14172-91-9Relevant articles and documents
Synthesis, photophysical properties and biological evaluation of β-alkylaminoporphyrin for photodynamic therapy
Liao, Ping-Yong,Wang, Xin-Rong,Gao, Ying-Hua,Zhang, Xiang-Hua,Zhang, Li-Jun,Song, Chun-Hong,Zhang, Dan-Ping,Yan, Yi-Jia,Chen, Zhi-Long
, p. 6040 - 6047 (2016)
A series of β-alkylaminoporphyrins conjugated with different amines at β position (D1–D3) or with electron-donating and electron-withdrawing substituents at phenyl position (D4–D6) were synthesized. Their photophysical and photochemical properties, intracellular localization, photocytotoxicities in vitro and vivo were also investigated. All target compounds exhibited no cytotoxicities in the dark and excellent photocytotoxicities against HeLa cells. Among them, D6 showed the highest phototoxicity and the lowest dark toxicity, which was more phototoxic than Hematoporphyrin monomethyl ether (HMME). In addition, D6 exhibited best photodynamic antitumor efficacy on BALB/c nude mice bearing HeLa tumor. Therefore, D6 is a powerful and promising antitumor photosensitizer for photodynamic therapy.
Copper based macromolecular catalysts for the hydroxylation of phenols
Anjali, Kaiprathu,Ganesh, Venkatachalam,Christopher, Jayaraj,Sakthivel, Ayyamperumal
, (2020)
Copper containing macromolecules, viz., Copper-meso-tetrakis-(4-carboxyphenyl)porphyrin (CuTCPP) and Copper-meso-tetra-phenylporphyrin (CuTPP) complexes were synthesized and heterogenized on the surface of aminated SBA-15 molecular sieves. The 1H NMR, mass spectral and elemental (CHN) analyses were performed to confirm the formation of these copper complexes (CuTCPP and CuTPP). The absence of 1H NMR signal, characteristic of N[sbnd]H bond (-2.79 ppm in TCPP and -2.74 ppm in TPP) in CuTCPP and CuTPP clearly confirms the incorporation of copper ion in to the cavities of the TCPP and TPP ligands. In addition, the decreased intensity of the soret band and the reduction of the number of Q bands also supports the formation of copper complexes. Further the homogeneous CuTCPP and CuTPP were grafted on the amino functionalized SBA-15. The grafting of copper complexes on amino functionalised SBA-15 was evident from the surface area analysis, powder XRD and N2 sorption isotherm. In the powder XRD, the shift in 2θ value compared to parent SBA-15 materials, and the broadening of the signal supports the grafting of copper complexes in to the amino functionalized SBA-15. Both homogeneous and heterogeneous copper macromolecular complexes were used as catalysts for the hydroxylation of phenolic compounds. The catalysts showed comparable conversion (72%) with the formation of ortho- and para- substituted products which have industrial importance. The hydroxylation reaction using the copper based macromolecular catalyst was found to be first order with an activation energy of 26.03 KJ/mol. Subsequently various substituted phenolic compounds, anisole and benzene also yielded the corresponding hydroxylated product with comparable conversion.
Influence of chloro-form on crystalline products yielded in reactions of 5,10,15,20-tetra-phenyl-porphyrin with HCl and copper(II) salts
Aparici Plaza, Luis,Chojnacki, Jaroslaw
, p. m24-m28 (2012)
Chloro-form was found to occupy the lattice of the protonated porphyrin and to promote crystallization of a different poly-morphic form of a metalloporphyrin. The structure of 5,10,15,20-tetra-phenyl-porphyrin-21,23-diium dichloride chloro-form octa-solvate, C44H32N4 2+·2Cl -·8CHCl3, (I), in the solid state is described and compared with related solvates. The porphyrin macrocycle displays a distorted saddle shape, with chloride anions above and below the ring. Seven chloro-form mol-ecules are bound via C - H...Cl hydrogen bonds, while the link with the eighth solvent mol-ecule is weaker. A new monoclinic polymorph of (5,10,15,20-tetra-phenyl-porphyrinato)copper(II), [Cu(C44H28N4)], (II), crystallized from chloro-form, is also presented.
Reactions of Chelate Complexes with Macrocyclic Ligands. Octaphenyltetraazaporphine and Its Derivatives
Mamardashvili,Chizhova,Berezin
, p. 348 - 351 (2003)
Coordination of three azaporphines, namely, octaphenyltetraazaporphine (I), octa(4-nitrophenyl)-tetraazaporphine (II), and octa(4-bromophenyl)- tetraazaporphine (III) with some chelate salts of copper and zinc (hydroxyquinolate (IV), α-nitroso-β-naphthola
Acid–base and coordination properties of Meso-substituted porphyrins in nonaqueous solutions
Pukhovskaya,Nam, Dao Tkhe,Fien, Chan Ding,Domanina,Ivanova, Yu. B.,Semeikin
, p. 1692 - 1702 (2017)
Acid–base and coordination properties of alkyl and aryl meso-substituted porphyrins are studied spectrophotometrically in nonaqueous solutions. It is found that the nature of the substituent greatly affects the basicity of ligands for porphyrins characterized by a flat structure of macrocycle. The electronic effects of substituents have a much weaker influence on the kinetics of complexing. These effects could be due to the opposite orientation of some factors: an increase in the basicity and stability of the N–H bonds of porphyrin reaction centers. Dissociation constants pKb of the cationic forms of meso-substituted derivatives of porphyrin are measured. The values of pKb are in good agreement with classic concepts of the nature of substituents, particularly those indirectly included in the macrocycle through phenyl buffer rings.
