“End-Only” Functionalized Oligo(phenylene ethynylene)s: Synthesis, Photophysical and Biocidal Activity

• Published in: The journal of physical chemistry letters Vol. 1; no. 21; pp. 3207 - 3212
• Main Authors: Zhou, Zhijun, Corbitt, Thomas S, Parthasarathy, Anand, Tang, Yanli, Ista, Linnea K, Schanze, Kirk S, Whitten, David G
• Format: Journal Article
• Language: English
• Published: American Chemical Society 04.11.2010
• Subjects: Biophysical Chemistry
• ISSN: 1948-7185; 1948-7185
• DOI: 10.1021/jz101088k

It is essential to develop alternative strategies to treat infections, especially those infections caused by Staphylococcus aureus, which is responsible for most skin infections. Among those strategies, light-induced inactivation of pathogens appears to be a promising candidate. We present four novel “end only” oligo(phenylene ethynylene)s (EO-OPE-1s) that have the ends functionalized with cationic groups and are powerful light-activated biocides against Escherichia coli, Staphylococcus epidermidis, and S. aureus. We have correlated the light-induced biocidal activities with singlet oxygen quantum yields Φ (1O2) of EO-OPE-1s, and a higher Φ (1O2) correlates with a better light-induced biocidal activity. Coupled with our previous work on the interactions of EO-OPE-1s with dioleoyl-sn-glycero-3-phosphocholine (DOPC)/cholesterol vesicles, we believe the biocidal process involves the following: (1) EO-OPE-1s penetrate the bacterial membrane, (2) EO-OPE-1s photosensitize the generation of singlet oxygen and/or other reactive oxygen species, and (3) singlet oxygen and/or reactive oxygen species trigger the cytotoxicity.