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P0115

Sigma-Aldrich

PAC-1

≥98% (HPLC)

Sinonimo/i:

(4-Benzylpiperazino)acetic acid (3-allyl-2-hyroxybenzylidene)hydrazide, 1-Piperazineacetic acid, 2-(phenylmethyl)-,[[2-hydroxy-3-(2-propenyl)phenyl]methylene]hyrrazide

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About This Item

Formula empirica (notazione di Hill):
C23H28N4O2
Numero CAS:
315183-21-2
Peso molecolare:
392.49
Numero MDL:
MFCD03302441
Codice UNSPSC:
12352200
ID PubChem:
329820019
NACRES:
NA.77

Livello qualitativo

100

Saggio

≥98% (HPLC)

Stato

solid

Colore

white

Solubilità

DMSO: ≥10 mg/mL
deionized water: ≤2 mg/mL

Temperatura di conservazione

room temp

Stringa SMILE

Oc1c(CC=C)cccc1\C=N\NC(=O)CN2CCN(CC2)Cc3ccccc3

InChI

1S/C23H28N4O2/c1-2-7-20-10-6-11-21(23(20)29)16-24-25-22(28)18-27-14-12-26(13-15-27)17-19-8-4-3-5-9-19/h2-6,8-11,16,29H,1,7,12-15,17-18H2,(H,25,28)/b24-16+
YQNRVGJCPCNMKT-LFVJCYFKSA-N

Descrizione generale

Procaspase-activating compound 1 (PAC-1) is an ortho-hydroxy N-acyl hydrazine compound. It is cytotoxic to a variety of cancer cells, such as lymphoma, leukaemia, breast carcinoma and glioblastoma. High doses of PAC-1 can promote neuroexcitation. It helps in the in vitro autoactivation of the proenzyme protease, which acts as a prototype for other protease activating compounds. PAC-1 dependant activation of procaspase-3 is associated with the chelation of zinc.

Azioni biochim/fisiol

PAC-1 is a caspase 3 activator.
PAC-1 is a caspase 3 activator. Caspase activation is a key strategy in cancer therapy. Caspase 3 is a key executioner caspase and direct effector of apoptosis. Hallmark of many cancers is the circumvention of signal in the activation of executioner caspases and loss of apoptotic response. EC50 for caspase 3 activation = 0.33 μM and caspase 7= 4.5 μM. The IC50 for apoptosis induction = 0.92 μM. Elevated caspase 3 level in cancerous cell lines and tissues allows PAC-1 to selectively induce apoptosis in tissues.

Caratteristiche e vantaggi

This compound is featured on the Caspases 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

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

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Certificati d'analisi (COA)

Lot/Batch Number
088K4703V
088K4703
057K4708

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Sigma-Aldrich

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Sigma-Aldrich

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Sodio idrossido

Targeting of C-type lectin-like receptor 2 or P2Y12 for the prevention of platelet activation by immunotherapeutic CpG oligodeoxynucleotides: comment.
U Flierl et al.
Journal of thrombosis and haemostasis : JTH, 16(1), 181-185 (2017-10-21)
Parallel synthesis and biological evaluation of 837 analogues of procaspase-activating compound 1 (PAC-1)
Hsu DC et al.
ACS Combinatorial Science, 14(1), 44-50 (2011)
Philipp Blüm et al.
Cellular & molecular immunology, 14(12), 986-996 (2016-04-19)
Hepatitis C virus (HCV) infection is a major problem worldwide. HCV is not limited to liver disease but is frequently complicated by immune-mediated extrahepatic manifestations such as glomerulonephritis or vasculitis. A fatal complication of HCV-associated vascular disease is thrombosis. Polyriboinosinic:polyribocytidylic
Michal Bijak et al.
International journal of biological macromolecules, 106, 878-884 (2017-08-27)
The primary biological function of platelets is to form hemostatic thrombi that prevent blood loss and maintain vascular integrity. These multi-responding cells are activated by different endogenous, physiological agonists due to the vast number of receptors present on the surface
Procaspase-3 activation as an anti-cancer strategy: structure- activity relationship of procaspase-activating compound 1 (PAC-1) and Its cellular co-localization with caspase-3
Peterson QP et al.
Journal of Medicinal Chemistry, 52(18), 5721-5731 (2009)
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