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P4394

Sigma-Aldrich

cis-Diammineplatinum(II) dichloride

≥99.99% (trace metal analysis), crystalline, anti-neoplastic agent drug

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
EC Number:
239-733-8
MDL number:
MFCD00011623
UNSPSC Code:
12352200
PubChem Substance ID:
24278632
NACRES:
NA.77

product name

cis-Diammineplatinum(II) dichloride, crystalline

form

crystalline

Quality Level

200

color

yellow

mp

270 °C (lit.)

antibiotic activity spectrum

neoplastics

mode of action

DNA synthesis | interferes

originator

Corden

SMILES string

N.N.Cl[Pt]Cl

InChI

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

InChI key

LXZZYRPGZAFOLE-UHFFFAOYSA-L

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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.

Storage and Stability

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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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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