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Isoginkgetin

Product Name
Isoginkgetin
CAS No.
548-19-6
Chemical Name
Isoginkgetin
Synonyms
ISOGINKGETIN;Isoginkgetin-RM;ISOGINKGETIN(SH);Isoginkgetin, >99%;Isoginkgo diflavone;ISOGINKGETIN(RG)(PLEASE CALL);4',4'''-Dimethylamentoflavone;4',4'''-Dimethoxyamentoflavone;Isoginkgetin, 98%, from Ginkgo biloba L.;5,5'',7,7''-Tetrahydroxy-4',4'''-dimethoxy-3''',8-biflavone
CBNumber
CB2675231
Molecular Formula
C32H22O10
Formula Weight
566.51
MOL File
548-19-6.mol
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Isoginkgetin Property

Melting point:
355℃
Boiling point:
843.6±65.0 °C(Predicted)
Density 
1.506
storage temp. 
2-8°C(protect from light)
solubility 
DMSO: 3 mg/ml; DMSO:PBS (pH 7.2) (1:7): 0.12 mg/ml
form 
powder
pka
6.16±0.40(Predicted)
color 
White-beige
InChIKey
HUOOMAOYXQFIDQ-UHFFFAOYSA-N
SMILES
C1(C2=CC=C(OC)C=C2)OC2=C(C3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C=4)=CC=C3OC)C(O)=CC(O)=C2C(=O)C=1
LogP
5.240 (est)
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
416154
Product name
Pre-mRNA Splicing Inhibitor, Isoginkgetin - CAS 548-19-6 - Calbiochem
Packaging
10mg
Price
$245
Updated
2024/03/01
Cayman Chemical
Product number
25104
Product name
Isoginkgetin
Purity
≥98%
Packaging
1mg
Price
$37
Updated
2024/03/01
Cayman Chemical
Product number
25104
Product name
Isoginkgetin
Purity
≥98%
Packaging
5mg
Price
$151
Updated
2024/03/01
Cayman Chemical
Product number
25104
Product name
Isoginkgetin
Purity
≥98%
Packaging
10mg
Price
$213
Updated
2024/03/01
Cayman Chemical
Product number
25104
Product name
Isoginkgetin
Purity
≥98%
Packaging
25mg
Price
$442
Updated
2024/03/01
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Isoginkgetin Chemical Properties,Usage,Production

Description

Isoginkgetin is a biflavonoid that has been found in G. biloba and is an inhibitor of pre-mRNA splicing. Isoginkgetin (33 μM) reduces the activity of an mRNA-dependent luciferase reporter by 5-fold, shifts the composition of total RNA extract from predominantly mRNA to pre-mRNA, and arrests cell growth in HEK293 cells. Isoginkgetin (10 μM) suppresses mouse lymphocyte proliferation induced by concanavalin A (Con A; ) and LPS by approximately 87 and 90%, respectively. It also suppresses arachidonic acid release induced by phorbol 12-myristate 13-acetate (PMA; ) and the calcium ionophore A23187 by 32.5 and 48.4%, respectively, in rat peritoneal macrophages when used at a concentration of 10 μM. Isoginkgetin (5-20 μM) reduces matrix metalloproteinase-9 (MMP-9) activity, expression, and mRNA levels in and decreases cell invasion by HT1080 fibrosarcoma cells in a concentration-dependent manner.

Definition

ChEBI: A biflavonoid resulting from the formal oxidative dimerisation between position 8 of one molecule of 5,7-dihydroxy-4'-methoxyflavone and the 3' position of another. Found in the leaves of Ginkgo biloba, it is a potent inhibitor of matrix metal oproteinase 9 (MMP-9).

Origin

Isoginkgetin (ISO), a member of the biflavonoid family, could promote autophagy in HCC cells and human colon carcinoma cells HCT 116. As a natural compound derived from Ginkgo biloba leaves, ISO possesses anti-tumor and anti-splicing functions. Nevertheless, ISO's low water solubility and poor bioavailability hinder its biomedical application [1].

General Description

A cell-permeable, naturally isolated Ginkgo biloba biflavanoid that acts as a general pre-mRNA splicing inhibitor (ICmax = 50 μM in splicing assays using HeLa nuclear extract) by blocking the spliceosome-meidated splicing process at the prespliceosome/A complex stage. Isoginkgetin treatment is shown to result in growth arrest in HEK293-derived cultures in a reversible manner without affecting cell viability (33 μM for 24 h).

