Characterization and properties of monoammine nitroimidazole complexes of platinum (PtCl sub 2 (NH sub 3 )(NO sub 2 Im)). Crystal and molecular structure of cis-Amminedichloro(1-((((2-hydroxyethyl)amino)carbonyl)methyl)-2-nitroimidazole)platinum(II)

Journal Article · Wed Nov 27 04:00:00 EST 1991 · Inorganic Chemistry; (United States)

DOI:https://doi.org/10.1021/ic00024a013· OSTI ID:7163401

Rochon, F D; Kong, Pichang; Melanson, R ^[1]; Skov, K A ^[2]; Farrell, N ^[3]

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1. Univ. du Quebec, Montreal (Canada)
2. British Columbia Cancer Research Centre, Vancouver (Canada)
3. Univ. of Vermont, Burlington (United States)

The characterization of monoammine(nitroimidazole)platinum(II) complexes of structure (PtCl{sub 2}(NH{sub 3})(NO{sub 2}Im)) (NO{sub 2}Im = 1-((((2-hydroxyethyl)amino)carbonyl)methyl)-2-nitroimidazole, Etanidazole (I), 1-(2-nitro-1-imidazolyl)-3-methoxy2-propanol, Misonidazole (II), and 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole, Metronidazole (III)) is reported. Both is cis and trans isomers may be isolated for II and III. The crystal structure of cis-amminedichloro(1-((((2-hydroxyethyl)amino)carbonyl)methyl)-2-nitroimidazole)platinum(II) has been determined by X-ray diffraction. The crystals are orthorhombic, space group Pnab with cell dimensions a = 14.867 (7) {angstrom}, b = 9.915 (5) {angstrom}, c = 19.015 (9) {angstrom}, and Z = 8. The structure was refined to R = 0.062 and R{sub w} = 0.052. Platinum has the expected square-planar coordination. The Pt-Cl bond trans to the nitroimidazole ligand is shorter (2.269 (3) {angstrom}) than normal. The dihedral angle between the platinum plane and the imidazole ring is 111{degree}, while the nitro group makes an angle of 31{degree} with the imidazole ring plane. Electrochemistry and {sup 195}Pt NMR data are also reported. The relevance of the chemical properties to their biological properties as radiosensitizers and hypoxic cytotoxins is discussed.

• OSTI ID: 7163401
• Journal Information: Inorganic Chemistry; (United States), Journal Name: Inorganic Chemistry; (United States) Vol. 30:24; ISSN 0020-1669; ISSN INOCA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
550600 -- Medicine
62 RADIOLOGY AND NUCLEAR MEDICINE
ANTIMITOTIC DRUGS
BIOLOGICAL EFFECTS
BOND ANGLE
BOND LENGTHS
CHEMICAL PROPERTIES
CHEMISTRY
COHERENT SCATTERING
COMPLEXES
CRYSTAL LATTICES
CRYSTAL STRUCTURE
DAYS LIVING RADIOISOTOPES
DIFFRACTION
DIMENSIONS
DRUGS
ELECTROCHEMISTRY
EVEN-ODD NUCLEI
HEAVY NUCLEI
INTERNAL CONVERSION RADIOISOTOPES
ISOMERIC TRANSITION ISOTOPES
ISOMERS
ISOTOPES
LENGTH
MOLECULAR STRUCTURE
NMR SPECTRA
NUCLEI
ORTHORHOMBIC LATTICES
PLATINUM 195
PLATINUM COMPLEXES
PLATINUM ISOTOPES
RADIOISOTOPES
RADIOSENSITIZERS
SCATTERING
SPECTRA
STABLE ISOTOPES
TRANSITION ELEMENT COMPLEXES
X-RAY DIFFRACTION