Young Key Shim

d-(+)-Galactose-Conjugated Single-Walled Carbon Nanotubes as New Chemical Probes for Electrochemical Biosensors for the Cancer Marker Galectin-3

d-(+)-Galactose-conjugated single-walled carbon nanotubes (SWCNTs) were synthesized for use as biosensors to detect the cancer marker galectin-3. To investigate the binding of galectin-3 to the d-(+)-galactose-conjugated SWCNTs, an electrochemical biosensor was fabricated by using molybdenum electrodes. The binding affinities of the conjugated SWCNTs to galectin-3 were quantified using electrochemical sensitivity measurements based on the differences in resistance together with typical I-V characterization. The electrochemical sensitivity measurements of the d-(+)-galactose-conjugated SWCNTs differed significantly between the samples with and without galectin-3. This indicates that d-(+)-galactose-conjugated SWCNTs are potentially useful electrochemical biosensors for the detection of cancer marker galectin-3.

Size-Dependent Photodynamic Activity of Gold Nanoparticles Conjugate of Water Soluble Purpurin-18-N-Methyl-D-Glucamine

Gold nanoparticles (GNPs) conjugates of water soluble ionic photosensitizer (PS), purpurin-18-N-methyl-D-glucamine (Pu-18-NMGA), were synthesized using various molar ratios between HAuCl4 and Pu-18-NMGA without adding any particular reducing agents and surfactants. The PS-GNPs conjugates showed long wavelength absorption of range 702–762 nm, and their different shapes and diameters depend on the molar ratios used in the synthesis. In vitro anticancer efficacy of the PS-GNPs conjugates was investigated by MTT assay against A549 cells, resulting in higher photodynamic activity than that of the free Pu-18-NMGA. Among the PS-GNPs conjugates, the GNPs conjugate from the molar ratio of 1 : 2 (Au(III): Pu-18-NMGA) exhibits the highest photodynamic activity corresponding to bigger size (~60 nm) of the GNPs conjugate which could efficiently transport the PS into the cells than that of smaller size of the GNPs conjugate.

Synthesis of methyl pyropheophorbide-a pyrazole derivatives and their in vitro cell viabilities on A549 cells

Porphyrins and chlorins containing acetylacetone residues on the peripheral substituents are known to readily react with hydrazine derivatives to form porphyrin and chlorin derivatives possessing a pyrazole moiety. In this study, we have carried out the synthesis of methyl pyropheophorbide-a derivatives containing a pyrazole moiety on its peripheral position. Moreover, we have examined a preliminary in vitro effect of these new derivatives on A549 cancer cell in photodynamic therapy.

Synthesis and Characterization of Novel Purpurinimides as Photosensitizers for Photodynamic Therapy

A series of novel purpurinimides with long wavelength absorption were designed and synthesized to develop novel and potential photosensitizers. These compounds were investigated through reduction, oxidation, rearrangement reaction and amidation reactions of methyl pheophorbide a. They demonstrated a considerable bathochromic shift of the major absorption band in the red region of the optical spectrum (695–704 nm). Newly synthesized purpurinimides were screened for their antitumor activities, and showed higher photodynamic efficiency against A549 cell lines as compared to purpurin-18 methyl ester. The results revealed the novel purpurinimides could be potential photosensitizers.

Efficient synthesis and in vitro photodynamic anticancer study of new purpurinimide-hydrazone conjugates

A series of new purpurinimide-hydrazone conjugates were synthesized, and their in vitro anticancer efficacy against A549 lung cancer cell lines was evaluated. It was found that the incorporation of the hydrazone group to the purpurinimide could increase their anticancer activities via a combination of photodynamic therapy and chemotherapy.

Synthesis and Biological Evaluation of New Imidazolium and Piperazinium Salts of Pyropheophorbide-a for Photodynamic Cancer Therapy

We have designed imidazolium and piperazinium salts of pyropheophorbide-a in order to develop effective photosensitizers which have good solubility in polar and non polar media and to reveal the possible influences of the piperazine and imidazole moieties on the biological activities of pyropheophorbide-a. The phototoxicity of those pyropheophorbide-a salts against A549 cells was studied in vitro and compared with that of pyropheophorbide-a. The result showed that complexing piperazine and imidazole into pyropheophorbide-a decreases its dark toxicity without greatly decreasing phototoxicity and, enhances its phototoxicity without greatly increasing dark toxicity, respectively. This work not only describes novel amphiphilic salt complexes of pyropheophobide-a which retain the biological activities of the parent compound pyropheophorbide-a and could be effective candidate for PDT, but also reveals the possibility of developing effective photosensitizers by complexing imidazole and piperazine into other hydrophobic photosensitizers.

Efficient photosensitization by a chlorin-polyoxometalate supramolecular complex.

The 4:1 supramolecular complexed ionic salt between pyridinium chlorin and polyanionic [α-SiMo12O40](4-) exhibits significantly enhanced photodynamic activity against A549 cell lines because of increased singlet oxygen photogeneration through high cellular penetration and localization of the chlorin molecules on the ionic salt into the cancer cell. Confocal laser scanning microscopy images clearly represent a higher uptake and photodynamic effect of this supramolecular complex corresponding to the lower IC50 value compared to the free chlorin.

Synthesis and photodynamic activities of novel water soluble purpurin-18-N-methyl-D-glucamine photosensitizer and its gold nanoparticles conjugate

A new type of water soluble ionic photosensitizer (PS), purpurin-18-N-methyl-D-glucamine (Pu-18-NMGA) has been synthesized and it was conjugated into gold nanoparticles (GNPs) stabilized by the PS without adding any particular reducing agents and surfactants. In vitro anticancer efficacy of the PS and its PS–GNPs conjugate against A549 lung cancer cell lines was evaluated. The PS–GNPs conjugate based on water-soluble Pu-18-NMGA afforded good PDT efficacy which was three times greater than that of the water-soluble PS.

Gadolinium complexes of chlorin derivatives applicable for MRI contrast agents and PDT

One of the ultimate goals of contrast agent (CA) research in magnetic resonance imaging (MRI) is to identify tumor-seeking materials. Thus, cancer diagnosis by Photodynamic Therapy (PDT) using photosensitizer will be one of the best tools for cancer research. By linking paramagnetic gadolinium [Gd(III)] ion to tumor selective chlorin-based photosensitizers, the cancer cell can be easily detected with high sensitivity and cured by appropriate laser irradiation simultaneously. The synthesis of monomer and dimer chlorin derivatives, such as pyropheophorbide-a and purpurin systems, conjugated with Gd(III) diethylenetriaminepentaacetic acid (DTPA) by means of diethylene-triaminepentaacetic dianhydride (caDTPA) for the evaluation as CAs for MRI was described in the present study.

Synthesis and photodynamic activity of new imidazole substituted pyropheophorbide-a derivatives

Two new imidazole substituted chlorin derivatives, namely (4-[1-imidazolyl]-phenyl)-amide pyropheophorbide-a and (3-[1-imidazolyl]-propyl)-amide pyropheophorbide-a have been synthesized. Their cell viabilities on A549 human lung adenocarcinoma cells were investigated and compared with that of pyropheophorbide-a. According to the phototoxicity study, (4-[1-imidazolyl]-phenyl)-amide pyropheophorbide-a and (3-[1-imidazolyl]-propyl)-amide pyropheophorbide-a were found superior to pyropheophorbide-a with respect to high phototoxicity. This work demonstrates that imidazole substituted chlorin derivatives could be a promising candidate for photodynamic therapy and are worth further investigations.