Latonduine-1-Amino-Hydantoin Hybrid, Triazole-Fused Latonduine Schiff Bases and Their Metal Complexes: Synthesis, X-ray and Electron Diffraction, Molecular Docking Studies and Antiproliferative Activity
A series of latonduine derivatives, namely 11-nitro-indolo[2,3-<i>d</i>]benzazepine-7-(1-amino-hydantoin) (<b>B</b>), triazole-fused indolo[2,3-<i>d</i>]benzazepine-based Schiff bases <b>HL<sup>1</sup></b> and <b>HL<sup>2</su...
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| Format: | Article |
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MDPI AG
2023-01-01
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| Series: | Inorganics |
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| Online Access: | https://www.mdpi.com/2304-6740/11/1/30 |
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| author | Christopher Wittmann Tim Gruene Alexander Prado-Roller Sandra Aranđelović Jóhannes Reynisson Vladimir B. Arion |
| author_facet | Christopher Wittmann Tim Gruene Alexander Prado-Roller Sandra Aranđelović Jóhannes Reynisson Vladimir B. Arion |
| author_sort | Christopher Wittmann |
| collection | DOAJ |
| description | A series of latonduine derivatives, namely 11-nitro-indolo[2,3-<i>d</i>]benzazepine-7-(1-amino-hydantoin) (<b>B</b>), triazole-fused indolo[2,3-<i>d</i>]benzazepine-based Schiff bases <b>HL<sup>1</sup></b> and <b>HL<sup>2</sup></b> and metal complexes [M(<i>p</i>-cymene)(HL<sup>1</sup>)Cl]Cl, where M = Ru (<b>1</b>), Os (<b>2</b>), and [Cu(HL<sup>2</sup>)Cl<sub>2</sub>] (<b>3</b>) were synthesized and characterized by spectroscopic techniques (UV–vis, <sup>1</sup>H, <sup>13</sup>C, <sup>15</sup>N–<sup>1</sup>H HSQC NMR) and ESI mass spectrometry. The molecular structures of <b>B</b> and <b>HL<sup>1</sup></b> were confirmed by single-crystal X-ray diffraction, while that of <b>3</b> by electron diffraction of nanometer size crystalline sample. Molecular docking calculations of species <b>B</b> in the binding pocket of PIM-1 enzyme revealed that the 1-amino-hydantoin moiety is not involved in any hydrogen-bonding interactions, even though a good accommodation of the host molecule in the ATP binding pocket of the enzyme was found. The antiproliferative activity of organic compounds <b>B</b>, <b>HL<sup>1</sup></b> and <b>HL<sup>2</sup></b>, as well as complexes <b>1</b>–<b>3</b> was investigated in lung adenocarcinoma A549, colon adenocarcinoma LS-174 and triple-negative breast adenocarcinoma MDA-MB-231 cells and normal human lung fibroblast cells MRC-5 by MTT assays; then, the results are discussed. |
| first_indexed | 2024-03-09T12:15:52Z |
| format | Article |
| id | doaj.art-72b6673b92dd4d1c9537f5344d2884b2 |
| institution | Directory Open Access Journal |
| issn | 2304-6740 |
| language | English |
| last_indexed | 2024-03-09T12:15:52Z |
| publishDate | 2023-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Inorganics |
| spelling | doaj.art-72b6673b92dd4d1c9537f5344d2884b22023-11-30T22:47:19ZengMDPI AGInorganics2304-67402023-01-011113010.3390/inorganics11010030Latonduine-1-Amino-Hydantoin Hybrid, Triazole-Fused Latonduine Schiff Bases and Their Metal Complexes: Synthesis, X-ray and Electron Diffraction, Molecular Docking Studies and Antiproliferative ActivityChristopher Wittmann0Tim Gruene1Alexander Prado-Roller2Sandra Aranđelović3Jóhannes Reynisson4Vladimir B. Arion5Institute of Inorganic Chemistry, University of Vienna, Währinger Strasse 42, A1090 Vienna, AustriaInstitute of Inorganic Chemistry, University of Vienna, Währinger Strasse 42, A1090 Vienna, AustriaInstitute of Inorganic Chemistry, University of Vienna, Währinger Strasse 42, A1090 Vienna, AustriaInstitute of Oncology and Radiology of Serbia, Pasterova 