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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

Quality Level

100

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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Roberto A Barrero et al.
BMC genomics, 12, 600-600 (2011-12-14)
Euphorbia fischeriana is an important medicinal plant found in Northeast China. The plant roots contain many medicinal compounds including 12-deoxyphorbol-13-acetate, commonly known as prostratin that is a phorbol ester from the tigliane diterpene series. Prostratin is a protein kinase C
Brian A DeChristopher et al.
Nature chemistry, 4(9), 705-710 (2012-08-24)
Bryostatin is a unique lead in the development of potentially transformative therapies for cancer, Alzheimer's disease and the eradication of HIV/AIDS. However, the clinical use of bryostatin has been hampered by its limited supply, difficulties in accessing clinically relevant derivatives
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
L Yu et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 19(3-4), 239-244 (2011-10-11)
Chinese jujube (also known as Chinese date) is the fruit of Ziziphus jujuba Mill. (Rhamnaceae). As a famous folk medicine, it is used as antidote in traditional Chinese formula, Shi Zao Decoction, to relieve the drastic inflammatory irritant nature of
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
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