- Molecular organogel-forming porphyrin derivative with hydrophobic l-glutamide
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An l-glutamide-functionalized tetraphenylporphyrin derivative has been newly synthesized. This can dissolve in various organic solvents to form nanofibrillar aggregates with both right-handed and left-handed chiral stacking structures among the porphyrin
- Jintoku, Hirokuni,Sagawa, Takashi,Sawada, Tsuyoshi,Takafuji, Makoto,Hachisako, Hiroshi,Ihara, Hirotaka
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- Synthesis and characterization of porous organic polymer containing tailored?AB3?metalloporphyrin: highly active?and reusable catalyst?for oxidation of benzyl alcohol
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In this work, a modern and attractive Cu(II) porphyrin‐based polymer network with high surface area was synthesized. This strategy prepares an easy approach to produce highly stable Cu-Porphyrin‐based polymer network. The organization of this catalyst was
- Mouradzadegun, Arash,Hamid, Sheida,Sheikhzadeh Takabi, Asiyeh
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- New photodynamic molecular beacons (PMB) as potential cancer-targeted agents in PDT
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Further improvements in Photodynamic therapy (PDT) necessitate that the dye targets more selectively tumour tissues or neovascularization than healthy cells. Different enzymes such as matrix metalloproteinases (MMPs) are overexpressed in tumour areas. Amo
- Stallivieri, Aurélie,Colombeau, Ludovic,Devy, Jér?me,Etique, Nicolas,Chaintreuil, Carine,Myrzakhmetov, Bauyrzhan,Achard, Mathilde,Baros, Francis,Arnoux, Philippe,Vanderesse, Régis,Frochot, Céline
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- Preparation and characterization of covalently bound tetraphenylporphyrin - Silica gel stationary phases for reversed-phase and anion-exchange chromatography
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A tetraphenylporphyrin-based stationary phase for high-performance liquid chromatography is prepared by attaching a p-carboxyphenyl derivative of the porphyrin to aminopropyl silica gel through an amide bond. This stationary-phase support is used for the
- Kibbey,Meyerhof
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- Chirally self-assembled porphyrin nanowires assisted by L-glutamide-derived lipid for excitation energy transfer
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An L-glutamide-functionalized tetraphenylporphyrin (1) has been newly synthesized and its self-assembling behavior in organic solvents is reported. 1 forms nanofibrous assemblies in a dilute solution to show specific induced circular dichroism at the abso
- Jintoku, Hirokuni,Sagawa, Takashi,Takafuji, Makoto,Ihara, Hirotaka
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- Synthesis, crystal structure and nonlinear optical properties of ferrocene-containing metalloporphyrins
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Five ferrocene-containing metalloporphyrins (Pd-P-Fc, Co-P-Fc, Cu-P-Fc, Zn-P-Fc and Ni-P-Fc) were synthesized and characterized. The crystal structure of Zn-P-Fc determined by using the single crystal diffraction technique belongs to the triclinic system. A typical aggregation of Zn-P-Fc occurs when the concentration of Zn-P-Fc is greater than 2.0 × 10?6 mol/L in solution. The strong interaction between the metalloporphyrin and the ferrocene group was inferred by the absorption spectra, fluorescence spectra and the DFT calculation. Good nonlinear optical properties of these materials were inferred from the low fluorescence quantum yields and the short fluorescence lifetimes. Zn-P-Fc and Pd-P-Fc exhibit great reverse saturable absorption properties for 7 ns laser with 532 nm wavelength, and the β values are 13.36 and 13.41 cm/GW, respectively.
- Guo, Fengqi,Huang, Xuewei,Wei, Fengli,Zhu, Yanyan
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- Anionic manganese meso-tetraphenyl porphine/oligonucleotide conjugates - Synthesis and utilization in chemiluminescent DNA-probe detection
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The synthesis and application of oligodeoxynucleotides derivatized by the water-soluble anionic manganese-(III)-5-(4-carboxyphenyl)-10,15,20-tris- (4-sulphonatophenyl)-porphine complex are described. These conjugates were found to be potent catalysts for
- Schubert,Kluetsch,Cech
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- Magnesium Tetraarylporphyrin Tweezer: A CD-Sensitive Host for Absolute Configurational Assignments of α-Chiral Carboxylic Acids
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A protocol to determine the absolute configuration of α-chiral carboxylic acids based on a modified circular dichroic (CD) exciton chirality method has been developed. The protocol relies on a host-guest complexation mechanism: the chiral substrates are derivatized to give bifunctional amide conjugates ("guests") that form complexes with a dimeric magnesium porphyrin host, Mg-T (T stands for "tweezer") that acts as a "receptor". The two porphyrins in the complex adopt a preferred helicity dictated by the substituents at the chiral center in accordance with their steric sizes (assigned on the basis of conformational energy A-values) and, consequently, with the absolute configuration of the substrates under investigation. This chiroptical method, verified with a variety of chiral substrates, has been demonstrated to be reliable and generally applicable, including natural products with complex structures. Molecular modeling, NMR, and FTIR experiments of selected host-guest complexes revealed the mode of ligation of the substrates to the magnesium porphyrin species and led to clarification of the structure of the complex. When oxygen functionalities were directly attached to the chiral center, the signs of the CD couplets were opposite to those predicted on the basis of steric size. NMR and molecular modeling experiments indicated that this apparent inconsistency was due to conformational characteristics of the guest molecules. The stereochemical analysis is shown to be a sensitive technique, not only for the determination of absolute configurations of substrates but also for elucidation of their solution conformations.
