All Photos(1)
Synonym(s):
(4-Benzylpiperazino)acetic acid (3-allyl-2-hyroxybenzylidene)hydrazide, 1-Piperazineacetic acid, 2-(phenylmethyl)-,[[2-hydroxy-3-(2-propenyl)phenyl]methylene]hyrrazide
Empirical Formula (Hill Notation):
C23H28N4O2
CAS Number:
Molecular Weight:
392.49
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
Quality Level
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’.
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
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.
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
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
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)
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)
Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.
Contact Technical Service