Improving regioselectivity in the rhodium catalyzed hydroformylation of protoporphyrin-IX and chlorophyll a derivatives

Peixoto, Andreia F.; Pereira, Mariette M.; Sousa, Andreia F.; Pais, Alberto A. C. C.; Neves, Maria G. P. M. S.; Silva, Artur M. S.; Cavaleiro, José A. S.

doi:10.1016/j.molcata.2005.04.008

Cited by 10 publications

(2 citation statements)

References 26 publications

(31 reference statements)

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“…The fact that the lowest concentration of PP-IX provoked a significant decrease in damage could be due to the fact that the porphyrin ring could make complexes or act as a chelator, introducing the chromium into the ring. PP-IX has been reported to be able to bind other metals such as zinc and nickel [36] . The different studies on the role of ferrochelatase have revealed that this enzyme catalyzes zinc as well as the iron chelating activity of protoporphyrin [14] .…”

Section: Discussionmentioning

confidence: 99%

Genetic damage induced by CrO3 can be reduced by low doses of Protoporphyrin-IX in somatic cells of Drosophila melanogaster

2014

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HighlightsExperimental data placed PP-IX as an effective antimutagen at low doses.PP-IX could acts through the formation of chemical complexes with the chromium.Low concentration of PP-IX reduced genetic damage of the radiomimetic CrO3.The ability of PP-IX to release electrons may have inactivated the free radicals.Ferrochelatase could participate in the chelating chromium reducing its mutagenicity.

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Section: Discussionmentioning

confidence: 99%

Genetic damage induced by CrO3 can be reduced by low doses of Protoporphyrin-IX in somatic cells of Drosophila melanogaster

2014

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“…Conformationally distorted porphyrins have been the subject of interest since it was apparent that heme proteins presented°mostly°nonplanar°heme°configurations° [23,°24]. The nonplanarity of several porphyrin type chromophores is thought to be related to their functions in natural°systems° [16,°17].°The°nonplanarity°of°the°porphy-rin core is dependent on the electronic and steric effects of meso and ␤-pyrrolic substituents and by the size and type of°the°metal°centers° [25][26][27][28].…”

Section: Semiempirical Calculationsmentioning

confidence: 99%

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

Izquierdo

Barros

Santana-Marques

et al. 2007

J. Am. Soc. Mass Spectrom.

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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 ␤-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 ␤-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. (J Am Soc Mass Spectrom 2007, 18, 218 -225 Viruses are responsible for a large number of infectious diseases. In particular, the Herpes simplex virus is one of the most common agents responsible for viral infections in man [5]. From preliminary virus inactivation studies carried out with Herpes simplex virus type 1 (HSV-1) using the cationic porphyrins 1 and 2 (Scheme 1), we have observed that despite their structural resemblance and their similar photocytotoxicity profiles, Compound 1 was very effective in the photoinactivation of the virus, whereas Compound 2 displayed no virucidal effect in the same conditions [6].Electrospray ionization mass spectrometry (ESI-MS) was successfully applied to characterize porphyrins as early as 1991 [7] and both ESI-MS [8 -11] and tandem mass spectrometry (ESI-MS/MS) [12,13] have been used to study neutral and cationic porphyrins since then. We wanted to know if the two porphyrin isomers, 1 and 2, could be differentiated by ESI-MS/MS and if the informa-

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Organic Synthesis and Reactivity of Porphyrins

Senge¹,

Meindl²

2022

Fundamentals of Porphyrin Chemistry

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Improving regioselectivity in the rhodium catalyzed hydroformylation of protoporphyrin-IX and chlorophyll a derivatives

Cited by 10 publications

References 26 publications

Genetic damage induced by CrO3 can be reduced by low doses of Protoporphyrin-IX in somatic cells of Drosophila melanogaster

Genetic damage induced by CrO3 can be reduced by low doses of Protoporphyrin-IX in somatic cells of Drosophila melanogaster

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

Organic Synthesis and Reactivity of Porphyrins

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