Tetraphenylporphyrin derivatives possessing piperidine group as potential agents for photodynamic therapy

Liao, Ping-Yong; Gao, Yan; Wang, Xinrong; Bao, Leilei; Bian, Jun; Hu, Tai‐Shan; Min, Zheng; Yan, Yuan; Chen, Zhilong

doi:10.1016/j.jphotobiol.2016.10.031

Cited by 13 publications

(7 citation statements)

References 31 publications

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“…Quinoline derivatives have attracted interest as photosensitizers in recent years attributed to their ability to absorb long‐wavelength light and high singlet oxygen generation efficiency [97–99] . Due to complex formation with DNA, molecules with quinoline rings were discovered to have DNA photocleavage activity [100] .…”

Section: Resultsmentioning

confidence: 99%

“…Quinoline derivatives have attracted interest as photosensitizers in recent years attributed to their ability to absorb long-wavelength light and high singlet oxygen generation efficiency. [97][98][99] Due to complex formation with DNA, molecules with quinoline rings were discovered to have DNA photocleavage activity. [100] Aromatic heterocycles as quinoline derivatives with a conjugated C=N bond system have a higher tendency for photochemical cleavage of DNA due to the development of a photoexcited (n-π*) state with radical properties.…”

Section: Dna Photocleavage Studiesmentioning

confidence: 99%

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Hantzsch‐Like Synthesis, DNA Photocleavage, DNA/BSA Binding, and Molecular Docking Studies of Bis(sulfanediyl)bis(tetrahydro‐5‐deazaflavin) Analogs Linked to Naphthalene Core

Ragheb

Abdelwahab

Darweesh

et al. 2022

Chemistry & Biodiversity

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The cyclocondensation reaction of aldehydes with dimedone and bis(6-aminopyrimidin-4-one) in acetic acid led to the formation of the corresponding bis (pyrimido[4,5-b]quinoline-4,6-diones) which are known as bis(sulfanediyl)bis(tetrahydro-5-deazaflavin) analogs in a single step. Also, bis(pyrimido[4,quinoline-4,6diones) which are linked to naphthyl core via phenoxymethyl linkage is prepared. The interactions of the synthesized compounds with DNA and bovine serum albumin (BSA) were studied. Gel electrophoresis assay was used to show the capability of the compounds to photocleave the supercoiled pBR322 plasmid DNA in UV-A (365 nm). Besides, the most photocleavable compound, bis(tetrahydropyrimido[4,5-b]quinoline-4,6-dione) linked to pyridin-3-yl at position-5 exhibits good binding affinities toward CT-DNA and BSA as supported by UV/VIS spectral studies. In addition to the experimental findings, a molecular docking simulation was performed to collect detailed binding data for this compound to both biomolecules.

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Section: Resultsmentioning

confidence: 99%

Section: Dna Photocleavage Studiesmentioning

confidence: 99%

Hantzsch‐Like Synthesis, DNA Photocleavage, DNA/BSA Binding, and Molecular Docking Studies of Bis(sulfanediyl)bis(tetrahydro‐5‐deazaflavin) Analogs Linked to Naphthalene Core

Ragheb

Abdelwahab

Darweesh

et al. 2022

Chemistry & Biodiversity

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“…Baldea et al demonstrated the meso-5,10,15,20-tetrakis (4-hydroxyphenyl) porphyrin (THOPP) induced apoptosis through caspase activation after PDT [53]. Liao et al reported TPP derivatives possessing piperidine groups induced cell death after PDT in the QBC-939 cholangiocarcinoma cell line and antitumor efficacy in QBC-939 tumor-bearing mice [54]. Roby et al described TPP free and TPP-loaded PEG-PE micelles induced apoptosis in murine Lewis lung carcinoma [55].…”

Section: Discussionmentioning

confidence: 99%

Photodynamic Therapy Activity of New Porphyrin-Xylan-Coated Silica Nanoparticles in Human Colorectal Cancer

