Dendritic near-IR absorbing zinc phthalocyanines for antimicrobial photodynamic therapy

Dominic K. Muli, Bradley L. Carpenter, Mayank Mayukh, Reza A. Ghiladi, Dominic V Mcgrath

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Design, synthesis, characterization, and photodynamic activity of dendritic, water-soluble zinc phthalocyanine (ZnPc) isomers 1a and 1b are described. Bearing terminal triethylene glycol (TEG) moieties as water solubilizing groups that were attached to the Pc core using Cu(I) catalyzed alkyne-azide cycloaddition (CuAAC), 1a and 1b are readily soluble in H<inf>2</inf>O, polar aprotic, and protic organic solvents. UV/Vis analyses indicate that the Q band of the non-peripheral ZnPc 1b is ca. 80 nm red-shifted relative to the peripheral one with absorption at 805 nm (distilled water). 1a and 1b have log D<inf>7.4</inf> values of 0.22 and 0.05, respectively, suggesting that the non-peripheral substitution improved the overall hydrophilicity. Aggregation studies indicate that non-peripherally substituted 1b is significantly less aggregated in aqueous media than peripherally substituted 1a. Singlet oxygen generation studies are reported. Both ZnPcs showed negligible dark toxicity on bacteria and yeast with 10 μM 1a and 1b. Illumination (400-850 nm) of Pseudomonas aeruginosa with 10 μM of 1a produced a 90% cell inactivation while Acinetobacter baumannii with 10 μM 1b showed detection limit (99.9999+%) cell inactivation, demonstrating the antimicrobial photoactivity of these dyes.

Original languageEnglish (US)
Pages (from-to)3541-3545
Number of pages5
JournalTetrahedron Letters
Volume56
Issue number23
DOIs
StatePublished - May 25 2015

Fingerprint

Photodynamic therapy
Photochemotherapy
Water
Bearings (structural)
Acinetobacter baumannii
Singlet Oxygen
Alkynes
Azides
Cycloaddition
Cycloaddition Reaction
Hydrophilicity
Lighting
Hydrophobic and Hydrophilic Interactions
Isomers
Yeast
Organic solvents
Pseudomonas aeruginosa
Toxicity
Limit of Detection
Bacteria

Keywords

  • Click chemistry
  • Methylene blue
  • Non-aggregated
  • Singlet oxygen
  • Water soluble

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Dendritic near-IR absorbing zinc phthalocyanines for antimicrobial photodynamic therapy. / Muli, Dominic K.; Carpenter, Bradley L.; Mayukh, Mayank; Ghiladi, Reza A.; Mcgrath, Dominic V.

In: Tetrahedron Letters, Vol. 56, No. 23, 25.05.2015, p. 3541-3545.

Research output: Contribution to journalArticle

Muli, Dominic K. ; Carpenter, Bradley L. ; Mayukh, Mayank ; Ghiladi, Reza A. ; Mcgrath, Dominic V. / Dendritic near-IR absorbing zinc phthalocyanines for antimicrobial photodynamic therapy. In: Tetrahedron Letters. 2015 ; Vol. 56, No. 23. pp. 3541-3545.
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AB - Design, synthesis, characterization, and photodynamic activity of dendritic, water-soluble zinc phthalocyanine (ZnPc) isomers 1a and 1b are described. Bearing terminal triethylene glycol (TEG) moieties as water solubilizing groups that were attached to the Pc core using Cu(I) catalyzed alkyne-azide cycloaddition (CuAAC), 1a and 1b are readily soluble in H2O, polar aprotic, and protic organic solvents. UV/Vis analyses indicate that the Q band of the non-peripheral ZnPc 1b is ca. 80 nm red-shifted relative to the peripheral one with absorption at 805 nm (distilled water). 1a and 1b have log D7.4 values of 0.22 and 0.05, respectively, suggesting that the non-peripheral substitution improved the overall hydrophilicity. Aggregation studies indicate that non-peripherally substituted 1b is significantly less aggregated in aqueous media than peripherally substituted 1a. Singlet oxygen generation studies are reported. Both ZnPcs showed negligible dark toxicity on bacteria and yeast with 10 μM 1a and 1b. Illumination (400-850 nm) of Pseudomonas aeruginosa with 10 μM of 1a produced a 90% cell inactivation while Acinetobacter baumannii with 10 μM 1b showed detection limit (99.9999+%) cell inactivation, demonstrating the antimicrobial photoactivity of these dyes.

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