22112-79-4Relevant articles and documents
Development of antimicrobial laser-induced photodynamic therapy based on ethylcellulose/chitosan nanocomposite with 5,10,15,20-tetrakis(M-hydroxyphenyl)porphyrin
Hasanin, Mohamed S.,Abdelraof, Mohamed,Fikry, Mohamed,Shaker, Yasser M.,Sweed, Ayman M. K.,Senge, Mathias O.
, (2021)
The development of new antimicrobial strategies that act more efficiently than traditional antibiotics is becoming a necessity to combat multidrug-resistant pathogens. Here we report the effi-cacy of laser-light-irradiated 5,10,15,20-tetrakis(m-hydroxyphenyl)porphyrin (mTHPP) loaded onto an ethylcellulose (EC)/chitosan (Chs) nanocomposite in eradicating multi-drug resistant Pseudomonas aeruginosa, Staphylococcus aureus, and Candida albicans. Surface loading of the ethylcelllose/chitosan composite with mTHPP was carried out and the resulting nanocomposite was fully characterized. The results indicate that the prepared nanocomposite incorporates mTHPP inside, and that the composite acquired an overall positive charge. The incorporation of mTHPP into the nanocomposite enhanced the photo-and thermal stability. Different laser wavelengths (458; 476; 488; 515; 635 nm), powers (5–70 mW), and exposure times (15–45 min) were investigated in the antimicrobial pho-todynamic therapy (aPDT) experiments, with the best inhibition observed using 635 nm with the mTHPP EC/Chs nanocomposite for C. albicans (59 ± 0.21%), P. aeruginosa (71.7 ± 1.72%), and S. aureus (74.2 ± 1.26%) with illumination of only 15 min. Utilization of higher doses (70 mW) for longer periods achieved more eradication of microbial growth.
Effects of substituents on the photophysical properties of symmetrical porphyrins
Ormond, Alexandra B.,Freeman, Harold S.
, p. 440 - 448 (2013)
Porphyrin compounds having groups that mimic the phenolic moiety of m- and p-isomers of 5,10,15,20-tetrakis(hydroxyphenyl) porphyrin (THPP) have been synthesized along with 5,10,15,20-tetrakis(heteroaryl) porphyrins bearing 2-thienyl and 5-thiazolyl groups. Absorption and fluorescence spectroscopy, including fluorescence lifetime (τf) and quantum yield (Φf) measurements, were employed to characterize the singlet excited state of all compounds, using 5,10,15,20-tetraphenylporphyrin (H 2TPP) as a standard (Φf = 0.12 in DMF). The generation of singlet oxygen by each porphyrin photosensitizer was measured as the singlet oxygen quantum yield (ΦΔ), using H2TPP as a standard (ΦΔ = 0.64 in DMF). Partition coefficients were determined using 2-octanol as the organic phase and PBS solution as the aqueous phase. Fluorescence quantum yields ranged from 0.01 to 0.18 for all compounds, with heteroaryl porphyrins having the lowest values. Singlet oxygen quantum yields ranged from 0.40 to 0.65, with heteroaryl porphyrins having the highest values, showing them to be better sensitizers than m- and p-THPP. Log P values were all >1 showing higher solubility in the 2-octanol layer.
Synthesis and biological distribution study of a new carbon-11 labeled porphyrin for PET imaging. Photochemical and biological characterization of the non-labeled porphyrin
Gonc?lves, Nuno P. F.,Sim?es, Ana V. C.,Abreu, Artur R.,Abrunhosa, Antero J.,D?browski, Janusz M.,Pereira, Mariette M.
, p. 946 - 955 (2015)
Ideal reaction conditions were found to promote the "cold" monomethylation of 5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrin with CH3I, at minute time scale, in the presence of base. The photophysical characterization, cellular uptake and dark cytotoxicity of the resulting monomethylated porphyrin were appraised. Moreover, the syntheses of the corresponding labeled porphyrin, using short-lived carbon-11, prepared in the automated radiolabeling system were efficiently performed. The purification of the labeled product was achieved via preparative HPLC with high radiochemical purity and specific radioactivity. Preliminary studies on the biodistribution of 5,10,15-tris(3-hydroxyphenyl)-20-(3-[11C]methoxyphenyl)porphyrin carried out in a BALB/C normal mouse, using PET imaging, showed that the liver is the main pathway for excretion.
New approach for the synthesis, docking of new porphyrins and their antitumor activity
Tawfik, Eman H.,Fadda, Ahmed A.,Soliman, Nanees N.,Abou-Zeid, Laila,Negm, Amr
, p. 251 - 259 (2019/02/24)
A new methodology for the synthesis of a new series of mesotetrakis[aryl]-21H,23H-porphyrin derivatives 5a-5d, 6a-6c, 7 and 8 is presented. Structures of new compounds were established based on both elemental and spectral data. Cytotoxicity activity of the newly synthesized compounds was investigated against two human cell lines MCF-7 and HepG2. Molecular docking was performed to investigate the binding between the most active porphyrin derivatives and Bcl-2 molecular biomarkers in HepG2 cells.
A four-phenyl porphine preparation method
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Paragraph 0060; 0110-0116, (2018/03/26)
The invention discloses a preparation method of meso-tetraphenylchlorin. The preparation method comprises the steps that 1, a mixed solution of pyrrole and aromatic aldehyde is prepared for standby; 2, a solvent is added into a polymerization reactor, nitrogen displacement is conducted till the concentration of tail oxygen is lower than 1%, the solvent is heated to backflow, the mixed solution obtained in the first step starts to be dropwise added, a reaction is started, after the mixed solution is dropwise added completely, the reaction is continuously conducted for 0.05 h to 0.5 h, and then the reaction is stopped; 3, oxygen-containing gas with the oxygen volume fraction ranging from 5% to 100% is fed into the polymerization reactor for oxidation, cooling is conducted after the oxidation is completed, filtration is conducted to obtain a filter cake and filtrate, and a product is obtained after the filter cake is washed and dried. The preparation method of the meso-tetraphenylchlorin has the advantages that the yield is high, safety and environmental protection are achieved, separation and purification are easy, and the product quality is stable.
