69458-21-5Relevant academic research and scientific papers
Novel porphyrin-quinone architectures via 1,3-dipolar cycloaddition reactions
Zhao, Shengxian,Neves, Maria G.P.M.S.,Tomé, Augusto C.,Silva, Artur M.S.,Cavaleiro, José A.S.
, p. 5487 - 5490 (2005)
Porphyrinic pyridinium ylides react with 1,4-benzoquinone and 1,4-naphthoquinone to afford novel meso-substituted indolizine porphyrins.
Reactive hydrogen sulfide fluorescent probe and preparation and application thereof
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Paragraph 0048; 0049, (2021/09/29)
The invention discloses a reactive hydrogen sulfide fluorescent probe and preparation and application thereof. The method comprises the following steps: dissolving 5-(4-pyridyl)-10, 15, 20-tri (4-sulfonyl phenyl) porphyrin (p-PyTS) and a 2-substituted benzoic acid-4-bromomethyl phenyl ester derivative (2-PBr) in dimethyl sulfoxide according to a molar ratio of 2: 1 to form a solution with 2-PBr of 0.2 mmol/mL, carrying out heating reflux reaction for 2 hours, and purifying to obtain the final product porphyrin-phenyl ester (p-Pium) probe. The probe is good in water solubility, a fluorescence signal is obviously enhanced when hydrogen sulfide in an aqueous solution is subjected to fluorescence detection, and the probe has relatively high sensitivity and selectivity; in combination with a laser confocal scanning microtechnique, fluorescence detection imaging of the probe on hydrogen sulfide in living cells can also be realized.
Crystal material containing metal iridium-monopyridyl porphyrin, and preparation method thereof
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Paragraph 0038; 0041; 0042, (2019/01/15)
The invention belongs to the field of laser protection materials, and discloses a nonlinear optical crystal material formed by coordination connection between a metal iridium dimer and 5,10,15-triphenyl-20-(4-pyridyl)porphyrin, and a preparation method th
Photodynamic effect of meso-(aryl)porphyrins and meso-(1-methyl-4-pyridinium)porphyrins on HaCaT keratinocytes
Slomp, Amanda M.,Barreira, Sandra M.W.,Carrenho, Luise Z.B.,Vandresen, Camila C.,Zattoni, Ingrid F.,Ló, Stephanie M.S.,Dallagnol, Juliana C.C.,Ducatti, Diogo R.B.,Orsato, Alexandre,Duarte, M. Eugênia R.,Noseda, Miguel D.,Otuki, Michel F.,Gon?alves, Alan G.
supporting information, p. 156 - 161 (2016/12/27)
Sixteen porphyrins, including neutral, anionic and cationic meso-(aryl)porphyrins and meso-(1-methyl-4-pyridinium)porphyrins were herein evaluated in terms of their photosensitizing properties against HaCaT keratinocytes. After an initial screening, the cationic porphyrins were studied in more details, by both determining their log POWand performing PDT assays in lower porphyrin concentrations. Porphyrins presenting two or more adjacent positively charged groups, directly linked to the macrocycle meso positions, appeared to be the most effective photosensitizers. The present study also included the dicationic 5,10-diphenyl-15,20-di(1-methylpyridinium-4-yl)porphyrin (14b), which has previously shown promising results on a psoriasis-like in vivo model. Overall results indicated that the beneficial effect related to porphyrins on psoriasis can be related to the decreasing of keratinocyte viability. Furthermore, some of the cationic porphyrins studied appeared as candidates to be utilized as photosensitizers for psoriasis treatment.
In vitro photodynamic inactivation of conidia of the phytopathogenic fungus Colletotrichum graminicola with cationic porphyrins
Vandresen, Camila Chevonica,Gon?alves, Alan Guilherme,Ducatti, Diogo Ricardo Bazan,Murakami, Fabio Seigi,Noseda, Miguel Daniel,Duarte, Maria Eugenia Rabello,Barreira, Sandra Mara Woranovicz
, p. 673 - 681 (2016/06/01)
Photodynamic inactivation (PDI) is an efficient approach for the elimination of a series of microorganisms; however, PDI involving phytopathogenic filamentous fungi is scarce in the literature. In the present study, we have demonstrated the photoinactivating properties of five cationic meso-(1-methyl-4-pyridinio)porphyrins on conidia of the phytopathogen Colletotrichum graminicola. For this purpose, photophysical properties (photostability and 1O2 singlet production) of the porphyrins under study were first evaluated. PDI assays were then performed with a fluence of 30, 60, 90 and 120 J cm-2 and varying the porphyrin concentration from 1 to 25 μmol L-1. Considering the lowest concentration that enabled the best photoinactivation, with the respective lowest effective irradiation time, the meso-(1-methyl-4-pyridinio)porphyrins herein studied could be ranked as follows: triple-charged 4 (1 μmol L-1 with a fluence of 30 J cm-2) > double-charged-trans2 (1 μmol L-1 with 60 J cm-2) > tetra-charged 5 (15 μmol L-1 with 90 J cm-2) > mono-charged 1 (25 μmol L-1 with 120 J cm-2). Double-charged-cis-porphyrin 3 inactivated C. graminicola conidia in the absence of light. Evaluation of the porphyrin binding to the conidia and fluorescence microscopic analysis were also performed, which were in agreement with the PDI results. In conclusion, the cationic porphyrins herein studied were considered efficient photosensitizers to inactivate C. graminicola conidia. The amount and position of positive charges are related to the compounds' amphiphilicity and therefore to their photodynamic activity.
