| Identification | Back Directory | [Name]
Prostratin, PKC activator | [CAS]
60857-08-1 | [Synonyms]
SA 101A
PROSTRATIN
NSC 623310
CCRIS 6292
Prostatin >99%
Stillingia Facto
13-O-Acetylphorbol
Prostratin, PKC activator
12-DEOXYPHORBOL 13-ACETATE
13-O-Acetyl-12-deoxyphorbol
12-Deoxyphorbol 13-Acetate, dPAc
Prostratin, PKC activator USP/EP/BP
(1aR,1bS,4aR,7aS,7bR,8R,9aS)-9a-(Acetyloxy)-1,1a,1b,4,4a,7a,7b,8,9,9a
-decahydro-4a,7b-dihydroxy-3-(hydroxyMethyl)-1,1,6,8-tetraMethyl-
(1aR)-9aα-Acetoxy-1,1aα,1bβ,4,4a,7aα,7b,8,9,9a-decahydro-4aβ,7bα-dihydroxy-3-hydroxymethyl-1,1,6,8α-tetramethyl-5H-cyclopropa[3,4]benz[1,2-e]azulen-5-one
(1aR)-1,1aα,1bβ,4,4a,7aα,7b,8,9,9a-Decahydro-4aβ,7bα-dihydroxy-9aα-acetoxy-3-(hydroxymethyl)-1,1,6,8α-tetramethyl-5H-cyclopropa[3,4]benzo[1,2-e]azulene-5-one
(1aR,1bS,4aR,7aS,7bR,8R,9aS)-9a-(Acetyloxy)-1,1a,1b,4,4a,7a,7b,8,9,9a -decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl- 5H-cyclopropa[3,4]benz[1,2-e]azulen-5-one
5H-Cyclopropa[3,4]benz[1,2-e]azulen-5-one, 9a-(acetyloxy)-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-, (1aR,1bS,4aR,7aS,7bR,8R,9aS)- | [Molecular Formula]
C22H30O6 | [MDL Number]
MFCD00674138 | [MOL File]
60857-08-1.mol | [Molecular Weight]
390.47 |
| Chemical Properties | Back Directory | [Melting point ]
216-219℃ | [Boiling point ]
550.5±50.0 °C(Predicted) | [density ]
1.31 | [storage temp. ]
-20°C | [solubility ]
Soluble in DMSO at 30mg/ml | [form ]
white powder | [pka]
11.40±0.70(Predicted) | [color ]
Off-white | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month. |
| Hazard Information | Back Directory | [Description]
Activation of latent reservoirs of HIV-infected cells is a treatment strategy designed to reduce viral load and eliminate the perpetuation of retroviral infection. Prostratin is a non-tumor promoting phorbol ester that potently induces HIV-1 reactivation in latent reservoirs of infected Jurkat-LAT-GFP cells with an IC50 value of ~0.5 μM. Originally, prostratin was isolated from plant sources including P. prostrata, E. cornigera, and H. nutans. The effects of prostratin are mediated through activation of NF-κB via protein kinase C and by downregulation of HIV-1 receptor CD4 expression and its co-receptors CXCR4 and CCR5. | [Uses]
Activation of latent reservoirs of HIV-infected cells is a treatment strategy designed to reduce viral load and eliminate the perpetuation of retroviral infection. Prostratin is a non-tumor promoting phorbol ester that potently induces HIV-1 reactivation in latent reservoirs of infected Jurkat-LAT-GFP cells . [Cayman Chemical]
| [Uses]
It is a protein kinase C activator found in the bark of the mamala tree of Samoa, Homalanthus nutans (Euphorbiaceae). Research indicated that prostratin has potential to be useful in the treatment of HIV as it flushes viral reservoirs in latently infected CD4+ T-cells. | [Definition]
ChEBI: A natural product found in Euphorbia fischeriana. | [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. | [storage]
Store at -20°C | [References]
1) Cashmore et al. (1976), The structure of prostratin: a toxic tetracyclic diterpene ester from Pimelea Prostrata; Tetrahedron Lett., 17 1737
2) Miana et al. (2015), Prostratin: An Overview; Mini Rev. Med. Chem., 15 1122
3) Shen et al. (2015), The protein kinase C agonist prostratin induces differentiation of human myeloid leukemia cells and enhances cellular differentiation by chemotherapeutic agents; Cancer Lett., 356 (2 Pt. B) 686
4) Biancotto et al. (2004), Dual role of prostratin in inhibition of infection and reactivation of human immunodeficiency virus from latency in primary blood lymphocytes and lymphoid tissue; J. Virol., 78 10507
5) Geribaldi-Doldan et al. (2015), 12-Deoxyphorbols Promote Adult Neurogenesis by Inducing Neural Progenitor Cell Proliferation via PKC activation ; Int. J, Neuropsychopharmacol., 19 pyv085 |
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