MNI-caged-L-glutamate

Catalog # Availability Size / Price Qty
1490/10
1490/50
Glutamate Receptor Compounds Small Molecule
1 Image
Description: Stable photoreleaser of L-glutamate
Alternative 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

Purity: ≥98%

Product Details
Citations (56)
Reviews (1)

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.
Tocris products are intended for laboratory research use only, unless stated otherwise.

Additional Information

Licensing Caveats:
Sold under license from the Medical Research Council
Other Product-Specific Information:

Background References

  1. 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
  2. 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
  3. Comparative analysis of inhibitory effects of caged ligands for the NMDA receptor.
    Maier et al.
    J.Neurosci.Methods, 2005;142:1
  4. Dendritic spine geometry is critical for AMPA receptor expression in hippocampal CA1 pyramidal neurons.
    Matsuzaki et al.
    Nat.Neurosci., 2001;4:1086
  5. Effects of aromatic substitutions on the photocleavage of 1-acyl-7-nitroindolines.
    Papageorgiou and Corrie
    Tetrahedron, 2000;56:8197

Product Datasheets

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Citations for MNI-caged-L-glutamate

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

56 Citations: Showing 1 - 10

  1. Neuronal morphologies built for reliable physiology in a rhythmic motor circuit.
    Authors: Otopalik Et al.
    Elife  2019;8
  2. Precise Temporal Regulation of Molecular Diffusion within Dendritic Spines by Actin Polymers during Structural Plasticity.
    Authors: Obashi Et al.
    Cell Rep  2019;27:1503
  3. The CaMKII/NMDA receptor complex controls hippocampal synaptic transmission by kinase-dependent and independent mechanisms.
    Authors: Incontro
    Nat Commun  2018;9:2069
  4. OXT functions as a spatiotemporal filter for excitatory synaptic inputs to VTA DA neurons.
    Authors: Xiao Et al.
    Elife  2018;7
  5. Sub-populations of Spinal V3 Interneurons Form Focal Modules of Layered Pre-motor Microcircuits.
    Authors: Chopek Et al.
    Cell Rep  2018;25:146
  6. Neuronal Activity and Intracellular Calcium Levels Regulate Intracellular Transport of Newly Synthesized AMPAR.
    Authors: Hangen Et al.
    Cell Rep  2018;24:1001
  7. Slow AMPAR Synaptic Transmission Is Determined by Stargazin and Glutamate Transporters.
    Authors: Lu Et al.
    Neuron  2017;96:73
  8. CaMKII Autophosphorylation Is Necessary for Optimal Integration of Ca2+ Signals during LTP Induction, but Not Maintenance.
    Authors: Chang Et al.
    Neuron  2017;94:800
  9. Formation and Maintenance of Functional Spines in the Absence of Presynaptic Glutamate Release.
    Authors: Sigler Et al.
    Neuron  2017;94:304
  10. Serotonin enhances excitability and gamma frequency temporal integration in mouse prefrontal fast-spiking interneurons.
    Authors: Athilingam Et al.
    Elife  2017;6
  11. When complex neuronal structures may not matter.
    Authors: Otopalik Et al.
    Elife  2017;6
  12. Activity-dependent trafficking of lysosomes in dendrites and dendritic spines.
    Authors: Goo Et al.
    J Cell Biol  2017;216:2499
  13. A Presynaptic Glutamate Receptor Subunit Confers Robustness to Neurotransmission and Homeostatic Potentiation.
    Authors: Kiragasi Et al.
    Cell Rep  2017;19:2694
  14. Stereotyped initiation of retinal waves by bipolar cells via presynaptic NMDA autoreceptors.
    Authors: Zhang Et al.
    Nat.Commun.  2016;7:12650
  15. A family of photoswitchable NMDA receptors.
    Authors: Berlin Et al.
    Elife  2016;5
  16. 17β-OEAcutely Potentiates Glutamatergic Synaptic Transmission in the Hippocampus through Distinct Mechanisms in Males and Females.
    Authors: Oberlander
    J Neurosci  2016;36:2677
  17. The Shaping of Two Distinct Dendritic Spikes by A-Type Voltage-Gated K(+) Channels.
    Authors: Yang Et al.
    J Neurosci  2015;9:469
  18. 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
  19. Optical control of NMDA receptors with a diffusible photoswitch.
    Authors: Laprell Et al.
    PLoS One  2015;6:8076
  20. Distribution and function of HCN channels in the apical dendritic tuft of neocortical pyramidal neurons.
    Authors: Harnett Et al.
    PLoS One  2015;35:1024
  21. Melanoma brain colonization involves the emergence of a brain-adaptive phenotype.
    Authors: Nygaard Et al.
    J Neurosci  2015;1:82
  22. 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