A non-covalent functionalization of copper tetraphenylporphyrin/chemically reduced graphene oxide nanocomposite for the selective determination of dopamine
Karuppiah, Chelladurai,Sakthinathan, Subramanian,Chen, Shen-Ming,Manibalan, Kesavan,Chen, Sin-Ming,Huang, Sheng-Tung
, p. 40 - 46 (2016)
A non-covalent functionalization based on a copper tetraphenylporphyrin/chemically reduced graphene oxide (Cu-TPP/CRGO) nanocomposite is demonstrated for selective determination of dopamine (DA) in pharmaceutical and biological samples. A homogeneous electron-rich environment can be created on the graphene surface by Cu-TPP due to the π-π non-covalent stacking interaction. The synthesized Cu-TPP/CRGO nanocomposite was characterized using scanning electron microscopy NMR, ultraviolet-visible and electrochemical impedance spectroscopies. The electrocatalytic activity of DA was evaluated using cyclic voltammetry and differential pulse voltammetry. The oxidation peak current (Ipa) of DA increased linearly with increasing concentration of DA in the range 2-200 μM. The detection limit was calculated as 0.76 μM with a high sensitivity of 2.46 μA μM-1 cm-2. The practicality of the proposed DA sensor was evaluated in DA hydrochloride injection, human urine and saliva, and showed satisfactory recovery results for the detection of DA. In addition, the Cu-TPP/CRGO nanocomposite-modified electrode showed excellent stability, repeatability and reproducibility towards the detection of DA.
Oxidation of benzyl alcohols to the corresponding carbonyl compounds catalyzed by copper (II) meso-tetra phenyl porphyrin as cytochrome P-450 model reaction
Rahimi, Rahmatolah,Gholamrezapor, Ensieh,Naimi-Jamal, Mohammad Reza
, p. 1561 - 1568 (2011)
The oxidation of benzyl alcohols has been studied in the presence of isobutyraldehyde as co-catalyst, molecular oxygen as oxidant and copper (II) meso-tetra phenyl porphyrin (CuTPP) as catalyst. The CuTPP catalyst exhibits good activity and high selectivity under mild conditions. The effects of temperature and solvents have also been investigated in this catalyst system.
Tuning the crystal structures of metal-tetraphenylporphines: Via a magnetic field
Chen, Chen,He, Xiao-Tong,Hong, Dan-Li,Wang, Jing-Wen,Luo, Yang-Hui,Sun, Bai-Wang
, p. 12570 - 12575 (2018)
In this work, two new single crystals of copper-tetraphenylporphine (Cu-TPP) (crystals 2 and 3), which were induced by external magnetic fields with strengths of 0.5 and 0.8 T, respectively, have been prepared and characterized by single-crystal X-ray diffraction and Hirshfeld surface analysis. Compared with the original Cu-TPP (crystal 1), crystals 2 and 3 exhibit significant differences in their unit cell parameters, crystalline stacking styles and intermolecular interactions, resulting in a compressed crystal packing. Here, the number of closer interactions (H?H, C?H/H?C) increased with the magnetic field strength, accompanied by a decrease in the number of π?π (C?C) interactions as a sacrifice. On considering the results of our previous work, the results here suggest that a magnetic field has a different influence on the crystallization process of mono-component and multi-component materials, which will certainly provide some suggestions for the design of crystallization strategies for other materials with the presence of an external magnetic field.
Thermokinetic studies of porphyrin complexation in non-aqueous solutions by heat conduction microcalorimetry
Ageeva,Utzig,Golubchikov,Zielenkiewicz
, p. 243 - 248 (1998)
Porphyrins are known as unique ligands forming some of the most stable complexes with various metal ions. In this work the thermokinetic investigations of complex formation of tetraphenylporphyrins with copper(II) acetate were carried out in two anhydrous organic solvents: acetic acid and DMF at 25°C. Measurements were performed in a heat conduction microcalorimeter [7] adapted for non-aqueous solvents. Total heat effects and thermokinetics were determined. The results were discussed together with spectrophotometric data. Taking into account the high stability of metalloporphyrin complexes, the heat of their formation is rather small (in the case of acetic acid ΔQ=32.7±1.2 kJ mol-1, for DMF ΔQ= 26.2±1.3 kJ mol-1). Such result can suggest that: 1) the stability of complexes is influenced strongly by an entropy factor, 2) the complexation involves breaking of the NH-bond in the porphyrin coordination centre, accompanied by high consumption of energy.
Ligand exchange in the complexone-porphyrin macrocycle system in reactions of copper(II) ethylenediaminetetraacetate with porphyrins and phthalocyanines
Mamardashvili,Berezin
, p. 529 - 533 (2006)
Complexation between 5,10,15,20-tetraphenylporphine H2TPP and tetra(tert-butyl)phthalocyanine H2(t-Bu)4Pc with copper(II) ethylenediaminetetraacetate in DMSO was studied by spectrophotometry. The kinetic parameters of the
