16834-13-2Relevant academic research and scientific papers
Thermochemistry of solution of some quaternized derivatives of tetra(4-pyridyl)porphine in water
Berezin,Berezina,Semeikin,V'Yugin
, p. 1955 - 1958 (2007)
Quaternized tetra(4-pyridyl)porphine derivatives: tetra(N-carboxymethyl-4- pyridyl)porphine tetrachloride, tetra(N-carboxymethyl-4-pyridyl)porphine tetrabromide, tetra(N-methyl-4-pyridyl)porphine tetraiodide, and tetra(N-ethoxycarbonylmethyl-4-pyridyl)porphine tetrachloride, were synthesized, isolated, and purified. The enthalpies of solution of these compounds in water at 298.15 K were determined calorimetrically. The effect of functional substituents in porphyrin ligands on the enthalpies of solution is discussed.
Bottom-Up Hierarchical Self-Assembly of Chiral Porphyrins through Coordination and Hydrogen Bonds
Oliveras-González, Cristina,Di Meo, Florent,González-Campo, Arántzazu,Beljonne, David,Norman, Patrick,Simón-Sorbed, Maite,Linares, Mathieu,Amabilino, David B.
, p. 15795 - 15808 (2015)
A series of chiral synthetic compounds is reported that shows intricate but specific hierarchical assembly because of varying positions of coordination and hydrogen bonds. The evolution of the aggregates (followed by absorption spectroscopy and temperature-dependent circular dichroism studies in solution) reveal the influence of the proportion of stereogenic centers in the side groups connected to the chromophore ring in their optical activity and the important role of pyridyl groups in the self-assembly of these chiral macrocycles. The optical activity spans 2 orders of magnitude depending on composition and constitution. Two of the aggregates show very high optical activity even though the isolated chromophores barely give a circular dichroism signal. Molecular modeling of the aggregates, starting from the pyridine-zinc(II) porphyrin interaction and working up, and calculation of the circular dichroism signal confirm the origin of this optical activity as the chiral supramolecular organization of the molecules. The aggregates show a broad absorption range, between approximately 390 and 475 nm for the transitions associated with the Soret region alone, that spans wavelengths far more than the isolated chromophore. The supramolecular assemblies of the metalloporphyrins in solution were deposited onto highly oriented pyrolitic graphite in order to study their hierarchy in assembly by atomic force microscopy. Zero and one-dimensional aggregates were observed, and a clear dependence on deposition temperature was shown, indicating that the hierarchical assembly took place largely in solution. Moreover, scanning electron microscopy images of porphyrins and metalloporphyrins precipitated under out-of-equilibrium conditions showed the dependence of the number and position of chiral amide groups in the formation of a fibrillar nanomaterial. The combination of coordination and hydrogen bonding in the complicated assembly of these molecules-where there is a clear hierarchy for zinc(II)-pyridyl interaction followed by hydrogen-bonding between amide groups, and then van der Waals interactions-paves the way for the preparation of molecular materials with multiple chromophore environments.
Novel Amphiphilic G-Quadruplex Binding Synthetic Derivative of TMPyP4 and Its Effect on Cancer Cell Proliferation and Apoptosis Induction
Chilakamarthi, Ushasri,Koteshwar, Devulapally,Jinka, Sudhakar,Vamsi Krishna, Narra,Sridharan, Kathyayani,Nagesh, Narayana,Giribabu, Lingamallu
, p. 6514 - 6527 (2018)
Porphyrins are well-known anticancer agents because of their high binding affinity for G-quadruplex DNA and excellent photophysical properties. Several studies carried out using TMPyP4 established it as an efficient chemotherapeutic and a photodynamic therapeutic (PDT) agent, but its use as a lead molecule has been restricted because of its high level of binding to double-stranded DNA (dsDNA), which may have side effects on normal cells and tissues. To minimize its interaction with dsDNA and to enhance internalization into cells, an analogue of TMPyP4 (5Me) was synthesized. Its selectivity for G-quadruplex DNA over dsDNA was evaluated by spectroscopic methods, and its role in stabilizing G-quadruplex DNA was assessed by fluorescence lifetime and thermal melting experiments. Biophysical studies indicated that 5Me interacts well with G-quadruplex DNA. In vitro cytotoxicity experiments with tumor cell lines (PANC-1, B16F10, and MDA MB 231) have revealed that 5Me can inhibit the growth of cancer cells comparable to TMPyP4. MTT and apoptotic assays demonstrated the ability of 5Me to specifically affect cancer cells over normal cells. Cell cycle analysis showed that 5Me, like TMPyP4, induces G2/M phase cell cycle arrest. In addition, 5Me is more effectively taken up by both cancer and normal cells than TMPyP4. In addition, we have noticed that 5Me is more efficient than TMPyP4 in inhibiting the growth of the cancer cells after irradiation with light (600-720 nm, 20 J/cm2, 50 mW/cm2). By and large, these experimental results indicate that 5Me can be an efficient chemotherapeutic as well as a PDT agent.