  23. 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
  24. Spatially reciprocal inhibition of inhibition within a stimulus selection network in the avian midbrain.
    Authors: Goddard Et al.
    PLoS One  2014;9:e85865
  25. Input integration around the dendritic branches in hippocampal dentate granule cells.
    Authors: Kamijo Et al.
    Cogn Neurodyn  2014;8:267
  26. Adult neurogenesis modifies excitability of the dentate gyrus.
    Authors: Ikrar Et al.
    Front Neural Circuits  2014;7:204
  27. Plasticity of binocularity and visual acuity are differentially limited by nogo receptor.
    Authors: Stephany Et al.
    J Neurosci  2014;34:11631
  28. Directional summation in non-direction selective retinal ganglion cells.
    Authors: Abbas Et al.
    PLoS Comput Biol  2013;9:e1002969
  29. Four-dimensional multi-site photolysis of caged neurotransmitters.
    Authors: Go Et al.
    Front Cell Neurosci  2013;7:231
  30. Rapid, activity-independent turnover of vesicular transmitter content at a mixed glycine/GABA synapse.
    Authors: Apostolides and Trussell
    J Neurosci  2013;33:4768
  31. 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
  32. Intrinsic connections in the anterior part of the bed nucleus of the stria terminalis.
    Authors: Turesson Et al.
    J Neurophysiol  2013;109:2438
  33. 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
  34. Mechanism of inhibition of the glutamate transporter EAAC1 by the conformationally constrained glutamate analogue (+)-HIP-B.
    Authors: Callender Et al.
    Biochemistry  2012;51:5486
  35. Alteration of synaptic network dynamics by the intellectual disability protein PAK3.
    Authors: Dubos Et al.
    J Neurosci  2012;32:519
  36. 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
  37. Neural circuit mechanisms for pattern detection and feature combination in olfactory cortex.
    Authors: Davison and Ehlers
    Neuron  2011;70:82
  38. Oligodendrocytes as regulators of neuronal networks during early postnatal development.
    Authors: Doretto Et al.
    PLoS One  2011;6:e19849
  39. Water and urea permeation pathways of the human excitatory amino acid transporter EAAT1.
    Authors: Vandenberg Et al.
    Biochem J  2011;439:333
  40. NMDA receptor signaling in oligodendrocyte progenitors is not required for oligodendrogenesis and myelination.
    Authors: Biase Et al.
    Oncoscience  2011;31:12650
  41. Hetero-oligomerization of neuronal glutamate transporters.
    Authors: Nothmann Et al.
    J Neurosci  2011;286:3935
  42. 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
  43. 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
  44. 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
  45. 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
  46. SLM Microscopy: Scanless Two-Photon Imaging and Photostimulation with Spatial Light Modulators.
    Authors: Nikolenko Et al.
    Front Neural Circuits  2009;2:5
  47. Robust short-latency perisomatic inhibition onto neocortical pyramidal cells detected by laser-scanning photostimulation.
    Authors: Brill and Huguenard
    J Neurosci  2009;29:7413
  48. 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
  49. 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
  50. Sequential changes in AMPA receptor targeting in the developing neocortical excitatory circuit.
    Authors: Brill and Huguenard
    J Reprod Dev  2008;28:13918
  51. 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
  52. 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
  53. 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
  54. Dendritic spines linearize the summation of excitatory potentials.
    Authors: Araya Et al.
    Proc Natl Acad Sci U S A  2006;103:18799
  55. The spine neck filters membrane potentials.
    Authors: Araya Et al.
    J Neurosci  2006;103:17961
  56. Astrocyte glutamate transporters regulate metabotropic glutamate receptor-mediated excitation of hippocampal interneurons.
    Authors: Huang Et al.
    J Neurosci  2004;24:4551

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Glutamate uncaging on dendritic spines
By Anonymous on 10/20/2017
Species: Rat

We buy this product in bulk for use in all of our uncaging experiments. High frequency uncaging next to dendritic spine head induces reliable spine growth, indicative of synapse strengthening.

We 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.

PMID: 23303946

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