Mechanism of action

Specifically, isoginkgetin impairs the production of matrix metalloproteinase 9 (MMP-9), a protein involved in tumor invasion and metastasis, via inhibition of the NF-κB pathway and upregulation of the MMP-9 inhibitor tissue inhibitor metalloproteinase 1 (TIMP-1) in human fibrosarcoma cells. Isoginkgetin inhibits the activity of the 20S proteasome, leading to a toxic accumulation of ubiquitinated proteins in the ER and the induction of apoptosis in cancer cell lines. Like other proteasome inhibitors, isoginkgetin also inhibits the NF-κB pathway, which relies on proteasomal degradation of the inhibitory protein IκBα for activation. Moreover, the disruption of proper protein clearance via proteasome inhibition results in the activation of lysosome regulator TFEB, UPR, and autophagy pathways[2].

storage

Store at -20°C

References

[1] Yang Wang . “Isoginkgetin synergizes with doxorubicin for robust co-delivery to induce autophagic cell death in hepatocellular carcinoma.” Acta Biomaterialia 153 (2022): Pages 518-528.
[2] Jessica Tsalikis. “Isoginkgetin, a Natural Biflavonoid Proteasome Inhibitor, Sensitizes Cancer Cells to Apoptosis via Disruption of Lysosomal Homeostasis and Impaired Protein Clearance.” Molecular and Cellular Biology 39 10 (2019).

Isoginkgetin Preparation Products And Raw materials

Raw materials

Preparation Products

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Isoginkgetin Suppliers

Huzhou ZhanShu Biotechnology Co.,Ltd
Tel
0572-8889530 18167260939
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zsubio@163.com
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China
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360
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Chembest Research Laboratories Limited
Tel
+86-21-20908456
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021-58180499
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sales@BioChemBest.com
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China
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6005
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BioBioPha Co., Ltd.
Tel
0871-65217109 13211707573;
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0871-65215563
Email
y.liu@mail.biobiopha.com
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China
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ShangHai YuanYe Biotechnology Co., Ltd.
Tel
021-61312847 13636370518
Fax
021-55068248
Email
shyysw007@163.com
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China
ProdList
4940
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Chengdu Biopurify Phytochemicals Ltd.
Tel
+86-028-82633397 18982077548
Fax
+86-28-82633165
Email
cwb1@biopurify.cn
Country
China
ProdList
2376
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60
Shanghai Winherb Medical Technology Co., Ltd.
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400-186-5138 13341702378
Fax
QQ:190129269
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winherb@126.com
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China
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1008
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Shanghai T&W Pharmaceutical Co., Ltd.
Tel
+86 21 61551611
Fax
+86 21 50676805
Country
China
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9891
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Shanghai Tauto Biotech Co., Ltd.
Tel
021-51320588
Fax
0086-21-51320502
Email
tauto@tautobiotech.com
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China
ProdList
3989
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66
TargetMol Chemicals Inc.
Tel
021-021-33632979 15002134094
Fax
021-33632979
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marketing@targetmol.com
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China
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7783
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Cheng Du Pufeide Biotechnology Co., Ltd.
Tel
028-82610909 13388174823
Fax
8171-1798
Email
scglp@glp-china.com
Country
China
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1064
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View Lastest Price from Isoginkgetin manufacturers

Shanghai Standard Technology Co., Ltd.
Product
Isoginkgetin 548-19-6
Price
US $0.00/mg
Min. Order
20mg
Purity
≥98%(HPLC)
Supply Ability
10 g
Release date
2020-05-12
Shanghai Standard Technology Co., Ltd.
Product
Isoginkgetin 548-19-6
Price
US $0.00/mg
Min. Order
20mg
Purity
≥98%(HPLC)
Supply Ability
10 g
Release date
2020-05-12

548-19-6, IsoginkgetinRelated Search:


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  • 2-(4-Methoxyphenyl)-8-[6-methoxy-3-(4-oxo-5,7-dihydroxy-4H-1-benzopyran-2-yl)phenyl]-5,7-dihydroxy-4H-1-benzopyran-4-one
  • 4',4'''-Dimethoxyamentoflavone
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  • 4',4'''-Dimethylamentoflavone
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  • 5,5'',7,7''-Tetrahydroxy-4',4'''-dimethoxy-3''',8-biflavone
  • ISOGINKGETIN(SH)
  • Isoginkgetin, 98%, from Ginkgo biloba L.
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