9, 2022 Phase 2
NCT05595499 Recruiting Procedure: Biospecimen Collection
Drug: Fisetin
Anatomic Stage I Breast Cancer AJCC v8
Anatomic Stage II Breast Cancer AJCC v8
Jonsson Comprehensive Cancer Center March 27, 2023 Phase 2
NCT04537299 Active, not recruiting Drug: Fisetin
Drug: Placebo
Covid19
SARS-CoV Infection
Mayo Clinic April 29, 2022 Phase 2
Biological Data
  • Effect of fisetin on microtubule assembly in vitro. (A) Graph of microtubule polymerization in the presence of fisetin (10 μM), paclitaxel (10 μM), and control. Tubulin polymerization was measured by spectrophotometer at 340 nm every 1 min for 60 min. Data form a typical experiment performed three times with similar results. (B) Representative immunofluorescence photomicrographs of PC-3 cells incubated with DMSO (Control) and fisetin (80 μM) for 0, 30, 60, 90 minutes. The microtubule network was analyzed with the Nikon confocal system. Microtubule networks (green fluorescence), nuclei labeled with DAPI (blue fluorescence). Scale bars, 25 μm and 50 μM. Images are representative of three independent experiments. (For interpretation of the references to color in this figure legend, the reader is referred to the web version of this article.)
  • Fisetin and taxol interact within the β-tubulin binding pocket. (A) X-Ray co-crystal structure of β-tubulin and taxol. (B) Superimposition of taxol and of fisetin (both from X-ray structure and from docking calculation) onto the β-tubulin biding site. (C) Amino acid binding pocket of taxol on β-tubulin. (D–G) Representative view of taxol derived from X-ray. (E–H) Representative view of taxol derived from docking. (F–I) Representative view of fisetin on the amino acid binding pocket on β-tubulin domain.
  • Effect of fisetin treatment on proteins associated with microtubule organization and cell cycle. (A–C) Representative blots showing the effect of fisetin treatment (0–80 μM) on α-tubulin acetylation, MT-associated proteins, and NudC protein respectively in PCa PC-3 and DU-145 cells. (D) The cell cycle distribution as analyzed by flow cytometry. PC-3 cells were treated with fisetin (0–80 μM) for 24 h. Data form a typical experiment performed three times with similar results.
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