scholarly journals Synthesis and photodynamic activity of diaryl-porphyrins characterized by the presence of nitro groups

2006 ◽  
Vol 10 (11) ◽  
pp. 1319-1326 ◽  
Author(s):  
Stefano Banfi ◽  
Enrico Caruso ◽  
Emanuele Fieni ◽  
Loredana Buccafurni ◽  
Marzia Bruna Gariboldi ◽  
...  
Keyword(s):  
Colon Adenocarcinoma ◽  
Aromatic Aldehydes ◽  
Human Colon ◽  
Halogen Lamp ◽  
Porfimer Sodium ◽  
Standard Procedures ◽  
Photodynamic Activity ◽  
Phenyl Rings ◽  
Meso Position

A panel of nitro substituted 5,15-diaryl-porphyrins, featuring nitro groups either on the phenyl rings or on one of the two free meso-positions, was synthesized. In the former category, compounds 5-(3-nitrophenyl)-15-phenylporphyrin, 5,15-di(3-nitrophenyl)porphyrin and 5-(4-nitrophenyl)-15-phenylporphyrin were obtained following standard procedures by reacting dipyrromethane and aromatic aldehydes. In the latter category, porphyrins 10-nitro-5,15-diphenylporphyrin, 10-nitro-5-(3-methoxyphenyl)-15-phenylporphyrin and 10-nitro-5,15-di(3-methoxyphenyl)porphyrin were generated by nitration of 5,15-diarylporphyrins with trifluoroacetic acid/sodium nitrite under particularly mild conditions. The new molecules bearing one or two nitro-groups were tested as photosensitizers during in vitro experiments on a human colon adenocarcinoma cell line (HCT116), and their effects were compared with those induced by temoporfin, porfimer sodium and by some previously published electron-rich diarylporphyrins. The results, expressed as IC50 values obtained by the MTT test following 24 h incubation with the photosensitizers and 2 h irradiation with a 500 W tungsten-halogen lamp, indicate that the presence of an electron withdrawing substituent, on a meso-position, decreases the photodynamic activity of the compound. Conversely, 5-(3-nitrophenyl)-15-phenylporphyrin, a non symmetrically substituted diarylporphyrin bearing both one electron-deficient and one lipophilic moiety, resulted in high phototoxic activity.

Synthesis and photobiological properties of novel silicon(IV) phthalocyanines axially modified by paracetamol and 4-hydroxyphenylacetamide

2009 ◽  
Vol 13 (12) ◽  
pp. 1227-1232 ◽  
Author(s):  
Jian-Dong Huang ◽  
Xiong-Jie Jiang ◽  
Xiao-Min Shen ◽  
Qing-Qing Tang
Keyword(s):  
Colon Adenocarcinoma ◽  
Human Colon ◽  
Biological Properties ◽  
Ht29 Cells ◽  
Adenocarcinoma Cells ◽  
Photodynamic Activity ◽  
Lower Singlet ◽  
Very High ◽  
Colon Adenocarcinoma Cells

Two novel axial-disubstituted silicon(IV) phthalocyanines (compounds 1 and 2) have been prepared by introducing paracetamol (a common antipyretic analgesic) or its isomer 4-hydroxyphenylacetamide at the axial positions of silicon(IV) phthalocyanine, respectively. Their photophysical and biological properties have been examined. Both compounds are highly soluble and exhibit very similar absorption spectra in N, N-dimethylformamide, which is typical for non-aggregated phthalocyanines. Both compounds are photocytotoxic against HT29 human colon adenocarcinoma cells. Compound 2 shows a very high in vitro photodynamic activity, with the IC50 value down to 15 nM. In contrast, compound 1 exhibits a much lower in vitro photodynamic activity toward HT29 cells, which can be attributed to its higher aggregating trend in the biological medium and lower singlet oxygen quantum yield.

scholarly journals Synthesis, Characterization, and In Vitro Photodynamic Activity of Novel Amphiphilic Zinc(II) Phthalocyanines Bearing Oxyethylene-Rich Substituents

