Betulinic acid(ALS357 Lupatic acid)

Molecular Weight (MW)	456.7
Formula	C30H48O3
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([C@]1(CC[C@H]2C(C)=C)[C@@]2([H])[C@@]3([H])CC[C@]4([H])[C@@]5(C)CC[C@H](O)C(C)(C)[C@]5([H])CC[C@@]4(C)[C@]3(C)CC1)O
Synonyms	Lupatic acid; ALS357; ALS 357; Betulic acid; ALS-357; Mairin.

Molecular Weight (MW)

456.7

Formula

C30H48O3

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([C@]1(CC[C@H]2C(C)=C)[C@@]2([H])[C@@]3([H])CC[C@]4([H])[C@@]5(C)CC[C@H](O)C(C)(C)[C@]5([H])CC[C@@]4(C)[C@]3(C)CC1)O

Synonyms

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

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 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.
Animal model	LNCaP tumor xenograft model
Formulation & Dosage	Diluted 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.

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 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.

Animal model

LNCaP tumor xenograft model

Formulation & Dosage

Diluted 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.

CAS NO:	472-15-1
规格:	≥98%

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