Diaminocyclohexanedichloroplatinum(II)
[CAS# 61848-66-6]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic hafnium, mercury, silver, platinum, etc.
• Name: Diaminocyclohexanedichloroplatinum(II)
• Molecular Formula: C₆H₁₄Cl₂N₂Pt
• Molecular Weight: 380.18
• CAS Registry Number: 61848-66-6
• EC Number: 685-481-0
• SMILES: C1CCC(C(C1)N)N.Cl[Pt]Cl

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Hazard Statements: H302-H312-H332-H351
• Precautionary Statements: P203-P261-P264-P270-P271-P280-P301+P317-P302+P352-P304+P340-P317-P318-P321-P330-P362+P364-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	3	H301
Reproductive toxicity	Repr.	2	H361
Respiratory sensitization	Resp. Sens.	1B	H334
Acute toxicity	Acute Tox.	3	H311
Respiratory sensitization	Resp. Sens.	1	H334
Acute toxicity	Acute Tox.	3	H331
Skin irritation	Skin Irrit.	2	H315
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Specific target organ toxicity - single exposure	STOT SE	3	H335
Carcinogenicity	Carc.	2	H351
Skin sensitization	Skin Sens.	1B	H317
Germ cell mutagenicity	Muta.	1B	H340
Carcinogenicity	Carc.	1A	H350
Reproductive toxicity	Repr.	1A	H360
Germ cell mutagenicity	Muta.	2	H341
Skin sensitization	Skin Sens.	1	H317

• Transport Information: UN 3467

Discovory and Applicatios

Diaminocyclohexanedichloroplatinum(II), often abbreviated as DACH-Pt, is a platinum-based compound with the chemical formula [PtCl₂(C₆H₁₂N₂)] that contains a platinum(II) center coordinated with two chloride ions and a bidentate ligand known as diaminocyclohexane (DACH). This complex is part of a broader class of platinum-based chemotherapeutic agents, which are widely used for their anticancer properties. Platinum compounds, particularly cisplatin, are well-known for their efficacy in treating various types of cancer, and DACH-Pt is one of the derivatives designed to improve upon the effectiveness and reduce the toxicity associated with cisplatin.

The development of DACH-Pt stems from the desire to enhance the pharmacological activity of platinum drugs while minimizing some of the severe side effects, such as nephrotoxicity and neurotoxicity, that are often seen with cisplatin. The diaminocyclohexane ligand in DACH-Pt plays a crucial role in modifying the compound’s overall interaction with DNA, which is essential for its antitumor activity.

Diaminocyclohexanedichloroplatinum(II) works by interacting with the DNA in cancer cells. Like other platinum-based drugs, DACH-Pt binds to the DNA strands, causing cross-links between the strands. This action inhibits the DNA replication process and transcription, leading to the death of rapidly dividing cancer cells. These DNA cross-links are particularly effective at inducing apoptosis (programmed cell death) in tumor cells, which is the mechanism that allows DACH-Pt to be used as an anticancer drug.

While cisplatin remains one of the most well-established platinum-based chemotherapeutic agents, its use is often limited by its toxic side effects. DACH-Pt, as a derivative, has been investigated for its potential to offer similar or improved anticancer activity with a reduced side effect profile. The diaminocyclohexane ligand in DACH-Pt is thought to help decrease the likelihood of certain side effects, such as nephrotoxicity, while still maintaining or enhancing the drug's anticancer efficacy. Additionally, the steric effects of the cyclohexane ring may influence the drug’s ability to interact with tumor DNA, possibly making it more selective for cancerous tissues.

The pharmacokinetics and bioavailability of DACH-Pt are also points of ongoing research. Studies have shown that DACH-Pt can be administered intravenously, where it undergoes rapid distribution throughout the body. Once inside the cancer cells, the platinum complex is activated and reacts with DNA. However, as with other platinum drugs, the exact mechanisms that determine its distribution, metabolism, and excretion are complex and are still being explored in clinical studies.

In terms of its clinical application, DACH-Pt has been investigated in preclinical models and some early-phase clinical trials. The drug has shown promising results in treating a variety of cancers, including ovarian cancer, lung cancer, and testicular cancer, among others. As with many experimental drugs, its full clinical potential is still under evaluation, but it holds promise for improving the therapeutic options available for patients with cancers that are resistant to traditional platinum-based therapies.

Overall, while DACH-Pt is not yet as widely used or established as cisplatin, it represents an important development in the field of platinum-based chemotherapy. Its potential for reduced toxicity, combined with its ability to target cancer cells effectively, makes it a compound of interest in cancer treatment research. Ongoing clinical trials and further studies will continue to define its role in the treatment of various cancers and help establish its place within the broader range of platinum-based chemotherapeutics.

References

1982. DNA crosslinking induced by 1,2-diaminocyclohexanedichloroplatinum(II) in murine leukemia L1210 cells and comparison with other platinum analogues. Biochimica et Biophysica Acta (BBA) - Gene Structure and Expression, 698(2).
DOI: 10.1016/0167-4781(82)90127-0

1986. High-performance liquid chromatographic separation of platinum complexes containing the cis-1,2-diaminocyclohexane carrier ligand. Analytical Biochemistry, 157(1).
DOI: 10.1016/0003-2697(86)90206-x

2012. Polymeric micelles incorporating (1,2-diaminocyclohexane)platinum (II) suppress the growth of orthotopic scirrhous gastric tumors and their lymph node metastasis. Journal of Controlled Release, 159(2).
DOI: 10.1016/j.jconrel.2012.01.038