2008 ◽  
Vol 2008 ◽  
pp. 1-8 ◽  
Author(s):  
Jian-Yong Liu ◽  
Xiong-Jie Jiang ◽  
Wing-Ping Fong ◽  
Dennis K. P. Ng
Keyword(s):  
High Efficiency ◽  
Culture Media ◽  
Fluorescence Emission ◽  
Colon Adenocarcinoma ◽  
Human Colon ◽  
Photodynamic Activity ◽  
Hepatocarcinoma Cells ◽  
Intracellular Fluorescence ◽  
Aggregation Tendency

Three novel zinc(II) phthalocyanines substituted with one or two 3,4,5-tris(3,6,9-trioxadecoxy)benzoxy group(s) have been prepared and spectroscopically characterized. These compounds are highly soluble and remain nonaggregated in N,N-dimethylformamide. Upon excitation, they exhibit a relatively weak fluorescence emission and high efficiency to generate singlet oxygen compared with the unsubstituted zinc(II) phthalocyanine. These amphiphilic photosensitizers formulated with Cremophor EL are highly photocytotoxic against HT29 human colon adenocarcinoma and HepG2 human hepatocarcinoma cells. The mono-α-substituted analogue 4 is particularly potent with IC50 values as low as 0.02 μM. The higher photodynamic activity of this compound can be attributed to its lower aggregation tendency in the culture media as shown by absorption spectroscopy and higher cellular uptake as suggested by the stronger intracellular fluorescence, resulting in a higher efficiency to generate reactive oxygen species inside the cells.

In Vitro and in Vivo Comparison of Binding of 99m-Tc-Iabeled Anti-CEA MAb F33-104 with 99m-Tc-labeled Anti-CEA MAb BW431/26

1999 ◽  
Vol 38 (04) ◽  
pp. 115-119
Author(s):  
N. Oriuchi ◽  
S. Sugiyama ◽  
M. Kuroki ◽  
Y. Matsuoka ◽  
S. Tanada ◽  
...  
Keyword(s):  
Nude Mice ◽  
Binding Capacity ◽  
Colon Adenocarcinoma ◽  
Human Colon ◽  
Cell Binding ◽  
Vitro Binding ◽  
Labeling Method ◽  
Human Colon Adenocarcinoma

Summary Aim: The purpose of this study was to assess the potential for radioimmunodetection (RAID) of murine anti-carcinoembryonic antigen (CEA) monoclonal antibody (MAb) F33-104 labeled with technetium-99m (99m-Tc) by a reduction-mediated labeling method. Methods: The binding capacity of 99m-Tc-labeled anti-CEA MAb F33-104 with CEA by means of in vitro procedures such as immunoradiometric assay and cell binding assay and the biodistribution of 99m-Tc-labeled anti-CEA MAb F33-104 in normal nude mice and nude mice bearing human colon adenocarcinoma LS180 tumor were investigated and compared with 99m-Tc-labeled anti-CEA MAb BW431/26. Results: The in vitro binding rate of 99m-Tc-labeled anti-CEA MAb F33-104 with CEA in solution and attached to the cell membrane was significantly higher than 99m-Tclabeled anti-CEA MAb BW431/261 (31.4 ± 0.95% vs. 11.9 ± 0.55% at 100 ng/mL of soluble CEA, 83.5 ± 2.84% vs. 54.0 ± 2.54% at 107 of LS 180 cells). In vivo, accumulation of 99m-Tc-labeled anti-CEA MAb F33-104 was higher at 18 h postinjection than 99m-Tc-labeled anti-CEA MAb BW431/26 (20.1 ± 3.50% ID/g vs. 14.4 ± 3.30% ID/g). 99m-Tcactivity in the kidneys of nude mice bearing tumor was higher at 18 h postinjection than at 3 h (12.8 ± 2.10% ID/g vs. 8.01 ± 2.40% ID/g of 99m-Tc-labeled anti-CEA MAb F33-104, 10.7 ± 1.70% ID/g vs. 8.10 ± 1.75% ID/g of 99m-Tc-labeled anti-CEA MAb BW431/26). Conclusion: 99m-Tc-labeled anti-CEA MAb F33-104 is a potential novel agent for RAID of recurrent colorectal cancer.

scholarly journals Antiproliferative Activity on Human Colon Adenocarcinoma Cells and In Vitro Antioxidant Effect of Anthocyanin-Rich Extracts from Peels of Species of the Myrtaceae Family

