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Preparation and characterization of a small library of symmetric trans-di(4-pyridyl)porphyrin dimers, obtained by either Glaser-Hay or Sonogashira coupling reactions from appropriately prepared trans-di-4-pyridylporphyrin precursors, is presented. The porphyrin dimers are differentiated by a phenyl-alkynyl bridge of increasing length at one meso-position, while for all the derivatives the two remaining opposite meso-positions are tailored with a phenyl moiety bearing a short polyether chain. Coordination of the four pyridyl groups with appropriate metal fragments may be exploited to construct tubular hollow structures, with varied internal sizes, depending on the choice of the porphyrin dimer component.

An efficient transition metal catalyzed procedure for the reductive alkylation of proteins has been developed. Imines formed from the condensation of aldehydes (1 mM) with lysine residues and the N-terminus can be reduced efficiently by a [Cp*Ir(4,4′-dime

The mixture of triterpenoids from birch bark and amphiphilic meso-arylprophyrins was used to develop spherical amorphous nanoparticles. The nanoparticles were studied with the methods of electron microscopy, dynamic light scattering, UV spectroscopy, and

Abstract: Mono- and diethylene oxide derivatives of tetra(p-hydroxyphenyl)porphyrin (THPP) with different conformation states are synthesized. These compounds exhibit high photosensitization activity in the generation of singlet oxygen in organic and aque

The synthesis of asymmetric meso-aryl-substituted porphyrins containing three 4-methoxycarbonylphenyl groups, and 4-hydroxyphenyl or 4-hydroxy-3-methoxyphenyl radicals or isomeric 3-and 4-pyridyl radicals as a forth substitute, is described. 4-Oxyalkyl derivatives are obtained. The ytterbium complexes of these porphyrins have been synthesized, and their spectral luminescence properties have been studied. A significant difference in the lifetimes of the excited state of ytterbium complexes of the esters and acids of asymmetric porphyrins has been shown. Pleiades Publishing, Ltd., 2011.

Targeted photodynamic therapy (PDT) is one of the promising approaches for the selective killing of cancerous cells without affecting the normal cells, and hence designing new strategies for targeted PDT is extremely important. Herein we report the design and synthesis of a new class of nanosheets derived from the self-assembly of the iodo-BODIPY-biotin conjugate as a photosensitizer for targeted PDT applications. The nanosheet exhibits a high extinction coefficient in the NIR region, high singlet oxygen efficiency, no toxicity in the dark and cell targeting ligands (biotin) on the surface, which are necessary features required for an ideal photosensitizer. Overexpression of sodium-dependent multivitamin transporters (SMVTs) in HeLa and A549 (biotin receptor positive cell lines) is explored for the selective uptake of the nanophotosensitizer through receptor mediated endocytosis (interaction between biotin and SMVT). Control experiments using a biotin receptor negative cell line (WI-38) are also carried out to confirm that the specific interaction between the SMVTs and biotin is mainly responsible for the selective uptake of the photosensitizer. Efficient killing of cancerous cells is demonstrated upon light irradiation through the generation of singlet oxygen and other reactive oxygen species around the cellular environment.

Multi-component polymers (MCPs) incorporate multiple components into the main chain or pendant group and have special functions. In this work, the small-molecule fluorescent boron-dipyrromethene (BODIPY), with ester groups and/or alkoxyl long chains, was synthesized first. Then, this small-molecule BODIPY and the components containing CC bonds (HD and PD) were reacted via the Heck coupling reaction to obtain macromolecular probes that perform different functions. With the help of ester groups and alkoxyl "tail", polymers MCP1 and MCP2 were soluble in a variety of water-miscible organic solvents. Moreover, MCP3 and MCP4 were completely soluble in water. These macromolecular probes showed sensitive and selective recognition toward Hg2+/Hg+ because of the introduced components (HD and PD) containing CC bonds. After binding to Hg2+/Hg+, MCP1 and MCP2 demonstrated fluorescence quenching and color changes, which allowed the dual-channel specific detection of Hg2+/Hg+. Compared with the probes containing HD, the probes containing PD showed higher sensitivity, and the good recognition ability caused the detection limit to be as low as 0.32 μM, which may be due to the "molecular wire"mechanism. The small-molecule components with different functional groups were polymerized into fluorescent polymer materials. This methodology endows the polymer probe with good solubility and high sensitivity, and the as-prepared polymers could sense metal ions in aqueous environments. This journal is

Despite being a clinically approved intervention for cancer, photodynamic therapy (PDT) still suffers from limitations. Prime among these is a therapeutic response that is mostly oxygen dependent. This limits the utility of PDT in treating hypoxic tumors