14, 11000 Belgrade, SerbiaSchool of Pharmacy and Bioengineering, Keele University, Hornbeam Building, Staffordshire ST5 5BG, UKInstitute of Inorganic Chemistry, University of Vienna, Währinger Strasse 42, A1090 Vienna, AustriaA series of latonduine derivatives, namely 11-nitro-indolo[2,3-<i>d</i>]benzazepine-7-(1-amino-hydantoin) (<b>B</b>), triazole-fused indolo[2,3-<i>d</i>]benzazepine-based Schiff bases <b>HL<sup>1</sup></b> and <b>HL<sup>2</sup></b> and metal complexes [M(<i>p</i>-cymene)(HL<sup>1</sup>)Cl]Cl, where M = Ru (<b>1</b>), Os (<b>2</b>), and [Cu(HL<sup>2</sup>)Cl<sub>2</sub>] (<b>3</b>) were synthesized and characterized by spectroscopic techniques (UV–vis, <sup>1</sup>H, <sup>13</sup>C, <sup>15</sup>N–<sup>1</sup>H HSQC NMR) and ESI mass spectrometry. The molecular structures of <b>B</b> and <b>HL<sup>1</sup></b> were confirmed by single-crystal X-ray diffraction, while that of <b>3</b> by electron diffraction of nanometer size crystalline sample. Molecular docking calculations of species <b>B</b> in the binding pocket of PIM-1 enzyme revealed that the 1-amino-hydantoin moiety is not involved in any hydrogen-bonding interactions, even though a good accommodation of the host molecule in the ATP binding pocket of the enzyme was found. The antiproliferative activity of organic compounds <b>B</b>, <b>HL<sup>1</sup></b> and <b>HL<sup>2</sup></b>, as well as complexes <b>1</b>–<b>3</b> was investigated in lung adenocarcinoma A549, colon adenocarcinoma LS-174 and triple-negative breast adenocarcinoma MDA-MB-231 cells and normal human lung fibroblast cells MRC-5 by MTT assays; then, the results are discussed.https://www.mdpi.com/2304-6740/11/1/30indolobenzazepinesantiproliferative activityruthenium(II)osmium(II)copper(II) |
| spellingShingle | Christopher Wittmann Tim Gruene Alexander Prado-Roller Sandra Aranđelović Jóhannes Reynisson Vladimir B. Arion Latonduine-1-Amino-Hydantoin Hybrid, Triazole-Fused Latonduine Schiff Bases and Their Metal Complexes: Synthesis, X-ray and Electron Diffraction, Molecular Docking Studies and Antiproliferative Activity Inorganics indolobenzazepines antiproliferative activity ruthenium(II) osmium(II) copper(II) |
| title | Latonduine-1-Amino-Hydantoin Hybrid, Triazole-Fused Latonduine Schiff Bases and Their Metal Complexes: Synthesis, X-ray and Electron Diffraction, Molecular Docking Studies and Antiproliferative Activity |
| title_full | Latonduine-1-Amino-Hydantoin Hybrid, Triazole-Fused Latonduine Schiff Bases and Their Metal Complexes: Synthesis, X-ray and Electron Diffraction, Molecular Docking Studies and Antiproliferative Activity |
| title_fullStr | Latonduine-1-Amino-Hydantoin Hybrid, Triazole-Fused Latonduine Schiff Bases and Their Metal Complexes: Synthesis, X-ray and Electron Diffraction, Molecular Docking Studies and Antiproliferative Activity |
| title_full_unstemmed | Latonduine-1-Amino-Hydantoin Hybrid, Triazole-Fused Latonduine Schiff Bases and Their Metal Complexes: Synthesis, X-ray and Electron Diffraction, Molecular Docking Studies and Antiproliferative Activity |
| title_short | Latonduine-1-Amino-Hydantoin Hybrid, Triazole-Fused Latonduine Schiff Bases and Their Metal Complexes: Synthesis, X-ray and Electron Diffraction, Molecular Docking Studies and Antiproliferative Activity |
| title_sort | latonduine 1 amino hydantoin hybrid triazole fused latonduine schiff bases and their metal complexes synthesis x ray and electron diffraction molecular docking studies and antiproliferative activity |
| topic | indolobenzazepines antiproliferative activity ruthenium(II) osmium(II) copper(II) |
| url | https://www.mdpi.com/2304-6740/11/1/30 |
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