1192552-64-9

Basic information

• Product Name: 1-Hydroxy-2,7-diaMino Mitosene (Mixture cis/trans)
• Synonyms: 1-Hydroxy-2,7-diaMino Mitosene (Mixture cis/trans)
• CAS NO: 1192552-64-9
• Molecular Formula: C14H16N4O5
• Molecular Weight: 320.30064
• Product Categories: Amines;Chiral Reagents;Heterocycles;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;Amines, Chiral Reagents, Heterocycles, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 1192552-64-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 560.8±50.0 °C(Predicted)
• Appearance: /
• Density: 1.90±0.1 g/cm3(Predicted)
• Storage Temp.: -86°C Freezer, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 13.10±0.50(Predicted)
• CAS DataBase Reference: 1-Hydroxy-2,7-diaMino Mitosene (Mixture cis/trans)(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Hydroxy-2,7-diaMino Mitosene (Mixture cis/trans)(1192552-64-9)
• EPA Substance Registry System: 1-Hydroxy-2,7-diaMino Mitosene (Mixture cis/trans)(1192552-64-9)

Safety Data

• Hazardous Substances Data: 1192552-64-9(Hazardous Substances Data)

Usage

Uses

Mitomycin (M371900) impurity.

Upstream product

• 50-07-7 mitomycin C 
• 127-09-3 sodium acetate 

Relevant articles and documents

Kinetics and mechanism of the acid hydrolysis of mitomycins

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Synthesis of Mitomycin C and decarbamoylmitomycin C N6 deoxyadenosine-adducts

Mitomycin C (MC), an anti-cancer drug, and its analog, decarbamoylmitomycin C (DMC), are DNA-alkylating agents. MC is currently used in the clinics and its cytotoxicity is mainly due to its ability to form Interstrand Crosslinks (ICLs) which impede DNA replication and, thereby, block cancer cells proliferation. However, both MC and DMC are also able to generate monoadducts with DNA. In particular, we recently discovered that DMC, like MC, can form deoxyadenosine (dA) monoadducts with DNA. The biological role played by these monoadducts is worthy of investigation. To probe the role of these adducts and to detect them in enzymatic digests of DNA extracted from culture cells treated by both drugs, we need access to reference compounds i.e. MC and DMC dA-mononucleoside adducts. Previous biomimetic methods used to generate MC and DMC mononucleoside adducts are cumbersome and very low yielding. Here, we describe the diastereospecific chemical synthesis of both C-1 epimers of MC and DMC deoxyadenosine adducts. The key step of the synthesis involves an aromatic substitution reaction between a 6-fluoropurine 2′-deoxyribonucleoside and appropriately protected stereoisomeric triaminomitosenes to form protected-MC-dA adducts with either an S or R stereochemical configuration at the adenine-mitosene linkage. Fluoride-based deprotection methods generated the final four reference compounds: the two stereoisomeric MC-dA adducts and the two stereoisomeric DMC-dA adducts. The MC and DMC-dA adducts synthesized here will serve as standards for the detection and identification of such adducts formed in the DNA of culture cells treated with both drugs.

Observations on the activation of mitomycin C. Requirements for C-10 functionalization

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