(R,R-1,2-Diaminocyclohexane)dinitratoplatinum
[CAS# 66900-68-3]

Identification

• Classification: Analytical chemistry >> Standard >> Pharmacopoeia standards and magazine standards
• Name: (R,R-1,2-Diaminocyclohexane)dinitratoplatinum
• Synonyms: (1R,2R)-1,2-Cyclohexanediaminedinitratoplatinum
• Molecular Formula: C₆H₁₄N₄O₆Pt
• Molecular Weight: 433.28
• CAS Registry Number: 66900-68-3
• EC Number: 814-400-5
• SMILES: C1CC[C@H]([C@@H](C1)N)N.[N+](=O)([O-])[O-].[N+](=O)([O-])[O-].[Pt+2]

Safety Data

• Hazard Symbols: GHS06;GHS07;GHS08 Danger
• Hazard Statements: H301-H317-H319-H334-H341-H351-H360-H361
• Precautionary Statements: P203-P233-P260-P261-P264-P264+P265-P270-P271-P272-P280-P284-P301+P316-P302+P352-P304+P340-P305+P351+P338-P318-P321-P330-P333+P317-P337+P317-P342+P316-P362+P364-P403-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Reproductive toxicity	Repr.	2	H361
Respiratory sensitization	Resp. Sens.	1	H334
Carcinogenicity	Carc.	2	H351
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	3	H301

Discovory and Applicatios

(R,R-1,2-Diaminocyclohexane)dinitratoplatinum is a platinum-based compound that belongs to the class of organoplatinum complexes, which are widely studied and used in cancer chemotherapy. This specific platinum complex incorporates the chiral ligand 1,2-diaminocyclohexane (DACH), known for its ability to induce stereochemistry in the platinum coordination sphere. The presence of the dinitrate ligands makes this compound an interesting candidate for research due to its potential therapeutic properties, as well as its structural and chemical similarity to other platinum-based anticancer drugs like cisplatin.

The discovery of platinum-based chemotherapy agents began with the serendipitous finding of cisplatin's anticancer effects in the 1960s. Since then, a variety of platinum complexes, including those with chiral ligands like DACH, have been developed in the search for more effective and less toxic chemotherapy options. The goal in developing these complexes is to improve upon the side effects of traditional platinum drugs such as cisplatin, which can cause nephrotoxicity, ototoxicity, and peripheral neuropathy.

(R,R-1,2-Diaminocyclohexane)dinitratoplatinum is one of the many derivatives synthesized to explore the effects of stereochemistry and ligand variation on the pharmacological properties of platinum drugs. The chiral DACH ligand is believed to influence the drug's interaction with DNA, the primary target for platinum-based drugs. These interactions occur when the platinum ion binds to the DNA, causing DNA crosslinks that prevent replication and transcription, ultimately leading to cell death. The use of DACH as a ligand may alter the drug's specificity and binding mode, potentially resulting in differences in toxicity and effectiveness compared to other platinum complexes.

The dinitrate ligands in this compound are also of interest because nitrates can play a role in the compound's reactivity and ability to form stable adducts with DNA. Nitrate groups in coordination compounds can undergo various transformations, including the release of nitro groups under certain conditions, which may have implications for the drug's activity and resistance mechanisms.

The potential application of (R,R-1,2-Diaminocyclohexane)dinitratoplatinum in cancer treatment is a subject of ongoing research. Studies are focused on evaluating the compound's cytotoxicity and its ability to overcome the mechanisms of resistance that often limit the effectiveness of other platinum-based agents. In particular, the introduction of chiral ligands and nitrate groups may offer new insights into improving the pharmacokinetics and pharmacodynamics of platinum drugs.

The compound's development is part of a broader effort to optimize platinum-based chemotherapy by improving their selectivity for cancer cells while reducing off-target toxicity. Chiral ligands like DACH have been shown to enhance the stability of platinum complexes and may also modify their interaction with biological molecules, potentially making them more effective or offering a different toxicity profile compared to other platinum-based drugs.

As with other platinum drugs, the clinical use of (R,R-1,2-Diaminocyclohexane)dinitratoplatinum would likely be in the context of combination therapies, where the platinum complex is used alongside other chemotherapeutic agents to enhance the overall efficacy of cancer treatment. The development of combination regimens aims to tackle cancer from multiple angles, including interfering with DNA repair, inhibiting cell proliferation, and activating immune responses.

The research into (R,R-1,2-Diaminocyclohexane)dinitratoplatinum continues, with studies focusing on its synthesis, stability, reactivity, and anticancer activity. These studies aim to determine whether this compound can provide a viable alternative to existing platinum-based treatments and contribute to the broader understanding of how structural modifications can impact drug efficacy.

In summary, (R,R-1,2-Diaminocyclohexane)dinitratoplatinum is an organoplatinum compound with potential applications in cancer chemotherapy. Its development highlights the ongoing efforts to improve the efficacy and reduce the toxicity of platinum-based drugs by modifying their structure, particularly through the use of chiral ligands and nitrate groups. Continued research is necessary to fully explore the therapeutic potential of this compound and its place in modern cancer treatment regimens.