Heteroatom‐substitued Dioxetanes and their Emerging Biomedical Applications

Abstract

Heteroatom‐substituted dioxetanes are one subclass of dioxetanes that have at least one heteroatom (such as O, S, N) at its two carbons of dioxetane structures. These are readily formed from the [2+2] cycloaddition reaction of heteroatom‐substituted alkenes and singlet oxygen ( 1 O 2 ). Due to their unique characteristics, such as chemiluminescence and spontaneous cleavage, heteroatom‐substituted dioxetanes have been used for a number of biomedical applications, for example biomedical analyses and light‐controlled drug release. A number of review papers and book chapters have been published for the biomedical analyses of chemiluminescence. However, no comprehensive review or book chapter for the applications to light‐controlled drug release have yet been published, although there have been very significant and interesting advances in the field in the last couple of years. In this chapter, we focus mainly on a new and exciting application of dioxetanes for light‐controlled drug release. In the latter part of this section, we also introduce briefly another new interesting application of dioxetane chemistry for hydrogen peroxide (H 2 O 2 ) imaging.

Targeting Photochemical Scalpels or Lancets in the Photodynamic Therapy Field—The Photochemist's Role

“…). Reports have described visible or NIR light to disconnect drugs from sensitizer molecules, as a means for simultaneous PDT and delivery of anti‐cancer drugs, such as paclitaxel . Related NIR uncaging and sensitization reactions have also been reported for cyanines and phthalocyanines .…”

Photoactive Fluoropolymer Surfaces That Release Sensitizer Drug Molecules

“…We 27,28 and others 29–31 have published papers devoted to 1 O 2 -based drug release and a book chapter has also appeared. 32 Singlet oxygen is a potentially therapeutic species and is photogenerated by PAHs, 33,34 chlorins, 35,36 porphyrins and phthalocyanines, and their fluorinated analogs. 37–41 In 2011, Röder et al reported the deposition of perfluorinated phthalocyanines on silica gel as a composite material for generating 1 O 2 for sterilization.…”

“…Visible light and NIR photocleavage reactions are known − and actually represent a burgeoning area of research. , For example, the sensitized generation of 1 O 2 ( 1 Δ g ) has been used with labile ethene linkers for photorelease reactions. We , and others − have published papers devoted to 1 O 2 -based drug release, and a book chapter has also appeared . Singlet oxygen is a potentially therapeutic species and is photogenerated by PAHs, , chlorins, , porphyrins and phthalocyanines, and their fluorinated analogues. − In 2011, Röder et al reported the deposition of perfluorinated phthalocyanines on silica gel as a composite material for generating 1 O 2 for sterilization .…”