Cyclophane-Sustained High Performance Porphyrins

NU 2020-089

INVENTORS
James F Stoddart*
Wenqi Liu

SHORT DESCRIPTION
High performance dyes for diagnosis and therapy

ABSTRACT
Porphyrins and metalloporphyrins are functional dyes with distinctive photo-physical properties, showing great potentials for biomedical applications. Meanwhile, practical applications of these dyes suffer from several well-known technical challenges including the poor solubility and heavy aggregation in water, fluorescence quenching, protonation and solvolysis under acid environments. Northwestern researchers have developed a molecular encapsulation technology using a cyclophane, XCage, to produce ultrastable porphyrins. The cyclophane used here is able to encapsulate both free base porphyrins and metallophorphyrins. The resulting complex is ultrastable, capable of withstanding extremely acidic environments.  The supramolecular complexes are stable at subnanomolar concentration in water on account of their high binding affinities. The molecular encapsulation improves the water solubility, prevents intermolecular aggregation, resists quenching and enhances fluorescence emission.  The unique encapsulation may prove to be quite general for a library of metalloporphyrins with a wide range of properties, leading to applications in nanotechnology, artificial photodevice fabrication, and biomedical science.

APPLICATION

• Fluorescence imaging
• Photodynamic therapy
• Photothermal therapy
• Magnetic resonance imaging

ADVANTAGES

• Ultrastability
• Applicability to a wide range of porphyrin structures without tedious chemical modifications on porphyrins
• Simplicity in enhancing solubilization, deaggregation and fluorescence

PUBLICATION
Liu W, Lin C, Weber J, Stern C, Young R, Wasielewski M and Stoddart JF (2020) Cyclophane-Sustained Ultrastable Porphyrins.  Journal of American Chemical Society.  142: 8938-8945.

IP STATUS
A US patent application has been filed.