- Proni, Gloria,Pescitelli, Gennaro,Huang, Xuefei,Nakanishi, Koji,Berova, Nina
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- Porphyrin-peptoid conjugates: Face-to-face display of porphyrins on peptoid helices
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Distance, orientation, and number controlled porphyrin-peptoid conjugates (PPCs) were efficiently synthesized. Cofacial (1, 2, and 4), slipped-cofacial (3), and unstructured (5) arrangements of porphyrins provided distinct optical and electronic propertie
- Kang, Boyeong,Chung, Solchan,Ahn, Young Deok,Lee, Jiyoun,Seo, Jiwon
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- Glycine-conjugated porphyrin fluorescent probe with iRGD for live cell imaging
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A porphyrin modified by glycine has been synthesized and developed as a near-infrared (NIR) fluorescence probe to detect tumor. Porphyrins’ longwavelength emission at ～650?nm can efficiently avoid the spectral crosstalk with Spontaneous fluorescence in th
- Zhang, Qian,Dong, Xue,Wang, Kun-Peng,Zhu, Ting-Ting,Sun, Feng-Nan,Meng, Shu-Xian,Feng, Ya-Qing
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- Synthesis, crystal structure, catalytic dimerization and S–H insertion of new porphyrin diazoketones
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Porphyrin diazoketones were synthesized from the corresponding porphyrin acetyl chloride by treatment with trimethylsilyldiazomethane in 60–80% yield. The solid-state structure of one of the two bis-diazo derivatives (trans isomer) was determined by singl
- Carrié, Daniel,Roisnel, Thierry,Simonneaux, Gérard
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- A novel apoA-I mimetic peptide suppresses atherosclerosis by promoting physiological HDL function in apoE?/? mice
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Background and Purpose: Apolipoprotein A-I (apoA-I) mimetic peptides (AAMPs) are short peptides that can mimic the physiological effects of apoA-I, including the suppression of atherosclerosis by reversely transporting peripheral cholesterol to the liver.
- Gou, Sanhu,Wang, Li,Zhong, Chao,Chen, Xinyue,Ouyang, Xu,Li, Beibei,Bao, Guangjun,Liu, Hui,Zhang, Yun,Ni, Jingman
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- Porphyrin substituted phosphoramidites: New building blocks for porphyrin-oligonucleotide syntheses
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Thymidine phosphoramidites containing trispyridylphenyl and tetraphenylporphyrin chromophores attached via a short amide linker in the 3′-position have been synthesized and used as building blocks in solid-phase synthesis of self-complementary 8-mer oligo
- Balaz, Milan,Holmes, Andrea E.,Benedetti, Michele,Proni, Gloria,Berova, Nina
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- An estradiol-porphyrin conjugate selectively localizes into estrogen receptor-positive breast cancer cells
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A conjugate of a C11-β-estradiol and an asymmetric tetraphenylporphyrin was synthesized to study its potential selective uptake by breast cancer cells naturally over-expressing the nuclear receptor for estrogen (ER). Competitive radioligand binding assays of this conjugate with recombinant ER showed that the conjugate bound to ER in a dose-dependent manner with an EC50 of 274 nM, compared with 1 nM for estradiol, the natural ligand. Cellular uptake studies with ER-positive MCF-7 and ER-negative HS578t human breast cancer cells revealed that, the conjugate was taken up by MCF-7 cells in a dose-dependent manner, which was obliterated by co-incubation with a large excess of estradiol. On the other hand there was very little uptake of the un-conjugated porphyrin by MCF-7 and Hs578t cells. HS578t cells also showed insignificant uptake of the conjugate under the conditions of our experiment. These results strongly suggested that specific interaction between the endogenous ER in MCF-7 cells and the estrogen part of the conjugate enabled these cells to selecti ely internalize the conjugate over the un-conjugated porphyrin. Therefore, ER-binding conjugates of estradiol and porphyrins could potentially be used for ER-targeted photodynamic therapy of hormone-sensitive cancers of breast, ovary, gonads etc. Copyright
- Swamy, Narasimha,James, David A,Mohr, Scott C,Hanson, Robert N,Ray, Rahul
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- Fluorescence resonance energy transfer in host-guest inclusion complexes of cyclodextrin-porphyrin composite in aqueous solution
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A composite of zinc tetraphenylporphyrin linked with β-cyclodextrin was prepared as a convenient scaffold for a self-assembled energy-transfer complex. The energy-transfer properties of the host-guest complexes were investigated for several guest molecule
- Hosokawa, Kiyotada,Miura, Yutaka,Kiba, Takayuki,Kakuchi, Toyoji,Sato, Shin-Ichiro
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- Synthesis and estrogen receptor binding affinity of a porphyrin- estradiol conjugate for targeted photodynamic therapy of cancer
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A tetraphenylporphyrin-C11-β-estradiol conjugate has been synthesized. Competitive binding assay of the conjugate with estrogen receptor (ER)-ligand-binding domain showed that the conjugate binds specifically to the protein with high affinity. Potential use of this conjugate to selectively deliver cytotoxic porphyrins to ER-positive cells in various carcinomas is discussed.
- James, David A.,Swamy, Narasimha,Paz, Nancy,Hanson, Robert N.,Ray, Rahul
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- The role of para-alkyl substituents on meso-phenyl porphyrin sensitised TiO2 solar cells: Control of the eTiO2/electrolyte + recombination reaction
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We aim to investigate the effect of adding hydrophobic alkyl chains substituents to unsymmetrical free base tetra-phenyl porphyrins used for the preparation of dye sensitised solar cells (DSSC). We have used two different unsymmetrical meso-tetraphenyl substituted free base porphyrins attending to two objectives: (1) to observe how the substitution of three para positions of the meso-phenyl groups with hydrophobic alkyl chains influences the formation of molecular aggregates onto the semiconductor nanoparticles and (b) to deduce the influence that the substitution exerts over the eTiO2/ electrolyte+ recombination reaction in operating devices. To achieve these goals we have focussed on the study of the electron transfer processes that take place at the different interfaces of the photovoltaic device using electrochemistry, steady-state and time resolved spectroscopic techniques. The Royal Society of Chemistry 2008.
