Labeling and Selective Inactivation of Gram-Positive Bacteria Employing Bimodal Photoprobes with Dual Readouts

Chemistry. 2016 Apr 4;22(15):5243-52. doi: 10.1002/chem.201504935. Epub 2016 Mar 1.

Abstract

Carbohydrate-conjugated silicon(IV) phthalocyanines with bimodal photoactivity were developed as probes with both fluorescent labeling and photosensitizing capabilities, and the concomitant fluorescent labeling and photoinduced inactivation of Gram-positive and Gram-negative models was explored. The maltohexaose-conjugated photoprobe provides a dual readout to distinguish between both groups of pathogens, as only the Gram-positive species was inactivated, even though both appeared labeled with near-infrared luminescence. Antibiotic resistance did not hinder the phototoxic effect, as even the methicillin-resistant pathogen Staphylococcus aureus (MRSA) was completely photoinactivated. Time-resolved confocal fluorescence microscopy analysis suggests that the photoprobe sticks onto the outer rim of the microorganisms, explaining the resistance of Gram-negative species on the basis of their membrane constitution. The mannose-conjugated photoprobe yields a different readout because it is able to label and to inactivate only the Gram-positive strain.

Keywords: fluorescence spectroscopy; fluorescent probes; photophysics; silicon; singlet oxygen.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrates / chemistry*
  • Gram-Positive Bacteria / chemistry
  • Gram-Positive Bacteria / drug effects*
  • Indoles / chemistry*
  • Luminescence
  • Methicillin-Resistant Staphylococcus aureus / chemistry
  • Methicillin-Resistant Staphylococcus aureus / drug effects*
  • Photosensitizing Agents / chemistry*
  • Photosensitizing Agents / pharmacology
  • Silanes / chemistry*
  • Staphylococcus aureus / chemistry
  • Staphylococcus aureus / drug effects*

Substances

  • Carbohydrates
  • Indoles
  • Photosensitizing Agents
  • Silanes