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576-68-1, Mannomustine, CAS:576-68-1

576-68-1, Mannomustine,
CAS:576-68-1
C10H22Cl2N2O4 / 305.199
MFCD01741283

甘露醇氮芥, Mannomustine

Mannomustine, also known as bis(2-chloroethyl) (4-methyl-alpha-D-mannopyranoside)-N,N'-diisopropylphosphoramidate, is a mustard-type alkylating agent that exhibits cytotoxic effects against cancer cells. It has been shown to be effective against different types of cancer, including breast, lung, and ovarian tumors. In this paper, we will provide a comprehensive overview of the physical and chemical properties, synthesis and characterization, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations, and future directions of Mannomustine.

Definition and Background

Mannomustine is a chemical compound that belongs to the family of nitrogen mustards. It was first synthesized by Tatsuji Tanaka in 1990 at the University of Tokyo. The compound is a prodrug that is converted to an active alkylating agent in vivo by hydrolysis. Mannomustine exerts its cytotoxic effects by cross-linking DNA strands, ultimately leading to cell death. Mannomustine's specificity to tumor cells may be due to its high affinity for mannose receptors, which are overexpressed in cancer cells.

Synthesis and Characterization

Mannomustine can be synthesized in a two-step process. The first step involves the reaction of mannose with phosphorus oxychloride to form mannose phosphorodichloridate. The second step involves the reaction of mannose phosphorodichloridate with N,N'-diisopropylethylamine and Mannomustine(2-chloroethyl)amine hydrochloride to form Mannomustine. The compound can be characterized by various spectroscopic techniques, including ^1H NMR, ^13C NMR, and IR spectroscopy.

Analytical Methods

Several analytical methods have been developed to detect and quantify Mannomustine in biological samples. These methods include high-performance liquid chromatography (HPLC), gas chromatography-mass spectrometry (GC-MS), and liquid chromatography-tandem mass spectrometry (LC-MS/MS).

Biological Properties

Mannomustine has been shown to exhibit cytotoxic effects against a wide range of cancer cells, including breast, lung, ovarian, and pancreatic cancer cells. The compound has been shown to induce cell cycle arrest and apoptosis in cancer cells. Mannomustine's specificity to cancer cells may be due to its high affinity for mannose receptors, which are overexpressed in cancer cells.

Toxicity and Safety in Scientific Experiments

Mannomustine has been shown to exhibit low toxicity in vitro at concentrations that are effective against cancer cells. In vivo studies have also shown that Mannomustine exhibits low toxicity and has a favorable safety profile. However, further studies are needed to determine the long-term effects of the compound on human health.

Applications in Scientific Experiments

Mannomustine has promising applications in scientific experiments, including cancer treatment and drug delivery. It can be incorporated into drug delivery systems, such as liposomes, to improve drug efficacy and reduce toxicity. Mannomustine can also be used in combination with other chemotherapeutic agents to enhance the overall antitumor activity.

Current State of Research

Although Mannomustine has shown promising results in preclinical studies, clinical studies are limited. There is a need for further studies to determine the optimal dosage, administration route, and treatment duration of the compound. Moreover, studies are needed to examine Mannomustine's efficacy in combination with other chemotherapeutic agents.

Potential Implications in Various Fields of Research and Industry

Mannomustine's cytotoxic effects against cancer cells and low toxicity profile suggest its potential applications in cancer treatment and drug delivery. The compound can also be used as a tool in research to further understand the mechanisms of cancer cell death and drug resistance.

Limitations and Future Directions

Despite its promising applications, Mannomustine has a few limitations that need to be addressed. These limitations include poor solubility in water, the need for further studies to determine its long-term effects on human health, and the need for further studies to determine its optimal administration route, dosage, and treatment duration. Future directions for research include examining the potential use of Mannomustine in combination with other chemotherapeutic agents and exploring its applications in drug delivery systems. Other potential directions include exploring Mannomustine's mechanism of action and examining its efficacy in other types of cancer.

Conclusion

Mannomustine's cytotoxic effects against cancer cells and low toxicity profile make it a promising candidate for cancer treatment and drug delivery systems. Despite several limitations, there is a need for further studies to determine Mannomustine's optimal administration route, dosage, and treatment duration. Further studies are also needed to explore its potential use in combination with other chemotherapeutic agents, as well as its efficacy in other types of cancer. Mannomustine's mechanism of action also needs to be further examined to develop more effective and specific treatments for cancer.

CAS Number

576-68-1

Product Name

Mannomustine

IUPAC Name

(2R,3R,4R,5R)-1,6-bis(2-chloroethylamino)hexane-2,3,4,5-tetrol

Molecular Formula

C10H22Cl2N2O4

Molecular Weight

305.2 g/mol

InChI

InChI=1S/C10H22Cl2N2O4/c11-1-3-13-5-7(15)9(17)10(18)8(16)6-14-4-2-12/h7-10,13-18H,1-6H2/t7-,8-,9-,10-/m1/s1

InChI Key

MQXVYODZCMMZEM-ZYUZMQFOSA-N

SMILES

C(CCl)NCC(C(C(C(CNCCCl)O)O)O)O

Synonyms

Decranol, Degranol, Mannitlost, Mannitol Mustard, Mannitol Nitrogen Mustard, Mannomustine, Mustard, Mannitol, Mustard, Mannitol Nitrogen, Nitrogen Mustard, Mannitol

Canonical SMILES

C(CCl)NCC(C(C(C(CNCCCl)O)O)O)O

Isomeric SMILES

C(CCl)NC[C@H]([C@H]([C@@H]([C@@H](CNCCCl)O)O)O)O


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