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    Betulinic acid (ALS357; Lupatic acid)
    Betulinic acid (ALS357; Lupatic acid)

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    This product is for research use only, not for human use. We do not sell to patients.
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    InvivoChem Cat #: V1401
    CAS #: 472-15-1Purity ≥98%

    Description: Betulinic acid (also known as ALS-357; LS-357; Mairin; Lupatic acid; Betulic acid) is a naturally occuring pentacyclic triterpenoid extracted from Syzigium claviflorum that displays anti-HIV and antitumor activity. Betulinic acid acts as an inhibitor of HIV-1 with an EC50 of 1.4 μ M. Betulinic acid selectively induces apoptosis in tumor cells by directly activating the mitochondrial pathway of apoptosis through a p53- and CD95-independent mechanism. Betulinic acid also displays TGR5 agonist activity (EC50 =1.04 μM).

    References: Planta Med. 1998 Oct;64(7):655-7; J Nat Prod. 1994 Feb;57(2):243-7.

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    Molecular Weight (MW)456.7 
    FormulaC30H48O3 
    CAS No.472-15-1 
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 20 mg/mL (43.8 mM) 
    Water: <1 mg/mL
    Ethanol: 10 mg/mL (21.9 mM) 
    Solubility (In vivo)

    Chemical Name: (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid

    InChi Key: QGJZLNKBHJESQX-FZFNOLFKSA-N

    InChi Code: InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1

    SMILES Code: O=C([[email protected]]1(CC[[email protected]]2C(C)=C)[[email protected]@]2([H])[[email protected]@]3([H])CC[[email protected]]4([H])[[email protected]@]5(C)CC[[email protected]](O)C(C)(C)[[email protected]]5([H])CC[[email protected]@]4(C)[[email protected]]3(C)CC1)O       

    SynonymsLupatic acid; ALS357; ALS 357; Betulic acid; ALS-357; Mairin.


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    In Vitro

    In vitro activity: 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. Betulinic acid also acts as anti-melanoma agent through inhibiting aminopeptidase N activity with IC50 of 7.3 μM. 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.


    Kinase Assay: 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 bromide.


    Cell Assay: CCK-8 is used in the assay. MDA-MB-231 cells are cultured in 96-well plates at a density of 2 × 103 cells/well and then treated with DMSO vehicle or various concentrations of Betulinic acid ranging from 5 µM to 160 µM in 100 µL of medium for the indicated times. After the treatment period, the medium in each well is replaced with 110 µL of medium containing 10 µL of the CCK-8 mixture, and the plates are incubated for 1 h and 30 min at 37°C. The absorbance at a wavelength of 450 nm is measured with a microplate reader.

    In VivoBetulinic 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. 
    Animal modelLNCaP tumor xenograft model 
    Formulation & DosageDiluted in corn oil containing 1% DMSO; 10, 20 mg/kg/d; p.o. administration
    References

    Planta Med. 1998 Oct;64(7):655-7; J Nat Prod. 1994 Feb;57(2):243-7. 



    These protocols are for reference only. InvivoChem does not independently validate these methods.

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