The (NHC)PdBr 2 (2-aminopyridine) complexes: synthesis, characterization, molecular docking study, and inhibitor effects
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ORIGINAL PAPER
The (NHC)PdBr2(2‑aminopyridine) complexes: synthesis, characterization, molecular docking study, and inhibitor effects on the human serum carbonic anhydrase and serum bovine xanthine oxidase Ferhat Türker1 · Samir Abbas Ali Noma1 · Aydın Aktaş1,2 · Khattab Al‑Khafaji3 · Tugba Taşkın Tok3,4 · Burhan Ateş1 · Yetkin Gök1 Received: 30 December 2019 / Accepted: 14 September 2020 © Springer-Verlag GmbH Austria, part of Springer Nature 2020
Abstract This study contains the synthesis, spectral analysis, and the enzyme inhibition effects of the Pd-based complexes bearing both 2-aminopyridine and N-heterocyclic carbene (NHC) ligands. The NHC ligand in the Pd-based complexes contains the 3-cyanobenzyl group. All new complexes were synthesized from (NHC)PdBr2(pyridine) complexes and 2-aminopyridine. These new complexes were characterized by using elemental analysis, 1H NMR, 13C NMR, and FT-IR spectroscopy techniques. Furthermore, inhibitor effects of these complexes were also tested toward some metabolic enzymes such as carbonic anhydrase and xanthine oxidase enzymes. The IC50 range for hCA I, hCA II, and XO were determined as 0.325–0.707, 0.238–0.636, and 0.576–1.693 μM, respectively. These data showed that Pd(II)–NHC complexes bearing 2-aminopyridine may be potent inhibitors of hCA and XO enzymes. Besides these applications, molecular docking was performed by using CDOCKER tool as a part of Discovery studio 2019, not only to determine the binding mode of synthesized inhibitors, but also to determine the correlation between the CDOCKER score values and IC50 values. We found a good correlation (R2 = 0.7403) between IC50 and the CDOCKER score of the inhibitors for XO. These findings could be a reference to start the development of effective medicine for XO. Graphic abstract
Keywords 2-Aminopyridine · Carbonic anhydrase · Enzyme inhibition · N-heterocyclic carbene · Molecular docking · Palladium complexes · Xanthine oxidase
Introduction Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00706-020-02687-2) contains supplementary material, which is available to authorized users. * Aydın Aktaş [email protected] Extended author information available on the last page of the article
Since half a century ago, the NHCs have attracted a great deal of interest as ligands in the fields of organic and organometallic chemistry after the discovery of the stable metal–NHC complexes by Wanzlick [1]. Surprisingly, NHCs have been overshadowed by metal-NHC complexes
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for 23 years. In the early 1990s, stable, isolated and storable crystal NHC 1,3-di(adamantyl)imidazol-2-ylidene (IAd) was reported by Arduengo et al. [2, 3]. The NHCs have important properties such as high reactivity, structural diversity, being a strong σ-donor and a weak π-acceptor. Furthermore, the stability of the metal–carbene bond in the metal–NHC complexes increased the interest in these complexes [4–9]. The NHCs can form stable complexes with almost all transition metals. Sta
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