Macrocyclic Gd3+ Complexes with Pendant Crown Ethers Designed for Binding Zwitterionic Neurotransmitters
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| Titel: | Macrocyclic Gd3+ Complexes with Pendant Crown Ethers Designed for Binding Zwitterionic Neurotransmitters |
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| Autoren: | Nikos K. Logothetis, Céline Landon, Hervé Meudal, Carlos Platas-Iglesias, Goran Angelovski, Fatima Oukhatar, Éva Tóth |
| Weitere Verfasser: | Frapart, Isabelle |
| Quelle: | Chemistry – A European Journal Oukhatar, F, Meudal, H, Landon, C, Logothetis, N K, Platas-Iglesias, C, Angelovski, G & Toth, E 2015, 'Macrocyclic Gd(3+) complexes with pendant crown ethers designed for binding zwitterionic neurotransmitters', Chemistry, vol. 21, no. 31, pp. 11226-37. https://doi.org/10.1002/chem.201500542 |
| Verlagsinformationen: | Wiley, 2015. |
| Publikationsjahr: | 2015 |
| Schlagwörter: | Macrocyclic Compounds/chemical synthesis/chemistry/*metabolism, Models, Molecular, Neurotransmitter Agents, Binding Sites, Macrocyclic Compounds, Magnetic Resonance Spectroscopy, Coordination Complexes/chemical synthesis/chemistry/*metabolism, Amino Acids/metabolism, Molecular, Gadolinium, 01 natural sciences, 3. Good health, 0104 chemical sciences, [SDV] Life Sciences [q-bio], Crown Ethers/chemical synthesis/chemistry/*metabolism, Models, Coordination Complexes, Crown Ethers, Luminescent Measurements, Potentiometry, Gadolinium/chemistry/*metabolism, Amino Acids, Neurotransmitter Agents/*metabolism |
| Beschreibung: | A series of Gd3+ complexes exhibiting a relaxometric response to zwitterionic amino acid neurotransmitters was synthesized. The design concept involves ditopic interactions 1) between a positively charged and coordinatively unsaturated Gd3+ chelate and the carboxylate group of the neurotransmitters and 2) between an azacrown ether appended to the chelate and the amino group of the neurotransmitters. The chelates differ in the nature and length of the linker connecting the cyclen‐type macrocycle that binds the Ln3+ ion and the crown ether. The complexes are monohydrated, but they exhibit high proton relaxivities (up to 7.7 mM−1 s−1 at 60 MHz, 310 K) due to slow molecular tumbling. The formation of ternary complexes with neurotransmitters was monitored by 1H relaxometric titrations of the Gd3+ complexes and by luminescence measurements on the Eu3+ and Tb3+ analogues at pH 7.4. The remarkable relaxivity decrease (≈80 %) observed on neurotransmitter binding is related to the decrease in the hydration number, as evidenced by luminescence lifetime measurements on the Eu3+ complexes. These complexes show affinity for amino acid neurotransmitters in the millimolar range, which can be suited to imaging concentrations of synaptically released neurotransmitters. They display good selectivity over non‐amino acid neurotransmitters (acetylcholine, serotonin, and noradrenaline) and hydrogenphosphate, but selectivity over hydrogencarbonate was not achieved. |
| Publikationsart: | Article |
| Sprache: | English |
| ISSN: | 1521-3765 0947-6539 |
| DOI: | 10.1002/chem.201500542 |
| Zugangs-URL: | https://pubmed.ncbi.nlm.nih.gov/26118946 https://hal.archives-ouvertes.fr/hal-01196981 https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.201500542 https://www.ncbi.nlm.nih.gov/pubmed/26118946 http://pubman.mpdl.mpg.de/pubman/item/escidoc:2272410 http://onlinelibrary.wiley.com/doi/10.1002/chem.201500542/abstract https://pubmed.ncbi.nlm.nih.gov/26118946/ http://hdl.handle.net/11858/00-001M-0000-002A-4576-B https://hal.science/hal-01196981v1 |
| Rights: | Wiley Online Library User Agreement |
| Dokumentencode: | edsair.doi.dedup.....72c90f1ca21bf08aa43c47017b8b784b |
| Datenbank: | OpenAIRE |
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Nájsť tento článok vo Web of Science | Abstract: | A series of Gd3+ complexes exhibiting a relaxometric response to zwitterionic amino acid neurotransmitters was synthesized. The design concept involves ditopic interactions 1) between a positively charged and coordinatively unsaturated Gd3+ chelate and the carboxylate group of the neurotransmitters and 2) between an azacrown ether appended to the chelate and the amino group of the neurotransmitters. The chelates differ in the nature and length of the linker connecting the cyclen‐type macrocycle that binds the Ln3+ ion and the crown ether. The complexes are monohydrated, but they exhibit high proton relaxivities (up to 7.7 mM−1 s−1 at 60 MHz, 310 K) due to slow molecular tumbling. The formation of ternary complexes with neurotransmitters was monitored by 1H relaxometric titrations of the Gd3+ complexes and by luminescence measurements on the Eu3+ and Tb3+ analogues at pH 7.4. The remarkable relaxivity decrease (≈80 %) observed on neurotransmitter binding is related to the decrease in the hydration number, as evidenced by luminescence lifetime measurements on the Eu3+ complexes. These complexes show affinity for amino acid neurotransmitters in the millimolar range, which can be suited to imaging concentrations of synaptically released neurotransmitters. They display good selectivity over non‐amino acid neurotransmitters (acetylcholine, serotonin, and noradrenaline) and hydrogenphosphate, but selectivity over hydrogencarbonate was not achieved. |
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| ISSN: | 15213765 09476539 |
| DOI: | 10.1002/chem.201500542 |