- Forneli, Amparo,Planells, Miquel,Sarmentero, Maria Angeles,Martinez-Ferrero, Eugenia,O'Regan, Brian C.,Ballester, Pablo,Palomares, Emilio
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- J-aggregate formation in bis-(4-carboxyphenyl)porphyrins in water:pH and counterion dependence
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The self aggregation behaviour of meso-tetraarylporphyrins containing two carboxyphenyl units in adjacent and opposite positions, respectively, 5,10-bis(4-carboxyphenyl)-15,20-diphenylporphyrin (DiCPP-adj) and 5,15-bis(4-carboxyphenyl)-10,20-diphenylporph
- Serra, Vanda Vaz,Andrade, Suzana M.,Neves, Maria G.P.M.S.,Cavaleiro, Jose A.S.,Costa, Silvia M.B.
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- Catalytic CO2-to-CO conversion in water by covalently functionalized carbon nanotubes with a molecular iron catalyst
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The covalent grafting of an Fe porphyrin on carbon nanotubes led to efficient electroreduction of CO2 into CO in water (pH 7.3). CO was obtained with high selectivity and turnover at 0.5 V overpotential. The grafting strategy may be further ext
- Maurin, Antoine,Robert, Marc
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- Synthesis and characterization of 5-(4-carboxyphenylspermine)-10,15,20-triphenylporphyrin
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We synthetized and characterized a mono spermine porphyrin derivative by NMR, UV-vis and fluorescence spectroscopy. The photophysical properties and the protonation equilibria of 5-(4-carboxyphenylspermine)-10,15,20-triphenylporphyrin have been investigated, showing that porphyrin does not aggregate in acidic solutions, differently from what occurs as soon as the core of the porphyrin is deprotonated. These aggregation processes have been detected by the rising of new fluorescence band and a significant splitting of the Soret band.
- Gangemi, Chiara M.A.,Randazzo, Rosalba,Gaeta, Massimiliano,Fortuna, Cosimo G.,Fragalà, Maria E.,Purrello, Roberto,D'Urso, Alessandro
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- Synthesis of flexible dimeric meso-tetrakis-porphyrins
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Monofunctionalisation of meso-tetrakis-porphyrins through introduction of a carboxylic group in the meso position of the phenyl group confers the necessary characteristics to anchor them through stable amide bonds to functionalised supports or to molecules. In this Letter we describe the synthesis, characterisation and photophysical evaluation of such a functionalised flexible dimeric porphyrin, bis-(meso-tetrakis-5,10,15-triphenyl-20-(p-carboxyphenyl)-porphyrinyl)-1,6-hexanediamide.
- Sobral, Abilio J.F.N.,Melo, Susana M.,Ramos, M. Luísa,Teixeira, Raquel,Andrade, Susana M.,Costa, Silvia M.B.
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- Folic acid conjugates with photosensitizers for cancer targeting in photodynamic therapy: Synthesis and photophysical properties
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Recent researches in photodynamic therapy have focused on novel techniques to enhance tumour targeting of anticancer drugs and photosensitizers. Coupling a photosensitizer with folic acid could allow more effective targeting of folate receptors which are
- Stallivieri, Aurélie,Colombeau, Ludovic,Jetpisbayeva, Gulim,Moussaron, Albert,Myrzakhmetov, Bauyrzhan,Arnoux, Philippe,Acherar, Samir,Vanderesse, Régis,Frochot, Céline
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- 3D-Network porous polymer bonded metalloporphyrin: An efficient and reusable catalyst for the Baeyer-Villiger oxidation
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A new, green catalyst was prepared through immobilization of metalloporphyrin on the surface of 3D-network polymer based on calix[4]resorcinarene (PC4RA), which efficiently catalyze B-V oxidation reaction using O2/benzaldehyde. The catalyst demonstrated excellent activity, which is highly potential for cyclic aliphatic ketones oxidation under mild conditions. IR spectroscopy, UV-Vis spectroscopy, thermal gravimetric analysis, energy dispersive spectroscopy and scanning electron microscopy are some of the spectroscopic methods used to characterize the new synthesized solid support.
- Hamid, Sheida,Mouradzadegun, Arash
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p. 171 - 179
(2021/12/06)
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- Metalloporphyrin compound as well as preparation method and application thereof
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The invention discloses a metalloporphyrin compound as well as a preparation method and application thereof, and belongs to the technical field of medicinal chemistry. The metalloporphyrin compound shown in the formula I (See the specification for reference), or an optical isomer, a pharmaceutically acceptable salt or a solvent compound of the metalloporphyrin compound has a specific human immunodeficiency virus RNA recognition effect and excellent human immunodeficiency virus reverse transcriptase inhibition capability. The invention also discloses an application of the compound in preparation of an HIV TAR RNA selective recognition reagent and an application of the compound in preparation of an HIV reverse transcriptase inhibitor.
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- Benzimidazolyl zinc porphyrin, benzimidazolyl porphyrin and synthesis method thereof
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The application discloses benzimidazolyl zinc porphyrin, benzimidazolyl porphyrin and a synthesis method thereof, wherein the structural formula of the benzimidazolyl zinc porphyrin is as shown in thespecification. The novel benzimidazolyl porphyrin, the
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Paragraph 0053-0058; 0066-0069; 0075-0078
(2019/08/02)
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- A cost-efficient method for unsymmetrical Meso-aryl porphyrin synthesis using NaY zeolite as an inorganic acid catalyst
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Herein we report the synthesis of unsymmetrical meso-aryl substituted porphyrins, using NaY zeolite as an inorganic acid catalyst. A comparative study between this method and the several synthetic strategies available in the literature was carried out. Our method presented a better, more cost-efficient rationale and displayed a significantly lower environmental impact. Furthermore, it was possible to verify the scalability of the process as well as the reutilization of the inorganic catalyst NaY (up to 6 times) without significant yield decrease. In addition, this method was applied to the synthesis of several other unsymmetrical porphyrins, from a low melting point porphyrin to mono-carboxylated halogenated unsymmetrical porphyrins, in yields higher than those found in the literature. Additionally, for the first time, two acetamide functionalized halogenated porphyrins were prepared in high yields. This methodology opens the way to the preparation of high yielding functionalized porphyrins, which can be easily immobilized for a variety of applications, either in catalysis or in biomedicine.
