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Chemical Structure| 548-19-6 Chemical Structure| 548-19-6

Structure of Isoginkgetin
CAS No.: 548-19-6

Chemical Structure| 548-19-6

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Isoginkgetin is a pre-mRNA splicing inhibitor. It also inhibits the activities of Akt, NF-κB, and MMP-9, inhibits the activity of the 20S proteasome, induces apoptosis, and activates autophagy.

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Product Details of Isoginkgetin

CAS No. :548-19-6
Formula : C32H22O10
M.W : 566.51
SMILES Code : O=C1C=C(C2=CC=C(OC)C=C2)OC3=C(C4=CC(C5=CC(C6=C(O)C=C(O)C=C6O5)=O)=CC=C4OC)C(O)=CC(O)=C13
MDL No. :MFCD00597035
InChI Key :HUOOMAOYXQFIDQ-UHFFFAOYSA-N
Pubchem ID :5318569

Safety of Isoginkgetin

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Related Pathways of Isoginkgetin

PI3K-AKT
pyroptosis

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
Huh7 20 μM 14 days ISO significantly inhibited colony formation in Huh7 cells. PMC10012924
U87MG glioblastoma cells 15 and 25 µM 1, 2, and 3 days Growth curves and MTT toxicity assays showed time and dose-dependent growth inhibition of U87MG after treatment with Iso (15/25 µM) for 1, 2, and 3 days. PMC9740329
HepG2 20 μM 24 h ISO induced autophagosome formation in HepG2 cells, as evidenced by increased LC3-II expression. PMC10012924
U87MG glioblastoma cells 15 and 25 µM 24 h The colony formation test showed that iso treatment for 24 h reduced colony formation. PMC9740329
Vero cells 22.81 μM (IC50) 24 hours To evaluate the antiviral activity of Isoginkgetin against SARS-CoV-2, results showed an IC50 of 22.81 μM, significantly inhibiting viral replication PMC8849861
BV2 cells 0.1 μM and 0.5 μM 24 hours To evaluate the effect of Isoginkgetin on the release of inflammatory mediators in LPS-activated BV2 cells. Results showed that Isoginkgetin significantly inhibited mRNA expression of IL-1β, IL-6, and COX-2, and reduced NO and ROS production. PMC8521360
U87MG glioblastoma cells 15 µM 24, 48, and 72 h The FACS analysis showed that treatment with Iso 15 µM determines a blockage of the cell cycle in the S1 phase. PMC9740329
Human liver microsomes 0.982 ± 0.006 μM (IC50) 30 minutes To evaluate the inhibitory effect of Isoginkgetin on CYP3A4, the results showed an IC50 of 0.982 ± 0.006 μM, indicating significant inhibition of CYP3A4. PMC8920304
H9C2 cardiomyocytes 10 μM 48 hours To evaluate the protective effect of IGK on PA-induced cardiomyocyte injury. Results showed that IGK significantly alleviated PA-induced cardiomyocyte hypertrophy and oxidative stress, and enhanced mitochondrial respiratory capacity. PMC9516449
Neonatal rat cardiomyocytes (NRCMs) 10 μM 48 hours To evaluate the protective effect of IGK on PA-induced cardiomyocyte injury. Results showed that IGK significantly alleviated PA-induced cardiomyocyte hypertrophy and oxidative stress, and enhanced mitochondrial respiratory capacity. PMC9516449
SMA type 1 patient fibroblasts 50 µM 6 hours Inhibited spliceosome assembly, significantly reduced SMN-C3 activity PMC5684323
HeLa cells 30 μM 6 hours To identify specific stages of mRNA synthesis influenced by IsoG, found that IsoG inhibits transcription elongation PMC5688950
HeLa S3 cells 30 μM 6 hours To investigate the effect of Isoginkgetin on the transcriptome of HeLa S3 cells, revealing widespread accumulation of RNA polymerase II at the 5' ends of genes, indicating its role as an RNA polymerase II elongation inhibitor. PMC7852222
Recombinant CES2 0.07 μM Evaluate the inhibitory potential of Isoginkgetin on CES2-catalyzed 4-MUA hydrolysis, showing potent inhibition PMC8167799
Human intestinal microsomes (HIMs) 0.94 μM Evaluate the inhibitory potential of Isoginkgetin on CES2-catalyzed irinotecan hydrolysis, showing potent inhibition PMC8167799
Human liver microsomes (HLMs) 32.24 nM Evaluate the inhibitory potential of Isoginkgetin on CES2-catalyzed FD hydrolysis, showing potent inhibition PMC8167799

