39050-26-5Relevant articles and documents
Interaction between novel porphyrin-dextran nanoparticles and human serum albumin
Zhang, Zhi,Guo, Qian-Ni,Lu, Yun-Guo,Jia, Tao,Yan, Kun,Li, Zao-Ying
, p. 264 - 270 (2010)
A novel porphyrin-dextran coated Fe3O4 nanoparticle (5) was designed and synthesized. The structure of 5 was confirmed by IR, UV-vis and inductively coupled plasma atomic emission spectrometry, and dynamic laser scattering (DLS); magnetic property was measured by a vibrating sample magnetometer (VSM). The interaction between compound 5 and human serum albumin (HSA) was investigated through UV-vis absorbance spectra and fluorospectrophotometer, compared with the 5-(4-aminophenyl)-10,15,20-tris-(4- sulfonatophenyl)porphyrin, trisodium salt (3). The results showed compound 5 containing porphyrin moiety and 3 could interact with HSA. The quenching constant (Ksv) was 4.739 × 105 M-1 for 3, and 2.846 × 105 M-1 for 5; the apparent affinity binding constant (KA) was 8.562 × 103 M-1 for 3, and 4.978 × 104 M-1 for 5.
One-Step Labeling of Collagen Hydrogels with Polydopamine and Manganese Porphyrin for Non-Invasive Scaffold Tracking on Magnetic Resonance Imaging
Szulc, Daniel Andrzej,Cheng, Hai-Ling Margaret
, (2019)
Biomaterial scaffolds are the cornerstone to supporting 3D tissue growth. Optimized scaffold design is critical to successful regeneration, and this optimization requires accurate knowledge of the scaffold's interaction with living tissue in the dynamic in vivo milieu. Unfortunately, non-invasive methods that can probe scaffolds in the intact living subject are largely underexplored, with imaging-based assessment relying on either imaging cells seeded on the scaffold or imaging scaffolds that have been chemically altered. In this work, the authors develop a broadly applicable magnetic resonance imaging (MRI) method to image scaffolds directly. A positive-contrast “bright” manganese porphyrin (MnP) agent for labeling scaffolds is used to achieve high sensitivity and specificity, and polydopamine, a biologically derived universal adhesive, is employed for adhering the MnP. The technique was optimized in vitro on a prototypic collagen gel, and in vivo assessment was performed in rats. The results demonstrate superior in vivo scaffold visualization and the potential for quantitative tracking of degradation over time. Designed with ease of synthesis in mind and general applicability for the continuing expansion of available biomaterials, the proposed method will allow tissue engineers to assess and fine-tune the in vivo behavior of their scaffolds for optimal regeneration.
Harnessing nature's insights: Synthetic small molecules with peroxidase-mimicking DNAzyme properties
Stefan, Loic,Xu, Hai-Jun,Gros, Claude P.,Denat, Franck,Monchaud, David
, p. 10857 - 10862 (2011)
Substitute features: The demonstration that small DNAs can acquire enzymatic properties (DNAzyme activity) is appealing since it makes protein-based biotechnologies simpler. Herein, two further simplifications of this process are proposed: the substitution of DNAs for small molecules, called DOTA-templated synthetic G-quartets (DOTASQ), and of hemin for the more practically convenient iron(III) porphyrin (FeTPPS; see scheme). Copyright
Photodegradation of Rhodamine B using Aqueous Free-Base Porphyrin and Metalloporphyrins of Divalent Metal Ions
Gokakakar, S. D.,Salker, A. V.
, p. 147 - 154 (2022/01/06)
The present study is focused on the photodegradation of rhodamine B using aqueous free-base photocatalysts in presence of solar radiation. All catalysts such as free-base tetrasodium meso-tetra(p-sulphonatophenyl)porphyrin (TPPS4) or abbreviated as TPS and substituting M = Co, Ni, Cu, Zn and Ag into the moiety of TPS to get metalloporphyrins, were synthesized. Further, they were characterized by UV-visible, IR and 1H MMR spectroscopic techniques. The photodegradation of rhodamine B of concentration 10-5 M was carried out with 5 mg of a photocatalyst of free-base and other metalloporphyrins. It was observed that these synthesized photocatalysts have shown the photodegradation efficiency to the extent of 100% within time period of 5 to 40 min. The process of degradation was verified with HPLC and ion-chromatography.
Porphyrin n-pincer pd(Ii)-complexes in water: A base-free and nature-inspired protocol for the oxidative self-coupling of potassium aryltrifluoroborates in open-air
Hanafiah, Marlia M.,Lakkaboyana, Sivarama Krishna,Lakshmidevi, Jangam,Marella, Ravi Kumar,Naidu, Bandameeda Ramesh,Prasad, Sana Siva,Venkateswarlu, Katta
, (2021/09/13)
Metalloporphyrins (and porphyrins) are well known as pigments of life in nature, since representatives of this group include chlorophylls (Mg-porphyrins) and heme (Fe-porphyrins). Hence, the construction of chemistry based on these substances can be based on the imitation of biological systems. Inspired by nature, in this article we present the preparation of five different porphyrin, meso-tetraphenylporphyrin (TPP), meso-tetra(p-anisyl)porphyrin (TpAP), tetra-sodium meso-tetra(p-sulfonatophenyl)porphyrin (TSTpSPP), meso-tetra(m-hydroxyphenyl)porphyrin (TmHPP), and meso-tetra(m-carboxyphenyl)porphyrin (TmCPP) as well as their N-pincer Pd(II)-complexes such as Pd(II)-meso-tetraphenylporphyrin (PdTPP), Pd(II)-meso-tetra(p-anisyl)porphyrin (PdTpAP), Pd(II)-tetrasodium meso-tetra(p-sulfonatophenyl)porphyrin (PdTSTpSPP), Pd(II)-meso-tetra(m-hydroxyphenyl)porphyrin (PdTmHPP), and Pd(II)-meso-tetra(m-carboxyphenyl)porphyrin (PdTmCPP). These porphyrin N-pincer Pd(II)-complexes were studied and found to be effective in the base-free self-coupling reactions of potassium aryltrifluoroborates (PATFBs) in water at ambient conditions. The catalysts and the products (symmetrical biaryls) were characterized using their spectral data. The high yields of the biaryls, the bio-mimicking conditions, good substrate feasibility, evading the use of base, easy preparation and handling of catalysts, and the application of aqueous media, all make this protocol very attractive from a sustainability and cost-effective standpoint.
