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P0077

Sigma-Aldrich

Prostratin

≥98% (HPLC)

Synonym(s):

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

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About This Item

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

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

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.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Kouki Matsuda et al.
Cell reports methods, 1(8), 100122-100122 (2022-04-28)
Persistence of HIV-1 latent reservoir cells during antiretroviral therapy (ART) is a major obstacle for curing HIV-1. Even though latency-reversing agents (LRAs) are under development to reactivate and eradicate latently infected cells, there are few useful models for evaluating LRA
Mélanie Bourjot et al.
Journal of natural products, 75(12), 2183-2187 (2012-12-12)
A chemical study of the Vietnamese plant species Trigonostemon howii led to the isolation of a new tigliane-type diterpenoid, trigowiin A (1), along with several known coumarins and phenylpropanoids. The planar structure and the relative configuration of compound 1 were
Marjan Hezareh
Drug news & perspectives, 18(8), 496-500 (2006-01-05)
The persistence of latent reservoirs of human immunodeficiency virus type 1 (HIV-1) represents a major barrier to virus eradication in patients on combination antiretroviral therapy. It has been suggested that treating infected individuals simultaneously with highly active antiretroviral therapy (HAART)
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)
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.
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Protein Kinase C (PKC)

Protein kinase C (PKC) is an AGC kinase that phosphorylates serine and threonine residues in many target proteins.

Protein Kinase C (PKC)

Protein kinase C (PKC) is an AGC kinase that phosphorylates serine and threonine residues in many target proteins.

Protein Kinase C (PKC)

Protein kinase C (PKC) is an AGC kinase that phosphorylates serine and threonine residues in many target proteins.

Protein Kinase C (PKC)

Protein kinase C (PKC) is an AGC kinase that phosphorylates serine and threonine residues in many target proteins.

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