Characterization of isomeric cationic porphyrins with beta-pyrrolic substituents by electrospray mass spectrometry: The singular behavior of a potential virus photoinactivator

• Type: Article in International Scientific Journal
• Date: 2007

Authors

Izquierdo, RA (Author) Other; Barros, CM (Author) Other; Santana Marques, MG (Author) Other; Ferrer Correia, AJ (Author) Other; Silva, EMP (Author) Other; Giuntini, F (Author) Other; Faustino, MAF (Author) Other; Tome, JPC (Author) Other; Tome, AC (Author) Other; Silva, AMS (Author) Other; Neves, GPMS (Author) Other; Cavaleiro, JAS (Author) Other; Peixoto, AF (Author) FCUP; Pereira, MM (Author) Other; Pais, AACC (Author) Other

Journal

Title: Journal of the American Society for Mass Spectrometry

Vol. 18

Pages: 218-225

ISSN: 1044-0305

Publisher: American Chemical Society

Indexing

ISI Web of Knowledge - 15 Citations

Scopus - 15 Citations

Other information

Authenticus ID: P-004-C2X

DOI: 10.1016/j.jasms.2006.09.010

Abstract (EN): 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. (c) 2007 American Society for Mass Spectrometry.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 8