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
C57BL/6J mice High-fat diet-induced obesity model Tail vein injection 0.5 mg/kg Once a week for 4 weeks To evaluate the protective effect of IGK on obesity-induced cardiomyopathy. Results showed that IGK significantly improved diastolic function, alleviated cardiac hypertrophy and fibrosis, activated Nrf2/ARE signaling pathway, and improved mitochondrial function in obese mice. PMC9516449
BALB/c nude mice HepG2 xenograft model Intraperitoneal injection 25 mg/kg and 50 mg/kg Once daily for 14 days ISO significantly reduced the volume and weight of HepG2 xenograft tumors. PMC10012924
Kunming mice LPS-induced depression model Intraperitoneal injection 4 mg/kg Once daily for 14 days To evaluate the effect of Isoginkgetin on LPS-induced depression-like behaviors. Results showed that Isoginkgetin significantly reversed LPS-induced depression-like behaviors, reduced serum IL-1β levels, and restored hippocampal neurotransmitter levels. PMC8521360
SD rats Needle puncture-induced intervertebral disc degeneration model Local injection 60 μg/mL Weekly for 8 weeks Evaluate the therapeutic effect of IGK@SeNP on intervertebral disc degeneration in vivo, showing significant preservation of disc height and water content PMC10029295

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

1.77mL

0.35mL

0.18mL

8.83mL

1.77mL

0.88mL

17.65mL

3.53mL

1.77mL

References

[1]O'Brien K, Matlin AJ, et al. The biflavonoid isoginkgetin is a general inhibitor of Pre-mRNA splicing. J Biol Chem. 2008 Nov 28;283(48):33147-54.

[2]Yoon SO, Shin S, et al. Isoginkgetin inhibits tumor cell invasion by regulating phosphatidylinositol 3-kinase/Akt-dependent matrix metalloproteinase-9 expression. Mol Cancer Ther. 2006 Nov;5(11):2666-75.

[3]Yoon SO, Shin S, Lee HJ, Chun HK, Chung AS. Isoginkgetin inhibits tumor cell invasion by regulating phosphatidylinositol 3-kinase/Akt-dependent matrix metalloproteinase-9 expression. Mol Cancer Ther. 2006 Nov;5(11):2666-75

[4]Tsalikis J, Abdel-Nour M, Farahvash A, Sorbara MT, Poon S, Philpott DJ, Girardin SE. Isoginkgetin, a Natural Biflavonoid Proteasome Inhibitor, Sensitizes Cancer Cells to Apoptosis via Disruption of Lysosomal Homeostasis and Impaired Protein Clearance. Mol Cell Biol. 2019 Apr 30;39(10):e00489-18

[5]Li P, Zhang F, Li Y, Zhang C, Yang Z, Zhang Y, Song C. Isoginkgetin treatment attenuated lipopolysaccharide-induced monoamine neurotransmitter deficiency and depression-like behaviors through downregulating p38/NF-κB signaling pathway and suppressing microglia-induced apoptosis. J Psychopharmacol. 2021 Jul 19:2698811211032473

[6]Heinhuis B, Plantinga TS, Semango G, Küsters B, Netea MG, Dinarello CA, Smit JWA, Netea-Maier RT, Joosten LAB. Alternatively spliced isoforms of IL-32 differentially influence cell death pathways in cancer cell lines. Carcinogenesis. 2016 Feb;37(2):197-205

[7]Lee SJ, Choi JH, Son KH, Chang HW, Kang SS, Kim HP. Suppression of mouse lymphocyte proliferation in vitro by naturally-occurring biflavonoids. Life Sci. 1995;57(6):551-8

 

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