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Carbazole appended trans-dicationic pyridinium porphyrin finds supremacy in DNA binding/photocleavage over a non-carbazolyl analogue

Dalton Transactions, ISSN: 1477-9234, Vol: 51, Issue: 33, Page: 12453-12466
2022
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  • Citations
    15
  • Captures
    13
  • Social Media
    136
    • Shares, Likes & Comments
      136
      • Facebook
        136

Article Description

A carbazolyl appended trans-pyridyl porphyrin (1) was synthesized and its dicationic form 2 was obtained by methylation of the pyridyl group. Copper and zinc complexes of porphyrin 2 (Cu(ii), 3; Zn(ii), 4) were isolated and characterized by various modern spectroscopic techniques. The DNA binding properties of 2, 3, and 4 have been explored against calf thymus-DNA (CT-DNA). DNA binding was quantized using the intrinsic binding constant (K) that was calculated by UV-visible absorption spectroscopy, and the value K = 1.6 × 10 M for compound 2 reveals a better interaction of 2 towards CT-DNA than those of 3 (3.1 × 10 M) and 4 (3.4 × 10 M), which follows the order 2 > 4 > 3. The fluorescence quenching efficiency and ethidium bromide quenching assay also indicated a good binding affinity of all the compounds towards CT-DNA. Furthermore, the spectroscopic data suggest that the possible mode of interaction is intercalation. The docking studies were in accordance with the experimental results. Notably, DNA cleavage studies reveal that 2 shows better damage than 3 and 4 which is in accordance with the binding affinity order 2 > 4 > 3. The observed quantum yield (2: 0.65, 3: 0.33, and 4: 0.97) and no change in DNA cleavage in the presence of NaN reveal the involvement of singlet oxygen. The singlet excited state lifetimes were in the range of 6.3-1.2 ns. Furthermore, these porphyrins can be investigated as interesting photosensitizers in photodynamic therapy and photochemotherapy.

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