Highly positive-charged zinc(II) phthalocyanine as non-aggregated and efficient antifungal photosensitizer

Bioorg Med Chem Lett. 2015 Jun 1;25(11):2386-9. doi: 10.1016/j.bmcl.2015.04.004. Epub 2015 Apr 7.

Abstract

A new tetra-α-substituted zinc(II) phthalocyanine containing dodeca-amino groups (compound 4) and its quaternized analogue (compound 5) have been prepared and evaluated for their photoactivities against Candida albicans. Compared with the dodeca-amino phthalocyanine 4, the dodeca-cationic phthalocyanine 5 exhibits a higher photodynamic inactivation against C. albicans with an IC90 value down to 1.46 μM, which can be attributed to its non-aggregated nature in aqueous environments and more efficient cellular uptake. More interestingly, 5 shows a higher photodynamic inactivation on C. albicans due to its stronger affinity to C. albicans cells than mammalian cells. These results suggest that the highly positive-charged phthalocyanine 5 is a potential non-aggregated antifungal photosensitizer, which shows some selectivity toward the fungus.

Keywords: Antifungal; Non-aggregated; Photodynamic inactivation; Photosensitizer; Zinc(II) phthalocyanine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemistry*
  • Antifungal Agents / pharmacology*
  • Candida albicans / drug effects*
  • Indoles / chemistry*
  • Isoindoles
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Photosensitizing Agents / chemistry*
  • Photosensitizing Agents / pharmacology*
  • Structure-Activity Relationship
  • Zinc Compounds

Substances

  • Antifungal Agents
  • Indoles
  • Isoindoles
  • Organometallic Compounds
  • Photosensitizing Agents
  • Zinc Compounds
  • Zn(II)-phthalocyanine