Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2020 Aug 21;13(17):3705.
doi: 10.3390/ma13173705.

Transition Metal Complexes with Flufenamic Acid for Pharmaceutical Applications-A Novel Three-Centered Coordination Polymer of Mn(II) Flufenamate

Michał Gacki  1 , Karolina Kafarska  1 , Anna Pietrzak  1 , Małgorzata Szczesio  1 , Izabela Korona-Głowniak  2 , Wojciech M Wolf  1
Affiliations

Transition Metal Complexes with Flufenamic Acid for Pharmaceutical Applications-A Novel Three-Centered Coordination Polymer of Mn(II) Flufenamate

Michał Gacki et al. Materials (Basel). .

Abstract

Five complexes of Mn(II), Co(II), Ni(II), Cu(II) and Zn(II) with non-steroidal anti-inflammatory drug, flufenamic acid were synthesized: (1) [Mn3(fluf)6EtOH)(H2O)]·3EtOH; (2) [Co(fluf)2(EtOH)(H2O)]·H2O; (3) [Ni(fluf)2(EtOH)(H2O)]·H2O; (4) [Cu(fluf)2·H2O]; (5) [Zn(fluf)2·H2O]. All complexes were characterized by elemental analysis (EA), flame atomic absorption spectrometry (FAAS), Fourier-transform infrared spectroscopy (FTIR), and thermogravimetric analysis (TGA). The crystal structure of 1 was determined by the single crystal X-ray diffraction technique. It crystallizes in the triclinic space group P with three independent Mn(II) cations, six coordinated flufenamato ligands augmented with water and ethanol molecules in the inner coordination sphere. In this crystal, manganese atoms are multiplied by symmetry and form infinite, polymeric chains which extend along the [001] dimension. The Hirshfeld Surface analysis revealed changes in interaction assemblies around all metal centers. The antioxidant and antimicrobial activities were established for all complexes and free ligand for comparison. All compounds exhibit good or moderate bioactivity against Gram-positive bacteria and yeasts.

Keywords: antioxidant activity; coordination polymer; flufenamic acid; non-steroidal anti-inflammatory drug-complex; thermal analysis.

PubMed Disclaimer

Conflict of interest statement

The authors declare that they have no conflict of interest.

Figures

Scheme 1
Scheme 1
Structural scheme of flufenamic acid 6.
Figure 1
Figure 1
(a) Asymmetric unit of 1. Manganese atoms are shown in black, oxygens are in red, ligands in the inner coordination sphere are in gray while non coordinating ethanol molecules are in green; (b) The coordination polymer chain. The constitutional repeating unit is shown in brackets; (c,d) Packing diagrams along [100] and [001], respectively. The coordination polymer chain is in black and red, while hydrogen bonding involving ethanol molecules is in blue.
Figure 2
Figure 2
The Hirshfeld Surface of Mn2+ centers in 1 with a normalized contact distance (dnorm) mapped on it. The parameter dnorm ranges from –0.76 to 0.76.
Figure 3
Figure 3
(a) Fingerprint plot for the Hirshfeld Surface of the metal centers Mn1, Mn2 and Mn3 of 1; (b) The percentage contribution of contacts of the Mn2+ in the coordination polymer of 1.
Figure 4
Figure 4
FTIR spectra of 1–5 complexes and free ligand 6.
Figure 5
Figure 5
Thermoanalytical curves for 1 (a), 2 (b), 3 (c), 4 (d) and 5 (e). TG is plotted in green, DTG is in blue, while DTA is in red.
See this image and copyright information in PMC

References

    1. Bagherzadeh M., Amini M., Boghaei D.M., Najafpour M.M., McKee V. Synthesis, X–ray structure, characterization and catalytic activity of a polymeric manganese(II) complex with iminodiacetate. Appl. Organomet. Chem. 2011;25:559–563. doi: 10.1002/aoc.1802. - DOI
    1. Keggin J.F., Miles F.D. Structures and formulæ of the prussian blues and related compounds. Nature. 1936;137:577–578. doi: 10.1038/137577a0. - DOI
    1. Batten S.R., Champness N.R. Coordination polymers and metal–organic frameworks: Materials by design. Philos. Trans. R. Soc. A Math. Phys. Eng. Sci. 2017;375 doi: 10.1098/rsta.2016.0032. - DOI - PMC - PubMed
    1. Ghasdian N., Liu Y., McHale R., He J., Miao Y., Wang X. Synthesis of Prussian Blue Metal Coordination Polymer Nanocubes via Cyanoferrate Monomer Design. J. Inorg. Organomet. Polym. Mater. 2013;23:111–118. doi: 10.1007/s10904-012-9748-y. - DOI
    1. Donaruma L.G., Block B.P., Loening K.L., Plate N., Tsuruta T., Buschbeck K.C., Powell W.H., Reedijk J. Nomenclature for regular single-strand and quasi single-strand inorganic and coordination polymers. Pure Appl. Chem. 1985;57:149–168.

LinkOut - more resources