Molecular Recognition of Imidazole-Based Drug Molecules by Cobalt(III)- and Zinc(II)-Coproporphyrins in Aqueous Media
The methods of <sup>1</sup>H NMR, spectrophotometric titration, mass spectrometry and elemental analysis are applied to determine the selective binding ability of Co(III)- and Zn(II)-coproporphyrins I towards a series of imidazole-based drug molecules with a wide spectrum of pharmacologi...
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MDPI AG
2023-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/3/964 |
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| author | Galina Mamardashvili Elena Kaigorodova Ivan Lebedev Nugzar Mamardashvili |
| author_facet | Galina Mamardashvili Elena Kaigorodova Ivan Lebedev Nugzar Mamardashvili |
| author_sort | Galina Mamardashvili |
| collection | DOAJ |
| description | The methods of <sup>1</sup>H NMR, spectrophotometric titration, mass spectrometry and elemental analysis are applied to determine the selective binding ability of Co(III)- and Zn(II)-coproporphyrins I towards a series of imidazole-based drug molecules with a wide spectrum of pharmacological activity (metronidazole, histamine, histidine, tinidazole, mercazolil, and pilocarpine) in phosphate buffer (pH 7.4) simulating the blood plasma environment. It is shown that in aqueous buffer media, Co(III)-coproporphyrin I, unlike Zn(II)-coproporphyrin I, binds two imidazole derivatives, and the stability of mono-axial Co-coproporphyrin imidazole complexes is two to three orders of magnitude higher than that of similar complexes of Zn-coproporphyrin I. The studied porphyrinates are found to have the highest binding ability to histamine and histidine due to the formation of two additional hydrogen bonds between the carboxyl groups of the porphyrinate side chains and the binding sites of the ligands in the case of histidine and a hydrogen bond between the amino group of the ligand and the carbonyl oxygen atom of the carboxyl group of the porphyrinate in the case of histamine. The structures of the resulting complexes are optimized by DFT quantum chemical calculations. The results of these studies may be of use in the design of biosensors, including those for the detection, control and verification of various veterinary drug residues in human food samples. |
| first_indexed | 2024-03-11T09:34:54Z |
| format | Article |
| id | doaj.art-f28c5a0669b142ea9bf73f7b5e378b64 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T09:34:54Z |
| publishDate | 2023-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-f28c5a0669b142ea9bf73f7b5e378b642023-11-16T17:25:41ZengMDPI AGMolecules1420-30492023-01-0128396410.3390/molecules28030964Molecular Recognition of Imidazole-Based Drug Molecules by Cobalt(III)- and Zinc(II)-Coproporphyrins in Aqueous MediaGalina Mamardashvili0Elena Kaigorodova1Ivan Lebedev2Nugzar Mamardashvili3G.A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences, Akademicheskay St. 1, Ivanovo 153045, RussiaG.A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences, Akademicheskay St. 1, Ivanovo 153045, RussiaG.A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences, Akademicheskay St. 1, Ivanovo 153045, RussiaG.A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences, Akademicheskay St. 1, Ivanovo 153045, RussiaThe methods of <sup>1</sup>H NMR, spectrophotometric titration, mass spectrometry and elemental analysis are applied to determine the selective binding ability of Co(III)- and Zn(II)-coproporphyrins I towards a series of imidazole-based drug molecules with a wide spectrum of pharmacological activity (metronidazole, histamine, histidine, tinidazole, mercazolil, and pilocarpine) in phosphate buffer (pH 7.4) simulating the blood plasma environment. It is shown that in aqueous buffer media, Co(III)-coproporphyrin I, unlike Zn(II)-coproporphyrin I, binds two imidazole derivatives, and the stability of mono-axial Co-coproporphyrin imidazole complexes is two to three orders of magnitude higher than that of similar complexes of Zn-coproporphyrin I. The studied porphyrinates are found to have the highest binding ability to histamine and histidine due to the formation of two additional hydrogen bonds between the carboxyl groups of the porphyrinate side chains and the binding sites of the ligands in the case of histidine and a hydrogen bond between the amino group of the ligand and the carbonyl oxygen atom of the carboxyl group of the porphyrinate in the case of histamine. The structures of the resulting complexes are optimized by DFT quantum chemical calculations. The results of these studies may be of use in the design of biosensors, including those for the detection, control and verification of various veterinary drug residues in human food samples.https://www.mdpi.com/1420-3049/28/3/964Co(III)-porphyrinsZn(II)-porphyrinsimidazoleaxial coordinationselective bindingmolecular recognition |
| spellingShingle | Galina Mamardashvili Elena Kaigorodova Ivan Lebedev Nugzar Mamardashvili Molecular Recognition of Imidazole-Based Drug Molecules by Cobalt(III)- and Zinc(II)-Coproporphyrins in Aqueous Media Molecules Co(III)-porphyrins Zn(II)-porphyrins imidazole axial coordination selective binding molecular recognition |
| title | Molecular Recognition of Imidazole-Based Drug Molecules by Cobalt(III)- and Zinc(II)-Coproporphyrins in Aqueous Media |
| title_full | Molecular Recognition of Imidazole-Based Drug Molecules by Cobalt(III)- and Zinc(II)-Coproporphyrins in Aqueous Media |
| title_fullStr | Molecular Recognition of Imidazole-Based Drug Molecules by Cobalt(III)- and Zinc(II)-Coproporphyrins in Aqueous Media |
| title_full_unstemmed | Molecular Recognition of Imidazole-Based Drug Molecules by Cobalt(III)- and Zinc(II)-Coproporphyrins in Aqueous Media |
| title_short | Molecular Recognition of Imidazole-Based Drug Molecules by Cobalt(III)- and Zinc(II)-Coproporphyrins in Aqueous Media |
| title_sort | molecular recognition of imidazole based drug molecules by cobalt iii and zinc ii coproporphyrins in aqueous media |
| topic | Co(III)-porphyrins Zn(II)-porphyrins imidazole axial coordination selective binding molecular recognition |
| url | https://www.mdpi.com/1420-3049/28/3/964 |
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