Heterocyclic Hemipiperazines: Water‐Compatible Peptide‐Derived Photoswitches

Abstract

Hemipiperazines are a recently discovered class of peptide-derived molecular photoswitches with high biocompatibility and therapeutic potential. Here, for the first time we describe photochromism of heterocyclic hemipiperazines. They demonstrate long thermal lifetimes, and enlarged band separation between photoisomers. Efficient photoisomerization occurs under aqueous conditions, although with a need for organic co-solvent. Bidirectional switching with visible light is observed for an extended aromatic system.

Reversible Influence of Hemipiperazine Photochromism on the Early Development of Zebrafish Embryo

“…[15] This endeavor involves the structural adaptation of the naturally occurring stilbenoid combretastatin A4, which yielded azobenzene-based photostatins [16] and a series of optimized derivatives based on various photochromic motifs. [7,17] Our group discovered [18] that another tubulin dynamics inhibitor, plinabulin 1, contains a previously unreported photochromic motif -hemipiperazine [19] -which enables significant photomodulation of the activity of 1 without additional structural modifications.…”