Reversible Photocontrol of Microtubule Stability by Spiropyran‐Conjugated Tau‐Derived Peptides

Abstract

Spatiotemporal modulation of microtubules by light has become an important aspect of the biological and nanotechnological applications of microtubules. We previously developed a Tau‐derived peptide as a binding unit to the inside of microtubules. Here, we conjugated the Tau‐derived peptide to spiropyran, which is reversibly converted to merocyanine by light, as a reversible photocontrol system to stabilize microtubules. Among the synthesized peptides with spiropyran/merocyanine at different positions, several peptides were bound to the inside of microtubules and stabilized the structures of microtubules. The peptide with spiropyran at the N‐terminus induced polymerization and stabilization of microtubules, whereas the same peptide with the merocyanine form did not exert these effects. Reversible formation of microtubules/tubulin aggregates was achieved using the peptide with spiropyran conjugated at the N‐terminus and irradiation with UV and visible light. Spiropyran‐conjugated Tau‐derived peptides would be useful for spatiotemporal modulation of microtubule stability through reversible photocontrol of binding.

Photoresponsive peptide materials: Spatiotemporal control of self-assembly and biological functions

“…7(c) ]. 115 Spiropyran was conjugated to the cysteine residues that were introduced to the different TMR-labeled TP positions. The peptide with spiropyran at the N-terminus (TMR-1-TP-SP) and the merocyanine form (TMR-1-TP-MC), among the four peptides with different positions of spiropyran, showed the largest difference in microtubule structures prepared with GTP, as TMR-1-TP-SP stabilized the microtubule structures but not TMR-1-TP-MC [ Fig.…”

New Triphenylphosphonium Salts of Spiropyrans: Synthesis and Photochromic Properties

“…Among the most studied classes of organic photochromic structures are spirocyclic compounds, such as spiropyrans, which are capable of switching between the usually colorless cyclic and colored merocyanine forms when exposed to external stimuli such as light [ 1 , 2 , 3 , 4 ], temperature [ 4 , 5 ], pressure [ 6 ], environmental polarity [ 2 , 7 ], pH [ 2 , 8 , 9 ], mechanical action [ 2 , 10 ], electric or magnetic field [ 2 , 3 ], which allows their use in memory elements [ 2 , 3 , 11 , 12 ], as optoelectronic devices [ 13 , 14 ], sensors [ 1 , 2 , 15 , 16 , 17 , 18 ], light-responsive materials in biology [ 2 , 19 , 20 , 21 ], etc.…”

“…Photochromic spiropyrans are promising agents for the creation of drugs of this kind, with a high selectivity and a high induced therapeutic effect, due to the ability to exist in two isomeric forms with different physicochemical properties. At the same time, in the global literature, there is only one work describing, using one example of water-soluble spiropyran, photoswitchable cytotoxicity towards Hek293 cancer cells [ 20 ]. This approach will make it possible to hope that the closed form will not cause a toxic effect and will easily pass through the cell membrane, while the open form, on the contrary, will lead to an induced cytotoxic effect.…”