Dimethyl and diethyl carbaporphyrin ketals inhibit the growth of Leishmania tarentolae promastigotes in vitro. The concentration dependency of the inhibitory effect was tested using the MTT assay. The presence of reactive oxygen species, such as singlet oxygen and superoxide, was detected using electron paramagnetic resonance spectroscopy with selected spin traps and confocal microscopy in cultures exposed to these carbaporphyrin ketals. These unique porphyrinoids show promise as potent inhibitors of Leishmania.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1016/j.bmc.2008.05.037 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
DDQ-supported alkoxylation of 2-aza-21-carbaporphyrin and noncatalyzed transetherification of its 3,21-dialkoxy derivatives.
J Org Chem
September 2012
Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education, Hunan, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan 411201, China.
An oxidative addition of primary alkoxyls into two sites of N-confused porphyrin (NCP) has been accomplished by means of alcohols in the presence of a stoichiometric amount of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). The resulting aromatic monocationic species 1-R(3) (R = Me, Et) were characterized by the NMR and, in the case of triethoxy-NCP, by monocrystal X-ray diffraction analysis. One alkoxy group is located in position 3, on the macrocycle's perimeter, while two -OR moieties are attached to the internal carbon (position 21) of the confused pyrrole.
View Article and Find Full Text PDFIn vitro and in vivo studies of the utility of dimethyl and diethyl carbaporphyrin ketals in treatment of cutaneous leishmaniasis.
Antimicrob Agents Chemother
October 2011
PECET, School of Medicine, Universidad de Antioquia, Carrera 53 No. 61-30, Medellín, Colombia.
Carbaporphyrin ketals are porphyrinoid compounds in which a pyrrole ring of a typical porphyrin macrocycle has been replaced by a ketal-substituted indene ring. It was recently demonstrated that these compounds are effective in vitro against Leishmania tarentolae. Their in vitro effectiveness is increased when they are exposed to visible light; they act as photosensitizers capable of mediating the production of reactive oxygen species (ROS).
View Article and Find Full Text PDFCarbaporphyrin ketals as potential agents for a new photodynamic therapy treatment of leishmaniasis.
Bioorg Med Chem
July 2008
Department of Chemistry, Illinois State University Normal, IL 61790-4160, USA.
Dimethyl and diethyl carbaporphyrin ketals inhibit the growth of Leishmania tarentolae promastigotes in vitro. The concentration dependency of the inhibitory effect was tested using the MTT assay. The presence of reactive oxygen species, such as singlet oxygen and superoxide, was detected using electron paramagnetic resonance spectroscopy with selected spin traps and confocal microscopy in cultures exposed to these carbaporphyrin ketals.
View Article and Find Full Text PDFRegioselective oxidations of benzocarbaporphyrins with ferric chloride: a facile synthesis of bridged [18]annulene ketals with strong absorptions in the far red and an unexpected halogenation reaction at the interior carbon atom.
J Org Chem
October 2003
Department of Chemistry, Illinois State University, Normal, Illinois 61790-4160, USA.
Benzocarbaporphyrins 4 were found to undergo regioselective oxidations with ferric chloride in methanol, ethanol, isopropyl alcohol, or ethylene glycol to give bridged benzo[18]annulene ketal derivatives 5 in excellent yields. These polar derivatives were generally isolated in a monoprotonated form and the corresponding free bases appeared to be relatively unstable. Addition of TFA resulted in the formation of spectroscopically distinct dications.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!