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P4394

Sigma-Aldrich

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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25 MG
€51.80
100 MG
€145.00
250 MG
€145.00
1 G
€436.00

€51.80

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25 MG
€51.80
100 MG
€145.00
250 MG
€145.00
1 G
€436.00

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

€51.80

Please contact Customer Service for Availability
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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[1]
  • in the inhibition of cell proliferation and chemosensitivity in ovarian cancer cell lines[2]
  • in MTT [3-(4,5-Dimethylthiazol-2-yl)-2,5-Diphenyltetrazolium Bromide] cell viability assay in oral squamous cell carcinoma[3]

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

Signal Word

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 Code

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
MKCW6651
MKCT7308
MKCS6808
MKCR6473
MKCP9505

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Role and regulation of proapoptotic Bax in oral squamous cell carcinoma and drug resistance
Alam M, et al.
Head & Neck (2018)
Calpain system protein expression and activity in ovarian cancer
Zhang S, et al.
Journal of Cancer Research and Clinical Oncology, 1-17 (2018)
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.
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
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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Questions

1–9 of 9 Questions  

  1. How to reconstitute Cisplatin (P4394)?

    1 answer

    1. The list of solvents and rates are as follows:
      Solvent M x 10E(2) %(w/v)
      H2O(after 24 hours)* 0.77 0.23
      (after 72 hours)* 0.83 0.25
      0.9% NaCl 0.50 0.15
      DMF 6.67 2.0
      DMA 6.00 1.8
      DMSO* 116.6 35.0
      *strongly discouraged
      DMSO inserts itself into the ligand

      Please see the link below to review this product datasheet for additional information:
      https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/310/148/p4394pis.pdf

      Helpful?

  2. How long can it be stored at -20°C when it is dissolved in PBS?

    1 answer

    1. The long term stability of this material in solution has not been determined. In general, it is recommended to prepare solutions fresh and protect from light. However, at -20°C, Cisplatin is completely stable over a span of 2 weeks according to the article below:
      https://onlinelibrary.wiley.com/doi/full/10.1002/%28SICI%291097-0142%2819970501%2979%3A9%3C1723%3A%3AAID-CNCR13%3E3.0.CO%3B2-%23

      Helpful?

  3. How should the Product cisplatin P4394, be stored?

    1 answer

    1. 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: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/310/148/p4394pis.pdf

      Helpful?

  4. What is the half-life of Cisplatin, Product P4394, in DMSO?

    1 answer

    1. At 37 °C, the half-life of cisplatin in DMSO is 60 minutes. In vivo the half-life of cisplatin is approximately 30 minutes.

      Helpful?

  5. Why should DMSO not be used as a solvent for cis-Diammineplatinum (II) dichloride?

    1 answer

    1. The divalent platinum has a high affinity for sulfur donor ligands and this will displace the chloride.  The use of DMSO as a solvent affects the instability of cisplatin and can affect biological activity.  Sundquist, W. I., et al., Inorg. Chem. 26:1524-1528, 1987.

      Helpful?

  6. How can solutions of Cisplatin, Product P4394, be stored?

    1 answer

    1. Sterile solutions in 0.9% sodium chloride protected from light are stable for 28 days at room temperature.

      Helpful?

  7. What is the toxicity of Cisplatin, Product P4394?

    1 answer

    1. This information can be found on the MSDS Section 11.

      Helpful?

  8. What is the Department of Transportation shipping information for this product?

    1 answer

    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

      Helpful?

  9. What is the best solvent to use for Cisplatin, Product P4394?

    1 answer

    1. Pharmaceutical injections of cisplatin are in 0.9% sodium chloride at 1 mg/ml.  A 0.1% solution in 0.9% sodium chloride solution has a pH range of 4.5-6.0 immediately after preparation and can be adjusted with HCl.

      Helpful?

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