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136587-07-0

136587-07-0 Structure

136587-07-0 Structure
IdentificationBack Directory
[Name]

3-Oxobetulin Acetate
[CAS]

136587-07-0
[Synonyms]

3-Oxobetulin Acetate
[Molecular Formula]

C32H50O3
[MDL Number]

MFCD32692729
[MOL File]

136587-07-0.mol
[Molecular Weight]

482.74
Chemical PropertiesBack Directory
[Melting point ]

77-79 °C
[Boiling point ]

532.7±23.0 °C(Predicted)
[density ]

1.019±0.06 g/cm3(Predicted)
[storage temp. ]

-20°C
[solubility ]

DMF: 30 mg/ml,DMSO: 10 mg/ml,Ethanol: 25 mg/ml
[form ]

A crystalline solid
Hazard InformationBack Directory
[Uses]

3-Oxobetulin acetate (28-O-Acetyl-3-Oxobetulin; 3-oxo-28-O-Acetylbetulin) is a derivative of betulin (HY-N0083), a cholesterol biosynthesis inhibitor. 3-Oxobetulin acetate inhibits the growth of P388 murine lymphocytic leukemia cells (EC50=0.12 μg/mL) and human MCF-7 breast cancer, SF-268 CNS cancer, H460 lung cancer, and KM20L2 colon cancer cells (GI50s=8, 10.6, 5.2, and 12.7 μg/mL), but not BxPC-3 pancreatic cancer cells or DU145 prostate cancer cells (GI50s=>10 μg/mL for both). 3-Oxobetulin acetate inhibits the replication of X4-tropic recombinant HIV (NL4.3-Ren) in MT-2 lymphoblastoid cells (IC50=13.4 μM). 3-Oxobetulin acetate is also effective against Listeria donovani amastigotes.
[Biological Activity]

3-Oxobetulin acetate is a derivative of the cholesterol biosynthesis inhibitor betulin .1 It inhibits the growth of P388 murine lymphocytic leukemia cells (EC50 = 0.12 μg/ml), as well as human MCF-7 breast, SF-268 CNS, H460 lung, and KM20L2 colon cancer cells (GI50s = 8, 10.6, 5.2, and 12.7 μg/ml, respectively), but not BxPC-3 pancreas or DU145 prostate cancer cells (GI50s = >10 μg/ml for both).2 3-Oxobetulin acetate inhibits replication of X4 tropic recombinant HIV (NL4.3-Ren) in MT-2 lymphoblastoid cells (IC50 = 13.4 μM).3 It is also active against L. donovani amastigotes when used at a concentration of 50 μM.1
[storage]

-20°C
[References]

1.Alakurtti, S., Bergstr?m, P., Sacerdoti-Sierra, N., et al.Anti-leishmanial activity of betulin derivativesJ. Antibiot. (Tokyo)63(3)123-126(2010) 2.Pettit, G.R., Melody, N., Hempenstall, F., et al.Antineoplastic agents. 595. Structural modifications of betulin and the X-ray crystal structure of an unusual betulin amine dimerJ. Nat. Prod.77(4)863-872(2014) 3.Callies, O., Bedoya, L.M., Beltrán, M., et al.Isolation, structural modification, and HIV inhibition of pentacyclic lupane-type triterpenoids from Cassine xylocarpa and Maytenus cuzcoinaJ. Nat. Prod.78(5)1045-1055(2015)
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