In tissue engineering collagen-derived materials rich in glycine, proline, and hydroxyproline have been used for the generation of gels on which cell proliferation can occur. Here we present the synthesis of a 34 amino acid long photoreactive collagen-like peptide that contains four units of the unnatural amino acid 5-carboxylic acid-7-nitroindoline built into the peptide backbone. The peptide was assembled by fragment condensation on Rink Amide resin. The photoreactive N-peptidyl-7-nitroindoline moieties are stable at ambient light, but undergo photolysis when illuminated with light of 350 nm. We demonstrate the ability of a photoreactive amino acid model compound and the collagen-like peptide to also undergo photolysis by a two-photon absorption process using a femtosecond laser at 710 nm. Mass spectrometry analysis revealed that the expected photohydrolysis products are formed when the peptide is irradiated under one-photon or two-photon absorption conditions at 350 nm or 710 nm, respectively. Upon two photon excitation, the molecular composition of a film made from our photoreactive peptide changes only at the laser focal volume. Therefore, this photoreactive peptide holds promise for the generation of three-dimensional matrices for tissue engineering, whose macroscopic structures can potentially be manipulated by femtosecond laser irradiation.

Synthesis of a novel photoreactive collagen-like peptide and its one and two-photon absorption properties

253rd National Meeting (2017)

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