8-Hydroxyquinoline-Amino Acid Hybrids and Their Half-Sandwich Rh and Ru Complexes: Synthesis, Anticancer Activities, Solution Chemistry and Interaction with Biomolecules
Solution chemical properties of two novel 8-hydroxyquinoline-D-proline and homo-proline hybrids were investigated along with their complex formation with [Rh(η<sup>5</sup>-C<sub>5</sub>Me<sub>5</sub>)(H<sub>2</sub>O)<sub>3</sub>]<sup>...
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MDPI AG
2021-10-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/22/20/11281 |
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| author | Tamás Pivarcsik Orsolya Dömötör János P. Mészáros Nóra V. May Gabriella Spengler Oszkár Csuvik István Szatmári Éva A. Enyedy |
| author_facet | Tamás Pivarcsik Orsolya Dömötör János P. Mészáros Nóra V. May Gabriella Spengler Oszkár Csuvik István Szatmári Éva A. Enyedy |
| author_sort | Tamás Pivarcsik |
| collection | DOAJ |
| description | Solution chemical properties of two novel 8-hydroxyquinoline-D-proline and homo-proline hybrids were investigated along with their complex formation with [Rh(η<sup>5</sup>-C<sub>5</sub>Me<sub>5</sub>)(H<sub>2</sub>O)<sub>3</sub>]<sup>2+</sup> and [Ru(η<sup>6</sup>-<i>p</i>-cymene)(H<sub>2</sub>O)<sub>3</sub>]<sup>2+</sup> ions by pH-potentiometry, UV-visible spectrophotometry and <sup>1</sup>H NMR spectroscopy. Due to the zwitterionic structure of the ligands, they possess excellent water solubility as well as their complexes. The complexes exhibit high solution stability in a wide pH range; no significant dissociation occurs at physiological pH. The hybrids and their Rh(η<sup>5</sup>-C<sub>5</sub>Me<sub>5</sub>) complexes displayed enhanced cytotoxicity in human colon adenocarcinoma cell lines and exhibited multidrug resistance selectivity. In addition, the Rh(η<sup>5</sup>-C<sub>5</sub>Me<sub>5</sub>) complexes showed increased selectivity to the chemosensitive cancer cells over the normal cells; meanwhile, the Ru(η<sup>6</sup>-<i>p</i>-cymene) complexes were inactive, most likely due to arene loss. Interaction of the complexes with human serum albumin (HSA) and calf-thymus DNA (ct-DNA) was investigated by capillary electrophoresis, fluorometry and circular dichroism. The complexes are able to bind strongly to HSA and ct-DNA, but DNA cleavage was not observed. Changing the five-membered proline ring to the six-membered homoproline resulted in increased lipophilicity and cytotoxicity of the Rh(η<sup>5</sup>-C<sub>5</sub>Me<sub>5</sub>) complexes while changing the configuration (L vs. D) rather has an impact on HSA or ct-DNA binding. |
| first_indexed | 2024-03-10T06:29:41Z |
| format | Article |
| id | doaj.art-44aaa2f0fa0d4a9d928e8ae83c9824e6 |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-10T06:29:41Z |
| publishDate | 2021-10-01 |
| publisher | MDPI AG |
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| series | International Journal of Molecular Sciences |
| spelling | doaj.art-44aaa2f0fa0d4a9d928e8ae83c9824e62023-11-22T18:36:57ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672021-10-0122201128110.3390/ijms2220112818-Hydroxyquinoline-Amino Acid Hybrids and Their Half-Sandwich Rh and Ru Complexes: Synthesis, Anticancer Activities, Solution Chemistry and Interaction with BiomoleculesTamás Pivarcsik0Orsolya Dömötör1János P. Mészáros2Nóra V. May3Gabriella Spengler4Oszkár Csuvik5István Szatmári6Éva A. Enyedy7MTA-SZTE Lendület Functional Metal Complexes Research Group, University of Szeged, Dóm Tér 7, H-6720 Szeged, HungaryMTA-SZTE Lendület Functional Metal Complexes Research Group, University of Szeged, Dóm Tér 7, H-6720 Szeged, HungaryMTA-SZTE Lendület Functional Metal Complexes Research Group, University of Szeged, Dóm Tér 7, H-6720 Szeged, HungaryCentre for Structural Science, Research Centre for Natural Sciences, Magyar Tudósok Körútja 2, H-1117 Budapest, HungaryMTA-SZTE Lendület Functional Metal Complexes Research Group, University of Szeged, Dóm Tér 7, H-6720 Szeged, HungaryInstitute of