P0077

Prostratin

≥98% (HPLC)

• Synonym(s): 12-Deoxyphorbol-13-acetate, CCRIS 6292, NSC 623310
• Empirical Formula (Hill Notation): C₂₂H₃₀O₆
• CAS Number: 60857-08-1
• Molecular Weight: 390.47
• MDL number: MFCD00674138
• UNSPSC Code: 12352200
• PubChem Substance ID: 329820006
• NACRES: NA.77

Properties

• Assay: ≥98% (HPLC)
• form: powder
• color: white
• solubility: DMSO: 10 mg/mL, clear
• storage temp.: −20°C
• SMILES string: C[C@@H]1C[C@]2(OC(C)=O)[C@H]([C@@H]3C=C(CO)C[C@@]4(O)[C@@H](C=C(C)C4=O)[C@@]13O)C2(C)C
• InChI: 1S/C22H30O6/c1-11-6-16-20(26,18(11)25)9-14(10-23)7-15-17-19(4,5)21(17,28-13(3)24)8-12(2)22(15,16)27/h6-7,12,15-17,23,26-27H,8-10H2,1-5H3/t12-,15+,16-,17-,20-,21+,22-/m1/s1
• InChI key: BOJKFRKNLSCGHY-HXGSDTCMSA-N

Description

Application

Prostratin has been used to reverse the latency of human immunodeficiency virus-1 (HIV-1) and to quantify the transcriptional activation of the long terminal repeat (LTR) in latently HIV-1-infected Jurkat (J-Lat) cell lines.

Biochem/physiol Actions

Prostratin, an unusual non-tumorigenic phorbol ester, is an activator of protein kinase C (PKC) and also an activator of nuclear factor KB (NF-KB) mediated through activation of the IKKs (IKB kinases). Prostratin exhibits potent in vitro activity by inducing HIV expression in latently infected cell lines and primary cells, thus antagonizing HIV latency. Activation of PKC and NF-kB has been proposed as the mechanism of action. Prostratin also inhibits HIV entry into target cells by down-regulating CD4 and CXCR4 receptors.

Features and Benefits

This compound is featured on the PKC page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves