22112-84-1Relevant articles and documents
Specific modification and self-transport of porphyrins and their multi-mechanism cooperative antitumor studies
Jia, Shuxin,Wang, Shaochen,Li, Shanshan,Hu, Peng,Yu, Shuling,Shi, Jiahua,Yuan, Jintao
, p. 3180 - 3191 (2021)
In order to reduce the toxicity and side effects of anti-tumor drugs and improve their therapeutic effect against cancer, photodynamic and chemical combination therapy has been exploited. However, the complicated preparation and metabolic toxicity of photosensitizer-loaded materials remain major obstacles for bioapplications. In this study, we designed and prepared a specific photosensitizer self-transporting drug-delivery system. First, 5,10,15,20-tetrakis(4-aminophenyl)-21H,23H-porphine (TAPP) was modified using specific molecules ofd-α-tocopheryl polyethylene glycol 1000 succinate (TPGS) with a certain antitumor effect, to prepare a specific fluorescent amphiphilic system (TAPP-TPGS). Then, the drug-loaded fluorescence nanomicelle (TAPP-TPGS/PTX) was formedviaself-assembly using the amphiphilic system and the anticancer drug paclitaxel (PTX). The carrier material could be used as a drug tracer and cancer therapy reagent to synergistically trace the chemotherapy drug and treat cancers. The biocompatibility and the enhanced antitumor effect of TAPP-TPGS/PTX were confirmed byin vitroandin vivoexperiments. To detect the synergistic anticancer effect enhanced by TPGS, TAPP-mPEG synthesized with a similar method as TAPP-TPGS was used for a comparative analysis. The results showed that the excellent synergistic anticancer effect of the TAPP-TPGS/PTX was enhanced due to the introduction of TPGS. Thus, the specific porphyrin self-transporting nanomicelle is a very promising carrier material for applications in biomedicine.
Further insight into aryl nitration of tetraphenylporphyrin
Xue, Zhi,Lee, Priscilla P.S.,Wang, Yanming,Kwong, Daniel W.J.,Li, Jing,Xin, John H.,Wong, Wai-Kwok,Cheuk, Kevin K.L.
, p. 6030 - 6035 (2011)
We report an in-depth study on meso-aryl nitration of tetraphenylporphyrin. In contrast to previous studies, new evidence reveals that tetrakis(p- nitrophenyl) derivative can be obtained as a major product. Successful isolation of the barely soluble product toward a remarkable yield of nearly 90% has been reached by means of a solid phase extraction technique. Distribution of different nitro-porphyrin components is reassessed with respect to varying acid content in the reactions. An ortho-effect model is proposed to describe the formation mechanism.
High-yielding syntheses of hydrophilic conjugatable chlorins and bacteriochlorins
McCarthy, Jason R.,Bhaumik, Jayeeta,Merbouh, Nabyl,Weissleder, Ralph
, p. 3430 - 3436 (2009)
Next-generation photodynamic therapy agents based upon the conjugation of multiple photosensitizers to a targeting backbone will allow for more efficacious light-based therapies. To this end, we have developed glucose-modified chlorins and bacteriochlorins featuring a reactive carboxylic acid linker for conjugation to targeting moieties. The photosensitizers were synthesized in relatively high yields from meso-tetra(p-aminophenyl)porphyrin, and resulted in neutral, hydrophilic chromophores with superb absorption profiles in the far-red and near-infrared portions of the electromagnetic spectrum. In addition, conjugation of these photosensitizers to a model nanoscaffold (crosslinked dextran-coated nanoparticles) demonstrated that the inclusion of hydrophilic sugar moieties increased the number of dyes that can be loaded while maintaining suspension stability. The described compounds are expected to be particularly useful in the synthesis of a number of targeted nanotherapeutic systems.
Synthesis and properties of 5,10,15,20-tetrakis[4-(3,5-dioctyloxybenzamido) phenyl]porphyrin and its metal complexes
Lian, Wenhui,Sun, Yuanyuan,Wang, Binbin,Shan, Ning,Shi, Tongshun
, p. 335 - 348 (2012)
A novel 5,10,15,20-tetrakis[4-(3,5-dioctyloxybenzamido)phenyl]-porphyrin and its transition metal complexes are reported in this paper. Their molecular structures were characterized by elemental analysis as well as IR, 1H-NMR and UV-Vis spectroscopy. Their spectroscopic properties were studied by Raman and fluorescence spectroscopy, and X-ray photoelectron spectroscopy (XPS). The fluorescence quantum yields were measured at room temperature. The fluorescence intensity of the porphyrin ligand was stronger than the intensity of the complexes. There were large differences in the Raman spectrum of the porphyrin ligand and those of the metal complexes due to changes in the symmetry of porphyrin plane. In the XPS spectra, the replacement of the free-base protons by a metal ion to form the metalloporphyrin not only increases the symmetry of the molecule, but also introduces an electron withdrawing group into the center of the porphyrin ligand, which increases the N1S binding energy.
Relative reactivities of activated carboxylic acids in amide-forming reactions employed for the synthesis of tetraphenylporphyrin libraries
Dombi, Kendra L.,Richert, Clemens
, p. 1265 - 1280 (2000)
Presented here is a method for rapidly testing the reactivity of carboxylic acids in amide-forming reactions. For this, a mixture of two acids, one a reference compound, and one acid whose reactivity is unknown, are coupled to an aminoacylated tetrakis(p-aminophenyl)porphyrin under typical peptide coupling conditions. The product distribution in the resulting library is analyzed via MALDI-TOF mass spectrometry to reveal the relative reactivity. This rapid reactivity test requires sub-nanomole quantities of acids, does not involve cleavage from a support or any potentially biasing work-up, and is automatable. Thus, it is well suited for testing building blocks for combinatorial syntheses. Further, it is demonstrated that step-wise coupling can produce near-statistically distributed libraries of porphyrins when acids of very different reactivity are employed.
SYNTHESIS OF TETRAPHENYLPORPHINS WITH ACTIVE GROUPS IN THE PHENYL RINGS. 1. PREPARATION OF TETRAKIS(4-AMINOPHENYL)PORPHIN
Semeikin, A. S.,Koifman, O. I.,Berezin, B. D.
, p. 1046 - 1047 (1982)
Condensation of p-nitrobenzaldehyde with pyrrole in propionic acid with added acetic anhydride gave tetrakis(4-nitrophenyl)porphin (24percent), by the reduction of which tetrakis(4-aminophenyl)porphin, which was also obtained by hydrolysis of tetrakis(4-acetamidophenyl)porphin, was synthesized.
Amino-metalloporphyrin polymers derived Fe single atom catalysts for highly efficient oxygen reduction reaction
Gan, Tao,He, Qian,He, Xiaohui,Ji, Hongbing,Meng, Yuying,Sun, Qingdi,Xiao, Huajian,Zhang, Hao,Zhang, Ying
, p. 810 - 817 (2020)
Recently, nitrogen-doped porous carbon supported single atom catalysts (SACs) have become one of the most promising alternatives to precious metal catalysts in oxygen reduction reaction (ORR) due to their outstanding performance, especially those derived from porphyrin-based materials. However, most of them involve other metal residuals, which would cause the tedious pre- and/or post-treatment, even mislead the mechanistic investigations and active-site identification. Herein, we report a precursor-dilution strategy to synthesize Fe SACs through the Schiff-based reaction via co-polycondensation of amino-metalloporphyrin, followed by pyrolysis at high temperature. Systematic characterization results provide the compelling evidence of the dominant presence of atomically dispersed Fe-Nx species. Our catalyst shows superior ORR performance with positive half-wave potential (E1/2=0.85 V vs. RHE) in alkaline condition and moderate activity (E1/2=0.68 V vs. RHE) under the acidic condition, excellent methanol tolerance and good long-term stability. All the results indicate Fe SACs would be a promising candidate for replacing the precious Pt in metal-air batteries and fuel cells.
Novel graphene capsule-aminoporphyrin nanohybrids: Preparation and application in photodynamic therapy of cancer
Liu, Guoli,Lv, Hongying,Zhao, Jing,Zhang, Shen,Sun, Shuqing
, p. 56062 - 56072 (2017)
In this work, we firstly prepared new sealed graphene capsules (GCs) that were about 300 nm in size and had different morphologies using a simple reduction method. The quality of the graphene oxide (GO) sheets and the concentration of hydrazine hydrate are proposed to be influencing factors for the formation of sealed graphene capsules. GCs are covalently functionalized with 5,10,15,20-tetra-(4-aminophenyl)porphyrin, forming dispersible GC-aminoporphyrins in aqueous solution. The observed fluorescence quenching of the GCs by the aminoporphyrin indicated that the GCs are electron donors and electron transfer occurs from the GCs to the aminoporphyrin. This F?rster Resonance Energy Transfer (FRET) between the GCs and aminoporphyrins is probably the reason for the enhancement of 1O2 generation of the GC-aminoporphyrins. More importantly, the as-prepared GC-aminoporphyrin nanohybrids as novel photosensitizers (PSs) with a short excitation wavelength can be used as PDT reagents for the treatment of malignant melanoma A375 with high efficiency. We expect that GC-aminoporphyrins will be promising PSs in future cancer therapy.
In situ bottom-up synthesis of porphyrin-based covalent organic frameworks
Tavakol, Elham,Kakekhani, Arvin,Kavani, Shayan,Tan, Peng,Ghaleni, Mahdi Mohammadi,Zaeem, Mohsen Asle,Rappe, Andrew M.,Nejati, Siamak
, p. 19560 - 19564 (2019)
Synthesis and processing of two-or three-dimensional covalent organic frameworks (COFs) have been limited by solvent intractability and sluggish condensation kinetics. Here, we report on the electrochemical deposition of poly(5,10,15,20-tetrakis(4-aminophenyl)porphyrin)-covalent organic frameworks (POR-COFs) via formation of phenazine linkages. By adjusting the synthetic parameters, we demonstrate the rapid and bottom-up synthesis of COF dendrites. Both experiment and density functional theory underline the prominent role of pyridine, not only as a polymerization promoter but as a stabilizing sublattice, cocrystallizing with the framework. The crucial role of pyridine in dictating the structural properties of such a cocrystal (Py-POR-COF) is discussed. Also, a structure-to-function relationship for this class of materials, governing their electrocatalytic activity for the oxygen reduction reaction in alkaline media, is reported.
Synthesis of novel porphyrin derivatives and their self-assemblies to enhance photocatalytic performance
Pei, Jinghe,Gao, Bo,Li, Yanhui,Duan, Qian
, p. 3454 - 3462 (2021)
Three new porphyrin derivatives were synthesized from tetra (4-aminophenyl) porphyrin (TAPP), namely tetra[p-(4-cyanophenylmethylene imino)]phenyl porphyrin (TCyPPP), tetra[p-(P-benzylidene)]phenyl porphyrin (TbePPP) and tetra[p-(4-pyridylimethylene imino)]phenyl porphyrin (TPyPPP). Based on the principle of self-assembly, three kinds of porphyrin derivatives were self-assembled to prepare three kinds of monomers. The structures were characterized clearly by UV-vis, FT-IR, 1H NMR and SEM. The photocatalytic performance study shows that the self-assemblies of the three porphyrin derivatives have stronger photocatalytic performance than their monomers. Moreover, the self-assemblies and their monomers have good photocatalytic stability. This journal is
