Document Detail


Characterization of isomeric cationic porphyrins with beta-pyrrolic substituents by electrospray mass spectrometry: the singular behavior of a potential virus photoinactivator.
MedLine Citation:
PMID:  17070697     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Electrospray ionization mass spectrometry (ESI-MS) and tandem mass spectrometry (ESI-MS/MS) have been used to differentiate the 2- and 4-methylpyridyl isomers of free-base and metallated cationic beta-vinylpyridylporphyrins. The analysis by ESI-MS/MS of the deuterated analogs and semiempirical calculations of structural and electronic parameters were also undertaken. The two free-base isomers are easily differentiated by ESI-MS/MS but the presence of a metallic center renders differentiation of the metallated isomers less effective. The data acquired show that of all the studied compounds, the free-base 2-methylpyridyl isomer, which was operative in the in vitro photoinactivation of Herpes simples virus, has a different gas-phase behavior. Local distortion of the macrocycle due to the presence of the beta-vinylpyridyl substituent occurs for all the compounds, but a different electron density distribution can account for the observed gas-phase behavior of this potential virus photoinactivator.
Authors:
Raul A Izquierdo; Cristina M Barros; M Graça Santana-Marques; A J Ferrer-Correia; Eduarda M P Silva; Francesca Giuntini; Maria A F Faustino; João P C Tomé; Augusto C Tomé; Artur M S Silva; Graça P M S Neves; J A S Cavaleiro; Andreia F Peixoto; Mariette M Pereira; Alberto A C C Pais
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Publication Detail:
Type:  Journal Article     Date:  2006-10-27
Journal Detail:
Title:  Journal of the American Society for Mass Spectrometry     Volume:  18     ISSN:  1044-0305     ISO Abbreviation:  J. Am. Soc. Mass Spectrom.     Publication Date:  2007 Feb 
Date Detail:
Created Date:  2007-01-30     Completed Date:  2007-04-26     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9010412     Medline TA:  J Am Soc Mass Spectrom     Country:  United States    
Other Details:
Languages:  eng     Pagination:  218-25     Citation Subset:  IM    
Affiliation:
Mass Spectrometry Laboratory, Department of Chemistry, University of Aveiro, Campus de Santiago, Aveiro, Portugal.
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MeSH Terms
Descriptor/Qualifier:
Antiviral Agents / analysis,  chemistry*
Cations / chemistry
Isomerism
Photochemistry
Porphyrins / analysis,  chemistry*
Spectrometry, Mass, Electrospray Ionization / methods*
Vinyl Compounds / analysis,  chemistry*
Virus Inactivation
Chemical
Reg. No./Substance:
0/Antiviral Agents; 0/Cations; 0/Porphyrins; 0/Vinyl Compounds; 0/tetraphenylporphyrin

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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