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Related CAS#:
552-54-5 20486-38-8
64527-08-8 52801-23-7
52801-24-8

552-54-5

552-54-5 structure
552-54-5 structure
  • Name: Rhamnazin
  • Chemical Name: 3',7-Di-O-methyl Quercetin
  • CAS Number: 552-54-5
  • Molecular Formula: C17H14O7
  • Molecular Weight: 330.29
  • Catalog: Signaling Pathways Protein Tyrosine Kinase/RTK VEGFR
  • Create Date: 2018-11-24 07:54:12
  • Modify Date: 2024-01-13 16:38:19
  • 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].
Name 3',7-Di-O-methyl Quercetin
Synonyms 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-
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
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.  

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
HS Code 2914509090
64527-08-8 structure

64527-08-8

~%

552-54-5 structure

552-54-5
Literature: Itokawa,H.; Oshida,Y. Phytochemistry (Elsevier), 1981 , vol. 20, p. 2421
90-19-7 structure

90-19-7

~%

552-54-5 structure

552-54-5
Literature: Kim, Bong-Gyu; Lee, Youngshim; Hur, Hor-Gil; Lim, Yoongho; Ahn, Joong-Hoon Phytochemistry, 2006 , vol. 67, # 4 p. 387 - 394
854873-13-5 structure

854873-13-5
857617-58-4 structure

857617-58-4

~%

552-54-5 structure

552-54-5
Literature: Kuhn; Loew Chemische Berichte, 1944 , vol. 77/79, p. 211,213
33554-60-8 structure

33554-60-8

~%

552-54-5 structure

552-54-5
Literature: Rao; Seshadri Journal of the Chemical Society, 1946 , p. 771
93876-67-6 structure

93876-67-6

~%

552-54-5 structure

552-54-5
Literature: Anand et al. Proceedings - Indian Academy of Sciences, Section A, 1949 , # 29 p. 203,207
80651-75-8 structure

80651-75-8

~%

552-54-5 structure

552-54-5
Literature: Nair, G. Aravindakshan; Joshua, C. P.; Nair, A. G. Ramachandran Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1981 , vol. 20, # 10 p. 939
17874-42-9 structure

17874-42-9

~%

552-54-5 structure

552-54-5
Literature: Rao; Seshadri Journal of the Chemical Society, 1946 , p. 771
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%

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