Synthesis of Amino Acid-Derived 1,2,3-Triazoles: Development of a Nontrivial Fluorescent Sensor in Solution for the Enantioselective Sensing of a Carbohydrate and Bovine Serum Albumin Interaction

Abstract

A series of amino acid-derived 1,2,3-triazoles presenting the amino acid and the aromatic moieties connected by a triazole-4-carboxylate spacer is discussed in this work. These compounds were achieved in good yields by organocatalytic enamine-azide [3 + 2] cycloadditions. One of the molecules obtained, bearing a 7-chloroquinoline moiety, was photoactive in the UV-violet region and was successfully employed as a probe for substrate-specific enantiomeric sensing using d-(-)-arabinose and l-(+)-arabinose. The potential application as a fluorescent probe to detect protein in phosphate buffer solution was also explored using as model bovine serum albumin (BSA). The studied compounds presented both suppression and association behavior in the presence of BSA. In addition, theoretical calculations were performed at levels ωB97XD/cc-pVDZ and PBE1PBE/6-311+G(d,p) together with the polarizable continuum model to understand the interaction of the molecules with the enantiomers.

<p>Novel Albumin Nanoparticle Enhanced the Anti-Insulin-Resistant-Hepatoma Activity of Metformin</p>

“…Hence, binding with metformin resulted in the transformation of the polarity around Tyr residues, while there was no change around Trp residues. 36 – 38

Figure 6 Synchronous fluorescence spectra of metformin with BSA with Δλ = 60 ( A ) or 15 ( B ) nm at 298 K. Protein concentrations and drug concentration are consistent with the steady-state fluorescence study.

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“…Hence, binding with metformin resulted in the transformation of the polarity around Tyr residues, while there was no change around Trp residues. [36][37][38] Conformational Studies by CD and 3D Fluorescence Spectroscopy CD spectroscopy was applied to monitor the content of the secondary structure of the protein. 39 Figure 7A shows the CD spectra of BSA with the addition of metformin of a 1:25 molar ratio, which was in line with the molar ratio in drug preparation.…”

Synthesis ofα‐Hydroxyphosphonates Containing Functionalized 1,2,3‐Triazoles

“…These structures are usually prepared by the thermal 1,3‐dipolar cycloaddition of azides with terminal alkynes, employing a catalytic amount of transition metal [46–55] . The synthesis of 1,2,3‐triazoles is a remarkable example of “Click‐Chemistry” reactions [56] …”

Glycoconjugates Based on Supramolecular Tröger’s Base Scaffold: Synthesis, Photophysics, Docking, and BSA Association Study

“…In this way, herein are described new Tröger’s base scaffolds presenting different glycosyl moieties linked by the 1,2,3-triazole core through copper-catalyzed azide–alkyne cycloaddition (Scheme 1). 39 Additionally, their photophysical properties were also studied using UV–vis and fluorescence spectroscopy. Furthermore, fluorescence titration and docking have been performed using bovine serum albumin (BSA) for association studies.…”