The present invention relates to a tumor targeting photodynamic therapeutic agent containing a compound represented by chemical formula 1. The compound according to the present invention can significantly improve cancer treatment efficiency.COPYRIGHT KIPO 2019

Photocages are light-sensitive chemical protecting groups that provide external control over when, where, and how much of a biological substrate is activated in cells using targeted light irradiation. Regrettably, most popular photocages (e.g., o-nitrobenzyl groups) absorb cell-damaging ultraviolet wavelengths. A challenge with achieving longer wavelength bond-breaking photochemistry is that long-wavelength-absorbing chromophores have shorter excited-state lifetimes and diminished excited-state energies. However, here we report the synthesis of a family of BODIPY-derived photocages with tunable absorptions across the visible/near-infrared that release chemical cargo under irradiation. Derivatives with appended styryl groups feature absorptions above 700 nm, yielding photocages cleaved with the highest known wavelengths of light via a direct single-photon-release mechanism. Photorelease with red light is demonstrated in living HeLa cells, Drosophila S2 cells, and bovine GM07373 cells upon ～5 min irradiation. No cytotoxicity is observed at 20 μM photocage concentration using the trypan blue exclusion assay. Improved B-alkylated derivatives feature improved quantum efficiencies of photorelease ～20-fold larger, on par with the popular o-nitrobenzyl photocages (?φ = 50-100 M-1 cm-1), but absorbing red/near-IR light in the biological window instead of UV light.

The present invention provides a porphyrin derivative having a hydrophilic polyethylene glycol group and a hydrophobic alkyl group, and a method for preparing the same. The porphyrin derivative of the present invention is excellent in anoxic oxygen produc

The invention belongs to the field of organic synthesis and drugs, and more specifically relates to a porphyrin compound which is high in water solubility and is capable of absorbing near infrared ray, and a preparation method and applications thereof. Ac

A major challenge in photodynamic cancer therapy (PDT) is avoiding PDT-induced hypoxia, which can lead to cancer recurrence and progression through activation of various angiogenic factors and significantly reduce treatment outcomes. Reported here is an acetazolamide (AZ)-conjugated BODIPY photosensitizer (AZ-BPS) designed to mitigate the effects of PDT-based hypoxia by combining the benefits of anti-angiogenesis therapy with PDT. AZ-BPS showed specific affinity to aggressive cancer cells (MDA-MB-231 cells) that overexpress carbonic anhydrase IX (CAIX). It displayed enhanced photocytotoxicity compared to a reference compound, BPS, which is an analogous PDT agent that lacks an acetazolamide unit. AZ-BPS also displayed an enhanced in vivo efficacy in a xenograft mouse tumor regrowth model relative to BPS, an effect attributed to inhibition of tumor angiogenesis by both PDT-induced ROS generation and CAIX knockdown. AZ-BPS was evaluated successfully in clinical samples collected from breast cancer patients. We thus believe that the combined approach described here represents an attractive therapeutic approach to targeting CAIX-overexpressing tumors.

A new series of N-methylfulleropyrrolidines bearing oligo(poly(ethylene oxide))-appended Percec monodendrons (fulleromonodendrons, 4a-f) have been synthesized. The substituted position of the oligo(poly(ethylene oxide)) chain(s) on the phenyl group of the Percec monodendron for 4a-f was varied, which is at the 4-, 2,4-, 3,5-, 3,4,5-, 2,3,4- and 2,4,6- position, respectively. 4a-e are obtained as solids at 25°C and can self-organize into lamellar phases as revealed by X-ray diffraction (XRD) and small-angle X-ray scattering (SAXS) measurements, while 4f appears as a viscous liquid. The substitution patterns of the oligo(poly(ethylene oxide)) chain(s) also significantly influence the solubility of 4a-f, especially in ethanol and water. Formation of self-organized supramolecular structures of 4d and 4e in water as well as 4d in ethanol is evidenced from UV-vis and dynamic light scattering (DLS) measurements. Further studies in water using various imaging techniques including transmission electron microscopy (TEM), freeze-fracture TEM (FF-TEM), cryo-TEM and atomic force microscopy (AFM) observations revealed the formation of well-defined vesicles for 4d and plate-like aggregates for 4e, indicating that the aggregation behavior of the fulleromonodendrons is highly dependent on their molecular structures. For 4d in ethanol, only irregular aggregates were noticed, indicating the solvent also plays a role on regulating the aggregation behavior. After functionalization with the Percec monodendrons, 4a-f can preserve the intriguing electrochemical properties of pristine C60 as revealed by cyclic voltammetries. The thermotropic properties of 4a-f have also been investigated. It was found that all of them show good thermal stability, but no mesophases were detected within the investigated temperature ranges. (Figure Presented).

