Barbigerone | CAS#75425-27-3 | tumor angiogenesis inhibitor

MedKoo Cat#: 562964 | Name: Barbigerone

Description:

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

Barbigerone is an inhibitor of tumor angiogenesis, growth and metastasis in melanoma.

Chemical Structure

Barbigerone

CAS#75425-27-3

Theoretical Analysis

MedKoo Cat#: 562964

Name: Barbigerone

CAS#: 75425-27-3

Chemical Formula: C23H22O6

Exact Mass: 394.1416

Molecular Weight: 394.42

Elemental Analysis: C, 70.04; H, 5.62; O, 24.34

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Barbigerone; Barubigeron;

IUPAC/Chemical Name

8,8-Dimethyl-3-(2,4,5-trimethoxyphenyl)pyrano[2,3-f]chromen-4-one

InChi Key

OBIUGMGQVQMVSK-UHFFFAOYSA-N

InChi Code

InChI=1S/C23H22O6/c1-23(2)9-8-13-17(29-23)7-6-14-21(24)16(12-28-22(13)14)15-10-19(26-4)20(27-5)11-18(15)25-3/h6-12H,1-5H3

SMILES Code

O=C1C(C2=CC(OC)=C(OC)C=C2OC)=COC3=C1C=CC4=C3C=CC(C)(C)O4

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

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 394.42 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

1: Li X, Wan L, Wang F, Pei H, Zheng L, Wu W, Ye H, Wang Y, Chen L. Barbigerone reverses multidrug resistance in breast MCF-7/ADR cells. Phytother Res. 2018 Apr;32(4):733-740. doi: 10.1002/ptr.6026. Epub 2018 Jan 24. PubMed PMID: 29368443. 2: Wei Z, Yang Y, Xie C, Li C, Wang G, Ma L, Xiang M, Sun J, Wei Y, Chen L. Synthesis and biological evaluation of pyranoisoflavone derivatives as anti-inflammatory agents. Fitoterapia. 2014 Sep;97:172-83. doi: 10.1016/j.fitote.2014.06.002. Epub 2014 Jun 9. PubMed PMID: 24924289. 3: Wang G, Wang F, Cao D, Liu Y, Zhang R, Ye H, Li X, He L, Yang Z, Ma L, Peng A, Xiang M, Wei Y, Chen L. Synthesis, structure-activity relationships and biological evaluation of barbigerone analogues as anti-proliferative and anti-angiogenesis agents. Bioorg Med Chem Lett. 2014 Jul 15;24(14):3158-63. doi: 10.1016/j.bmcl.2014.04.121. Epub 2014 May 16. PubMed PMID: 24863745. 4: Yang JH, Hu J, Wan L, Chen LJ. Barbigerone inhibits tumor angiogenesis, growth and metastasis in melanoma. Asian Pac J Cancer Prev. 2014;15(1):167-74. PubMed PMID: 24528020. 5: Qiu N, Cheng X, Wang G, Wang W, Wen J, Zhang Y, Song H, Ma L, Wei Y, Peng A, Chen L. Inclusion complex of barbigerone with hydroxypropyl-β-cyclodextrin: preparation and in vitro evaluation. Carbohydr Polym. 2014 Jan 30;101:623-30. doi: 10.1016/j.carbpol.2013.09.035. Epub 2013 Sep 23. PubMed PMID: 24299819. 6: Li X, Wang X, Ye H, Peng A, Chen L. Barbigerone, an isoflavone, inhibits tumor angiogenesis and human non-small-cell lung cancer xenografts growth through VEGFR2 signaling pathways. Cancer Chemother Pharmacol. 2012 Sep;70(3):425-37. doi: 10.1007/s00280-012-1923-x. Epub 2012 Jul 20. PubMed PMID: 22814678. 7: Ye H, Zhong S, Li Y, Tang M, Peng A, Hu J, Shi J, He S, Wu W, Chen L. Enrichment and isolation of barbigerone from Millettia pachycarpa Benth. using high-speed counter-current chromatography and preparative HPLC. J Sep Sci. 2010 Apr;33(8):1010-7. doi: 10.1002/jssc.200900641. PubMed PMID: 20187026. 8: Li ZG, Zhao YL, Wu X, Ye HY, Peng A, Cao ZX, Mao YQ, Zheng YZ, Jiang PD, Zhao X, Chen LJ, Wei YQ. Barbigerone, a natural isoflavone, induces apoptosis in murine lung-cancer cells via the mitochondrial apoptotic pathway. Cell Physiol Biochem. 2009;24(1-2):95-104. doi: 10.1159/000227817. Epub 2009 Jul 1. PubMed PMID: 19590197. 9: Gong T, Wang DX, Chen RY, Liu P, Yu DQ. Novel benzil and isoflavone derivatives from Millettia dielsiana. Planta Med. 2009 Feb;75(3):236-42. doi: 10.1055/s-0028-1112203. Epub 2009 Jan 12. PubMed PMID: 19140097. 10: Gong T, Wang HQ, Chen RY. [Isoflavones from vine stem of Millettia dielsiana]. Zhongguo Zhong Yao Za Zhi. 2007 Oct;32(20):2138-40. Chinese. PubMed PMID: 18306746. 11: Wangensteen H, Alamgir M, Rajia S, Samuelsen AB, Malterud KE. Rotenoids and isoflavones from Sarcolobus globosus. Planta Med. 2005 Aug;71(8):754-8. PubMed PMID: 16142641. 12: Yenesew A, Derese S, Midiwo JO, Oketch-Rabah HA, Lisgarten J, Palmer R, Heydenreich M, Peter MG, Akala H, Wangui J, Liyala P, Waters NC. Anti-plasmodial activities and X-ray crystal structures of rotenoids from Millettia usaramensis subspecies usaramensis. Phytochemistry. 2003 Oct;64(3):773-9. PubMed PMID: 13679101.