Nobiletin | CAS#478-01-3 | anti-tumor agent

MedKoo Cat#: 561504 | Name: Nobiletin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Nobiletin has anti-inflammatory and anti-tumor invasion, proliferation, and metastasis activity in vitro and in animal studies. Nobiletin was also found to potentially inhibit cartilage degradation.

Chemical Structure

Nobiletin

CAS#478-01-3

Theoretical Analysis

MedKoo Cat#: 561504

Name: Nobiletin

CAS#: 478-01-3

Chemical Formula: C21H22O8

Exact Mass: 402.1315

Molecular Weight: 402.40

Elemental Analysis: C, 62.68; H, 5.51; O, 31.81

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 230.00
25mg	USD 350.00
50mg	USD 630.00

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Related CAS #

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Synonym

Nobiletin; Hexamethoxyflavone; NOB;

IUPAC/Chemical Name

2-(3,4-Dimethoxyphenyl)-5,6,7,8-tetramethoxychromen-4-one

InChi Key

MRIAQLRQZPPODS-UHFFFAOYSA-N

InChi Code

InChI=1S/C21H22O8/c1-23-13-8-7-11(9-15(13)24-2)14-10-12(22)16-17(25-3)19(26-4)21(28-6)20(27-5)18(16)29-14/h7-10H,1-6H3

SMILES Code

O=C1C=C(C2=CC=C(OC)C(OC)=C2)OC3=C1C(OC)=C(OC)C(OC)=C3OC

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Nobiletin is a retinoid acid receptor-related orphan receptors (RORs) agonist.

In vitro activity:

Nobiletin, up to 100 μM without cytotoxicity, significantly decreased motility, migration and invasion as well as enzymatic activities, protein levels and mRNA expressions of matrix metalloproteinase (MMP)-2 and MMP-9 in U2OS and HOS cells. In addition to inhibition of extracellular signal-regulated kinase (ERK) and c-Jun N-terminal kinase (JNK), the inhibitory effect of nobiletin on the DNA-binding activity of the transcription factor nuclear factor-kappa B (NF-κB), cAMP response element-binding protein (CREB), and specificity protein 1 (SP-1) in U2OS and HOS cells. Reference: Oncotarget. 2016 Jun 7;7(23):35208-23. https://pubmed.ncbi.nlm.nih.gov/27144433/

In vivo activity:

When administered to diet-induced obese (DIO) mice, NOB (nobiletin) strongly counteracted metabolic syndrome and augmented energy expenditure and locomotor activity in a Clock gene-dependent manner. In db/db mutant mice, the clock is also required for the mitigating effects of NOB on metabolic disorders. In DIO mouse liver, NOB enhanced clock protein levels and elicited pronounced gene expression remodeling. Reference: Cell Metab. 2016 Apr 12;23(4):610-21. https://pubmed.ncbi.nlm.nih.gov/27076076/

	Solvent	mg/mL	mM
Solubility
	DMF	15.0	37.28
	DMF:PBS (pH 7.2) (1:1)	0.5	1.24
	DMSO	46.7	115.97
	Ethanol	1.7	4.10

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 402.40 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Takito J, Kimura J, Kajima K, Uozumi N, Watanabe M, Yokosuka A, Mimaki Y, Nakamura M, Ohizumi Y. Nerve growth factor enhances the CRE-dependent transcriptional activity activated by nobiletin in PC12 cells. Can J Physiol Pharmacol. 2016 Jul;94(7):728-33. doi: 10.1139/cjpp-2015-0394. Epub 2016 Feb 12. PMID: 27128150. 2. Cheng HL, Hsieh MJ, Yang JS, Lin CW, Lue KH, Lu KH, Yang SF. Nobiletin inhibits human osteosarcoma cells metastasis by blocking ERK and JNK-mediated MMPs expression. Oncotarget. 2016 Jun 7;7(23):35208-23. doi: 10.18632/oncotarget.9106. PMID: 27144433; PMCID: PMC5085222. 3. Nohara K, Mallampalli V, Nemkov T, Wirianto M, Yang J, Ye Y, Sun Y, Han L, Esser KA, Mileykovskaya E, D'Alessandro A, Green CB, Takahashi JS, Dowhan W, Yoo SH, Chen Z. Nobiletin fortifies mitochondrial respiration in skeletal muscle to promote healthy aging against metabolic challenge. Nat Commun. 2019 Aug 28;10(1):3923. doi: 10.1038/s41467-019-11926-y. PMID: 31462679; PMCID: PMC6713763. 4. He B, Nohara K, Park N, Park YS, Guillory B, Zhao Z, Garcia JM, Koike N, Lee CC, Takahashi JS, Yoo SH, Chen Z. The Small Molecule Nobiletin Targets the Molecular Oscillator to Enhance Circadian Rhythms and Protect against Metabolic Syndrome. Cell Metab. 2016 Apr 12;23(4):610-21. doi: 10.1016/j.cmet.2016.03.007. PMID: 27076076; PMCID: PMC4832569.

In vitro protocol:

In vivo protocol:

1. Nohara K, Mallampalli V, Nemkov T, Wirianto M, Yang J, Ye Y, Sun Y, Han L, Esser KA, Mileykovskaya E, D'Alessandro A, Green CB, Takahashi JS, Dowhan W, Yoo SH, Chen Z. Nobiletin fortifies mitochondrial respiration in skeletal muscle to promote healthy aging against metabolic challenge. Nat Commun. 2019 Aug 28;10(1):3923. doi: 10.1038/s41467-019-11926-y. PMID: 31462679; PMCID: PMC6713763. 2. He B, Nohara K, Park N, Park YS, Guillory B, Zhao Z, Garcia JM, Koike N, Lee CC, Takahashi JS, Yoo SH, Chen Z. The Small Molecule Nobiletin Targets the Molecular Oscillator to Enhance Circadian Rhythms and Protect against Metabolic Syndrome. Cell Metab. 2016 Apr 12;23(4):610-21. doi: 10.1016/j.cmet.2016.03.007. PMID: 27076076; PMCID: PMC4832569.

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