Betulinic acid

Catalog No.S3603

Betulinic acid, a pentacyclic triterpenoid from Syzigium claviflorum, is a inhibitor of HIV-1 with EC50 of 1.4 μ M. Phase 1/2.

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Betulinic acid Chemical Structure

Betulinic acid Chemical Structure
Molecular Weight: 456.7

Validation & Quality Control

Quality Control & MSDS

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Betulinic acid is available in the following compound libraries:

Product Information

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Product Description

Biological Activity

Description Betulinic acid, a pentacyclic triterpenoid from Syzigium claviflorum, is a inhibitor of HIV-1 with EC50 of 1.4 μ M. Phase 1/2.
Targets HIV-1 [1] Eukaryotic topoisomerase I [3] Aminopeptidase N [2]
IC50 1.4 μM(EC50) 5 μM 7.3 μM
LD50
In vitro Betulinic acid shows anti-HIV activity by blocking HIV replication in H9 lymphocytes with an EC50 value of 1.4 μM and inhibiting uninfected H9 cell growth with an IC50 value of 13 μM. [1] Betulinic acid also acts as anti-melanoma agent through inhibiting aminopeptidase N activity with IC50 of 7.3 μM. [2] In addition, Betulinic acid inhibits eukaryotic topoisomerase I activity with IC50 of 5 μM and can be exploited as a strong candidate for anti-tumor drug. [3]
In vivo Betulinic acid inhibits prostate cancer cell and tumor (xenograft) growth in athymic nude mice bearing LNCaP cells and this is due, in part, to proteasome-dependent downregulation of Sp1, Sp3, Sp4 and several Sp-regulated genes. [4]
Features

Protocol(Only for Reference)

Kinase Assay: [3]

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

Cell Assay: [1]

Cell lines H9 lymphocytes
Concentrations
Incubation Time 3 days
Method H9 lymphocytes ( 1 × 107 cells/ml) are incubated in the presence or absence of HIV-1 (IIIB isolate) for 1 h at 37 °C. Cells are washed thoroughly to remove unadsorbed virions and resuspended in culture medium. Betulinic acid (diluted in test medium) is added to the culture medium. After incubation for 3 days at 37 °C, the cell densities of uninfected cultures are determined to assess toxicity of betulinic acid. A p24 antigen capture assay is used to determine the level of HIV infection in HIV-treated culture

Animal Study: [4]

Animal Models LNCaP tumor xenograft model
Formulation Diluted in corn oil containing 1% DMSO
Dosages 10 and 20 mg/kg/d
Administration Orally
Solubility 1% DMSO/30% polyethylene glycol/1% Tween 80, pH 4, 10 mg/mL
* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Conversion of different model animals based on BSA

SpeciesWeight (kg)Body Surface Area (m2)Km factor
Baboon120.620
Dog100.520
Monkey30.2412
Rabbit1.80.1512
Guinea pig0.40.058
Rat0.150.0256
Hamster0.080.025
Mouse0.020.0073
Animal A (mg/kg) = Animal B (mg/kg) multiplied by  Animal B Km
Animal A Km

Value based on data from FDA Draft Guidelines: Center for Drug Evaluation and Research, Center for Biologics Evaluation and Research. (2002) Estimating the safe starting dose in clinical trials for therapeutics in adult healthy volunteers, U.S. Food and Drug Administration, Rockville, Maryland, USA.

For example, to convert the dose of resveratrol used in a mouse (22.4 mg/kg) to a dose based on surface area for rat, multiply 22.4 mg/kg by the Km factor for a mouse and then divide by the Km factor for a rat. This calculation results in a rat equivalent dose for resveratrol of 11.2 mg/kg.

Rat dose (mg/kg) = mouse dose (22.4 mg/kg) ×  mouse Km(3)  = 11.2 mg/kg
rat Km(6)
1

References

[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.

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Chemical Information

Download Betulinic acid SDF
Molecular Weight (MW) 456.7
Formula

C30H48O3

CAS No. 472-15-1
Storage 3 years -20℃Powder
6 months-80℃in DMSO
Synonyms
Chemical Name Lup-20(29)-en-28-oic acid,3-hydroxy-,(3β)-

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Tech Support & FAQs

Answers to questions you may have can be found in the inhibitor handling instructions. Topics include how to prepare stock solutions, how to store inhibitors, and issues that need special attention for cell-based assays and animal experiments.

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