865668-82-2Relevant 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.
Formation and Isolation of a Four-Electron-Reduced Porphyrin Derivative by Reduction of a Stable 20π Isophlorin
Suzuki, Wataru,Kotani, Hiroaki,Ishizuka, Tomoya,Shiota, Yoshihito,Yoshizawa, Kazunari,Kojima, Takahiko
supporting information, p. 1973 - 1977 (2018/01/27)
The two-electron reduction of a diprotonated dodecaphenylporphyrin derivative by Na2S2O4 gave a corresponding isophlorin (Iph) selectively. Formation of Iph was confirmed by spectroscopic measurements and the isolation of tetramethylated Iph. Further reduction of Iph proceeded to form an unprecedented four-electron-reduced porphyrin (IphH2), which was fully characterized by spectroscopic and X-ray crystallographic analysis. IphH2, with a unique conformation, could be oxidized to reproduce the starting porphyrin, resulting in a proton-coupled four-electron reversible redox system.
Synthesis, spectral, structural and antimicrobial studies of fluorinated porphyrins
Kooriyaden, Fasalu Rahman,Sujatha, Subramaniam,Arunkumar, Chellaiah
, p. 66 - 74 (2015/06/08)
Abstract We have reported the synthesis, spectral and anti-microbial studies of 5,10,15,20-tetrakis(4′-trifluoromethylphenyl)porphyrin derivatives, MT(4′-CF3P)Ps where M = 2H, 1; Fe(II), 2; Ni(II), 3; Cu(II), 4; Zn(II), 5 and Pt(II), 6. The opt