Conformational-Switch Based Strategy Triggered by [18] π Heteroannulenes toward Reduction of Alpha Synuclein Oligomer Toxicity
Chakraborty, Ritobrita,Sahoo, Sumit,Halder, Nyancy,Rath, Harapriya,Chattopadhyay, Krishnananda
, p. 573 - 587 (2018/10/31)
A water-soluble meso-carboxy aryl substituted [18] heteroannulene (porphyrin) and its Zn-complex have been found to be viable in targeting α-Syn aggregation at all its key microevents, namely, primary nucleation, fibril elongation, and secondary nucleation, by converting the highly heterogeneous and cytotoxic aggresome into a homogeneous population of minimally toxic off-pathway oligomers, that remained unexplored until recently. With the EC50 and dissociation constants in the low micromolar range, these heteroannulenes induce a switch in the secondary structure of toxic prefibrillar on-pathway oligomers of α-Syn, converting them into minimally toxic nonseeding off-pathway oligomers. The inhibition of the aggregation and the reduction of toxicity have been studied in vitro as well as inside neuroblastoma cells.
A putative heme manganese(v)-oxo species in the C-H activation and epoxidation reactions in an aqueous buffer
Harmalkar, Dinesh S.,Santosh,Shetgaonkar, Siddhi B.,Sankaralingam, Muniyandi,Dhuri, Sunder N.
, p. 12900 - 12906 (2019/08/28)
A water-soluble manganese(v)-oxo species 1 was generated in the reaction of [Mn(iii)(TPPS)Cl] 2 (TPPS = 5,10,15,20-tetrakis(4-sulfonatophenyl)-21H,23H-porphine) and iodosylbenzene (PhIO) in a 2:1 aqueous buffer (pH = 10.4):acetonitrile (CH3CN) mixture. The formula of the EPR silent species 1 is proposed as [Mn(v)(O)(TPPS)Cl] based on the Soret band (422 nm) and Q bands (520, 660 nm) in its UV-vis spectrum and its reaction with thioanisole, regenerating 2 and methyl phenyl sulfoxide. The reactivity of 1 was investigated in the C-H activation of alkyl hydrocarbons and epoxidation of cyclohexene. Based on the observation of the linear correlation of the logarithm of the second rate constant (logk2′) and the bond dissociation energy (BDE, kcal mol-1) of alkyl hydrocarbons along with a large kinetic isotope effect (KIE = 8.5) for xanthene vs. xanthene-d2, we propose H-atom abstraction as the rate determining step in the C-H activation reactions. On the other hand, in contrast to the C-H activation reaction, cyclohexene, which has a weak C-H bond (BDE = 82.5 kcal mol-1), undergoes an epoxidation reaction.
5-Phenyl-10,15,20-Tris(4-sulfonatophenyl)porphyrin: Synthesis, catalysis, and structural studies
Arlegui, Aitor,El-Hachemi, Zoubir,Crusats, Joaquim,Moyano, Albert
, (2019/01/04)
A convenient protocol for the preparation of 5-phenyl-10,15,20-tris(4-sulfonatophenyl) porphyrin, a water-soluble porphyrin with unique aggregation properties, is described. The procedure relies on the one-pot reductive deamination of 5-(4-aminophenyl)-10,15,20-tris(4-sulfonatophenyl)porphyrin, that can be in turn easily obtained from 5,10,15,20-tetraphenylporphyrin by a known three-step sequence involving mononitration, nitro to amine reduction and sulfonation of the phenyl groups. This method provides the title porphyrin in gram scale, and compares very favorably with the up to now only described procedure based on the partial sulfonation of TPP, that involves a long and tedious chromatographic enrichment of the final compound. This has allowed us to study for the first time both the use of its zwitterionic aggregate as a supramolecular catalyst of the aqueous Diels–Alder reaction, and the morphology of the aggregates obtained under optimized experimental conditions by atomic force microscopy and also by transmission electron cryomicroscopy.
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.
Catalytic Aerobic Oxidation of Biomass-based Furfural into Maleic Acid in Aqueous Phase with Metalloporphyrin Catalysts
Huang, Yi,Wu, Chunyan,Yuan, Wenwen,Xia, Yongmei,Liu, Xiang,Yang, Huamei,Wang, Haijun
, p. 786 - 794 (2017/07/24)
Catalytic oxidation of renewable furfural into valuable maleic acid in aqueous solutions using metalloporphyrin catalysts was investigated for the first time. The synthesized catalysts were characterized by FT-IR, UV–vis, 1H NMR, elemental analysis, and TGA. The catalysts varied in metal active sites and functional groups, which had different effects on their catalytic activity. Furthermore, the effects of temperatures, reaction time, catalyst loading, and oxygen pressure were studied in detail. Maleic acid could be achieved in 44% yield by using FeT(p-Cl)PPCl as catalyst under optimal conditions. Finally, FeT(p-Cl)PPCl could be reused in five consecutive runs without a significant loss of activity.
