Synthesis and in vitro biological evaluation of novel water‐soluble porphyrin complexes for cancer photodynamic therapy

2022 ◽  
Author(s):  
Bingjie Hou ◽  
Yuanwen Zhang ◽  
Cuili Li ◽  
Xueqin Sun ◽  
Xiaoxia Feng ◽  
...  
Keyword(s):  
Photodynamic Therapy ◽  
Biological Evaluation ◽  
Water Soluble ◽  
Water Soluble Porphyrin

Cytotoxic and antitumoral activity of N-(9H-purin-6-yl) benzamide derivatives and related water-soluble prodrugs

2021 ◽  
Vol 14 ◽  
Author(s):  
Emeline Cros-Perrial ◽  
Steve Saulnier ◽  
Muhammad Zawwad Raza ◽  
Rémi Charmelot ◽  
David Egron ◽  
...  
Keyword(s):  
Cancer Cell ◽  
Molecular Mechanisms ◽  
Biological Evaluation ◽  
Water Soluble ◽  
Antitumoral Activity ◽  
Cell Cycle Distribution ◽  
Synergistic Activity ◽  
Benzamide Derivatives

Background: The development of small molecules as cancer treatments is still of both interest and importance. Objective: Having synthesized and identified the initial cytotoxic activity of a series of chemically related N-(9H-purin-6-yl) benzamide derivatives, we continued their evaluation on cancer cell models. We also synthesized water-soluble prodrugs of the main compound and performed in vivo experiments. Method: We used organic chemistry to obtain compounds of interest and prodrugs. The biological evaluation included MTT assays, synergy experiments, proliferation assays by CFSE, cell cycle distribution and in vivo antitumoral activity. Results: Our results show activities on cancer cell lines ranging from 3-39 µM for the best compounds, with both induction of apoptosis and decrease in cell proliferation. Two compounds evaluated in vivo showed weak antitumoral activity. In addition, the lead compound and its prodrug had a synergistic activity with the nucleoside analogue fludarabine in vitro and in vivo. Conclusion: Our work allowed us to gain better knowledge on the activity of N-(9H-purin-6-yl) benzamide derivatives and showed new examples of water-soluble prodrugs. More research is warranted to decipher the molecular mechanisms of the molecules.

scholarly journals A Luminescent, Water-Soluble Ir(III) Complex as a Potential Photosensitizer for Two-Photon Photodynamic Therapy

2021 ◽  
Vol 11 (24) ◽  
pp. 11596
Author(s):  
Elisabeta I. Szerb ◽  
Sharmistha Chatterjee ◽  
Massimo La Deda ◽  
Giovanna Palermo ◽  
Lucie Sancey ◽  
...  
Keyword(s):  
Photodynamic Therapy ◽  
Water Soluble ◽  
In Vitro Experiments ◽  
Time Resolved Fluorescence ◽  
Time Resolved ◽  
Biologically Relevant ◽  
Two Photon ◽  
Fluorescence Measurements ◽  
Detection Probe

This work reports the study of two-photon induced properties of a highly luminescent cyclometalated Ir(III) complex, [Ir(ppy)2(en)] OOCCH3 (1), ppy = 2-phenylpyridine, en = ethylenediamine. Steady-state and time-resolved fluorescence measurements were performed by exciting 1 at the biologically relevant wavelength of 800 nm, whereas, the generation of singlet oxygen (1O2) was evaluated using 9,10-Anthracenediyl-bis(methylene)dimalonic acid (ABDA) as a detection probe. Preliminary in vitro experiments with U87-MG cells were performed, showing the potential of this compound as a two-photon photodynamic therapy (2P-PDT) agent at NIR wavelengths.

Photophysical properties and intracellular imaging of water-soluble porphyrin dimers for two-photon excited photodynamic therapy

2009 ◽  
Vol 7 (5) ◽  
pp. 889 ◽  
Author(s):  
Marina K. Kuimova ◽  
Hazel A. Collins ◽  
Milan Balaz ◽  
Emma Dahlstedt ◽  
James A. Levitt ◽  
...  
Keyword(s):  
Photodynamic Therapy ◽  
Photophysical Properties ◽  
Water Soluble ◽  
Intracellular Imaging ◽  
Two Photon ◽  
Water Soluble Porphyrin ◽  
Porphyrin Dimers

scholarly journals Two-Photon Photodynamic Therapy by Water-Soluble Self-Assembled Conjugated Porphyrins

2013 ◽  
Vol 2013 ◽  
pp. 1-11 ◽  
Author(s):  
Kazuya Ogawa ◽  
Yoshiaki Kobuke
Keyword(s):  
Photodynamic Therapy ◽  
Singlet Oxygen ◽  
Cross Section ◽  
Water Soluble ◽  
Photon Absorption ◽  
Time Resolved ◽  
Two Photon Absorption ◽  
Two Photon ◽  
Luminescence Measurement ◽  
Water Soluble Porphyrin

Studies on two-photon absorption (2PA) photodynamic therapy (PDT) by using three water-soluble porphyrin self-assemblies consisting of ethynylene-linked conjugatedbis(imidazolylporphyrin) are reviewed. 2PA cross-section values in water were obtained by an open aperture Z-scan measurement, and values were extremely large compared with those of monomeric porphyrins such as hematoporphyrin. These compounds were found to generate singlet oxygen efficiently upon one- as well as two-photon absorption as demonstrated by the time-resolved luminescence measurement at the characteristic band of singlet oxygen at 1270 nm and by using its scavenger. Photocytotoxicities for HeLa cancer cells were examined and found to be as high as those of hematoporphyrin, demonstrating that these compounds are potential candidates for 2PA-photodynamic therapy agents.

