Silicon(IV) Phthalocyanine-Decorated Cyclodextrin Vesicles as a Self-Assembled Phototherapeutic Agent against MRSA.
The host-guest complexation of a tailored Si(IV) phthalocyanine with supramolecular β-cyclodextrin vesicles (CDV) was studied, revealing a reduced aggregation of the photoactive center upon binding to the CDV, even in aqueous environments. For this purpose, a photosensitizing unit axially decorated with one adamantyl group and one pyridinium moiety on the other side was obtained by two successive click reactions on a bis-azido-functionalized derivative of Si(IV) phthalocyanine. To evaluate its potential as a photosensitizer against antibiotic-resistant bacteria, comparative studies of the photophysical properties including absorption and emission spectroscopy, lifetimes as well as fluorescence and singlet oxygen quantum yields were determined for the Si(IV) phthalocyanine alone and upon self-assembly on the CDV surface. In vitro phototoxicity against the methicillin-resistant Staphylococcus aureus (MRSA) USA300 was evaluated, showing an almost complete inactivation.
Physikalisches Institut and CeNTech, Westfälische Wilhelms-Universität Münster , Heisenbergstrasse 11, 48149 Münster, Germany.|European Institute for Molecular Imaging , Waldeyerstrasse 15, 48149 Münster, Germany.
Anzhela
A
Galstyan
Organic Chemistry Institute, Westfälische Wilhelms-Universität Münster , Corrensstrasse 40, 48149 Münster, Germany.
Ulrike
U
Kauscher
Institute for Medical Microbiology, University Hospital Münster , Domagkstrasse 10, 48149 Münster, Germany.
Desiree
D
Block
Organic Chemistry Institute, Westfälische Wilhelms-Universität Münster , Corrensstrasse 40, 48149 Münster, Germany.
Bart Jan
BJ
Ravoo
Physikalisches Institut and CeNTech, Westfälische Wilhelms-Universität Münster , Heisenbergstrasse 11, 48149 Münster, Germany.
Cristian A
CA
Strassert
D000890:Anti-Infective Agents / Q000737:chemistry / Q000494:pharmacology; D003505:Cyclodextrins / Q000737:chemistry* / Q000494:pharmacology / Q000627:therapeutic use*; D007211:Indoles / Q000737:chemistry*; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D017646:Organosilicon Compounds / Q000737:chemistry*; D017319:Photosensitizing Agents / Q000494:pharmacology / Q000627:therapeutic use; D010789:Phototherapy / Q000379:methods*; D013203:Staphylococcal Infections / Q000628:therapy*
D000890:Anti-Infective Agents; D003505:Cyclodextrins; D007211:Indoles; D017646:Organosilicon Compounds; D017319:Photosensitizing Agents; C082854:silicon phthalocyanine
MRSA; cyclodextrin vesicle; phthalocyanine; self-assembly; singlet oxygen