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Relevant academic research and scientific papers

Two-photon excited organic nanoparticles for chemo-photodynamic therapy

Drug molecules assembling nanomedicines possess several advantages, including precise molecular structure, various combinations of therapeutic agents and high content of drugs. In this work, paclitaxel dimer and two-photo photosensitizer were devised and synthesized, which could coassemble into nanoparticles (Co-NPs) in aqueous medium through nanoprecipitation method. As-synthesized Co-NPs possess the uniform size of about 80 nm and great stability in physiological condition, and could produce the singlet oxygen upon near-infrared light irradiation. The Co-NPs indicate enhanced cellular uptake and endosomal escape upon irradiation, which result in the synergistic enhancement of cytotoxicity towards cancer cells and growth inhibition of human cervical cancer tumors. We believed this combination therapy based on organic nanoparticles represent a new and important development in the cancer therapy.

Synthesis and structural study of organic two-photon-absorbing cycloalkanone chromophores

The three organic two-photon-absorbing cycloalkanone chromophores 2,4-bis[4-(diethylamino)benzylidene]cyclobutanone, C26H32N2O (I), 2,5-bis[4-(diethylamino)benzylidene]cyclopentanone, C27H34N2O (II), and 2,6-bis[4-(diethylamino)benzylidene]cyclohexanone, C28H36N2O (III), were obtained by a reaction between 4-(diethylamino)benzaldehyde and the corresponding cycloalkanone and were characterized by single-crystal X-ray diffraction studies, as well as density functional theory (DFT) quantum-chemical calculations. Molecules of this series have three main fragments, i.e. central acceptor (A) and two terminal donors (D 1 and D 2) and represent examples of the D 1-π-A-π-D 2 molecular design. All three compounds crystallize with two crystallographically independent molecules in the asymmetric unit (A and B) and are distinguished by the conformations of both the molecular Et2N - C6H4 - C=C - C(=O) - C=C - C6H4 - NEt2 backbone (arcuate or linear) and the terminal diethylamino substituents (syn- or antiperiplanar to the plane of the molecule). The central four- and five-membered rings in I and II are almost planar, and the six-membered ring in III adopts a sofa conformation. In the crystals of I-III, the two independent molecules A and B form hydrogen-bonded [A?B] dimers via intermolecular C - H?O hydrogen bonds. Furthermore, the [A?B] dimers in I are bound by intermolecular C - H?O hydrogen bonds into two-tier puckered layers, whereas in the crystals of II and III, the [A?B] dimers are stacked along the c and a axes, respectively. Taking into account the decreasing steric strain upon expanding the central ring, compound I might be more efficient as a two-photon absorption chromophore than compounds II and III, which corresponds to the results of spectroscopic studies.

Effects of novel diarylpentanoid analogues of curcumin on secretory phospholipase A2, cyclooxygenases, lipo-oxygenase, and microsomal prostaglandin e synthase-1

Arachidonic acid and its metabolites have generated a heightened interest due to their significant role in inflammation. Inhibiting the enzymes involved in arachidonic acid metabolism has been considered as the synergistic anti-inflammatory effect. A series of novel curcumin diarylpentanoid analogues were synthesized and evaluated for their inhibitory effects on activity of secretory phospholipase A2, cyclooxygenases, soybean lipo-oxygenase as well as microsomal prostaglandin E synthase-1. Among the curcumin analogues, compounds 3, 6, 9, 12, and 17 exhibited strong inhibition of secretory phospholipase A2 activity, with IC50 values ranging from 5.89 to 11.02 μm. Seven curcumin analogues 1, 3, 6, 7, 9, 11, and 12 showed inhibition of cyclooxygenases-2 with IC50 values in the range of 46.11 to 94.86 μm, which were lower than that of curcumin. Compounds 3, 6, 7, 12, and 17 showed strong inhibition of lipo-oxygenase enzyme activity. Preliminary screening of diarylpentanoid curcumin analogues for microsomal prostaglandin E synthase-1 activity revealed that four diarylpentanoid curcumin analogues 5, 6, 7, and 13 demonstrated higher inhibition of microsomal prostaglandin E synthase-1 activity with IC50 ranging from 2.41 to 4.48 μm, which was less than that of curcumin. The present results suggest that some of these diarylpentanoid analogues were able to inhibit the activity of these enzymes. This raises the possibility that diarylpentanoid analogues of curcumin might serve as useful starting point for the design of improved anti-inflammatory agents. A series of novel diarylpentanoid analogues of curcumin was synthesized by direct coupling of the appropriate aromatic aldehyde with three ketones, namely cyclohexanone, acetone, and cyclopentanone, under base-catalyzed Claisen-Schmidt condensation reaction. These analogues were screened for their inhibitory effects on the activity of secretory phospholipase A2 (sPLA2), cyclooxygenases, soybean lipo-oxygenase as well as microsomal prostaglandin E synthase-1 using in vitro assays.

Effect of alicyclic ring size on the photophysical and photochemical properties of bis(arylidene)cycloalkanone compounds

A series of bis(arylidene)cycloalkanone compounds based on cyclobutanone, cyclopentanone, cyclohexanone and cycloheptanone, C4-C7, respectively, with a D-π-A-π-D structure containing the same donor and acceptor but different alicyclic rings was prepared. The effects of alicyclic ring size on the photophysical, photochemical and electrochemical properties of these compounds were investigated systematically. We found that an increase of the number of carbons in the central alicyclic ring leads to changes in geometry, which has significant effects on the conjugation, and photophysical and photochemical properties. These effects include decreases in the fluorescence quantum yield, transient lifetimes, peak extinction coefficients, and the singlet oxygen quantum yield with the increase of the ring size. The one-photon absorption spectra, the two-photon absorption (2PA) spectra, and the fluorescence spectra all show a hypsochromic shift with increasing ring size. The results of this study provide guidance for the design of new cycloketone-based D-π-A-π-D 2PA compounds for photopolymerization and photodynamic therapy applications.

Polyethylene glycol-functionalized benzylidene cyclopentanone dyes for two-photon excited photodynamic therapy

A series of polyethylene glycol-functionalized benzylidene cyclopentanone dyes with varying lipid/water partition coefficients were synthesized in high yields by a simple process. Detailed characterization and systematic studies of these molecules, including linear and nonlinear photophysical properties, reactive oxygen yields, and in vitro photodynamic therapy (PDT) activities, were conducted. Four of these dyes exhibited good solubility in PBS (>2 mg ml-1, which is sufficient for clinical venous injection), high reactive oxygen yields, large two-photon absorption and low dark toxicity, under the therapy dosage. Among them, two dyes could be absorbed efficiently by human rectal cancer 1116 cells, and presented strong two-photon excited PDT activity in in vitro cell experiments.