Rhamnazin

Names

[ CAS No. ]:
552-54-5

[ Name ]:
Rhamnazin

[Synonym ]:
3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxychromen-4-one
Rhamnazin
3,4',5-Trihydroxy-3',7-dimethoxyflavone
3,5-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-4H-1-benzopyran-4-one
Flavone, 3,4',5-trihydroxy-3',7-dimethoxy-
T66 BO EVJ CR DQ CO1& DQ GQ IO1
3,5-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-4H-chromen-4-one
3',7-Dimethylquercetin
rhamnacene
4H-1-Benzopyran-4-one, 3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-

Biological Activity

[Description]:

Rhamnazin is an orally active inhibitor of VEGFR2 signaling with an IC50 of 4.68 μM against VEGFR2 kinase. Rhamnazin shows potent antiangiogenic activity and antitumor efficacy[1]. Rhamnazin shows antioxidant and anti-inflammatory properties[2].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Protein Tyrosine Kinase/RTK >> VEGFR

[Target]

VEGFR2:4.68 μM (IC50)

[In Vitro]

Rhamnazin (5-40 μM) 抑制 VEGF 诱导的 HUVECs 增殖、迁移和成管[1]。 Rhamnazin (0-20 μM) 降低 VEGFR-2 酪氨酸激酶活性和 VEGFR-2 信号通路[1]。 Rhamnazin (0-40 μM; 24 h) 抑制乳腺癌细胞增殖和 VEGFR2 信号通路[1]。 Cell Migration Assay [1] Cell Line: HUVECs Concentration: 0, 10, 15 and 20 μM Incubation Time: 6 h Result: Strongly inhibited the migration of HUVECs. Western Blot Analysis[1] Cell Line: HUVECs Concentration: 0, 10, 15 and 20 μM Incubation Time: 24 h Result: Decreased VEGF binding to VEGFR2. Reduced VEGF-stimulated phosphorylation of VEGFR2 and its downstream MAPK, AKT, and STAT3 in HUVECs in a concentrationdependent manner. Cell Proliferation Assay[1] Cell Line: HCC1937, T-47D, SK-BR-3, MCF-7 and MDA-MB-231 Concentration: 0, 10, 15, 20, 30 and 40 μM Incubation Time: 24 h Result: Inhibited cell growth with IC50s of 19, 27, 32, 41 and 64 μM against MDA-MB-231, MCF-7, SK-BR-3, T-47D and HCC1937 in the presence of VEGF, respectively.

[In Vivo]

Rhamnazin (200 mg/kg; i.g.; daily for 25 days) 抑制小鼠乳腺癌生长和血管生成[1]。 Rhamnazin (5-20 mg/kg; i.p.; once) 在大鼠急性肺损伤模型中显示出较强的抗氧化和抗炎作用[2]。 Animal Model: BALB/c nude mice, breast cancer xenograft model[1] Dosage: 200 mg/kg Administration: Intragastric administration, daily for 25 days Result: Dramatically suppressed tumor volumes by 47% compared with the vehicle group. Showed a significant reduction of pVEGFR2Tyr951-positive cells in tumors. Resulted in downregulation of VEGFR2 downstream molecules phosphorylation including MAPK, AKT and STAT3.

[References]

[1]. Yu Y, et al. Rhamnazin, a novel inhibitor of VEGFR2 signaling with potent antiangiogenic activity and antitumor efficacy. Biochem Biophys Res Commun. 2015 Mar 20;458(4):913-9.

[2]. Wu G, et al. ANTIOXIDANT AND ANTI-INFLAMMATORY EFFECTS OF RHAMNAZIN ON LIPOPOLYSACCHARIDE-INDUCED ACUTE LUNG INJURY AND INFLAMMATION IN RATS. Afr J Tradit Complement Altern Med. 2017 Jun 5;14(4):201-212.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
591.6±50.0 °C at 760 mmHg

[ Melting Point ]:
214-215℃

[ Molecular Formula ]:
C₁₇H₁₄O₇

[ Molecular Weight ]:
330.29

[ Flash Point ]:
221.2±23.6 °C

[ Exact Mass ]:
330.073944

[ PSA ]:
109.36000

[ LogP ]:
2.26

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.681

Safety Information

[ HS Code ]:
2914509090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914509090

[ Summary ]:
HS:2914509090 other ketones with other oxygen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%