Bretin

Pinon

Bouramtane

et al. 2019

Cancers

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Photodynamic therapy (PDT) using porphyrins has been approved for treatment of several solid tumors due to the generation of cytotoxic reactive oxygen species (ROS). However, low physiological solubility and lack of selectivity towards tumor sites are the main limitations of their clinical use. Nanoparticles are able to spontaneously accumulate in solid tumors through an enhanced permeability and retention (EPR) effect due to leaky vasculature, poor lymphatic drainage, and increased vessel permeability. Herein, we proved the added value of nanoparticle vectorization on anticancer efficacy and tumor-targeting by 5-(4-hydroxyphenyl)-10,15,20-triphenylporphyrin (TPPOH). Using 80 nm silica nanoparticles (SNPs) coated with xylan-TPPOH conjugate (TPPOH-X), we first showed very significant phototoxic effects of TPPOH-X SNPs mediated by post-PDT ROS generation and stronger cell uptake in human colorectal cancer cell lines compared to free TPPOH. Additionally, we demonstrated apoptotic cell death induced by TPPOH-X SNPs-PDT and the interest of autophagy inhibition to increase anticancer efficacy. Finally, we highlighted in vivo, without toxicity, elevated anticancer efficacy of TPPOH-X SNPs through improvement of tumor-targeting compared to a free TPPOH protocol. Our work demonstrated for the first time the strong anticancer efficacy of TPPOH in vitro and in vivo and the merit of SNPs vectorization.

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“…PDT is an emerging therapeutic procedure in cancer treatment that has attracted significant attention due to its high selectivity, non-invasive nature and minimal side effects, when compared to conventional therapy (Liao et al, 2016 ). Photosensitizer (PS) selection, tissue oxygen levels, and light wavelength are all key factors of PDT.…”

Section: Chemotherapy and Phototherapymentioning

confidence: 99%

A Review of Mesoporous Silica Nanoparticle Delivery Systems in Chemo-Based Combination Cancer Therapies

Gao

Shen

et al. 2020

Front. Chem.

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Chemotherapy is an important anti-tumor treatment in clinic to date, however, the effectiveness of traditional chemotherapy is limited by its poor selectivity, high systemic toxicity, and multidrug resistance. In recent years, mesoporous silica nanoparticles (MSNs) have become exciting drug delivery systems (DDS) due to their unique advantages, such as easy large-scale production, adjustable uniform pore size, large surface area and pore volumes. While mesoporous silica-based DDS can improve chemotherapy to a certain extent, when used in combination with other cancer therapies MSN based chemotherapy exhibits a synergistic effect, greatly improving therapeutic outcomes. In this review, we discuss the applications of MSN DDS for a diverse range of chemotherapeutic combination anti-tumor therapies, including phototherapy, gene therapy, immunotherapy and other less common modalities. Furthermore, we focus on the characteristics of each nanomaterial and the synergistic advantages of the combination therapies. Lastly, we examine the challenges and future prospects of MSN based chemotherapeutic combination therapies.

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Tetraphenylporphyrin derivatives possessing piperidine group as potential agents for photodynamic therapy

Cited by 13 publications

References 31 publications

Hantzsch‐Like Synthesis, DNA Photocleavage, DNA/BSA Binding, and Molecular Docking Studies of Bis(sulfanediyl)bis(tetrahydro‐5‐deazaflavin) Analogs Linked to Naphthalene Core

Hantzsch‐Like Synthesis, DNA Photocleavage, DNA/BSA Binding, and Molecular Docking Studies of Bis(sulfanediyl)bis(tetrahydro‐5‐deazaflavin) Analogs Linked to Naphthalene Core

Photodynamic Therapy Activity of New Porphyrin-Xylan-Coated Silica Nanoparticles in Human Colorectal Cancer

A Review of Mesoporous Silica Nanoparticle Delivery Systems in Chemo-Based Combination Cancer Therapies

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