Synthesis and Photophysical Studies of a Pyrenylindole and a Phenalenoindole Obtained from Dehydroamino Acid Derivatives – Application as Fluorescent Probes for Biological Systems

Abstract

Two pyrenyl-dehydroamino acid derivatives were cyclized by a metal-assisted C-N intramolecular cyclization developed in our research group, to give a pyrenylindole and a phenalenoindole. The pyrenylindole was inserted into a peptide by solid-phase coupling, with use of a 2-chlorotrityl chloride resin and a Fmoc strategy. The photophysical properties of the pyrenylindole and phenalenoindole in several solvents were studied and showed that these compounds can be used as fluorescence probes. The results obtained with the peptide labelled with the pyrenylindole moiety show potential for use of this compound as a fluorescence label avoiding the aggre-

Supramolecular Peptide Amphiphile Vesicles through Host–Guest Complexation

“…[16,17] One of the larger macrocycles in this family, CB [8], can be used as a "molecular handcuff" to join two molecules together in a non-covalent fashion, [18,19] and has been applied to form biomaterials such as polymer-protein conjugation and protein dimerization. [29] Herein, we utilize a functional pyrene bearing an imidazolium group both as a fluorescence sensor and as a guest for CB [8] [30] and linked it to a simple peptide sequence (1). [25][26][27][28] Pyrene and its derivatives have been widely used as fluorescence probes in a large number of complex systems, on account of their high fluorescence quantum yields, long excited state lifetimes and the ability to form excimers.…”

Synthesis and photophysical studies of new pyrenylamino acids

“…[6][7][8] Previously, we have reported the synthesis of several new pyrenylamino acid derivatives. 9,10 These compounds were prepared from dehydroamino acid derivatives using several types of reactions, namely Michael additions, substitution reactions and palladium catalyzed crosscouplings. The photophysical properties of some of these compounds showed their potential utility as fluorescence probes for biological systems.…”

[2]Benzothiophene bent-shaped liquid crystals

“…for molecules which absorb light with an electric field only along a particular molecular direction and with strong emission in the visible range. Among such materials, anthraquinone, naphthalimide [23,24], acenequinone [25], oligothiophenes [26,27], benzothiadiazole [28][29][30], perylene [31,32], cyanine derivatives [33], pyrene [34][35][36], oxadiazole [37][38][39] and BODIPY-dyes [40,41] belong to those * Corresponding author. Email: Jiri.Svoboda@vscht.cz that have been most intensively studied.…”