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<p>Carboxylato-type transition metal complexes with agaric acid, a bioactive natural compound derived from citric acid, were prepared, and tested <italic>in vitro</italic> for their antimicrobial activity and cytotoxicity. The products as well as agaric acid itself are amphiphilic compounds containing a hydrophilic head (citric acid moiety) and a hydrophobic tail (non-polar alkyl chain). The putative composition of the carboxylates was assigned on grounds of elemental analysis, infrared (IR) and high-resolution mass spectra (HR-MS), as well as in analogy with known complexes containing the citrate moiety. The metal carboxylates showed interesting activity in several microbial strains, especially against <italic>S. aureus</italic> (vanadium complex; MIC = 0.05 mg/ml). They were also tested for their cytotoxic activity in hepatocytes, the highest activity having been found in the copper(II) and manganese(II) complexes. Further research based on these preliminary results is needed in order to evaluate the influence of parameters like stability of the metal complexes in solution on the bioactivity of the complexes.</p>
</abstract>

Carboxylato-type transition metal complexes with agaric acid, a bioactive natural compound derived from citric acid, were prepared, and tested in vitro for their antimicrobial activity and cytotoxicity. The products as well as agaric acid itself are amphiphilic compounds containing a hydrophilic head (citric acid moiety) and a hydrophobic tail (non-polar alkyl chain). The putative composition of the carboxylates was assigned on grounds of elemental analysis, infrared (IR) and high-resolution mass spectra (HR-MS), as well as in analogy with known complexes containing the citrate moiety. The metal carboxylates showed interesting activity in several microbial strains, especially against S. aureus (vanadium complex; MIC = 0.05 mg/ml). They were also tested for their cytotoxic activity in hepatocytes, the highest activity having been found in the copper(II) and manganese(II) complexes. Further research based on these preliminary results is needed in order to evaluate the influence of parameters like stability of the metal complexes in solution on the bioactivity of the complexes.

Antimicrobial activity and cytotoxicity of transition metal carboxylates derived from agaric acid

Department of Chemical Theory of Drugs, Faculty of Pharmacy

Department of Cellular and Molecular Biology of Drugs, Faculty of Pharmacy

European Pharmaceutical Journal

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Carboxylato-type transition metal complexes with agaric acid, a bioactive natural compound derived from citric acid, were prepared, and tested in vitro for...

Comp. Nr.	Starting metal salt	Yield	Colour	Molar conductivity	Assumed composition	Elemental analysis theor.		Elemental analysis exp.
		%		μS·mol⁻¹·cm²		% C	% H	% C	%H
1	CoCl₂·6H₂O	96	pink	9	Co(L-2H)(2H₂O)	51.84	8.31	51.70	8.55
2	CuCl₂·2H₂O	75	light blue	3	Cu(L-2H)(2H₂O)	51.44	8.25	51.17	8.03
3	NiCl₂·6H₂O	82	light-green	10	Ni(L-2H)(3H₂O)	50.17	8.43	50.19	8.46
4	La(NO₃)₃·6H₂O	87	white	2	La(L-3H)(2H₂O)	44.90	7.02	44.91	7.19
5	VOSO₄·5H₂O	84	grey-blue	11	VO(L-2H)(3H₂O)	49.34	8.28	49.30	8.03
6	FeCl₃·6H₂O	86	light-brown	3	Fe(L-3H)(3H₂O)	50.46	8.28	50.50	7.95
7	MnCl₂·2H₂O	95	brownish-white	5	Mn(L-2H)(2H₂O)	52.27	8.37	52.79	8.30

Substance	ν_as(COO⁻) ^a	ν_s(COO⁻) ^b	Δν(COO⁻) ^c	ν(C=O)	m/z theor. ^d	m/z found
1 (Co)	1590	1394	196	1704	472.1872	472.1875
2 (Cu)	1567	1417	150	1704	476.1836	476.1839
3 (Ni)	1575	1417	158	1704	471.1893	471.1899
4 (La)	1558	1403	155	---	(552.1603)	---
5 (V)	1563	1423	140	1705	480.1928	480.1932
6 (Fe)	1539	1440	99	---	468.1811	468.1816
7 (Mn)	1569	1409	160	1703	(468.1920)	---
8 (L)	---	---	---	1691	415.2696	415.2701

Substance Nr.	Metal	MIC (mg/ml)
Substance Nr.	Metal	S. aureus	E. coli	C. albicans
1	Co	0.22	0.44	0.88
2	Cu	0.44	1.75	0.44
3	Ni	>3.5	1.75	0.88
4	La	1.75	1.75	1.75
5	V	0.05	3.5	0.88
6	Fe	3.5	0.88	0.44
7	Mn	3.5	3.5	0.44
8	(ligand)	1.75	3.5	0.88

Antimicrobial activity and cytotoxicity of transition metal carboxylates derived from agaric acid

Article Category: Original Paper

Published Online: Jul 25, 2021

Page range: 46 - 53

Received: Nov 13, 2020

Accepted: Mar 01, 2021

DOI: https://doi.org/10.2478/afpuc-2020-0018

Keywords
Bioinorganic chemistry, metallodrugs, agaric acid, anticancer, antimicrobial, amphiphilic compounds

© 2021 L. Habala et al., published by Sciendo

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Figure 1

Figure 2

Figure 3

The prepared metal carboxylates.

Characteristic signals in IR and HR-MS spectra.

Antimicrobial activity of metal carboxylates and the ligand (MIC = minimum inhibitory concentration).

Antimicrobial activity and cytotoxicity of transition metal carboxylates derived from agaric acid

Article Category: Original Paper

Published Online: Jul 25, 2021

Page range: 46 - 53

Received: Nov 13, 2020

Accepted: Mar 01, 2021

DOI: https://doi.org/10.2478/afpuc-2020-0018

KeywordsBioinorganic chemistry, metallodrugs, agaric acid, anticancer, antimicrobial, amphiphilic compounds

© 2021 L. Habala et al., published by Sciendo

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Figure 1

Figure 2

Figure 3

The prepared metal carboxylates.

Characteristic signals in IR and HR-MS spectra.

Antimicrobial activity of metal carboxylates and the ligand (MIC = minimum inhibitory concentration).

Keywords
Bioinorganic chemistry, metallodrugs, agaric acid, anticancer, antimicrobial, amphiphilic compounds