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P0077

Sigma-Aldrich

Prostratin

≥98% (HPLC)

Sinonimo/i:

12-Deoxyphorbol-13-acetate, CCRIS 6292, NSC 623310

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About This Item

Formula empirica (notazione di Hill):
C22H30O6
Numero CAS:
60857-08-1
Peso molecolare:
390.47
Numero MDL:
MFCD00674138
Codice UNSPSC:
12352200
ID PubChem:
329820006
NACRES:
NA.77

Livello qualitativo

100

Saggio

≥98% (HPLC)

Forma fisica

powder

Colore

white

Solubilità

DMSO: 10 mg/mL, clear

Temperatura di conservazione

−20°C

Stringa SMILE

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
BOJKFRKNLSCGHY-HXGSDTCMSA-N

Applicazioni

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.

Azioni biochim/fisiol

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.

Caratteristiche e vantaggi

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

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

Certificati d'analisi (COA)

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Sheena M Saayman et al.
Molecular therapy : the journal of the American Society of Gene Therapy, 24(3), 488-498 (2015-11-20)
HIV-1 provirus integration results in a persistent latently infected reservoir that is recalcitrant to combined antiretroviral therapy (cART) with lifelong treatment being the only option. The "shock and kill" strategy aims to eradicate latent HIV by reactivating proviral gene expression
Joaquín Rullas et al.
Antiviral therapy, 9(4), 545-554 (2004-10-01)
Induction of HIV expression through lymphocyte activation has been proposed as a strategy to purge latent reservoirs. Prostratin is a non-tumourogenic phorbol ester that delays HIV replication in vitro, but paradoxically activates HIV expression in latently infected cells. To get
Samuel A Williams et al.
The Journal of biological chemistry, 279(40), 42008-42017 (2004-07-31)
A subset of quiescent memory CD4 T cells harboring integrated but transcriptionally silent proviruses poses a currently insurmountable barrier to the eradication of the human immunodeficiency virus (HIV) in infected patients. Induction of HIV gene expression in these latently infected
Zichong Li et al.
Nucleic acids research, 41(1), 277-287 (2012-10-23)
Latent HIV reservoirs are the primary hurdle to eradication of infection. Identification of agents, pathways and molecular mechanisms that activate latent provirus may, in the presence of highly active antiretroviral therapy, permit clearance of infected cells by the immune system.
Flow cytometric analysis of drug-induced HIV-1 transcriptional activity in A2 and A72 J-Lat cell lines
Daniela B and Melanie O
Bio-protocol, 7(10) (2017)
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