Pharmaceutical Chemistry and Stereochemistry Research Group of Hungarian Academy of Sciences, University of Szeged, Eötvös U. 6, H-6720 Szeged, HungaryInstitute of Pharmaceutical Chemistry and Stereochemistry Research Group of Hungarian Academy of Sciences, University of Szeged, Eötvös U. 6, H-6720 Szeged, HungaryMTA-SZTE Lendület Functional Metal Complexes Research Group, University of Szeged, Dóm Tér 7, H-6720 Szeged, HungarySolution chemical properties of two novel 8-hydroxyquinoline-D-proline and homo-proline hybrids were investigated along with their complex formation with [Rh(η<sup>5</sup>-C<sub>5</sub>Me<sub>5</sub>)(H<sub>2</sub>O)<sub>3</sub>]<sup>2+</sup> and [Ru(η<sup>6</sup>-<i>p</i>-cymene)(H<sub>2</sub>O)<sub>3</sub>]<sup>2+</sup> ions by pH-potentiometry, UV-visible spectrophotometry and <sup>1</sup>H NMR spectroscopy. Due to the zwitterionic structure of the ligands, they possess excellent water solubility as well as their complexes. The complexes exhibit high solution stability in a wide pH range; no significant dissociation occurs at physiological pH. The hybrids and their Rh(η<sup>5</sup>-C<sub>5</sub>Me<sub>5</sub>) complexes displayed enhanced cytotoxicity in human colon adenocarcinoma cell lines and exhibited multidrug resistance selectivity. In addition, the Rh(η<sup>5</sup>-C<sub>5</sub>Me<sub>5</sub>) complexes showed increased selectivity to the chemosensitive cancer cells over the normal cells; meanwhile, the Ru(η<sup>6</sup>-<i>p</i>-cymene) complexes were inactive, most likely due to arene loss. Interaction of the complexes with human serum albumin (HSA) and calf-thymus DNA (ct-DNA) was investigated by capillary electrophoresis, fluorometry and circular dichroism. The complexes are able to bind strongly to HSA and ct-DNA, but DNA cleavage was not observed. Changing the five-membered proline ring to the six-membered homoproline resulted in increased lipophilicity and cytotoxicity of the Rh(η<sup>5</sup>-C<sub>5</sub>Me<sub>5</sub>) complexes while changing the configuration (L vs. D) rather has an impact on HSA or ct-DNA binding.https://www.mdpi.com/1422-0067/22/20/11281multidrug resistancesolution speciationcytotoxicityorganometallicDNA bindingalbumin binding |
| spellingShingle | Tamás Pivarcsik Orsolya Dömötör János P. Mészáros Nóra V. May Gabriella Spengler Oszkár Csuvik István Szatmári Éva A. Enyedy 8-Hydroxyquinoline-Amino Acid Hybrids and Their Half-Sandwich Rh and Ru Complexes: Synthesis, Anticancer Activities, Solution Chemistry and Interaction with Biomolecules International Journal of Molecular Sciences multidrug resistance solution speciation cytotoxicity organometallic DNA binding albumin binding |
| title | 8-Hydroxyquinoline-Amino Acid Hybrids and Their Half-Sandwich Rh and Ru Complexes: Synthesis, Anticancer Activities, Solution Chemistry and Interaction with Biomolecules |
| title_full | 8-Hydroxyquinoline-Amino Acid Hybrids and Their Half-Sandwich Rh and Ru Complexes: Synthesis, Anticancer Activities, Solution Chemistry and Interaction with Biomolecules |
| title_fullStr | 8-Hydroxyquinoline-Amino Acid Hybrids and Their Half-Sandwich Rh and Ru Complexes: Synthesis, Anticancer Activities, Solution Chemistry and Interaction with Biomolecules |
| title_full_unstemmed | 8-Hydroxyquinoline-Amino Acid Hybrids and Their Half-Sandwich Rh and Ru Complexes: Synthesis, Anticancer Activities, Solution Chemistry and Interaction with Biomolecules |
| title_short | 8-Hydroxyquinoline-Amino Acid Hybrids and Their Half-Sandwich Rh and Ru Complexes: Synthesis, Anticancer Activities, Solution Chemistry and Interaction with Biomolecules |
| title_sort | 8 hydroxyquinoline amino acid hybrids and their half sandwich rh and ru complexes synthesis anticancer activities solution chemistry and interaction with biomolecules |
| topic | multidrug resistance solution speciation cytotoxicity organometallic DNA binding albumin binding |
| url | https://www.mdpi.com/1422-0067/22/20/11281 |
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