Molecules ◽  
2021 ◽  
Vol 26 (3) ◽  
pp. 564
Author(s):  
Nayara Simas Frauches ◽  
Júlia Montenegro ◽  
Thuane Amaral ◽  
Joel Pimentel Abreu ◽  
Gabriela Laiber ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Phenolic Compounds ◽  
Colon Adenocarcinoma ◽  
Human Colon ◽  
Native Plant ◽  
Total Anthocyanin ◽  
Adenocarcinoma Cells ◽  
Human Colon Adenocarcinoma ◽  
Colon Adenocarcinoma Cells

There is a significant indication of the beneficial health effects of fruit rich diets. Fruits of native plant species have noticeably different phytochemicals and bioactive effects. The aim of this work was to characterize and compare the constituents of jabuticaba (Myrciaria jaboticaba, MJ), jamun-berry (Syzygium cumini, SC), and malay-apple (Syzygium malaccense, SM) extracts and their influence on antioxidant activity in vitro and antiproliferative effects on human colon adenocarcinoma cells. According to the results, dried peel powders (DP) have a high anthocyanin content, phenolic compounds, and antioxidant activity when compared to freeze dried extracts (FD). M. jaboticaba dried peel powder extract had a higher total anthocyanin and phenolic compounds content (802.90 ± 1.93 and 2152.92 ± 43.95 mg/100 g, respectively). A reduction in cell viability of HT-29 cells after treatment with M. jaboticaba extracts (DP-MJ and FD-MJ) was observed via MTT assay. Flow cytometry showed that the treatment with the anthocyanin-rich extracts from MJ, SC, and SM had an inhibitory impact on cell development due to G2/M arrest and caused a rise in apoptotic cells in relation to the control group. The findings of this study highlight the potential of peel powders from Myrtaceae fruits as an important source of natural antioxidants and a protective effect against colon adenocarcinoma.

scholarly journals Effect of β-carotene-rich tomato lycopene β-cyclase (tlcy-b) on cell growth inhibition in HT-29 colon adenocarcinoma cells

2008 ◽  
Vol 102 (2) ◽  
pp. 207-214 ◽  
Author(s):  
Paola Palozza ◽  
Diana Bellovino ◽  
Rossella Simone ◽  
Alma Boninsegna ◽  
Francesco Cellini ◽  
...  
Keyword(s):  
Cell Growth ◽  
Growth Inhibition ◽  
Colon Adenocarcinoma ◽  
Human Colon ◽  
Cell Growth Inhibition ◽  
Adenocarcinoma Cells ◽  
Ht 29 ◽  
Colon Adenocarcinoma Cells ◽  
Β Carotene

Lycopene β-cyclase (tlcy-b) tomatoes, obtained by modulating carotenogenesis via genetic engineering, contain a large amount of β-carotene, as clearly visible by their intense orange colour. In the present study we have subjected tlcy-b tomatoes to an in vitro simulated digestion and analysed the effects of digestate on cell proliferation. To this aim we used HT-29 human colon adenocarcinoma cells, grown in monolayers, as a model. Digested tomatoes were diluted (20 ml, 50 ml and 100 ml/l) in culture medium and added to the cells for different incubation times (24 h, 48 h and 72 h). Inhibition of cell growth by tomato digestate was dose-dependent and resulted from an arrest of cell cycle progression at the G0/G1 and G2/M phase and by apoptosis induction. A down-regulation of cyclin D1, Bcl-2 and Bcl-xl expression was observed. We also found that heat treatment of samples before digestion enhanced β-carotene release and therefore cell growth inhibition. To induce with purified β-carotene solubilised in tetrahydrofuran the same cell growth inhibition obtained with the tomato digestate, a higher amount of the carotenoid was necessary, suggesting that β-carotene micellarised during digestion is utilised more efficiently by the cells, but also that other tomato molecules, reasonably made available during digestion, may be present and cooperate with β-carotene in promoting cell growth arrest.

scholarly journals Salecan-Clay Based Polymer Nanocomposites for Chemotherapeutic Drug Delivery Systems; Characterization and In Vitro Biocompatibility Studies