The invention relates to a preparation method of a non-ionic fullerene-containing amphiphilic molecule. According to the invention, oligomeric ethylene glycol monomethyl ether bromo-derivative and hydroxy benzene (naphthalene, pyrene) formaldehyde are used as raw materials to synthesize an intermediate product oligomeric ethylene glycol monomethyl ether substituted benzene (naphthalene, pyrene) formaldehyde; and then, oligomeric ethylene glycol monomethyl ether substituted benzene (naphthalene, pyrene) formaldehyde is used as a donor unit and fullerene is used as a receptor so as to synthesize the non-ionic fullerene-containing amphiphilic molecule. The target product obtained has advantages of novel structure, high heat stability and adjustable solubility, can form a self-assembly structure in a solution and under the solvent-free condition, and is suitable for fields of surface chemistry, supramolecular self-assembly, photoelectronic device and the like.

In recent years, we have developed a low molecular weight hydrogelator system that is formed in situ under ambient conditions through catalysed hydrazone formation between two individually non-gelating components. In this contribution, we describe a molecular toolbox based on this system which allows us to (1) investigate the limits of gel formation and fine-tuning of their bulk properties, (2) introduce multicolour fluorescent probes in an easy fashion to enable high-resolution imaging, and (3) chemically modify the supramolecular gel fibres through click and non-covalent chemistry, to expand the functionality of the resultant materials. In this paper we show preliminary applications of this toolbox, enabling covalent and non-covalent functionalisation of the gel network with proteins and multicolour imaging of hydrogel networks with embedded mammalian cells and their substructures. Overall, the results show that the toolbox allows for on demand gel network visualisation and functionalisation, enabling a wealth of applications in the areas of chemical biology and smart materials.

A series of amphiphilic porphyrins appended with pyridinium cation and/or polyethylene glycol have been synthesized and fully characterized by 1H NMR, IR and MALDI-TOF-MS. Their photophysical properties were determined and the singlet oxygen (

A Bodipy-based energy transfer cassette with a singlet oxygen reactive linker between the donor and acceptor modules has an interesting emergent property, if the acceptor module is also a photosensitizer. Singlet oxygen produced by the photosensitizer rea

Logical progress: Independent molecular logic gates have been designed and characterized. Then, the individual molecular logic gates were coerced to work together within a micelle. Information relay between the two logic gates was achieved through the intermediacy of singlet oxygen. Working together, these concatenated logic gates result in a self-reporting and activatable photosensitizer. GSH=glutathione. Copyright

A dye sensitized solar cell, comprising a-heteroleptic polypyridil complex of Ru, Os or Fe. The donating ligand has an extended conjugated n-system increasing the light absorbance and keeing the LUMO energy level higher than that of the anchoring ligand. A compacting compound whose molecular structure comprises a terminal group, a hydrophobic part and an anchoring′ group may be co-adsorbed together with the dye on the semi-conductive metal oxide layer of the photoanode, forming a dense mixed self-assembled monolayer.

A series of asymmetric tetraarylporphyrins was synthesized from pyrrole, para-substituted oligo- or poly(ethylene glycol) monomethyl ether benzaldehyde and from 4-hydroxybenzaldehyde etherified with diethyl bromomalonate according to the Lindsey method. A

The present invention relates to the imidazole derivative of the following formula (I) wherein R1 is hydrogen, optionally substituted alkyl and the like, R2 is hydrogen, optionally substituted alkyl and the like, R3is optionally substituted heteroaryl, R4 is optionally substituted cycloalkyl, optionally substituted phenyl and the like, provided that when R1 is hydrogen, and R2 and R4 are the same or different and each is phenyl or phenyl substituted by halogen atom, lower alkyl or lower alkoxy, R3 is benzothiazolyl or thiazolyl substituted by phenyl, the imidazole derivative of the following formula (XII) wherein R6 is optionally substituted phenyl or optionally substituted heteroaryl and R7 is substituted phenyl, and pharmaceutically acceptable salts thereof. The compounds of the formulas (I) and (XII) and pharmaceutically acceptable salts thereof of the present invention inhibit IL-4 and IL-5 production by Th2 cells and are effective for the prophylaxis and treatment of allergic diseases such as atopic dermatitis, bronchial asthma, allergic rhinitis and the like.

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