Catalog Number: 1490
Alternate Names: 4-Methoxy-7-nitroindolinyl-caged-L-glutamate, MNI glutamate
Chemical Name: (S)-α-Amino-2,3-dihydro-4-methoxy-7-nitro-δ-oxo-1H-indole-1-pentanoic acid
Biological Activity
MNI-caged glutamate that rapidly and efficiently releases glutamate (Cat. No. 0218) when photolysed (300 - 380 nm excitation). Water-soluble, highly resistant to hydrolysis, stable at neutral pH, and pharmacologically inactive at neuronal glutamate receptors (up to mM concentrations). 2.5-fold more efficient at releasing L-glutamate than NI-caged L-glutamate.

View more information regarding MNI-caged-L-glutamate.

Technical Data
  • M.Wt:
    323.3
  • Formula:
    C14H17N3O6
  • Solubility:
    Soluble to 50 mM in water with gentle warming
  • Purity:
    >98%
  • Storage:
    Store at -20°C
  • CAS No:
    295325-62-1
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis. All Tocris products are intended for laboratory research use only.
Additional Information
Licensing Caveats:
Sold under license from the Medical Research Council
Other Product-Specific Information:
Background References
  1. Photochemical and pharmacological evaluation of 7-nitroindolinyl- and 4-methoxy-7-nitroindolinyl-amino acids as novel, fast caged neurotransmitters.
    Canepari et al.
    J.Neurosci.Methods, 2001;112:29
  2. Dendritic spine geometry is critical for AMPA receptor expression in hippocampal CA1 pyramidal neurons.
    Matsuzaki et al.
    Nat.Neurosci., 2001;4:1086
  3. New caged neurotransmitter analogs selective for glutamate receptor sub-types based on methoxynitroindoline and nitrophenylethoxycarbonyl caging groups.
    Palma-Cerda et al.
    Neuropharmacology., 2012;63:624
  4. Comparative analysis of inhibitory effects of caged ligands for the NMDA receptor.
    Maier et al.
    J.Neurosci.Methods, 2005;142:1
  5. Effects of aromatic substitutions on the photocleavage of 1-acyl-7-nitroindolines.
    Papageorgiou and Corrie
    Tetrahedron, 2000;56:8197
Citations:

The citations listed below are publications that use Tocris products. Selected citations for MNI-caged-L-glutamate include:

41 Citations: Showing 1 - 10
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  1. Stereotyped initiation of retinal waves by bipolar cells via presynaptic NMDA autoreceptors.
    Authors: Zhang Et al.
    Nat.Commun. 2016;7:12650
  2. The Shaping of Two Distinct Dendritic Spikes by A-Type Voltage-Gated K(+) Channels.
    Authors: Yang Et al.
    J Neurosci 2015;9:469
  3. Highly differentiated cellular and circuit properties of infralimbic pyramidal neurons projecting to the periaqueductal gray and amygdala.
    Authors: Ferreira Et al.
    Nat Commun 2015;9:161
  4. Optical control of NMDA receptors with a diffusible photoswitch.
    Authors: Laprell Et al.
    PLoS One 2015;6:8076
  5. Distribution and function of HCN channels in the apical dendritic tuft of neocortical pyramidal neurons.
    Authors: Harnett Et al.
    PLoS One 2015;35:1024
  6. Melanoma brain colonization involves the emergence of a brain-adaptive phenotype.
    Authors: Nygaard Et al.
    J Neurosci 2015;1:82
  7. The Functional Organization of Neocortical Networks Investigated in Slices with Local Field Recordings and Laser Scanning Photostimulation.
    Authors: Erlandson Et al.
    Front Cell Neurosci 2015;10:e0132008
  8. Fast Decay of CaMKII FRET Sensor Signal in Spines after LTP Induction Is Not Due to Its Dephosphorylation.
    Authors: Otmakhov Et al.
    Front Cell Neurosci 2015;10:e0130457
  9. Spatially reciprocal inhibition of inhibition within a stimulus selection network in the avian midbrain.
    Authors: Goddard Et al.
    PLoS One 2014;9:e85865
  10. Input integration around the dendritic branches in hippocampal dentate granule cells.
    Authors: Kamijo Et al.
    Cogn Neurodyn 2014;8:267
  11. Adult neurogenesis modifies excitability of the dentate gyrus.
    Authors: Ikrar Et al.
    Front Neural Circuits 2014;7:204
  12. Plasticity of binocularity and visual acuity are differentially limited by nogo receptor.
    Authors: Stephany Et al.
    J Neurosci 2014;34:11631
  13. Directional summation in non-direction selective retinal ganglion cells.
    Authors: Abbas Et al.
    PLoS Comput Biol 2013;9:e1002969
  14. Four-dimensional multi-site photolysis of caged neurotransmitters.
    Authors: Go Et al.
    Front Cell Neurosci 2013;7:231
  15. Rapid, activity-independent turnover of vesicular transmitter content at a mixed glycine/GABA synapse.
    Authors: Apostolides and Trussell
    J Neurosci 2013;33:4768
  16. Molecular layer perforant path-associated cells contribute to feed-forward inhibition in the adult dentate gyrus.
    Authors: Li Et al.
    Proc Natl Acad Sci U S A 2013;110:9106
  17. Intrinsic connections in the anterior part of the bed nucleus of the stria terminalis.
    Authors: Turesson Et al.
    J Neurophysiol 2013;109:2438
  18. Withdrawal from cocaine self-administration alters NMDA receptor-mediated Ca2+ entry in nucleus accumbens dendritic spines.
    Authors: Ferrario Et al.
    PLoS One 2012;7:e40898
  19. Mechanism of inhibition of the glutamate transporter EAAC1 by the conformationally constrained glutamate analogue (+)-HIP-B.
    Authors: Callender Et al.
    Biochemistry 2012;51:5486
  20. Alteration of synaptic network dynamics by the intellectual disability protein PAK3.
    Authors: Dubos Et al.
    J Neurosci 2012;32:519
  21. Increased excitatory synaptic input to granule cells from hilar and CA3 regions in a rat model of temporal lobe epilepsy.
    Authors: Zhang Et al.
    J Neurosci 2012;32:1183
  22. Neural circuit mechanisms for pattern detection and feature combination in olfactory cortex.
    Authors: Davison and Ehlers
    Neuron 2011;70:82
  23. Oligodendrocytes as regulators of neuronal networks during early postnatal development.
    Authors: Doretto Et al.
    PLoS One 2011;6:e19849
  24. Water and urea permeation pathways of the human excitatory amino acid transporter EAAT1.
    Authors: Vandenberg Et al.
    Biochem J 2011;439:333
  25. NMDA receptor signaling in oligodendrocyte progenitors is not required for oligodendrogenesis and myelination.
    Authors: Biase Et al.
    Oncoscience 2011;31:12650
  26. Hetero-oligomerization of neuronal glutamate transporters.
    Authors: Nothmann Et al.
    J Neurosci 2011;286:3935
  27. Dysregulation of presynaptic calcium and synaptic plasticity in a mouse model of 22q11 deletion syndrome.
    Authors: Earls Et al.
    J Biol Chem 2010;30:15843
  28. Mechanism of cation binding to the glutamate transporter EAAC1 probed with mutation of the conserved amino acid residue Thr101.
    Authors: Tao Et al.
    J Biol Chem 2010;285:17725
  29. Discovery of a Novel Chemical Class of mGlu(5) Allosteric Ligands with Distinct Modes of Pharmacology.
    Authors: Hammond Et al.
    ACS Chem Neurosci 2010;1:702
  30. High precision and fast functional mapping of cortical circuitry through a novel combination of voltage sensitive dye imaging and laser scanning photostimulation.
    Authors: Xu Et al.
    J Neurophysiol 2010;103:2301
  31. SLM Microscopy: Scanless Two-Photon Imaging and Photostimulation with Spatial Light Modulators.
    Authors: Nikolenko Et al.
    Front Neural Circuits 2009;2:5
  32. Robust short-latency perisomatic inhibition onto neocortical pyramidal cells detected by laser-scanning photostimulation.
    Authors: Brill and Huguenard
    J Neurosci 2009;29:7413
  33. Synaptic circuit abnormalities of motor-frontal layer 2/3 pyramidal neurons in an RNA interference model of methyl-CpG-binding protein 2 deficiency.
    Authors: Wood Et al.
    Proc Natl Acad Sci U S A 2009;29:12440
  34. Differential distribution of endoplasmic reticulum controls metabotropic signaling and plasticity at hippocampal synapses.
    Authors: Holbro Et al.
    Proc Natl Acad Sci U S A 2009;106:15055
  35. Sequential changes in AMPA receptor targeting in the developing neocortical excitatory circuit.
    Authors: Brill and Huguenard
    J Reprod Dev 2008;28:13918
  36. Natural oligomers of the Alzheimer amyloid-beta protein induce reversible synapse loss by modulating an NMDA-type glutamate receptor-dependent signaling pathway.
    Authors: Shankar Et al.
    J Neurosci 2007;27:2866
  37. Neutralization of the aspartic acid residue Asp-367, but not Asp-454, inhibits binding of Na+ to the glutamate-free form and cycling of the glutamate transporter EAAC1.
    Authors: Tao Et al.
    J Biol Chem 2006;281:10263
  38. Blockade of mGluR1 receptor results in analgesia and disruption of motor and cognitive performances: effects of A-841720, a novel non-competitive mGluR1 receptor antagonist.
    Authors: El-Kouhen Et al.
    Br J Pharmacol 2006;149:761
  39. Dendritic spines linearize the summation of excitatory potentials.
    Authors: Araya Et al.
    Proc Natl Acad Sci U S A 2006;103:18799
  40. The spine neck filters membrane potentials.
    Authors: Araya Et al.
    J Neurosci 2006;103:17961
  41. Astrocyte glutamate transporters regulate metabotropic glutamate receptor-mediated excitation of hippocampal interneurons.
    Authors: Huang Et al.
    J Neurosci 2004;24:4551
Expand to show all 41 Citations
Average Rating: 5 (Based on 1 review)

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 Glutamate uncaging on dendritic spines 1490
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 Glutamate uncaging on dendritic spines 1490
: Glutamate uncaging on dendritic spines [1490]

Other Experimental Details

Other Experimental DetailsWe resuspend in ACSF and found that we can freeze and reuse the solution. However, when suspended in HBSS it is no longer effective after freezing.

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