Oxygen sensing materials based on mesoporous silica MCM-41 and Pt(II)-porphyrin complexes
Zhang, Huidong,Sun, Yinghui,Ye, Kaiqi,Zhang, Ping,Wang, Yue
, p. 3181 - 3186 (2005)
The preparation and properties of luminescent oxygen sensing materials based on two Pt(II)-porphyrin complexes: platinum meso-tetrakis(4-N-methylpyridyl)porphyrin (PtTMPyP4+) and platinum meso-tetrakis(4-N-pyridyl)porphyrin (PtTPyP) assembled in mesoporous silica (MCM-41) are described. The luminescence of Pt(II)-porphyrin/MCM-41 assembly materials can be extremely quenched by molecular oxygen with good sensitivity (I0/I100 > 7) and rapid response times (4+/MCM-41 (20 mg g-1) exhibits very high sensitivity (I0/I00 > 50). Even when the concentration of oxygen is 1%, the luminescence intensity of PtTMPyP 4+/MCM-41 (20 mg g-1) can be quenched by 83.33%. The Royal Society of Chemistry 2005.
Synthesis, RNA binding and nuclease activity of porphyrin-hydroxamic acid derivatives
Marketaki, Maria,Touloupakis, Eleftherios,Charalambidis, Georgios,Chalbot, Marie-Cécile,Ghanotakis, Demetrios F.,Coutsolelos, Athanassios G.
, p. 997 - 1005 (2012)
The interaction modes and nuclease activity against RNA of methylpyridiniumyl/phenyl-hydroxamic acid porphyrin adducts have been investigated. These compounds are derived from the tetracationic meso-tetrakis(N-methyl-4-pyridiniumyl)porphyrin (H2TMPyP-4) by replacing one or two pyridinium rings with a phenyl group. This group is bearing an aliphatic chain of three carbon atoms in the para position to a hydroxamic acid. A different interaction mode is observed depending on the number of charges and hydroxamic acid function. The nuclease activity of the porphyrin adducts against RNA has been demonstrated. Also the effect of the presence of various lanthanide ions on the porphyrin nuclease activity has been tested.
A platinum functional porphyrin conjugate: An excellent cancer killer for photodynamic therapy
Hu, Xiaojun,Ogawa, Kazuma,Li, Siqiaozhi,Kiwada, Tatsuto,Odani, Akira
, p. 790 - 796 (2019)
A novel tetracationic porphyrin-platinum(II) conjugate was synthesized and characterized. This complex, 4Pt(dach)ClTPyP, showed reasonable water solubility, lack of aggregation, and high singlet oxygen quantum yield. It also exhibited low dark cytotoxicity and excellent photocytotoxicity (Colon26: 0.17 μM; Sarcoma180: 0.25 M). The mechanisms of cell death have been investigated and are attributed to high singlet oxygen generation, internalization into nucleus, and a caspase-3 induced apoptosis pathway. In the in vivo photodynamic therapy (PDT) assay, 4Pt(dach)ClTPyP completely killed tumor tissue, not simply displaying inhibition of tumor growth, and no recurrence was seen 18 days later after a single administration. All these findings of 4Pt(dach)ClTPyP shed light on a potential clinical use for cancer PDT in the future.
