PristimerinA triterpenoid and inducer of caspase-dependent apoptosis

Pristimerin (CAS 1258-84-0)

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Synonym: Celastrol methyl ester
Application: A triterpenoid and inducer of caspase-dependent apoptosis
CAS Number: 1258-84-0
Purity: ≥97%
Molecular Weight: 464.64
Molecular Formula: C30H40O4
* Refer to Certificate of Analysis for lot specific data (including water content).
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An triterpenoid and an antitumor agent. Induces caspase-dependent apoptosis by inhibiting the chymotrypsin-like activity of the proteasome.


References

Structure of pristimerin: A.B. Kulkarni & R.C. Shah; Nature 173, 1237 (1954) The triterpenoid quinonemethide pristimerin inhibits induction of inducible nitric oxide synthase in murine macrophages: V.M. Dirsch, et al.; Eur. J. Pharmacol. 336, 211 (1997) Novel quinone methides from Salacia kraussii with in vitro antimalarial activity: J.N. Figueiredo, et al.; J. Nat. Prod. 61, 718 (1998) Insecticidal activity of Maytenus species (Celastraceae) nortriterpene quinone methides against codling moth, Cydia pomonella (L.) (Lepidoptera: tortricidae): J. Avilla, et al.; J. Agric. Food Chem. 48, 88 (2000) Release of intermediate reactive hydrogen peroxide by macrophage cells activated by natural products: R.R. Moreira, et al.; Biol. Pharm. Bull. 24, 201 (2001) Antitumor agents. 228. five new agarofurans, Reissantins A-E, and cytotoxic principles from Reissantia buchananii: F.R. Chang, et al.; J. Nat. Prod. 66, 1416 (2003) Antifungal properties of pristimerin and celastrol isolated from Celastrus hypoleucus: D.Q. Luo, et al.; Pest Manag. Sci. 61, 85 (2005) Pristimerin induces caspase-dependent apoptosis in MDA-MB-231 cells via direct effects on mitochondria: C.C. Wu, et al.; Mol. Cancer Ther. 4, 1277 (2005) Anticytomegalovirus activity of pristimerin, a triterpenoid quinone methide isolated from Maytenus heterophylla (Eckl. & Zeyh.): T. Murayama, et al.; Antivir. Chem. Chemother. 18, 133 (2007) Antigiardial activity of triterpenoids from root bark of Hippocratea excelsa: G.J. Mena-Rejón, et al.; J. Nat. Prod. 70, 863 (2007) Pristimerin induces apoptosis by targeting the proteasome in prostate cancer cells: H. Yang, et al.; J. Cell. Biochem. 103, 234 (2008) Antiproliferative activity of pristimerin isolated from Maytenus ilicifolia (Celastraceae) in human HL-60 cells: P.M. Costa, et al.; Toxicol. in vitro 22, 854 (2008) Identification of a potent natural triterpenoid inhibitor of proteosome chymotrypsin-like activity and NF-kappaB with antimyeloma activity in vitro and in vivo: R.E. Tiedemann, et al.; Blood 113, 4027 (2009) Reactive oxygen species-dependent activation of Bax and poly(ADP-ribose) polymerase-1 is required for mitochondrial cell death induced by triterpenoid pristimerin in human cervical cancer cells: J.Y. Byun, et al.; Mol. Pharmacol. 76, 734 (2009) Triterpenoids as new promising anticancer drugs: A. Petronelli, et al.; Anticancer Drugs 20, 880 (2009) Discovery of potent and reversible monoacylglycerol lipase inhibitors: A.R. King, et al.; Chem. Biol. 16, 1045 (2009)

Appearance :
Crystalline
Physical State :
Solid
Derived From :
Tripterygium wilfordii Hook.F.
Solubility :
Soluble in DMSO (≥5 mg/mL), ethyl acetate, ethanol (~3 mg/mL), and DMF (~30 mg/mL). Insoluble in water.
Storage :
Store at -20° C
Melting Point :
217.5-218° C
Boiling Point :
607.7° C at 760 mmHg
Density :
1.16 g/cm3
Refractive Index :
n20D 1.58
Optical Activity :
α20/D -167°, c = 1 in chloroform; α24.5/D -157.43°, c = 0.1 in methanol
IC50 :
MAGL: IC50 = 93 nM; HL-60 : IC50 = 200 nM (human); MCF7: IC50 = 400 nM (human); L1210 : IC50 = 0.36 µg/mL (mouse); Plasmodium falciparum: IC50 = 0.27 µg/mL; P388 : IC50 = 0.12 µg/mL (mouse); Plasmodium falciparum: EC5050 = >820 nM; 20S proteasome: IC50 = 2.2 µM (rabbit); 26S proteasome: IC50 = 3.0 µM (human)
Ki Data :
3C-like protease of SARS coronavirus : Ki= 3100 nM
pK Values :
pKa: 8.60 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
RTECS :
RC4905000
PubChem CID :
159516
Merck Index :
14: 10370
MDL Number :
MFCD01711331
SMILES :
CC1=C(C(=O)C=C2C1=CC=C3C2(CCC4(C3(CCC5(C4CC(CC5)(C)C(=O)OC)C)C)C)C)O

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Certificate of Analysis

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