- Calvete, Mário J. F.,Dias, Lucas D.,Henriques, César A.,Pinto, Sara M. A.,Carrilho, Rui M. B.,Pereira, Mariette M.
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supporting information
(2017/06/08)
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- Endosome Targeting meso-Tetraphenylchlorin-Chitosan Nanoconjugates for Photochemical Internalization
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Four amphiphilic covalently linked meso-tetraphenylchlorin-chitosan nanoconjugates were synthesized and evaluated for use in photochemical internalization (PCI) in vitro and in vivo. The synthetic protocol for the preparation of two different hydrophobic chlorin photosensitizers, 5-(4-aminophenyl)-10,15,20-triphenylchlorin and 5-(4-carboxyphenyl)-10,15,20-triphenylchlorin, was optimized. These monofunctional photosensitizers were covalently attached to carrier chitosan via silyl-protected 3,6-di-O-tert-butyldimethylsilyl-chitosan (Di-TBDMS-chitosan) with 0.10 degree of substitution per glucosamine (DS). Hydrophilic moieties such as trimethylamine and/or 1-methylpiperazine were incorporated with 0.9 DS to give fully water-soluble conjugates after removal of the TBDMS groups. A dynamic light scattering (DLS) study confirmed the formation of nanoparticles with a 140-200 nm diameter. These nanoconjugates could be activated at 650 nm (red region) light, with a fluorescence quantum yield (ΦF) of 0.43-0.45, and are thus suitable candidates for use in PCI. These nanoconjugates were taken up and localized in the endocytic vesicles of HCT116/LUC human colon carcinoma cells, and upon illumination they substantially enhanced plasmid DNA transfection. The nanoconjugates were also evaluated in preliminary in vivo experiments in tumor-bearing mice, showing that the nanoconjugates could induce a strong photodynamic therapy (PDT) and also PCI effects in treatment with bleomycin.
- Gaware, Vivek S.,H?kerud, Monika,Juzeniene, Asta,H?gset, Anders,Berg, Kristian,Másson, Már
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p. 1108 - 1126
(2017/04/26)
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- Syntheses of asymmetric zinc porphyrins bearing different pseudo-pyridine substituents and their photosensitization for visible-light-driven H2 production activity
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A series of asymmetric zinc porphyrin (ZnPy) derivatives bearing different external substituents were synthesized and used to sensitize Pt-loaded graphitic carbon nitride (Pt/g-C3N4) for photocatalytic H2 production. Among them, ZnPy-1 has one benzoic acid and three phenyls as peripheral substituents, while ZnPy-2, ZnPy-3, and ZnPy-4 contain one benzoic acid and three pseudo-pyridines with different N-atom positions. The experimental results indicate that the pseudo-pyridine substitution for the phenyls in ZnPy-1 lead to enhanced photosensitization with an order of ZnPy-1 420 nm) irradiation. ZnPy-4-sensitized Pt/g-C3N4 (ZnPy-4-Pt/g-C3N4) exhibits the best average H2 production activity of 524 μmol h-1 with an extremely high turnover number (TON) of 11 089 h-1, which is much higher than that (328 μmol h-1) of ZnPy-2-Pt/g-C3N4 with a TON of 6942 h-1. Also, ZnPy-4-Pt/g-C3N4 shows a much higher apparent quantum yield (AQY) of 32.3% than that (11.5%) of ZnPy-2-Pt/g-C3N4 under 420 nm monochromatic light irradiation. The different N-atom positions in the pseudo-pyridines result in different interactions of the ZnPy dyes with a sacrificial reagent, which then strongly influences the photoactivity for H2 production. The present results demonstrate the molecular engineering aspect of ZnPy dyes in which fine-tuning of molecular structures is crucial for improving the photocatalytic H2 production activity of dye-sensitized semiconductors.
- Zheng, Ya,Wang, Jinming,Zhang, Jing,Peng, Tianyou,Li, Renjie
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p. 8219 - 8228
(2017/07/10)
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- Synthetic Methodology for the Fabrication of Porous Porphyrin Materials with Metal-Organic-Polymer Aerogels
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A promising fabrication strategy used for designing porous porphyrin materials and a group of rigid carboxyl porphyrins based metal-organic-polymer aerogels (MOPAs) has been proposed recently. These newly synthesized MOPAs were exemplarily characterized by FT-IR, UV-vis-DRS, EDS, PXRD, TGA, SEM, TEM, and gas sorption measurements. A gelation study has shown that solvents, molar ratio, temperature, and peripheral carboxyl number in porphyrins all affect gel generation. The MOPA series exhibit eminent thermal stability, high removal efficiency in dye adsorption, versatile morphologies, and permanent tunable porosity; also the BET surface areas fall within the range 249-779 m2 g-1. All of the mentioned properties are significantly superior to some other porous materials, which enable these compounds to be potential candidates for dye uptake, gas storage, and separation.
