Synthesis and antiproliferative activity of hindered, chiral 1,2-diaminodiamantane platinum(II) complexes
Platinum-based antineoplastic agents play a major role in the treatment of numerous types of cancer. A new bulky, lipophilic, and chiral ligand based on 1,2-diaminodiamantane in both of its enantiomeric forms was employed for the preparation of new platinum(ii) complexes with chloride and oxalate ligands. The dichloride complexes have a higher solubility and were evaluated as anti-proliferation agents for human ovarian cancer cell lines A2780 and cisplatin-resistant A2780cis. Its R,R-enantiomer showed increased efficacy compared to cisplatin for both cancer cell lines. A chromatographic approach was used to estimate the solvent partition coefficient of the dichloride complex. The binding of diamondoid-based platinum complexes to nucleotides was tested for both enantiomers with guanosine monophosphate (GMP) and deoxyguanosine monophosphate (dGMP) and occurs at a similar or faster rate for both isomers compared to cisplatin despite greatly increased steric demand. These findings highlight the potential in 1,2-diaminodiamantane as a viable pharmacophore.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2020 |
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| Erschienen: |
2020 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:49 |
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| Enthalten in: |
Dalton transactions (Cambridge, England : 2003) - 49(2020), 40 vom: 20. Okt., Seite 14009-14016 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Bakhonsky, Vladyslav V [VerfasserIn] |
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| Links: |
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| Themen: |
49DFR088MY |
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| Anmerkungen: |
Date Completed 20.07.2021 Date Revised 20.07.2021 published: Print Citation Status MEDLINE |
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| doi: |
10.1039/d0dt02391d |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM31648086X |
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| 100 | 1 | |a Bakhonsky, Vladyslav V |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Synthesis and antiproliferative activity of hindered, chiral 1,2-diaminodiamantane platinum(II) complexes |
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| 500 | |a Date Revised 20.07.2021 | ||
| 500 | |a published: Print | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Platinum-based antineoplastic agents play a major role in the treatment of numerous types of cancer. A new bulky, lipophilic, and chiral ligand based on 1,2-diaminodiamantane in both of its enantiomeric forms was employed for the preparation of new platinum(ii) complexes with chloride and oxalate ligands. The dichloride complexes have a higher solubility and were evaluated as anti-proliferation agents for human ovarian cancer cell lines A2780 and cisplatin-resistant A2780cis. Its R,R-enantiomer showed increased efficacy compared to cisplatin for both cancer cell lines. A chromatographic approach was used to estimate the solvent partition coefficient of the dichloride complex. The binding of diamondoid-based platinum complexes to nucleotides was tested for both enantiomers with guanosine monophosphate (GMP) and deoxyguanosine monophosphate (dGMP) and occurs at a similar or faster rate for both isomers compared to cisplatin despite greatly increased steric demand. These findings highlight the potential in 1,2-diaminodiamantane as a viable pharmacophore | ||
| 650 | 4 | |a Journal Article | |
| 650 | 7 | |a Antineoplastic Agents |2 NLM | |
| 650 | 7 | |a Coordination Complexes |2 NLM | |
| 650 | 7 | |a Ligands |2 NLM | |
| 650 | 7 | |a Organoplatinum Compounds |2 NLM | |
| 650 | 7 | |a Platinum |2 NLM | |
| 650 | 7 | |a 49DFR088MY |2 NLM | |
| 650 | 7 | |a Guanosine Monophosphate |2 NLM | |
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| 650 | 7 | |a Cisplatin |2 NLM | |
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| 700 | 1 | |a Pashenko, Aleksander A |e verfasserin |4 aut | |
| 700 | 1 | |a Becker, Jonathan |e verfasserin |4 aut | |
| 700 | 1 | |a Hausmann, Heike |e verfasserin |4 aut | |
| 700 | 1 | |a De Groot, Huub J M |e verfasserin |4 aut | |
| 700 | 1 | |a Overkleeft, Herman S |e verfasserin |4 aut | |
| 700 | 1 | |a Fokin, Andrey A |e verfasserin |4 aut | |
| 700 | 1 | |a Schreiner, Peter R |e verfasserin |4 aut | |
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