Water-soluble meso-thienyl BODIPY therapeutics: Synthesis, characterization, exploring photophysicochemical and DNA/BSA binding properties

Karanlık, Ceren Can; Karanlık, Gürkan; Erdoğmuş, Alı

doi:10.1016/j.jphotochem.2023.114581

Cited by 12 publications

(6 citation statements)

References 74 publications

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“…However, it has been concluded that the singlet oxygen generation capacity is reduced by replacing heavy atoms with aryl or heteroaryl groups with coupling type reactions at these positions. In our study, the ability of compounds 2–4 to produce singlet oxygen is that the sulfur groups in their structures induce ISC 38–42 …”

Section: Resultsmentioning

confidence: 70%

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Synthesis and characterization of novel BODIPYs and their antioxidant, antimicrobial, photodynamic antimicrobial, antibiofilm and DNA interaction activities

Karanlık

Özdemir

et al. 2023

Photochem & Photobiology

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In the current study, we synthesized and characterized new BODIPY derivatives (1–4) having pyridine or thienyl‐pyridine substituents at meso‐ position and 4‐dibenzothienyl or benzo[b]thien‐2‐yl moieties at 2‐,6‐ positions. We investigated fluorescence properties and the ability to form singlet oxygen. In addition, various biological activities of BODIPYs such as DPPH scavenging, DNA binding/cleavage ability, cell viability inhibition, antimicrobial activity, antimicrobial photodynamic therapy (aPDT) and biofilm inhibition properties were performed. BODIPY derivatives BDPY‐3 (3) and BDPY‐4 (4) have high fluorescence quantum yields as 0.50 and 0.61 and 1O2 quantum yields were calculated as 0.83 for BDPY‐1 (1), 0.12 for BDPY‐2 (2), 0.11 for BDPY‐3 and 0.23 for BDPY‐4. BODIPY derivatives BDPY‐2, BDPY‐3 and BDPY‐4 displayed 92.54 ± 5.41%, 94.20 ± 5.50%, and 95.03 ± 5.54% antioxidant ability, respectively. BODIPY compounds showed excellent DNA chemical nuclease activity. BDPY‐2, BDPY‐3 and BDPY‐4 also exhibited 100% APDT activity against E. coli at all tested concentrations. In addition to these, they demonstrated a highly effective biofilm inhibition activity against Staphyloccous aureus and Pseudomans aeruginosa. BDPY‐4 showed the most effective antioxidant and DNA cleavage activity, while BDPY‐3 exhibited the most effective antimicrobial and antibiofilm activity.

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Section: Resultsmentioning

confidence: 70%

“…In our study, the ability of compounds 2-4 to produce singlet oxygen is that the sulfur groups in their structures induce ISC. [38][39][40][41][42]…”

Section: Singlet Oxygen Quantum Yieldsmentioning

confidence: 99%

Synthesis and characterization of novel BODIPYs and their antioxidant, antimicrobial, photodynamic antimicrobial, antibiofilm and DNA interaction activities

Karanlık

Özdemir

et al. 2023

Photochem & Photobiology

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“…Nonintercalative binding shows up as hyperchromic and blue-shifted . The experiment was carried out following the reported procedure and explained in the Supporting Information. An increasing concentration of CT-DNA (CT-DNA; 0–20 μM) is added to a fixed concentration of GaPc (50 μM) to perform an absorption titration.…”

Section: Resultsmentioning

confidence: 99%

Hybrid Sono-Photodynamic Combination Therapy Mediated by Water-Soluble Gallium Phthalocyanine Enhances the Cytotoxic Effect against Breast Cancer Cell Lines

Turkkol,

Can Karanlık,

Calıskan

et al. 2024

ACS Appl. Bio Mater.

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Breast cancer is a life-threatening disease that is gaining increasing importance due to its rising incidence, highlighting the need for novel treatment methods with the least disadvantages. Recently, scientists have focused on developing therapeutic treatment modalities for effective cancer treatment. In contrast to conventional cancer treatment methods such as immunotherapy, surgery, chemotherapy, or radiotherapy, photodynamic therapy (PDT) is gaining prominence. Besides, sonodynamic treatment (SDT) is a noninvasive therapeutic approach that uses ultrasound to induce high tissue penetration. In both methods, sensitizers are activated to generate cytotoxic reactive oxygen species such as •OH and 1O2. In particular, the combined use of hybrid and complementary treatment methods has become an important modality in cancer treatment in recent years. Sono-photodynamic therapy (SPDT), which is an important method applied in combination with PDT and SDT, has started to be preferred in terms of reducing potential side effects compared to monotherapy. One of the most important types of sensitizers used in PDT and SDT is known as phthalocyanines (Pcs). Motivated by these facts, this research presents the sono-photochemical, in vitro cytotoxicity, and theoretical evaluation of water-soluble gallium phthalocyanine (GaPc). The results indicate that the quantum yield of the generation of singlet oxygen increased in sono-photochemical studies (ΦΔ = 0.94), compared to photochemical studies (ΦΔ = 0.72). In vitro analyses revealed that GaPc did not exhibit significant cytotoxic effects at the specified varying concentration doses (1–20 μM). Furthermore, GaPc-mediated SPDT triggered cell death by inducing reactive oxygen species formation in the breast cancer cell line (MCF-7). The interaction mechanism of the GaPc with EGFR and VEGFR2 target proteins, which are critical regulators of metastasis, proliferation, and angiogenesis, was investigated by molecular docking simulation. GaPc has effective binding affinities against target proteins, and this affinity was found to be the highest against VEGFR2. Molecular docking results showed a good correlation with the obtained biological results. Eventually, this molecular building of the efficient water-soluble phthalocyanine-based sensitizer is a potential therapeutic for PDT, SDT, and SPDT applications.

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“…It should be noted that among these compounds two are water soluble and may become promising photosensitizers since water solubility represents an important characteristic of good photosensitizers. 38,39 DFT (density functional theory) calculations 40 were carried out to determine the molecular geometries of new compounds, the electronic absorption and other excited state properties, the impact of introducing different substituents onto the BODIPY core, the frontier molecular HOMO and LUMO orbitals and other important chemical descriptors of the synthesized compounds.…”

Section: Introductionmentioning

confidence: 99%

BODIPY derivatives modified with carborane clusters: synthesis, characterization and DFT studies

et al. 2023

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Water-soluble meso-thienyl BODIPY therapeutics: Synthesis, characterization, exploring photophysicochemical and DNA/BSA binding properties

Cited by 12 publications

References 74 publications

Synthesis and characterization of novel BODIPYs and their antioxidant, antimicrobial, photodynamic antimicrobial, antibiofilm and DNA interaction activities

Synthesis and characterization of novel BODIPYs and their antioxidant, antimicrobial, photodynamic antimicrobial, antibiofilm and DNA interaction activities

Hybrid Sono-Photodynamic Combination Therapy Mediated by Water-Soluble Gallium Phthalocyanine Enhances the Cytotoxic Effect against Breast Cancer Cell Lines

BODIPY derivatives modified with carborane clusters: synthesis, characterization and DFT studies

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