- Zhao, Xin,Yuan, Lin,Zhang, Zeng-Qi,Wang, Yong-Song,Yu, Qiong,Li, Jun
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p. 5287 - 5296
(2016/06/14)
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- Symmetrical acid anhydride keymolecular pliers series containing porphyrin compound and its preparation method
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The invention provides acid-anhydride-bond-containing symmetric molecular tweezer series porphyrin compounds and a preparation method thereof. The structural formula is disclosed in the specification, wherein M=H2, Zn, MnCl, Cu, Ni or Co. The molecular fo
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Paragraph 0058; 0059
(2017/01/12)
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- COMPOUND AND METHOD
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The present invention provides a method of expressing an antigenic molecule or a part thereof on the surface of a cell using a photochemical internalisation method and a virosome or a virus-like particle (VLP) which comprises the antigenic molecule. In preferred embodiments the antigenic molecule is an antigen from influenza or papillomavirus. The method may be used to stimulate an immune response and for various therapeutic or prophylactic methods. Pharmaceutical compositions or kits comprising the components for use in the method, cells produced by the method and their use in therapy and prophylaxis also form aspects of the invention.
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Page/Page column 33
(2016/03/22)
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- COMPOUND AND METHOD
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The present invention provides a method of expressing an antigenic molecule or a part thereof on the surface of a cell using a photochemical internalisation method in which a cytokine, preferably GM-CSF, is used to enhance the method. The method may be used to stimulate an immune response and for various therapeutic or prophylactic methods. Pharmaceutical compositions or kits comprising the components for use in the method, cells produced by the method and their use in therapy and prophylaxis also form aspects of the invention.
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Page/Page column 35
(2016/03/22)
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- Preparation of Co-N-C supported on silica spheres with high catalytic performance for ethylbenzene oxidation
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In this study, Co-N-C supported on silica spheres is prepared through heat-treatment of supported metalloporphyrin in an N2 atmosphere. The catalytic performance of the catalysts for ethylbenzene oxidation is investigated and these catalysts are characterized by techniques such as BET, FT-IR, UV-vis, TEM and XPS. In comparison with other catalysts such as supported cobalt porphyrin and unsupported cobalt porphyrin, Co-N-C supported on silica spheres shows much higher catalytic activity for ethylbenzene oxidation (15.7%) and selectivity to acetophenone (76.5%). In addition, the catalyst can retain its high catalytic activity after several reuses. The results show that the high catalytic performance of the catalyst may be attributed to the formation of Co-N4-C sites during the heat-treatment and supported Co-N-C catalysts may be beneficial to yield more Co-N4-C sites. This journal is
- Liu, Zhigang,Ji, Lintao,Dong, Xulong,Li, Zhen,Fu, Lingling,Wang, Qiuan
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p. 6259 - 6264
(2015/03/05)
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- Synthesis of Porphyrin-CdSe Quantum Dot Assemblies: Controlling Ligand Binding by Substituent Effects
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Cadmium selenide quantum dots of 2.2-2.3 nm diameter were prepared by phosphorus-free methods using oleic acid as stabilizing surface ligand. Ligand exchange monitored quantitatively by 1H NMR spectroscopy gave an estimate of 30-38 monodentate ligands per nanocrystal, with a ligand density of 1.8-2.3 nm-2. The extent of ligand exchange with macrocycles carrying one or more functional groups was investigated, with the aim of producing nanocrystal-macrocycle conjugates with a limited number of coligands. Metal-free porphyrins are able to sequester the Cd2+ ions from the Cd(oleate)2 outer layer of the nanocrystals. Zinc porphyrin complexes carrying one carboxylate function displace oleate efficiently to give porphyrin/CdSe composites with porphyrins stacked upright on the crystal surface. Porphyrins with four potential ligating sites are able to bind to the crystal surface only if the donors are at the end of sufficiently long and flexible tethers. High-dilution methods allowed the synthesis and isolation of well-defined composites of composition [CdSe{porphyrin}2], where porphyrin = 5,10,15,20-tetrakis{3-(carboxy-n-alkyloxy)phenyl}porphyrinato zinc (n = 5 or 10) and 5,10,15,20-tetrakis{3-(11-undecenyloxythiol)phenyl}-porphyrinato zinc. Comparison of the composition data obtained by 1H NMR spectroscopy with luminescence quenching behavior suggests a dependence of quenching efficiency on the tether length. Luminescence quenching was also observed for porphyrins that, according to 1H NMR results, do not undergo surface ligand exchange.
- Chambrier, Isabelle,Banerjee, Chiranjib,Remiro-Buenama?ana, Sonia,Chao, Yimin,Cammidge, Andrew N.,Bochmann, Manfred
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supporting information
p. 7368 - 7380
(2015/08/18)
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- Trilobolide-porphyrin conjugates: On synthesis and biological effects evaluation
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Trilobolide (Tb), a potent natural counterpart of thapsigargin, is a sesquiterpene lactone of guaianolide type isolated from horse caraway (Laser trilobum, L. Borkh). Tb exerts remarkable pharmacological properties based on irreversible inhibition of sarc
- Tomanová, Pavla,Rimpelová, Silvie,Jurá?ek, Michal,Budě?ínsky, Milo?,Vejvodová, Lucie,Ruml, Tomá?,Kmoní?ková, Eva,Dra?ar, Pavel B.
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supporting information
p. 8 - 12
(2015/03/31)
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- Immobilization of metalloporphyrin on a silica shell with bimetallic oxide core for ethylbenzene oxidation
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In this study, metalloporphyrin has been immobilized on a core-shell structured SiO2@CeO2 doped with transition metals such as Fe, Cu, Co and Mn. The as-prepared catalysts have been characterized via N2 adsorption-desorption, XRD, TEM, FT-IR spectroscopy, and UV-vis spectroscopy. It is found that metalloporphyrin is anchored onto a SiO2 shell with a thickness of about 20 nm and on a MOx/CeO2 core (M = Fe, Cu, Co and Mn) with a diameter about 120 nm, which may benefit the diffusion of substrates through the pores in the thin shell into the metal oxide cores and the formation of a synergistic effect between metalloporphyrin and metal oxides. Moreover, CoTPP-(MOx/CeO2)@SiO2 catalysts (M = Fe, Cu, Co and Mn) exhibit different physical and chemical properties, such as surface areas, particle sizes and catalytic performances owing to the addition of transition metals into CeO2. Moreover, the catalyst doped with Co exhibits a higher catalytic performance than the other catalysts for ethylbenzene oxidation. Thus, the addition of transition metals, such as Co, Cu, Fe and Mn, plays an important role in the catalytic performance of the catalysts for ethylbenzene oxidation via adjusting the physical and chemical properties of the core-shell catalysts.
