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P0115

Sigma-Aldrich

PAC-1

≥98% (HPLC)

Synonym(s):

(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

Empirical Formula (Hill Notation):
C23H28N4O2
CAS Number:
315183-21-2
Molecular Weight:
392.49
MDL number:
MFCD03302441
UNSPSC Code:
12352200
PubChem Substance ID:
329820019
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

color

white

solubility

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

storage temp.

room temp

SMILES string

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+

InChI key

YQNRVGJCPCNMKT-LFVJCYFKSA-N

General description

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.

Biochem/physiol Actions

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.

Features and Benefits

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

WGK

WGK 3

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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Derivatives of procaspase-activating compound 1 (PAC-1) and their anticancer activities
Roth SH and Hergenrother JP
Current Medicinal Chemistry, 23(3), 201-241 (2016)
Yingxue Qi et al.
Journal of hematology & oncology, 11(1), 117-117 (2018-09-19)
Platelet glycoprotein Ibα (GPIbα) extracellular domain, which is part of the receptor complex GPIb-IX-V, plays an important role in tumor metastasis. However, the mechanism through which GPIbα participates in the metastatic process remains unclear. In addition, potential bleeding complication remains
Patrice Marques et al.
Frontiers in immunology, 8, 1766-1766 (2018-01-13)
Cardiovascular disease (CVD) is a major comorbidity in chronic obstructive pulmonary disease (COPD). Although the mechanism of its development remains largely unknown, it appears to be associated with cigarette consumption and reduced lung function. Therefore, the aim of this study
Amelie Vallet-Courbin et al.
PloS one, 12(1), e0170305-e0170305 (2017-01-27)
Cells of the innate and adaptive immune system are key factors in the progression of atherosclerotic plaque, leading to plaque instability and rupture, potentially resulting in acute atherothrombotic events such as coronary artery disease, cerebrovascular disease and peripheral arterial disease.
Huitong Peng et al.
International journal of general medicine, 13, 791-802 (2020-10-30)
Little is known about the relationship between the level of platelet NOD-like receptor protein 3 (NLRP3) and the severity of acute coronary syndrome (ACS) or the prognostic value of platelet NLRP3 for percutaneous coronary intervention (PCI). Platelets collected from 25
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