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<p>A comparative analysis was carried out to examine the effect of solvent nature and the specific features of molecular structure on aggregation behavior, pH stability, hydrophobicity, and antimicrobial activity of 2-iodo-tetramethyl-ethyl-BODIPY (where BODIPY is boron(<span>iii</span>) dipyrromethene) (<b>1</b>), 2,6-diiodo-tetramethyl-BODIPY (<b>2</b>), and 2,6-diiodo-tetramethyl-BODIPY containing an ester residue of butanoic acid (<b>3</b>) in the <i>meso</i>-spacer as potential photosensitizers for antimicrobial photodynamic therapy. All the studied compounds demonstrated a sufficiently high stability in both acidic and alkaline media. The introduction of iodine atoms into the pyrrole rings and the substitution of the hydrogen atom at the <i>meso</i>-position of the BODIPY core with an ester residue significantly (up to ∼1.4 times) increase the hydrophobicity of the luminophores compared to the tetramethylated analogue. In this case, compound <b>1</b> exhibits bactericidal activity against <i>Staphylococcus aureus</i> under irradiation at a wavelength of 530 nm, compound <b>2</b> demonstrates an activity that is 16 times lower, and BODIPY <b>3</b> does not show any antimicrobial activity under these experimental conditions.</p>

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Effect of structural and solvation factors on aggregation, pH stability, lipophilicity, and antimicrobial activity of mono- and diiodo-substituted boron(iii) dipyrromethene luminophores

  • 期刊论文

  • 发表日期：

    2025年4月1日

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  • G. B. Guseva,
  • D. R. Baidamshina,
  • U. D. Paramonova,
  • E. Y. Trizna,
  • A. R. Kayumov,
  • S. A. Lisovskaya,
  • I. R. Gilfanov,
  • L. E. Nikitina,
  • E. V. Antina

摘要

A comparative analysis was carried out to examine the effect of solvent nature and the specific features of molecular structure on aggregation behavior, pH stability, hydrophobicity, and antimicrobial activity of 2-iodo-tetramethyl-ethyl-BODIPY (where BODIPY is boron(iii) dipyrromethene) (1), 2,6-diiodo-tetramethyl-BODIPY (2), and 2,6-diiodo-tetramethyl-BODIPY containing an ester residue of butanoic acid (3) in the meso-spacer as potential photosensitizers for antimicrobial photodynamic therapy. All the studied compounds demonstrated a sufficiently high stability in both acidic and alkaline media. The introduction of iodine atoms into the pyrrole rings and the substitution of the hydrogen atom at the meso-position of the BODIPY core with an ester residue significantly (up to ∼1.4 times) increase the hydrophobicity of the luminophores compared to the tetramethylated analogue. In this case, compound 1 exhibits bactericidal activity against Staphylococcus aureus under irradiation at a wavelength of 530 nm, compound 2 demonstrates an activity that is 16 times lower, and BODIPY 3 does not show any antimicrobial activity under these experimental conditions.