Betulinic acid - CAS 472-15-1
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Not Intended for Therapeutic Use. For research use only.
Apoptosis Inducer
betulinic acid is a pentacyclic lupane-type triterpene derivative of betulin with antiinflammatory, anti-HIV and antineoplastic activities. Betulinic acid induces apoptosis through induction of changes in mitochondrial membrane potential, production of reactive oxygen species, and opening of mitochondrial permeability transition pores, resulting in the release of mitochondrial apogenic factors, activation of caspases, and DNA fragmentation.
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Mairin; Acronym: BA; Code name: ALS-357.
1. Synthesis, biology and clinical significance of pentacyclic triterpenes: a multi-target approach to prevention and treatment of metabolic and vascular diseases
Huaming Sheng and Hongbin Sun*. Nat. Prod. Rep., 2011, 28, 543–593
Interestingly, Selzer et al. reported that treatment of human melanoma cells by betulinic acid resulted in phosphorylation and activation of Akt, followed by phosphorylation and inactivation of GSK-3. Qiu et al. also observed the activation of Akt in melanoma cells by treatment with betulinic acid. However, the molecular mechanism by which betulinic acid induces Akt activation is still unclear.
2. First self-assembly study of betulinic acid, a renewable nano-sized, 6-6-6-6-5 pentacyclic monohydroxy triterpenic acid
Braja Gopal Bag* and Shib Shankar Dash. Nanoscale, 2011, 3, 4564–4566
The morphology of the gels was studied by optical and electronic microscopy. Fibrillar networks having fibers of 1–4micrometre cross-sections and >100 micrometre lengths were observed in a gel of betulinic acid in o-dichlorobenzene (Fig. 2). Helical ribbon-like fibers with optical birefringence of 15–30 micrometre cross-sections and upto 300 micrometre lengths were observed in a gel of betulinic acid in nitrobenzene under polarized light (Fig. 3). Spherulitic images were also observed in this case along with the fibers (Fig. 3 and 4b). Only spherulitic images were observed in a gel of betulinic acid in o-xylene (1.06% w/v) (Fig. 4(a)).
3. Lipase dissolution and stabilization in ether-functionalized ionic liquids
Hua Zhao,* Cecil L. Jones and Janet V. Cowins. Green Chem., 2009, 11, 1128–1138
Due to the low solubility of betulinic acid in many organic solvents, its synthesis and derivatization are limited to several solvents, such as dichloromethane, chloroform, acetone, THF, DMF, pyridine, benzene, etc. Most of these solvents (except pyridine) do not dissolve significant amounts of betulinic acid. Therefore, the efficiency ofmany reactions is limited by the poor reactant solubility. However, as discussed previously, ILs (such as 3 and 4) can dissolve high concentrations of betulinic acid even at ambient temperature. Unlike pyridine being basic, these ILs are neutral and even compatible with the lipase. For these reasons, ether-functionalized ILs (3 and 4) could be suitable media for chemical and enzymatic modification of betulinic acid.
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