Cyanine Modification Tuned for Amine Photorelease

Abstract

Cyanines are emerging as useful agents for photoreleasing biological compounds because of their capability of utilizing near‐infrared (NIR) light. Another benefit is their ability to self‐sensitize to produce singlet oxygen for the release of aryl amines, a process that has not been as feasible in the past. Here, we highlight the paper by Schnermann et al. (https://doi.org/10.1111/php.13090), which reports on a cyanine conjugate for heterolytic photocleavage of aryl amines. This paper is timely—delving into a photorelease mechanism involving a domino rearrangement and β‐elimination triggered by NIR light.

Bioorthogonal chemistry for prodrug activation in vivo

“…Later, this strategy was followed and extended by two groups to liberate aryl amines similarly in vitro . 128,129…”

“…Later, this strategy was followed and extended by two groups to liberate aryl amines similarly in vitro. 128,129 On the other hand, the axial Si-O and Si-C bonds of silicon phthalocyanines (SiPcs) exhibit NIR light-induced dissociation. The bond dissociation energies are around 80 kcal mol À1 and 40 kcal mol À1 , respectively.…”

Long-wavelength photoremovable protecting groups: On the way to in vivo application

“…4-hydroxycyclofen bearing such caging group showed significant cytotoxicity against breast cancer MCF-7 cells under irradiation. Later this method was extended by two groups to uncage the aryl amines by similar oxidation pathway [38], [39]. Conjugation of cyanine dyes with antibodies and cytotoxic drugs provides unique possibilities to tumor targeted drug release [40], [41].

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