Nivitol
Nivitol (UP302) is a natural phenolic compound discovered from Dianella ensifolia and also acts as a Tyrosinase inhibitor. Nivitol competitively and reversibly inhibits tyrosinase, suppressing melanin production. Nivitol inhibits homogentisate 1,2-dioxygenase (HGD). In human leukemia cells, Nivitol inhibits PI3K/AKT pathway phosphorylation, increases ROS, decreases mitochondrial membrane potential, and induces G2/M cell cycle arrest, apoptosis, and PINK1/Parkin-mediated mitophagy. Nivitol exhibits inhibition of tumor growth in the MV411 xenograft mouse model. Nivitol is used for research on exogenous ochronosis, hyperpigmentation, and leukemia.
For research use only. We do not sell to patients.
- CAS No.: 869743-37-3
- Formula: C18H22O4
- Molecular Weight:302.37
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
To place orders, for customer services and technical support, please contact: MedChemExpress USA
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Biological Activity
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Chemical Information
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Biological Activity
Description
IC50 & Target
[3]|
Bax |
Akt |
PI3K |
Bcl-2 |
Caspase 3 |
Cellular Effect
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| B16-F1 | IC50 |
15 μM
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Inhibition of melanin production in murine B16-F1 melanoma cells incubated for 72 hrs in the presence of 2 nM alpha-MSH measured by absorbance at 490 nm.
Inhibition of melanin production in murine B16-F1 melanoma cells incubated for 72 hrs in the presence of 2 nM alpha-MSH measured by absorbance at 490 nm.
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18758104 |
In Vitro
Nivitol (UP302) is a novel, potent, competitive, and reversible mushroom tyrosinase inhibitor with a Ki of 0.3 μM; it inhibits DOPA oxidase activity in B16-F1 mouse melanoma cell homogenates with an IC50 of 12 μM[2].
Nivitol (0-62 μM; 72 h) inhibits melanin production in B16-F1 cells and primary human epidermal melanocytes with IC50 values of 15 μM and 8 μM, respectively, and exhibits no cytotoxicity at concentrations up to 62 μM[2].
Nivitol (0.05-0.1%; 4-14 days) significantly inhibits melanogenesis in reconstructed human skin[2].
Nivitol (UP302) (20-120 μM; 48 h) inhibits the growth of MV411 and K562 human leukemia cell lines[3].
Nivitol (30-120 μM; 16 h) induces ROS production and decreases mitochondrial membrane potential in MV411 and K562 cells[3].
Nivitol (40-100 μM; 16 h) induces apoptosis in MV411 and K562 cells[3].
UP302 (30-90 μM; 16 h) alters the expression of apoptosis-related proteins in MV411 and K562 cells; activates mitophagy through the PINK1/Parkin pathway; inhibits the activation of the PI3K/AKT signaling pathway[3].
UP302 (50-100 μM; 16-48 h) induces autophagy and mitophagy in MV411 and K562 cells, and UP302-induced autophagy exerts a protective effect on leukemia cells MV411 and K562[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:MV411 and K562
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Concentration:20, 40, 60, 80, 100, 120 μM
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Incubation Time:48 h
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Result:Exhibited antiproliferative activity against leukemia cells MV411 and K562.
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Cell Line:MV411 and K562
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Concentration:0, 40, 60, 80, 100 μM
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Incubation Time:16 h
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Result:Significantly increased apoptosis in both MV411 and K562 compared to the control group.
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Cell Line:MV411 and K562
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Concentration:30, 60, 90 μM
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Incubation Time:16 h
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Result:Overexpressed AIF, Bax, and active-caspase 3.
Down-regulated relative protein levels of Bcl-2 compared with the control group.\nDramatically increased levels of LC3-II compared with the control group.
Upregulated expression levels of both PINK1 and Parkin.\nSignificantly inhibited the phosphorylation of PI3K/AKT.
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Cell Line:MV411 and K562
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Concentration:100 μM
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Incubation Time:48 h with or
without pretreatment with 20μM Chloroquine (HY-17589A) for 60
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Result:Significantly increased the number of apoptotic cells after autophagy inhibition.
Showed apoptosis of tumor cells in the combination group.
Parmacokinetics
| Species | Dose | Route | T1/2 | Vd | CL | MRT |
|---|---|---|---|---|---|---|
| Rat[4] | 5 mg/kg | i.v. | 0.87 h | 6.90 L/kg | 5.89 L/kg | 0.34 h |
In Vivo
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:BALB/c nude mice (female, 4 weeks old, received a subcutaneous injection of 8×106 cells (100μl cell suspension) in the right back)[3]
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Dosage:10 mg/kg
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Administration:i.p.; every two days; two weeks
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Result:Significantly reduced tumor volume compared to the control group.
Showed no significant difference in body weight among the groups.
Showed blood biochemical indicators for liver (ALT, AST), kidney (CREA, urea, UA), and heart (CK) functions all within the normal reference range.
Showed no prominent abnormal structures in H&E staining of major organs (heart, liver, spleen, lung, and kidney) compared to the PBS group.
Chemical Information
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CAS No. 869743-37-3
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Molecular Weight 302.37
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Formula C18H22O4
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SMILES
OC1=CC=C(C(O)=C1)CCCC2=CC=C(OC)C(=C2OC)C
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Synonyms
UP302
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation
References
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Nivitol Related Classifications
HY-108046 Related Classifications
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