Barbigerone

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MedKoo CAT#: 562964

CAS#: 75425-27-3

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


Price and Availability

Size Price Shipping out time Quantity
Inquire bulk and customized quantity

Pricing updated 2020-10-20. Prices are subject to change without notice.

Barbigerone is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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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


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


Technical Data

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


References

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.