Abstract
New water-soluble tetra-substituted derivatives of p-tert-butylthiacalix[4]arene containing fragments of L-tryptophan in cone and 1,3-alternate conformations were obtained. It was shown that the resulting compounds form stable, positively charged aggregates of 86–134 nm in diameter in water at a concentration of 1 × 10−4 M as confirmed by dynamic light scattering, scanning electron microscopy and transmission electron microscopy. It was established that these aggregates are fluorescently active and chiral. A distinctive feature of the compounds is the pronounced dependence of their spectral (emission and chiroptical) properties on the polarity of the solvent and the length of the linker between the macrocyclic and fluorophore parts of the molecule.
Highlights
Fluorescently active compounds have become a high demand in nanotechnology, biotechnology and medicinal chemistry [1,2]
N-bromoacetyl-L-tryptophan ethyl ester 3 was obtained by the acylation of L-tryptophan ethyl ester hydrochloride 2 with bromoacetyl bromide carried out in benzene at room temperature according to the literature procedure [39] (Scheme 1)
Using the dynamic light scattering (DLS) method, it was shown that the resulting compounds formed stable positively charged aggregates of 86–134 nm in size in water at a concentration of 1 × 10−4 M
Summary
Fluorescently active compounds have become a high demand in nanotechnology, biotechnology and medicinal chemistry [1,2]. Nanoparticles that consist of covalently or non-covalently bound fluorescent compounds are widely used due to attractive physical and chemical properties [3,4]. Water-soluble stable fluorescent nanoparticles open up new opportunities for the design of particles that can be traced throughout the body, for example, for the delivery of therapeutic agents [5], synthetic vectors for gene therapy [6] and contrast agents for magnetic resonance imaging [7,8]. Supramolecular particles can consist of various organic or inorganic components. Most of the fluorescent water-soluble nanoparticles described in the literature are metal-based (silver, gold, copper, etc.) [9,10,11,12]. Noncovalent self-assembly is a promising approach for creating fluorescent organic nanoparticles. Special attention is focused on the use of building blocks for the prepa-
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