A supramolecular bifunctional artificial enzyme with superoxide dismutase and glutathione peroxidase activities
Yu, Shuangjiang,Huang, Xin,Miao, Lu,Zhu, Junyan,Yin, Yanzhen,Luo, Quan,Xu, Jiayu,Shen, Jiacong,Liu, Junqiu
, p. 159 - 164 (2010)
For constructing a bifunctional antioxidative enzyme with both superoxide dismutase (SOD) and glutathione peroxidase (GPx) activities, a supramolecular artificial enzyme was successfully constructed by the self-assembly of the Mn(III)meso-tetra[1-(1-adamantyl methyl ketone)-4-pyridyl] porphyrin (MnTPyP-M-Ad) and cyclodextrin-based telluronic acid (2-CD-TeO3H) through host-guest interaction in aqueous solution. The self-assembly of the adamantyl moieties of Mn(III) porphyrin and the β-CD cavities of 2-CD-TeO3H was demonstrated by the NMR spectra. In this supramolecular enzyme model, the Mn(III) porphyrin center acted as an efficient active site of SOD and tellurol moiety endowed GPx activity. The SOD-like activity (IC50) of the new catalyst was found to be 0.116 μM and equals to 2.56% of the activity of the native SOD. Besides this, supramolecular enzyme model also showed a high GPx activity, and a remarkable rate enhancement of 27-fold compared to the well-known GPx mimic ebselen was observed. More importantly, the supramolecular artificial enzyme showed good thermal stability.
Synthesis and characterization of a new magnetic nanocomposite with metalloporphyrin (Co-TPyP) and sulfated tin dioxide (Fe3O4@SnO2/SO42-), and investigation of its photocatalytic effects in the degradation of Rhodamine B
Ghafuri, Hossein,Mohammadi, Fatemeh,Rahimi, Rahmatallah,Mohammadiyan, Esmaeel
, p. 83947 - 83953 (2016)
To achieve the synthesis of (Fe3O4@SnO2/SO42-), after the preparation of magnetic nanoparticles of Fe3O4 (MNP), tin dioxide was supported on the MNP, and it was sulfated using ammonium sulfate. To improve the photocatalytic activity of this magnetic nanocatalyst, after the synthesis of 5,10,15,20-tetra(4-pyridyl) porphyrin and its cobalt metalloporphyrin, (Co-TPyP) was stabilized on Fe3O4@SnO2/SO42-. The structure and morphology were characterized by XRD, EDX, FT-IR, SEM and FE-SEM. The X-ray diffraction studies showed tetragonal SnO2 and the orthorhombic structure of Fe3O4. The Fe3O4@SnO2/SO42- is an acidic heterogeneous nanocatalyst with excellent magnetic properties and can be easily separated from the reaction mixture by an external magnetic field. The photocatalytic activity was investigated by studying the photodegradation of Rhodamine B (RhB) in aqueous solution under visible light irradiation. The simplicity of the workup processes, the low cost of the catalyst and its high efficiency in the degradation of RhB are outstanding advantages of this procedure.
Synthesis and photophysical properties of the photoactivatable cationic porphyrin 5-(4-N-dodecylpyridyl)-10,15,20-tri(4-N-methylpyridyl)-21H,23H-porphyrin tetraiodide for anti-malaria PDT
Stallivieri, Aurélie,Le Guern, Florent,Vanderesse, Régis,Meledje, Esme,Jori, Giulio,Frochot, Céline,Acherar, Samir
, p. 1290 - 1295 (2015)
This article describes a new synthetic method for obtaining three water soluble porphyrins. The more sophisticated porphyrin [5-(4-N-dodecylpyridyl)-10,15,20-tri(4-N-methylpyridyl)-21H,23H-porphyrin tetraiodide], also named C12 porphyrin, was obtained through a three step methodology. The improvements, compared to syntheses described in the literature, mostly concern the purification procedures. The photophysical properties of the three porphyrins are described and the C12 porphyrin presents a very good 1O2 yield compared to its chemical intermediates. This porphyrin seems to be a very promising candidate for PDT applications.
Synthesis and Antimicrobial Activity of a Pyridine Complex of (Acetato)[5,10,15,20-tetrakis(N-methylpyridin- 4-yl)porphinato]manganese(III) Tetratosylate
Ovchenkova,Bichan,Lyubimtsev,Garasko,Lomova
, p. 1657 - 1662 (2018)
Aiming at preparation of new biologically active donor?acceptor complexes, a water-soluble manganese(III) complex with 5,10,15,20-tetrakis(N-methylpyridin-4-yl)porphine tetratosylate was synthesized and its reaction with pyridine was studied by spectrophotometry using the molar ratio method. In water a 1: 1 donor?acceptor complex with pyridine is formed. The chemical structure of the compounds was established by spectral methods. (Acetato)[5,10,15,20-tetrakis(N-methylpyridin-4-yl)porphinato]manganese(III) tetratosylate and especially its donor?acceptor complex with pyridine showed an antifungal activity against Candida albicans.
