Source:http://linkedlifedata.com/resource/pubmed/id/20392126
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| Predicate | Object |
|---|---|
| rdf:type | |
| lifeskim:mentions | |
| pubmed:issue |
10
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| pubmed:dateCreated |
2010-5-10
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| pubmed:abstractText |
Nitrosamines are well-known for their toxic and carcinogenic properties. The metabolic activation of nitrosamines occurs via interaction with the heme-containing cytochrome P450 enzymes. We report the preparation and structural characterization of a number of nitrosamine adducts of synthetic iron porphyrins. The reactions of the cations [(por)Fe(THF)(2)]ClO(4) (por = TPP, TTP, OEP) with dialkylnitrosamines (R(2)NNO; R(2) = Me(2), Et(2), (cyclo-CH(2))(4), (cyclo-CH(2))(5), (PhCH(2))(2)) in toluene generate the six-coordinate high-spin (S = 5/2) [(por)Fe(ONNR(2))(2)]ClO(4) compounds and a five-coordinate intermediate-spin (S = 3/2) [(OEP)Fe(ONNMe(2))]ClO(4) derivative in 57-72% yields (TPP = 5,10,15,20-tetraphenylporphyrinato dianion, TTP = 5,10,15,20-tetra-p-tolylporphyrinato dianion, OEP = 2,3,7,8,12,13,17,18-octaethylporphyrinato dianion). The N-O and N-N vibrations of the coordinated nitrosamine groups in [(por)Fe(ONNR(2))(2)]ClO(4) occur in the 1239-1271 cm(-1) range. Three of the six-coordinate [(por)Fe(ONNR(2))(2)]ClO(4) compounds and one five-coordinate [(OEP)Fe(ONNMe(2))]ClO(4) compound have been characterized by single crystal X-ray crystallography. All the nitrosamine ligands in these complexes bind to the ferric centers via a sole eta(1)-O binding mode. No arylnitrosamine adducts were obtained from the reactions of the precursor compounds [(por)Fe(THF)(2)]ClO(4) with three arylnitrosamines (Ph(2)NNO, Ph(Me)NNO, Ph(Et)NNO). However, prolonged exposure of [(por)Fe(THF)(2)]ClO(4) to these arylnitrosamines resulted in the formation of the known five-coordinate (por)Fe(NO) derivatives. The latter (por)Fe(NO) compounds were obtained more readily by the reactions of the three arylnitrosamines with the four-coordinate (por)Fe(II) precursors.
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| pubmed:grant | |
| pubmed:commentsCorrections |
http://linkedlifedata.com/resource/pubmed/commentcorrection/20392126-11233208,
http://linkedlifedata.com/resource/pubmed/commentcorrection/20392126-11942786,
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http://linkedlifedata.com/resource/pubmed/commentcorrection/20392126-9625726
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| pubmed:language |
eng
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| pubmed:journal | |
| pubmed:citationSubset |
IM
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| pubmed:chemical | |
| pubmed:status |
MEDLINE
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| pubmed:month |
May
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| pubmed:issn |
1520-510X
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| pubmed:author | |
| pubmed:issnType |
Electronic
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| pubmed:day |
17
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| pubmed:volume |
49
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| pubmed:owner |
NLM
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| pubmed:authorsComplete |
Y
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| pubmed:pagination |
4405-19
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| pubmed:dateRevised |
2011-9-26
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| pubmed:meshHeading |
pubmed-meshheading:20392126-Crystallography, X-Ray,
pubmed-meshheading:20392126-Cytochrome P-450 Enzyme System,
pubmed-meshheading:20392126-Electron Spin Resonance Spectroscopy,
pubmed-meshheading:20392126-Freezing,
pubmed-meshheading:20392126-Heme,
pubmed-meshheading:20392126-Models, Molecular,
pubmed-meshheading:20392126-Molecular Conformation,
pubmed-meshheading:20392126-Nitrosamines,
pubmed-meshheading:20392126-Protein Binding,
pubmed-meshheading:20392126-Temperature
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| pubmed:year |
2010
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| pubmed:articleTitle |
Five- and six-coordinate adducts of nitrosamines with ferric porphyrins: structural models for the Type II interactions of nitrosamines with ferric cytochrome P450.
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| pubmed:affiliation |
Department of Chemistry and Biochemistry, University of Oklahoma, 620 Parrington Oval, Norman, Oklahoma 73019, USA.
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| pubmed:publicationType |
Journal Article,
Research Support, U.S. Gov't, Non-P.H.S.,
Research Support, Non-U.S. Gov't,
Research Support, N.I.H., Extramural
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