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Merck

P4394

cis-Diammineplatinum(II) dichloride

≥99.99% (trace metal analysis), crystalline, macrophage activator

Synonym(s):

cis-Dichlorodiammine platinum(II), cis-Platinum(II) diammine dichloride, Cisplatin

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About This Item

Linear Formula:
Pt(NH3)2Cl2
CAS Number:
15663-27-1
Molecular Weight:
300.05
NACRES:
NA.77
PubChem Substance ID:
24278632
UNSPSC Code:
12352200
EC Number:
239-733-8
MDL number:
MFCD00011623

Key Documents

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Product Name

cis-Diammineplatinum(II) dichloride, crystalline

InChI key

LXZZYRPGZAFOLE-UHFFFAOYSA-L

InChI

1S/2ClH.2H3N.Pt/h2*1H;2*1H3;/q;;;;+2/p-2

SMILES string

N.N.Cl[Pt]Cl

form

crystalline

color

yellow

mp

270 °C (lit.)

antibiotic activity spectrum

neoplastics

mode of action

DNA synthesis | interferes

originator

Corden

Quality Level

200

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Application

cis-Diammineplatinum(II) dichloride has been used:
  • in cell viability measurement in cochlear explants
  • in the inhibition of cell proliferation and chemosensitivity in ovarian cancer cell lines
  • in MTT [3-(4,5-Dimethylthiazol-2-yl)-2,5-Diphenyltetrazolium Bromide] cell viability assay in oral squamous cell carcinoma

Biochem/physiol Actions

Potent chemoimmunotherapeutic drug; stimulates the immune responses by activating macrophages and other cells of the immune system. Cisplatin-treated macrophages show increased antigen presentation function in vitro. Treatment increased cellular NF-κB content and translocation in macrophages. Cisplatin effects are regulated by kinases, phosphatases, and Ca2+/calmodulin. Forms cytotoxic adducts with the DNA dinucleotide d(pGpG), inducing intrastrand crosslinks.
Potent platinum-based antineoplastic agent. Forms cytotoxic adducts with the DNA dinucleotide d(pGpG), inducing intrastrand cross-links.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Caspases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Corden. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Preparation Note

This product is to be stored in room temperature. Keep the product tightly closed in a well-ventilated place. Dry. Please view the Safety Data Sheet for more information.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Carc. 1B - Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP9505
MKCN8054
MKCM2435
MKCL0026
MKCJ4107

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Calpain system protein expression and activity in ovarian cancer
Zhang S, et al.
Journal of Cancer Research and Clinical Oncology, 1-17 (2018)
Role and regulation of proapoptotic Bax in oral squamous cell carcinoma and drug resistance
Alam M, et al.
Head & Neck (2018)
Lin Hou et al.
Life sciences, 232, 116561-116561 (2019-06-28)
The poor prognosis of ovarian cancer is mainly caused by chemotherapy resistance. Studies show that the Bcl-2 inhibitor ABT737 can significantly improve the effect of cisplatin and induce mitochondrial pathway apoptosis. However, the mechanism of ABT737 increases sensitivity to cisplatin
Yi-Long Wu et al.
The Lancet. Oncology, 14(8), 777-786 (2013-06-21)
The results of FASTACT, a randomised, placebo-controlled, phase 2 study, showed that intercalated chemotherapy and erlotinib significantly prolonged progression-free survival (PFS) in patients with advanced non-small-cell lung cancer. We undertook FASTACT-2, a phase 3 study in a similar patient population.
Qianqian Yang et al.
Free radical biology & medicine, 120, 342-355 (2018-02-20)
Phosphatase and tensin homologue (PTEN)-induced putative kinase 1 (PINK1) gene encodes a serine/threonine kinase, which acts as a molecular sensor of mitochondrial health necessary for mitochondrial quality control. The present study was designed to examine whether PINK1 expressed in C57BL/6
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