- Photoactivatable AMPA for the study of glutamatergic neuronal transmission using two-photon excitation
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We report a photoactivatable agonist of the AMPA subtype of ionotropic glutamate receptors, TMP-CyHQ-AMPA, which was designed to study the fast excitatory transmission between neurons. Upon visible light excitation, TMP-CyHQ-AMPA quantitatively released AMPA in high quantum yield on an ultra-short timescale. Intriguingly, the photolyisis can be carried out using 2-photon excitation (2PE) with remarkable efficiency, giving a two-photon uncaging action cross section (δu) value of 1.71 GM. TMP-CyHQ-AMPA is soluble in pysiological buffer and no hydrolysis was detected in the absence of light. Molecular docking experiments indicated that the photocaging strategy abolishes the affinity of AMPA for the GluR2 receptor and no GABAergic effects (as commonly observed in caged glutamates) are expected. TMP-CyHQ-AMPA can be used to study glutamatergic neuronal transmission with exceptional spatial-temporal resolution in complex tissue preparations.
- Asad, Naeem,Deodato, Davide,Dore, Timothy M.
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p. 5589 - 5594
(2021/07/02)
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- Nitrile Oxide Cycloaddition of Non-activated Alkynes: A Novel Approach to the Synthesis of Neuroactive Isoxazoles
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A general method for the unprecedented 1,3-dipolar cycloaddition of bromonitrile oxide to distributed non-activated alkynes provides a useful alternative route to the neuropharmacological tools AMPA and 4-methylhomoibotenic acid.
- Pevarello, Paolo,Amici, Raffaella,Colombo, Maristella,Varasi, Mario
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p. 2151 - 2152
(2007/10/02)
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- Equilibrium control in bromomethylation: An expedient route to 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid (AMPA)
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The excitatory amino acid 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid (AMPA) has been prepared in gram quantities in 42% total yield by a three-step procedure from 3-hydroxy-5-methylisoxazole. It is shown how bromomethylation may be optimized through control of the involved equilibria and how N-protecting methoxymethyl groups can be removed.
- Begtrup,Slok
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p. 861 - 863
(2007/10/02)
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