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Butein

$198

  • Brand : BIOFRON

  • Catalogue Number : BF-B3003

  • Specification : 98%

  • CAS number : 487-52-5

  • Formula : C15H12O5

  • Molecular Weight : 272.3

  • Volume : 20mg

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Catalogue Number

BF-B3003

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

272.3

Appearance

Powder

Botanical Source

herb of Broussonetia kazinoki

Structure Type

Flavonoids

Category

SMILES

C1=CC(=C(C=C1C=CC(=O)C2=C(C=C(C=C2)O)O)O)O

Synonyms

IUPAC Name

Density

1.5±0.1 g/cm3

Solubility

DMSO : ≥ 35 mg/mL (128.56 mM)
*"≥" means soluble, but saturation unknown.

Flash Point

307.1±26.6 °C

Boiling Point

560.9±50.0 °C at 760 mmHg

Melting Point

216°C

InChl

InChI=1S/C15H12O5/c16-10-3-4-11(14(19)8-10)12(17)5-1-9-2-6-13(18)15(20)7-9/h1-8,16,18-20H/b5-1+

InChl Key

AYMYWHCQALZEGT-ORCRQEGFSA-N

WGK Germany

RID/ADR

HS Code Reference

2914500000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:487-52-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31759370

Abstract

Background: Oral squamous cell carcinoma (OSCC) is one of the most predominant cancers in India. With advances in the field of oncology, a number of therapies have emerged; however, they are minimally effective. Consequently, there is a need to develop safe and effective regimens for the treatment of OSCC. Butein, a tetrahydroxychalcone has been found to exhibit potent antioxidant, anti-inflammatory, and also anti-tumor effects against several cancer types. However, its effect on OSCC is not studied yet.

Methods: The effect of butein on the viability, apoptosis, migration and invasion of OSCC cells was evaluated using MTT, colony formation, PI/FACS, live and dead, scratch wound healing, and matrigel invasion assays. Further Western blot analysis was done to evaluate the expression of different proteins involved in the regulation of cancer hallmarks.

Results: This is the first report exemplifying the anti-cancer effect of butein against OSCC. Our results showed that butein exhibited potent anti-proliferative, cytotoxic, anti-migratory, and anti-invasive effects in OSCC cells. It suppressed the expression of NF-κB and NF-κB-regulated gene products such as COX-2, survivin and MMP-9 which are involved in the regulation of different processes like proliferation, survival, invasion, and metastasis of OSCC cells. Conclusion Collectively, these results suggest that butein has immense potential in the management of OSCC. Nonetheless, in vivo validation is critical before moving to clinical trials.

KEYWORDS

NF-KB; Proliferation; butein; oral squamous cell carcinoma; survival.

Title

An Investigation on the Therapeutic Potential of Butein, A Tretrahydroxychalcone Against Human Oral Squamous Cell Carcinoma

Author

Devivasha Bordoloi 1, Javadi Monisha 1, Nand Kishor Roy 1, Ganesan Padmavathi 1, Kishore Banik 1, Choudhary Harsha 1, Hong Wang 2 3, Alan Prem Kumar 2, Frank Arfuso 4, Ajaikumar B Kunnumakkara 5

Publish date

2019 Nov 1;

PMID

31665136

Abstract

Drug resistance is the leading cause of breast cancer-related mortality in women, and triple negative breast cancer (TNBC) is the most aggressive subtype, affecting African American women more aggressively compared to Caucasians women. Of all cancer-related deaths, 15 to 20% are associated with inflammation, where proinflammatory cytokines have been implicated in the tumorigenesis process. The current study investigated the effects of the polyphenolic compound butein (2′,3,4,4′-tetrahydroxychalcone) on cell proliferation and survival, as well as its modulatory effect on the release of proinflammatory cytokines in MDA-MB-231 (Caucasian) and MDA-MB-468 (African American) TNBC cell. The results obtained showed that butein decreased cell viability in a time and dose-dependent manner, and after 72-h of treatment, the cell proliferation rate was reduced in both cell lines. In addition, butein was found to have higher potency in MDA-MB-468, exhibiting anti-proliferative effects in lower concentrations. Apoptosis assays demonstrated that butein (50 μM) increased apoptotic cells in MDA MB-468, showing 60% of the analyzed cells in the apoptotic phase, compared to 20% in MDA-MB-231 cells. Additionally, butein downregulated both protein and mRNA expression of the proinflammatory cytokine, CCL2, and IKBKE in TNFα-activated Caucasian cells, but not in African Americans. This study demonstrates butein potential in cancer cell suppression showing a higher cytotoxic, anti-proliferative, and apoptotic effects in African Americans, compared to Caucasians TNBC cells. It also reveals the butein inhibitory effect on CCL2 expression with a possible association with IKBKE downregulation in MDA-MB-231 cells only, indicating that Caucasians and African Americans TNBC cells respond differently to butein treatment. The obtained findings may provide an explanation regarding the poor therapeutic response in African American patients with advanced TNBC.

Title

The inhibitory effects of butein on cell proliferation and TNF-α-induced CCL2 release in racially different triple negative breast cancer cells

Author

Patricia Mendonca 1, Ainsley Horton 1, David Bauer 1, Samia Messeha 1, Karam F A Soliman 1

Publish date

2019 Oct 30

PMID

31329291

Abstract

The effects of chalcone and butein on the induction of the superoxide anion (O2 – )-generating system were studied in U937 cells by all-trans retinoic acid (RA). The chalcone skeleton, a common structural motif in them, significantly enhanced the transcription of gp91-phox in an epigenetic manner. In contrast, chalcone and butein showed opposite effects on the induction of the O2 – -generating activity by RA and the expression of gp91-phox protein. Chalcone inhibited, whereas butein promoted, the induction of O2 – -generating activity by RA and the expression of gp91-phox protein. These data raise the possibility that modification of the chalcone skeleton could produce more effective differentiation-promoting agents.

KEYWORDS

butein; chalcone; gp91-phox; superoxide.

Title

Chalcone skeleton promotes transcription of gp91-phox gene but inhibits expression of gp91-phox protein, and hydroxyl groups in hydroxychalcones participate in the stable expression of gp91-phox protein

Author

Hidehiko Kikuchi 1, Hitomi Mimuro 2 3, Harishkumar Madhyastha 4, Futoshi Kuribayashi 5

Publish date

2019 Oct;


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