Water-soluble porphyrin-based logic gates

2012 ◽  
Vol 16 (01) ◽  
pp. 72-76 ◽  
Author(s):  
Lili Li ◽  
Peiying Cai ◽  
Yuefei Deng ◽  
Liutao Yang ◽  
Xuan He ◽  
...  
Keyword(s):  
Metal Ions ◽  
Logic Gates ◽  
Water Soluble ◽  
Porphyrin Molecule ◽  
Acid Base ◽  
Fluorescent Spectra ◽  
Simple Logic ◽  
Logic Operations ◽  
Water Soluble Porphyrin

A series of simple logic gates based on a water-soluble porphyrin molecule, 5,10,15,20-tetrakis-(4-sulfonatophenyl)porphyrin (TPPS4) is designed. Logic operations, including OR, NOR, INHIBIT and AND, have been built by two inputs of acid/base or metal ions (Al3+ and/or Sn4+) and two outputs of UV-vis absorption and fluorescent spectra. An OFF–ON switch triggered by Al3+ ion in vitro is developed based on TPPS4.

scholarly journals HPMA-Based Copolymers Carrying STAT3 Inhibitor Cucurbitacin-D as Stimulus-Sensitive Nanomedicines for Oncotherapy

Pharmaceutics ◽  
2021 ◽  
Vol 13 (2) ◽  
pp. 179
Author(s):  
Marina R. Tavares ◽  
Klára Hrabánková ◽  
Rafał Konefał ◽  
Martin Kaňa ◽  
Blanka Říhová ◽  
...  
Keyword(s):  
Biological Evaluation ◽  
Water Soluble ◽  
Anticancer Effect ◽  
Polymer Carrier ◽  
Polymer Conjugate ◽  
Reversible Addition ◽  
Cucurbitacin D ◽  
Effective Delivery ◽  
Potential Component

The study describes the synthesis, physicochemical properties, and biological evaluation of polymer therapeutics based on N-(2-hydroxypropyl)methacrylamide (HPMA) copolymers intended for a tumor-targeted immuno-oncotherapy. Water-soluble linear and cholesterol-containing HPMA precursors were synthesized using controlled reversible addition–fragmentation chain transfer polymerization to reach molecular weight Mn about 2 × 104 g·mol−1 and low dispersity. These linear or self-assembled micellar conjugates, containing immunomodulatory agent cucurbitacin-D (CuD) or the anticancer drug doxorubicin (Dox) covalently bound by the hydrolytically degradable hydrazone bond, showed a hydrodynamic size of 10–30 nm in aqueous solutions. The CuD-containing conjugates were stable in conditions mimicking blood. Importantly, a massive release of active CuD in buffer mimicking the acidic tumor environment was observed. In vitro, both the linear (LP-CuD) and the micellar (MP-CuD) conjugates carrying CuD showed cytostatic/cytotoxic activity against several cancer cell lines. In a murine metastatic and difficult-to-treat 4T1 mammary carcinoma, only LP-CuD showed an anticancer effect. Indeed, the co-treatment with Dox-containing micellar polymer conjugate and LP-CuD showed potentiation of the anticancer effect. The results indicate that the binding of CuD, characterized by prominent hydrophobic nature and low bioavailability, to the polymer carrier allows a safe and effective delivery. Therefore, the conjugate could serve as a potential component of immuno-oncotherapy schemes within the next preclinical evaluation.

Facile synthesis of a highly water-soluble graphene conjugated chlorophyll-a photosensitizer composite for improved photodynamic therapy in vitro

2017 ◽  
Vol 41 (18) ◽  
pp. 10069-10082 ◽  
Author(s):  
Hongyue Zhang ◽  
Jianjun Cheng ◽  
Wenting Li ◽  
Guanghui Tan ◽  
Zhiqiang Wang ◽  
...  
Keyword(s):  
Photodynamic Therapy ◽  
Chlorophyll A ◽  
Water Solubility ◽  
Water Soluble ◽  
Facile Synthesis ◽  
Pyropheophorbide A

Graphene conjugated withp-bromo-phenylhydrazone-methyl pyropheophorbide-a (BPMppa, 683 nm), which is derived from a chlorophyll-aphotosensitizer, shows significantly improved water-solubility and PDT efficiency.

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