Coupling 6-chloro-3-methyluracil with copper: structural features, theoretical analysis, and biofunctional properties

As nucleobases in RNA and DNA, uracil and 5-methyluracil represent a recognized class of bioactive molecules and versatile ligands for coordination compounds with various biofunctional properties. In this study, 6-chloro-3-methyluracil (Hcmu) was used as an unexplored building block for the self-assembly generation of a new bioactive copper(ii) complex, [Cu(cmu)2(H2O)2]·4H2O (1). This compound was isolated as a stable crystalline solid and fully characterized in solution and solid state by a variety of spectroscopic methods (UV-vis, EPR, fluorescence spectroscopy), cyclic voltammetry, X-ray diffraction, and DFT calculations. The structural, topological, H-bonding, and Hirshfeld surface features of1were also analyzed in detail. The compound1shows a distorted octahedral {CuN2O4} coordination environment with twotranscmu−ligands adopting a bidentate N,O-coordination mode. The monocopper(ii) molecular units participate in strong H-bonding interactions with water molecules of crystallization, leading to structural 0D → 3D extension into a 3D H-bonded network with atfz-dtopology. Molecular docking and ADME analysis as well as antibacterial and antioxidant activity studies were performed to assess the bioactivity of1. In particular, this compound exhibits a prominent antibacterial effect against Gram negative (E. coli, P. aeruginosa) and positive (S. aureus, B. cereus) bacteria. The obtained copper(ii) complex also represents the first structurally characterized coordination compound derived from 6-chloro-3-methyluracil, thus introducing this bioactive building block into a family of uracil metal complexes with notable biofunctional properties. © The Royal Society of Chemistry 2021.

Kumar B.1 , Das T.1 , Das S. 1, 2 , Maniukiewicz W.3 , Nesterov D.S. 4 , Kirillov A.M. 4, 5 , Das S. 1, 2
Royal Society of Chemistry
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  • 1 Department of Chemistry, National Institute of Technology Patna, Ashok Rajpath, Patna, 800005, India
  • 2 Department of Life Science and Biotechnology, Jadavpur University, 188 Raja S.C. Mallick Rd, Kolkata, 700032, India
  • 3 Institute of General and Ecological Chemistry, Lodz University of Technology, Żeromskiego 116, Łódź, Poland
  • 4 Centro de Química Estrutural and Departamento de Engenharia Química, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, Lisbon, 1049-001, Portugal
  • 5 Research Institute of Chemistry, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya st., Moscow, 117198, Russian Federation
Ключевые слова
Complex networks; Complexation; Copper compounds; Cyclic voltammetry; Electron spin resonance spectroscopy; Escherichia coli; Fluorescence spectroscopy; Ligands; Metal complexes; Molecules; Solid solutions; Spectroscopic analysis; A-stable; Bioactive molecules; Bioactives; Biofunctional; Building blockes; Coordination compounds; Copper complexes; Nucleobases; Property; Structural feature; Aromatic compounds
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