22112-89-6Relevant articles and documents
Synthesis of mono- And disubstituted porphyrins: A- and 5,10-A 2-type systems
Ryppa, Claudia,Senge, Mathias O.,Hatscher, Sabine S.,Kleinpeter, Erich,Wacker, Philipp,Schilde, Uwe,Wiehe, Arno
, p. 3427 - 3442 (2005)
General syntheses have been developed for meso-substituted porphyrins with one or two substituents in the 5,10-positions and no β substituents. 5-Substituted porphyrins with only one meso substituent are easily prepared by an acid-catalyzed condensation of dipyrromethane, pyrrole-2-carbaldehyde, and an appropriate aldehyde using a "[2+1+1]" approach. Similarly, 5,10-disubstituted porphyrins are accessible by simple condensation of unsubstituted tripyrrane with pyrrole and various aldehydes using a "[3+1]" approach. The yields for these reactions are low to moderate and additional formation of either di- or monosubstituted porphyrins due to scrambling of the intermediates is observed. However, the reactions can be performed quite easily and the desired target compounds are easily removed due to large differences in solubility. A complementary and more selective synthesis involves the use of organolithium reagents for SNAr reactions. Reaction of in situ generated porphyrin (porphine) with 1.1-8 equivalents of RLi gave the monosubstituted porphyrins, while reaction with 3-6 equivalents of RLi gave the 5,10-disubstituted porphyrins in yields ranging from 43 to 90%. These hitherto almost inaccessible compounds complete the series of different homologues of A-, 5,15-A2-, 5,10-A2-, A3-, and A4-type porphyrins and allow an investigation of the gradual influence of type, number, and regiochemical arrangement of substituents on the properties of meso-substituted porphyrins. They also present important starting materials for the synthesis of ABCD porphyrins and are potential synthons for supramolecular materials requiring specific substituent orientations.
Core–shell poly-methyl methacrylate nanoparticles covalently functionalized with a non-symmetric porphyrin for anticancer photodynamic therapy
Ballestri, Marco,Caruso, Enrico,Guerrini, Andrea,Ferroni, Claudia,Banfi, Stefano,Gariboldi, Marzia,Monti, Elena,Sotgiu, Giovanna,Varchi, Greta
, p. 169 - 177 (2018)
Photodynamic therapy (PDT) is an anticancer modality that exploits singlet oxygen and other reactive oxygen species, that are formed by selective irradiation of photosensitive molecules, to kill cancer cells. Most photosensitizers (PS) are hydrophobic and poorly soluble in water and several nanoplatforms have been established to achieve a more efficient delivery. Moreover, the covalent binding of the PS to nanoparticles could in principle reduce unwanted bleaching of the PS, while preserving its photodynamic activity. In this study we report the synthesis of a novel non-symmetrical diaryl-porphyrin suitably modified with a polymerizable pendant, that was used for the preparation of core-shell poly-methyl methacrylate nanoparticles covalently loaded with the diaryl-porphyrin (PMMA@PorVa). Particles, which were prepared with two different porphyrin loadings, are spherical in shape and with a narrow hydrodynamic diameter around 70 nm and a positive zeta potential. Their photo-toxicity was tested against the human colon carcinoma cell line HCT116 and the human ovarian adenocarcinoma cell line SKOV3. PMMA@PorVa were able to inhibit tumor cells proliferation similarly to the free porphyrin, thus confirming that the covalent attachment of the PS to PMMA nanoparticles allows to preserve PS photodynamic activity and in vitro efficacy. Flow cytometric analysis of apoptotic cells demonstrates that, especially in SKOV3 cells, the free diaryl-porphyrin is more effective in inducing apoptosis.
Exploration of meso-substituted formylporphyrins and their Grignard and Wittig reactions
Dahms, Katja,Senge, Mathias O.,Bakar, M. Bakri
, p. 3833 - 3848 (2007)
Formylporphyrins were prepared by using either the 1,3-dithian-2-yl residue as a precursor for the CHO group or by the Vilsmeier reaction. Two synthetic routes for the introduction of the 1,2-dithian-2-yl group were explored. Furthermore, reactions of the
METHOD FOR PREPARING PORPHYRIN DERIVATE
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Paragraph 0070; 0074-0095, (2019/05/22)
The present invention relates to a method for manufacturing porphyrin derivatives, comprising a step of oxidizing porphyrinogen by oxygen bubbling under a metal catalyst to synthesize porphyrin derivatives. Therefore, since the method for manufacturing porphyrin derivatives of the present introduced a method of oxidization using oxygen bubbling under the metal catalyst without using a quinone-based oxidizing agent, it is possible to increase the yield of porphyrin derivatives and have an effect that a refining process is very easy.COPYRIGHT KIPO 2019
