132345-39-2Relevant academic research and scientific papers
β-Maleimide substituted meso-arylporphyrins: Synthesis, transformations, physico-chemical and antitumor properties
Ol'shevskaya, Valentina A.,Alpatova, Viktoriya M.,Radchenko, Alexandra S.,Ramonova, Alla A.,Petrova, Albina S.,Tatarskiy, Victor V.,Zaitsev, Andrei V.,Kononova, Elena G.,Ikonnikov, Nikolay S.,Kostyukov, Alexey A.,Egorov, Anton E.,Moisenovich, Mikhail M.,Kuzmin, Vladimir A.,Bragina, Natalya A.,Shtil, Alexander A.
, (2019/08/12)
The maleimide moiety is widely used in drug design. To explore the properties of maleimide containing photosensitizers we obtained a series of new β-maleimide functionalized meso-arylporphyrins through acylation of β-amino group in porphyrins with maleic anhydride followed by condensation of maleic acid monoamides. The selective reactivity of porphyrin maleimides toward thiols was demonstrated using mercaptocarboranes and cysteine. New derivatives retained the ability of tetrapyrrolic macrocyclic compounds to absorb light in visible spectral region and to generate triplet states and reactive oxygen species upon photoactivation. Importantly, illumination of cells loaded with a cell permeable 2-{3-[(o-carboran-1′-yl)thio]pyrrolidine-2,5-dione-1-yl}-5,10,15,20-tetraphenylporphyrin triggered rapid (within the initial minutes) generation of superoxide anion radical concomitantly with a decrease of mitochondrial membrane potential, and then the loss of the plasma membrane integrity and cell death. Thus, the maleimide-substituted porphyrins represent a new chemotype of polyfunctionalized compounds for an in-depth investigation as photosensitizers in cancer and beyond.
Beta-(2,3-dihydro-naphthyl[1,2,e]-m-oxazinyl) tetraphenylporphyrin, and preparation method and application thereof
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, (2017/05/12)
The invention discloses beta-(2,3-dihydro-naphthyl[1,2,e]-m-oxazinyl)tetraphenylporphyrin of which the structural general formula is disclosed as Formula (I) or Formula (II), and a preparation method and application thereof. The preparation method comprises the following steps: 1) preparing 5,10,15,20-tetraphenyl porphyrin from pyrrole and benzaldehyde, carrying out coordination with copper to obtain 5,10,15,20-tetraphenyl copper porphyrins, carrying out regioselective nitration to obtain beta-nitro-substituted-5,10,15,20-tetraphenyl copper porphyrins, carrying out decoppering and reduction to obtain beta-amino-substituted-5,10,15,20-tetraphenyl porphyrins, and reacting with acetate to obtain beta-amino-substituted-tetraphenyl metalloporphyrins (beta-NH2-MTPP); 2) carrying out condensation reaction on the beta-NH2-MTPP, formaldehyde and 2-naphthol, separating the product by column chromatography to obtain a beta-(2,3-dihydro-1H-naphthyl[1,2,e]-m-oxazinyl)-substituted tetraphenyl porphyrin metal complex; and decoppering to obtain the beta-(2,3-dihydro-naphthyl[1,2,e]-m-oxazinyl)tetraphenylporphyrin. The compounds can be used for preparing photodynamic-therapy photosensitizers and antineoplastic drugs with small toxic and side effects and high activity.