- Zhao, Sufang,Chen, Yuan,Liu, Zhigang
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p. 33299 - 33305
(2015/04/27)
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- Microwave-assisted synthesis of zinc 5-(4-carboxyphenyl)-10,15,20-triphenylporphyrin and zinc 5-(4-carboxyphenyl)-10,15,20-triphenylchlorin
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The microwave-assisted synthesis of zinc 5-(4-carboxyphenyl)-10,15,20-triphenylporphyrin and zinc 5-(4-carboxyphenyl)-10,15,20-triphenylchlrorin are described and compared to classic conditions of synthesis in terms of time of reaction and yields obtained
- Chouikrat, Rima,Champion, Aymeric,Vanderesse, Régis,Frochot, Céline,Moussaron, Albert
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p. 595 - 600
(2015/05/05)
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- CONJUGATE OF A PHOTOSENSITISER AND CHITOSAN AND USES THEREOF
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The present invention relates to novel chitosan-based conjugates, e.g. nanocarriers, comprising a derivative of the biocompatible polymer chitosan conjugated to a photosensitising agent, and uses thereof in photochemical internalisation (PCI) and photodynamic therapy (PDT). The invention also relates to the use of the novel conjugates of the invention in treatment or prevention of diseases, particularly cancer, and for vaccination purposes.
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Paragraph 0287-0288
(2015/07/27)
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- Influence of heat treatment on catalytic performance of Co-N-C/SiO2 for selective oxidation of ethylbenzene
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The effect of heat treatment on the Co-N-C/SiO2 catalysts prepared through supported metalloporphyrin has been investigated for selective oxidation of ethylbenzene. And techniques such as BET, XRD, FT-IR, UV-vis, TEM, TG-DTA and XPS are used to explore the relationship between heat temperature and the catalytic performance of the catalysts. The results show that Co-N-C/SiO2 catalyst heated at 500 °C exhibits much higher activity for ethylbenzene oxidation compared with its counterparts such as Co-N-C/SiO2 catalysts heated at 300 °C, 400 °C, 600 °C and 700 °C, respectively. This may be attributed to the formation of much more Co-N4-C active sites on the surface of Co-N-C/SiO2 catalyst heated at 500 °C.
- Liu, Zhi-Gang,Ji, Lin-Tao,Liu, Jia,Fu, Ling-Ling,Zhao, Su-Fang
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p. 315 - 321
(2014/12/10)
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- Immobilization of cobalt porphyrin on CeO2@SiO2 core-shell nanoparticles as a novel catalyst for selective oxidation of diphenylmethane
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In this study, CeO2@SiO2 core-shell nanoparticles have been synthesized and used as supports to graft cobalt porphyrin via an amide bond. The catalyst was characterized using techniques such as FT-IR, UV-vis, SEM, TEM and BET. The re
- Guo, Xiang,Li, Yuan-Yuan,Shen, Dan-Hua,Song, Yuan-Yuan,Wang, Xiao,Liu, Zhi-Gang
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- CONJUGATE OF A PHOTOSENSITISER AND CHITOSAN AND USES THEREOF
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The present invention relates to novel chitosan-based conjugates, e.g. nanocarriers, comprising a derivative of the biocompatible polymer chitosan conjugated to a photosensitising agent, and uses thereof in photochemical internalisation (PCI) and photodynamic therapy (PDT). The invention also relates to the use of the novel conjugates of the invention in treatment or prevention of diseases, particularly cancer, and for vaccination purposes.
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Page/Page column 70
(2014/01/09)
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- Photostability of a dyad of magnesium porphyrin and fullerene and its application to photocurrent conversion
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A new type of acceptor-donor2 dyad system containing two magnesium porphyrin molecules and a fullerene molecule is much more stable than the magnesium porphyrin itself. When it is fabricated into a binary system using imidazole carboxylic acid as a linker to indium tin oxide, the molecule effects efficient photocurrent generation that surpasses the device using the corresponding zinc porphyrin. This journal is
- Ichiki, Takahiko,Matsuo, Yutaka,Nakamura, Eiichi
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supporting information
p. 279 - 281
(2013/02/22)
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- Facile synthesis, characterization, and fluorescence studies of novel porphyrin appended thiazoles
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A facile and high yielding synthesis of porphyrin appended thiazoles from the reaction of 5-(4-thiocarboxamidophenyl)-10,15,20-triphenylporphyrin with α-bromo ketones has been described. The fluorescence studies of synthesized porphyrin appended thiazoles in chloroform indicate that porphyrin π system is not greatly perturbed by substitution of a thiazole moiety at meso-phenyl ring even in the excited state.
- Mishra, Bhupendra,Shekar, K. P. Chandra,Kumar, Anil,Phukan,Mitra,Kumar, Dalip
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p. 125 - 128
(2013/04/10)
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- Bimolecular catalysis and turnover from a macromolecular host system
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The synthesis of a globular macromolecule and its application as a bimolecular catalyst are reported. The macromolecular structure supports (at least) two zinc-metalated porphyrin units, each capable of binding a single reactant. The proximity of the two
- Ellis, Adam,Gooch, David,Twyman, Lance J
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p. 5364 - 5371
(2013/07/26)
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- A broad-band capturing and emitting molecular triad: Synthesis and photochemistry
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A novel broad-band capturing and emitting supramolecular triad useful for solar energy harvesting and building optoelectronic devices is reported. The Royal Society of Chemistry 2013.
