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Betulinic acid

Catalog No. T2830   CAS 472-15-1
Synonyms: ALS-357, Lupatic acid, Betulic acid

Betulinic acid (ALS-357) is a pentacyclic lupane-type triterpene derivative of betulin (isolated from the bark of Betula alba, the common white birch) which has antiretroviral, antimalarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase.

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Betulinic acid Chemical Structure
Betulinic acid, CAS 472-15-1
Pack Size Availability Price/USD Quantity
50 mg In stock $ 33.00
100 mg In stock $ 48.00
500 mg In stock $ 174.00
1 mL * 10 mM (in DMSO) In stock $ 54.00
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Purity: 99.7%
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Biological Description
Chemical Properties
Storage & Solubility Information
Description Betulinic acid (ALS-357) is a pentacyclic lupane-type triterpene derivative of betulin (isolated from the bark of Betula alba, the common white birch) which has antiretroviral, antimalarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase.
Targets&IC50 HIV-1:1.4 μM(EC50), Aminopeptidase N:7.3 μM, Eukaryotic topoisomerase I:5 μM
In vitro In LNCaP cell cultures of athymic nude mice, Betulinic acid inhibits the growth of prostate cancer cells and tumors (xenografts). This inhibitory effect is partly due to the downregulation of protease-dependent Sp1/3/4 and several SP-regulated genes.
In vivo As an anti-melanoma agent, Betulinic acid inhibits the activity of aminopeptidase N (IC50: 7.3 μM). It exhibits anti-HIV properties by blocking HIV replication in H9 lymphocytes (EC50: 1.4 μM) and inhibiting the growth of uninfected H9 cells (IC50: 13 μM). Moreover, Betulinic acid shows potential as an anti-cancer candidate, suppressing the activity of eukaryotic topoisomerase I (IC50: 5 μM).
Kinase Assay Topoisomerase I-DNA interaction: Annealed 25-mer duplex of oligonucleotide-1 and oligonicleotide-2 is incubated with 25 or 50 units of rat liver topoisomerase I at 8 °C for 15 min in the presence or absence of betulinic acid in binding buffer. After incubation the reaction mixtures are electrophoresed in 7% non-denaturing polyacrylamide gel at 4 °C in 0.167 × TBE buffer and DNA bands are stained with ethidium bromid
Source
Synonyms ALS-357, Lupatic acid, Betulic acid
Molecular Weight 456.7
Formula C30H48O3
CAS No. 472-15-1

Storage

Powder: -20°C for 3 years | In solvent: -80°C for 1 year

Solubility Information

Ethanol: 10 mg/mL (21.89 mM)

H2O: < 1 mg/mL (insoluble or slightly soluble)

DMSO: 16 mg/mL (35 mM)

TargetMolReferences and Literature

1. Fujioka T, et al. J Nat Prod, 1994, 57(2), 243-247. 2. Melzig MF, et al. Planta Med, 1998, 64(7), 655-657. 3. Chowdhury AR, et al. Med Sci Monit, 2002, 8(7), BR254-265. 4. Chintharlapalli S, et al. Cancer Res, 2007, 67, 2816-2823. 6. Kalra J, et al. Betulinic acid alleviates dextran sulfate sodium-induced colitis and visceral pain in mice. Naunyn Schmiedebergs Arch Pharmacol. 2017 Dec 26. 7. Tangliang Zhao1*, Yi Bao1*,Xinxin Gan1, et al. DNA methylation-regulated QPCT promotes sunitinib resistance by increasing HRAS stability in renal cell carcinoma. Theranostics. 2019, Vol. 9, Issue 22

TargetMolCitations

1. Tangliang Zhao1*, Yi Bao1*,Xinxin Gan1*, Jie Wang1*, Qiong Chen1*, Zhihui Dai2*, Bing Liu 1, Anbang Wang1, Shuhan Sun2, Fu Yang2,3, Linhui Wang1 DNA methylation-regulated QPCT promotes sunitinib resistance by increasing HRAS stability in renal cell carcinoma. Theranostics. 2019, Vol. 9, Issue 21

Related compound libraries

This product is contained In the following compound libraries:
Anti-Parasitic Compound Library Tobacco Monomer Library Anti-Cancer Active Compound Library Miao medicine Compound Library Anti-Cancer Drug Library Anti-Cancer Clinical Compound Library Antiparasitic Natural Product Library Oxidation-Reduction Compound Library Anti-Ovarian Cancer Compound Library Anti-Aging Compound Library

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Keywords

Betulinic acid 472-15-1 Apoptosis Autophagy DNA Damage/DNA Repair Metabolism Microbiology/Virology NF-Κb Proteases/Proteasome NF-κB Mitophagy Aminopeptidase Topoisomerase Endogenous Metabolite HIV Protease Human immunodeficiency virus HIV Nuclear factor-kappaB inhibit Nuclear factor-κB ALS357 Inhibitor Mitochondrial Autophagy ALS-357 Lupatic acid ALS 357 Betulic acid inhibitor

 

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