Materials ◽  
2020 ◽  
Vol 13 (23) ◽  
pp. 5389
Author(s):  
Paula Ecaterina Florian ◽  
Madalina Icriverzi ◽  
Claudia Mihaela Ninciuleanu ◽  
Elvira Alexandrescu ◽  
Bogdan Trica ◽  
...  
Keyword(s):  
Structural Parameters ◽  
Colon Adenocarcinoma ◽  
Human Colon ◽  
Chemotherapeutic Agents ◽  
In Vitro Biocompatibility ◽  
Synthetic Hydrogel ◽  
Mdbk Cells ◽  
Subsequent Effect ◽  
Ht 29

Salecan is a microbial polysaccharide suitable to obtain hydrogel for biomedical applications due to the excellent hydrophilicity and biocompatibility properties. In this work, Salecan of different concentrations was introduced into polymethacrylic acid (PMAA) in the presence of clay to form novel semi synthetic hydrogel nanocomposites systems and loaded afterwards with doxorubicin (DOX). The physical–chemical characteristics of the nanocomposites systems and their effect on the viability, and morphology of MDBK (Madin–Darby bovine kidney), HT-29 human colorectal adenocarcinoma and Colo 205 human colon adenocarcinoma cell lines were investigated. DOX release from the nanocomposite systems, cell up-take and subsequent effect on cell proliferation was also analyzed. It was found that Salecan concentration determined the swelling behavior, structural parameters and morphological features of the nanocomposite systems. The hydrogen bonds strongly influenced the formation of PMAA–Salecan–clay systems, each component bringing its own contribution, thus demonstrating the achievement of an advanced crosslinked network and a more compacted hydrogel nanocomposite morphology. All the synthesized nanocomposites had negligible toxicity to normal MDBK cells and chemoresistent HT-29 cell line, whereas in the case of Colo 205 cells a decrease by 40% of the cell viability was obtained for the sample containing the highest amount of Salecan. This effect was correlated with the lowest pore size distribution leading to highest available specific surface area and entrapped amount of DOX which was further released from the nanocomposite sample. Corroborating all the data it can be suggested that the synthesized nanocomposites with Salecan and clay could be good candidates as vehicles for chemotherapeutic agents.

Association of DNA repair inhibition and radiofrequency ablation in the treatment of xenografted colorectal cancer.

2012 ◽  
Vol 30 (4_suppl) ◽  
pp. 215-215
Author(s):  
Flavien Devun ◽  
Julian Biau ◽  
Jian-sheng Sun ◽  
Alban Denys ◽  
Marie Dutreix
Keyword(s):  
Colorectal Cancer ◽  
Dna Repair ◽  
Radiofrequency Ablation ◽  
Median Survival ◽  
Tumor Resection ◽  
Hepatic Metastases ◽  
Colon Adenocarcinoma ◽  
Human Colon ◽  
Heat Sensitivity

215 Background: Most of the patients with advanced colorectal cancer will develop liver metastasis, even after primary tumor resection. Although surgical resection remains the gold standard treatment of hepatic metastases, only few patients are eligible to curative resection. Radiofrequency ablation (RFA) is the most common curative alternative. Dbait are new molecules that inhibit DNA double-strand breaks repair. In vitro, Dbait has shown to increase cell death after hyperthermia. Here, we have assessed the combination of Dbait and RFA in the treatment of human colorectal cancer model xenografted in nude mice. Methods: 98 mice were flank-grafted with HT29 (human colon adenocarcinoma). When tumor reached 500 mm3, mice were sham treated (n=19), treated by Dbait via local injections (n=20), treated by RFA using an incomplete ablation scheme (n=20) or treated by combination of Dbait and RFA (n=39 separated in two Dbait regimens). After RFA, 39 mice were sacrificed for blinded pathological study, and 59 others were followed for survival analysis. Results: Mice treated by RFA-Dbait had significantly longer survival as compared to RFA alone (median survival: 56 vs 39 days, p<0.05) while RFA improved survival as compared to controls (median survival: 39 vs 28 days, p<0.05). Pathological studies of tumor slice have demonstrated significant decrease of tumor area and cancer cell viability in the RFA-Dbait group. Conclusions: While the implication of DNA repair activity in heat sensitivity remains unclear, our results show that the addition of Dbait to RFA enhances the antitumor response in this model and provide an experimental basis for the use of Dbait as an additional therapy to RFA. [Table: see text]

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