Synthesis of a new chlorin photosensitizer for photodynamic therapy against colon cancer

Chen, Jianjiao; Chen, Zhiqiang; Tan, Li‐Tao; Yang, Jie; Shen, Lei; Deng, Jun; Jiang, Xin; Zou, Dengfeng

doi:10.1039/d2qm00046f

Cited by 4 publications

(2 citation statements)

References 32 publications

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“…An essential tactic for finding new anti-cancer medications with high efficacy and low toxicity is the development of anti-colorectal active analogs based on recognized inhibitors. Through chemical modification of the NSAIDs with promising anti-cancer actions, it is possible to completely increase the anti-cancer potency 50) . Our goal is to create novel anti-cancer drugs, and our lead molecule is isokaempferide.…”

Section: Anticancer Resultsmentioning

confidence: 99%

Anti-collagenase, Anti-elastase, Anti-urease, and Anti-cancer Potentials of Isokaempferide as Natural Compound: In vitro and in silico Study

Yin,

Zhang,

Huang

et al. 2024

J. Oleo Sci.

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Section: Anticancer Resultsmentioning

confidence: 99%

Anti-collagenase, Anti-elastase, Anti-urease, and Anti-cancer Potentials of Isokaempferide as Natural Compound: In vitro and in silico Study

Yin,

Zhang,

Huang

et al. 2024

J. Oleo Sci.

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“…The well-known approach to improve the phototoxicity of cyanine dyes is based on the introduction of heavy atoms such as iodine [23][24][25], which significantly increases the probability of intersystem crossing (ISC) from the singlet to the triplet state due to enhanced spin-orbit coupling resulting in the elevated rates of cytotoxic species generation [26]. The enhancement of PDT and APDT efficacy owing to the "heavy atom effect" has been previously reported in the example of cyanine dyes [27][28][29] among the photosensitizers of other dye classes [30,31].…”

Section: Introductionmentioning

confidence: 99%

Effect of Solubilizing Group on the Antibacterial Activity of Heptamethine Cyanine Photosensitizers

et al. 2023

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Antibiotic resistance of pathogenic bacteria dictates the development of novel treatment modalities such as antimicrobial photodynamic therapy (APDT) utilizing organic dyes termed photosensitizers that exhibit a high cytotoxicity upon light irradiation. Most of the clinically approved photosensitizers are porphyrins that are poorly excitable in the therapeutic near-IR spectral range. In contrast, cyanine dyes function well in the near-IR region, but their phototoxicity, in general, is very low. The introduction of iodine atoms in the cyanine molecules was recently demonstrated to greatly increase their phototoxicity. Herein, we synthesized a series of the new iodinated heptamethine cyanine dyes (ICy7) containing various solubilizing moieties, i.e., negatively charged carboxylic (ICy7COOH) and sulfonic (ICy7SO3H) groups, positively charged triphenylphosphonium (ICy7PPh3), triethylammonium (ICy7NEt3) and amino (ICy7NH2) groups, and neutral amide (ICy7CONHPr) group. The effect of these substituents on the photodynamic eradication of Gram-positive (S. aureus) and Gram-negative (E. coli and P. aeruginosa) pathogens was studied. Cyanine dyes containing the amide and triphenylphosphonium groups were found to be the most efficient for eradication of the investigated bacteria. These dyes are effective at low concentrations of 0.05 µM (33 J/cm2) for S. aureus, 50 µM (200 J/cm2) for E. coli, and 5 µM (100 J/cm2) for P. aeruginosa and considered, therefore, promising photosensitizers for APDT applications. The innovation of the new photosensitizers consisted of a combination of the heavy-atom effect that increases singlet oxygen generation with the solubilizing group’s effect improving cell uptake, and with effective near-IR excitation. Such a combination helped to noticeably increase the APDT efficacy and should pave the way for the development of more advanced photosensitizers for clinical use.

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Porphyrin photosensitizers compatible with both aqueous and non-aqueous conditions: Acid dependent spectral, solubility and photocatalytic properties of meso-tetra(pyridyl)porphyrins

Khaledian,

Zakavi

2024

Inorganic Chemistry Communications

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Synthesis of a new chlorin photosensitizer for photodynamic therapy against colon cancer

Abstract: Photodynamic therapy (PDT) shows tremendous potential for treatment of cancer due to its advantages of non-invasiveness, low systemic toxicity. Phorphrine compounds are potentially translatable photosensitizers with excellent biocompatibility for PDT....

Cited by 4 publications

References 32 publications

Anti-collagenase, Anti-elastase, Anti-urease, and Anti-cancer Potentials of Isokaempferide as Natural Compound: <i>In vitro</i> and <i>in silico</i> Study

Anti-collagenase, Anti-elastase, Anti-urease, and Anti-cancer Potentials of Isokaempferide as Natural Compound: <i>In vitro</i> and <i>in silico</i> Study

Effect of Solubilizing Group on the Antibacterial Activity of Heptamethine Cyanine Photosensitizers

Porphyrin photosensitizers compatible with both aqueous and non-aqueous conditions: Acid dependent spectral, solubility and photocatalytic properties of meso-tetra(pyridyl)porphyrins

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