- Bandi, Venugopal,Ohkubo, Kei,Fukuzumi, Shunichi,D'Souza, Francis
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supporting information
p. 2867 - 2869
(2013/04/24)
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- Synthesis and DNA photocleavage studies of novel porphyrin diarylthiazoles
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A convenient and regioselective synthesis of porphyrin diarylthiazoles is reported via the reactions of alkynyl(aryl)iodonium tosylates and porphyrin thioamides. Among the synthesized porphyrin diarylthiazoles, compounds 6d and 6f have shown significant i
- Kumar, Dalip,Chandrashekar,Mishra, Bhupendra
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p. 1073 - 1079
(2014/01/06)
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- Metalloporphyrins immobilized on core-shell CeO2@SiO2 nanoparticles prepared by a double-coating method for oxidation of diphenyl methane
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Metalloporphyrins immobilized on CeO2@SiO2 core-shell nanoparticles were synthesized by a double-coating method and used for catalytic oxidation of diphenyl methane. A variety of characterization techniques including FT-IR, UV-vis, SEM, TEM, XRD, N2 adsorption-desorption and TGA were employed. The results show that the catalyst consists of regular nanoparticles (around 400 nm) with core-shell structure and metalloporphyrins were immobilized on CeO2@SiO2 core-shell nanoparticles via amide bonds. Moreover, these new developed catalysts for solvent-free selective oxidation of diphenyl methane exhibited an excellent catalytic activity, selectivity and stability. Furthermore, these catalysts could be reused 6 times without significant loss of their catalytic activity and the used catalysts maintained nearly the same physicochemical properties as the fresh.
- Guo, Xiang,Li, Yuan-Yuan,Shen, Dan-Hua,Gan, Jie,Tian, Mi,Liu, Zhi-Gang
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experimental part
p. 30 - 35
(2012/03/27)
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- Surface-functionalized hexagonal mesoporous silica supported 5-(4-carboxyphenyl)-10,15,20-triphenyl porphyrin manganese(III) chloride and their catalytic activity
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Manganese(III) 5-(4-carboxyphenyl)-10,15,20-triphenyl porphyrin chloride (Mn(TCPP)Cl) was grafted through amide bond on silica zeolite Y (HY), zeolite beta (Hβ) and hexagonal mesoporous silica (HMS). XRD, ICP-AES, N2 physisorption, SEM, TEM, FTIR and thermal analysis were employed to analyse these novel heterogeneous materials. These silica supported catalysts were shown to be used for epoxidation and good shape selectivity was observed. The effect of support structure on catalytic performance was also discussed. The catalytic activity remained when the catalysts were recycled five times. The energy changes about epoxidation of alkenes by NaIO4 and H2O 2 were also computationally calculated to explain the different catalytic efficiency.
- Zhang, Wei-Jie,Jiang, Ping-Ping,Zhang, Ping-Bo,Zheng, Jia-Wei,Li, Haiyang
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p. 4015 - 4022
(2013/08/23)
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- Conformational preference in bis(porphyrin) tweezer complexes: A versatile chirality sensor for α-chiral carboxylic acids
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Metallated porphyrin tweezers have demonstrated a remarkable ability to function as reporters of absolute stereochemistry for a number of different classes of organic molecules. Flexibility in binding, however, can result in an ensemble of different Exciton Coupled Circular Dichroism (ECCD) active conformations that could lead to variable results. Linker flexibility was found to be a key determinant of binding conformation. Experimental results indicate that a balance between linker flexibility and rigidity could yield an optimum porphyrin tweezer that stabilizes a common conformation for all bound chiral guests. This leads to a more simplified approach to absolute stereochemical determination of asymmetry for small organic molecules. This was demonstrated by the use of a C3-linked zincated porphyrin tweezer that yields a common conformational preference for a variety of α-chiral carboxylic acids derivatized with a diamine carrier. Copyright
- Tanasova, Marina,Borhan, Babak
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supporting information; experimental part
p. 3261 - 3269
(2012/07/01)
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- Photodynamic Molecular Beacons triggered by MMP-2 and MMP-9: Influence of the distance between photosensitizer and quencher onto photophysical properties and enzymatic activation
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Angiogenesis is a key step in the tumoral progression process. It is characterized by an over-expression of a number of matrix metalloproteinases (MMP). Among these MMPs, gelatinases (MMP-2 and MMP-9) are known to play a critical role in tumor angiogenesis and the growth of many cancers. Photodynamic Molecular Beacons (PMB) can be designed for cancer treatment by associating a chlorin-like photosensitizer and a black hole quencher linked by a gelatinase substrate peptide with the aim of silencing photosensitizer toxicity in non-targeted cells and restore its toxicity only in surrounding gelatinases. This article provides a report on the synthesis and photophysical and biochemical studies of new families of PMB, using tetraphenylchlorin and a black hole quencher as a donor-acceptor pair, and MMP specific sequence (H-Gly-Pro-Leu-Gly-Ile-Ala-Gly-Gln-Lys-OH or H-Pro-Leu-Gly-Leu-OH) to keep them in close proximity. Different spacers were used to evaluate the influence of the distance between the photosensitizer and the quencher on the photophysical properties and enzymatic activation of the PMB. Time-resolved quenching experiments were performed and FRET energy transfer could be observed. Photosensitizers' triplet state band in transient absorption disappears in PMB. However, even if both MMP-2 and MMP-9 were found to efficiently cleave the peptide alone, no cleavage was observed for all PMB. Further studies would be required to assess the ability of the PMB constructs to retain the sensitivity of the peptide linker to be cleaved by matrix metalloproteinases.
