Direct Construction of Corrole‐Peptide Conjugates by Controllable Bilane Formation on Resin

Abstract

Corroles have attracted increasing research interests in recent decades owing to their unique properties over porphyrins. However, the relatively inefficient and tedious synthetic procedures of corrole building blocks with functional groups for bioconjugation hindered their bioapplications. Herein, we report a highly efficient protocol to synthesize corrole-peptide conjugates with good yields (up to 63 %) without using prepared corrole building blocks. By condensing two À COOH-bearing-dipyrromethane molecules onto an aldehyde group on resin-bound peptide chains in a controllable manner, a series of desired products with long (up to 25 residues) and bioactive peptide chains were obtained with at most one chromatographic purification. The synthesized compounds exhibited potential applications as chelators for metal ions for biomedical applications, as building blocks for supramolecular materials, as well as targeted fluorescent probes.

Construction of 5-Fluorouracil and Gallium Corrole Conjugates for Enhanced Photodynamic Therapy

“…25 In addition, the corrole macrocycle has a direct pyrrole−pyrrole linkage, which makes it more easily metabolized after PDT. 26 Although there have been reports about the synthesis of corrole conjugates for antitumor application such as cyclodextrin, 27 coumarin, 28 amino acid, 29 protein, 30 peptide, 31 and siRNA 32 conjugates, the synthesis of corrole and the chemotherapeutic drug conjugate and its application in chemo-photodynamic combination therapy have not been reported so far.…”