Photoactivatable Caged Cyclic RGD Peptide for Triggering Integrin Binding and Cell Adhesion to Surfaces

Abstract

We report on the synthesis and properties of a photoactivatable caged RGD peptide and its application for phototriggering integrin and cell binding to surfaces. We analyzed in detail (i) the differences in the integrin binding affinity of the caged and uncaged forms via quartz crystal microbalance (QCM) studies, (ii) the efficiency and yield of the photolytic uncaging reaction, (iii) the biocompatibility of the photolysis byproducts and irradiation conditions and (iv) the possibility of site, temporal and density control of integrin binding and, therefore, human cell attachment, (v) the possibility of in situ generation of cell patterns and cell gradients by controlling the exposure. These studies provide a clear picture of the potential and limitations of caged ligands for integrin-mediated cell adhesion and demonstrate the application of this approach to control and study other types of cell interactions and response.

Ethyl substituted coumarin-4-yl derivatives as photoremovable protecting groups for amino acids with improved stability for SPPS

“…1 H NMR (300 MHz, CDCl 3 ) ı 7.37 (d, 1H, J = 9 Hz), 6.51 (dd, 1H, J = 9.3 Hz, 2.4 Hz), 6.39 (d, 1H, J = 2.7 Hz), 6.23 (s, 1H), 5.09 (q, 1H, J = 6.6 Hz), 3.34 (q, 4H, J = 6.9 Hz), 1.49 (d, 3H, J = 6.6 Hz), 1.41 (t, 3H, J = 6.9 Hz). 13 …”

“…13 C NMR spectra were recorded on a Bruker Spectrospin 75 Hz. ESI-MS spectra were recorded using a QTos Ultima 3 (Micromass/Waters, Manchester, UK).…”

“…Diverse photolabile protecting groups have been used for caging of various functional groups (i.e. phosphates, thiols, alcohols and carboxylic acids) [9] and applied to generate caged neurotransmitters [10], nucleotides [11,12] or peptides [13,14].…”

Engineering the matrix microenvironment for cell delivery and engraftment for tissue repair

“…Future cell-based strategies must consider the temporal and spatial complexities of the in vivo environment and the effect or role of cellular retention and engraftment for regenerative medicine. In addition to strategies previously mentioned, future considerations for engineering a cell delivery vehicle include dynamic or triggered changes in bioactivity [54,55], as well as multiple growth factor delivery for synergistic effects in directing cell fate [56]. Understanding, harnessing, and engineering these aspects into a cell-delivery vehicle may finally enable us to use cells to their full potential as a tissue repair therapy strategy.…”

Selective Cell Recruitment and Spatially Controlled Cell Attachment on Instructive Chitosan Surfaces Functionalized with Antibodies

“…Published works report the coating or tailoring of biomaterials with bioactive molecules, such as fibronectin [3], laminin [4], growth factors [5,6] or their integrin-binding epitopes including RGD [7,8] and GFOGER [9]. These studies report the influence of such biomolecules in cell adhesion, differentiation or proliferation.…”