- Verhille,Benachour,Ibrahim,Achard,Arnoux,Barberi-Heyob,André,Allonas,Baros,Vanderesse,Frochot
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p. 5580 - 5594
(2013/02/25)
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- Synthesis, photophysical and electochemical properties of amide-bridged porphyrin-anthraquinone dimers
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Photoinduced electron-transfer processes of two newly synthesized porphyrin-anthraquinone dyads bridged with amide were studied with the UV-visible, fluorescence and transient absorption spectra. Results indicated that the intramolecular electron-transfer might take place via the excited states of the 5-(4-carboxyphenyl)-10,15,20-triphenylporphyrin unit to the anthraquinone moiety.
- Liu, Li-Zeng,Liu, Dong-Zhi,Tao, Min-Li,Zhou, Xue-Qin,Li, Wei
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experimental part
p. 3490 - 3492
(2012/07/28)
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- Introducing structural flexibility into porphyrin-DNA zipper arrays
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A more flexible nucleotide building block for the synthesis of new DNA based porphyrin-zipper arrays is described. Changing the rigid acetylene linker between the porphyrin substituent and the 2′-deoxyuridine to a more flexible propargyl amide containing
- Brewer, Ashley,Siligardi, Guiliano,Neylon, Cameron,Stulz, Eugen
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supporting information; experimental part
p. 777 - 782
(2011/03/22)
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- Synthesis, characterization and application of trans-D-B-A-porphyrin based dyes in dye-sensitized solar cells
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A series of metal-free trans-D-B-A porphyrin dyes have been synthesized and characterized as photo-sensitizers for dye-sensitized solar cells (DSSCs). These dye molecules contain a porphyrin unit as a π-bridge, a substituted phenyl group as an electron do
- Pasunooti, Kalyan Kumar,Song, Jun-Ling,Chai, Hua,Amaladass, Pitchamuthu,Deng, Wei-Qiao,Liu, Xue-Wei
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p. 219 - 225
(2012/01/13)
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- Supramolecular chirality in solvent-promoted aggregation of amphiphilic porphyrin derivatives: Kinetic studies and comparison between solution behavior and solid-state morphology by AFM topography
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The solvent-promoted aggregation behavior of some amphiphilic porphyrin derivatives bearing chiral functionality in the form of a charged L-proline group has been investigated by UV/Vis, resonance light scattering, fluorescence and circular dichroism spectroscopy. The investigated macro- cycles give rise to aggregates featuring supramolecular chirality with high el- lipticity. Kinetic studies reveal peculiar differences in the fashion of aggregation, depending on the intimate nature of the chiral functionality, namely, cat- ionic (nitrogen-quaternized L-proline, 3H2) or anionic (carboxylate residue, 6H2) group. Formation of anionic 6H2 aggregates shows a diffusion-limited kinetic behavior. AFM topography studies show formation of tighter globular structures. On the other hand, the corresponding 3H2 aggregates are formed by a cooperative, fractal-type decay, and appear as long-fibrous, looser structures. In the templated aggregation of 3H2 over preformed 6H2 aggregates, AFM images show formation of globular structures with reduced sizes, as a likely consequence of shorter in- terchromophore distances, due to favorable Coulombic interactions. The results obtained show an interesting parallelism between the solution behavior and the solid-state aggregate structures, corroborating the sergeant- soldier effect observed in the templat- ed aggregation. The results presented give important insights for understanding the complex mechanisms involved in these issues, which are of key importance for the development of chiral supramolecular materials and stereose- lective sensors and devices. 2010 Wiley-VCH Verlag GmbH & Co. KGaA.
- Monti, Donato,De Rossi, Massimo,Sorrenti, Alessandro,Laguzzi, Giuseppe,Gatto, Emanuela,Stefanelli, Manuela,Venanzi, Mariano,Luvidi, Loredana,Mancini, Giovanna,Paolesse, Roberto
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supporting information; experimental part
p. 860 - 870
(2010/06/20)
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- Site-specific prodrug release using visible light
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Using a photosensitization-singlet oxygenation-dioxetane cleavage strategy, a photodynamic prodrug system has been developed, whereby drugs bearing carbonyl groups can first be attached to a photosensitizer to give a photosensitizer-drug complex and then released from the complex upon visible light irradiation. Visible light, which has good penetration through tissue, generates singlet oxygen via the photosensitizer, which then releases the prodrug when and where required. With this system, drug mimics and methyl esters of NSAIDs have been successfully incorporated with photosensitizers related to verteporfin and then released by visible light illumination in high to quantitative yields within minutes. Copyright
- Jiang, Michael Y.,Dolphin, David
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p. 4236 - 4237
(2008/10/09)
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- Synthesis of glycoporphyrin derivatives and their antiviral activity against herpes simplex virus types 1 and 2
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Studies on the synthesis, structural elucidation, and antiviral evaluation of several carbohydrate-substituted meso-tetraarylporphyrins against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) are described. The potential of those photosensitizers, and of their precursors, on the photoinactivation of HSV-1 and HSV-2 was examined in Vero cells. Their virucidal and viral replication effects were assessed under white light, at their maximum noncytotoxic concentrations. The highest inhibitory effects on viral replication, for both viruses, were obtained with the glycoporphyrins where the sugar moiety bears unprotected hydroxyl groups. Strong inhibition of virus yield was observed even at concentrations much lower than their maximum noncytotoxic concentrations. These compounds can be postulated to be useful as potential drugs for the treatment of herpes simplex viruses infections.
- Tome, Joao P.C.,Neves, Maria G.P.M.S.,Tome, Augusto C.,Cavaleiro, Jose A.S.,Mendonca, Ana F.,Pegado, Ines N.,Duarte, Ricardo,Valdeira, Maria L.
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p. 3878 - 3888
(2007/10/03)
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