Hyperporphyrin effects in the spectroscopy of protonated porphyrins with 4-aminophenyl and 4-pyridyl meso substituents
Wang, Chenyi,Wamser, Carl C.
, p. 3605 - 3615 (2014/06/09)
Spectrophotometric titrations for a full series of 4-aminophenyl/4-pyridyl meso-substituted porphyrins were carried out using methanesulfonic acid in DMSO to study the hyperporphyrin effect across different substitution patterns. The series included zero, one, two (cis and trans), three, and four meso(4-aminophenyl) groups, with the remaining meso substituents being 4-pyridyl groups. The peripheral pyridyl groups consistently protonate before the interior porphyrin pyrrole nitrogens, which protonate before the aminophenyl groups. Aminophenyl substituents increase the basicity of the pyrrole nitrogens and lead to distinctive hyperporphyrin spectra with a broad Soret band and a strong red absorption. The structure proposed to give rise to these spectra is the previously proposed charge-transfer interaction between the aminophenyl and the protonated pyrrole. A novel hyperporphyrin structure involving charge-transfer interactions between two peripheral substituents is also proposed in one case, the triply protonated (+3) porphyrin with three aminophenyls and one pyridyl substituent; two of the aminophenyl groups delocalize the charges on the interior nitrogens, while the third aminophenyl group delocalizes with the protonated pyridyl.
Two-photon oxygen sensing with quantum dot-porphyrin conjugates
Lemon, Christopher M.,Karnas, Elizabeth,Bawendi, Moungi G.,Nocera, Daniel G.
, p. 10394 - 10406 (2013/10/01)
Supramolecular assemblies of a quantum dot (QD) associated to palladium(II) porphyrins have been developed to detect oxygen (pO2) in organic solvents. Palladium porphyrins are sensitive in the 0-160 Torr range, making them ideal phosphors for i
Correlation of photodynamic activity and singlet oxygen quantum yields in two series of hydrophobic monocationic porphyrins
Deda, Daiana K.,Pavani, Christiane,Caritá, Eduardo,Baptista, Maurício S.,Toma, Henrique E.,Araki, Koiti
experimental part, p. 55 - 63 (2012/07/14)
The photodynamic properties of eight hydrophobic monocationic methyl and ruthenium polypyridine complex derivatives of free-base and zinc(II) meso-triphenyl-monopyridylporphyrin series were evaluated and compared using HeLa cells as model. The cream-like
Synthesis and cancer cell cytotoxicity of water-soluble gold(III) substituted tetraarylporphyrin
Sun, Liang,Chen, Huasheng,Zhang, Zonglei,Yang, Qian,Tong, Haibo,Xu, Aihua,Wang, Cunde
experimental part, p. 47 - 52 (2012/06/18)
The synthesis of novel substituted gold(III) tetraarylporphyrins with aqueous solubility has been carried out. The analogs ClAuTPP(CH 3Py+?I-), ClAuTCPPNa, ClAuTPPCO 2Na, ClAuTSPPNa and ClAuTPPNH2?HCl were evaluated for their in vitro cytotoxic activity against sarcoma 180 mouse tumor and SGC-7901 human gastric cancer cell line panel. Compound ClAuTCPPNa exhibited significant growth inhibitory properties against sarcoma 180 mouse tumor and SGC-7901 human gastric cancer cell examined, and afforded IC50 values 2?HCl was an effective inhibitor of sarcoma 180 mouse tumor and SGC-7901 human gastric cancer cell growth, but generally less effective as a cytotoxic agent. Thus, the substituted gold(III) porphyrin ClAuTCPP-Na + and ClAuTPPNH2?HCl with aqueous solubility were regarded as useful lead compounds for further structural optimization.
Synthesis and biological evaluation of gold(III) substituted tetraarylporphyrin chlorides as anticancer reagents
Chen, Huasheng,Yang, Qian,Sun, Liang,Zhang, Zonglei,Tong, Haibo,Xu, Aihua,Wang, Cunde
experimental part, p. 190 - 194 (2011/07/29)
Substituted gold(III) tetraarylporphyrins have been synthesised. The analogues TPPAuCl (TPP = tetraphenylporhyrin), MeOTPPAuCl, TMOPPAuCl, MeO 2CTPPAuCl, O2NTPPAuCl and PyTPPAuCl were evaluated for their in vitro cytotoxic activity a
