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MNI-caged-L-glutamate | CAS No. 295325-62-1 | Glutamate Receptor Compounds
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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: ≥99%

Product Details
Citations (61)
Reviews (1)

Biological Activity

MNI-caged-L-glutamate is a form of glutamate linked to a photo-protecting group, 4-methoxy-7-nitroindolinyl (MNI); it rapidly and efficiently releases L-glutamate (Cat. No. 0218) by photolysis (300 - 380 nm excitation) with a quantum yield in the 0.065-0.085 range. It is also suitable for use with two-photon uncaging microscopy (cross-section of 0.06 GM at 730 nm). MNI-caged-L-glutamate is optically compatible with other chromophores used for fluorescence imaging, such as GFP, YFP and most Ca2+ dyes. MNI-caged-L-glutamate is 2.5-fold more efficient at releasing L-glutamate than NI-caged L-glutamate. MNI-caged-L-glutamate is water-soluble, stable at neutral pH, highly resistant to hydrolysis and pharmacologically inactive at neuronal glutamate receptors and transporters (up to mM concentrations). MNI-caged-L-glutamate can be used for in situ studies of fast synaptic glutamate receptors.

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

Technical Data

Soluble to 50 mM in water
Store at -20°C

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

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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:

61 Citations: Showing 1 - 10

  1. Ketamine Rapidly Enhances Glutamate-Evoked Dendritic Spinogenesis in Medial Prefrontal Cortex Through Dopaminergic Mechanisms
    Authors: Wu Et al.
    Biol.Psychiatry  2021;89:1096
  2. Stress undermines reward-guided cognitive performance through synaptic depression in the lateral habenula
    Authors: Nuno-Perez
    Neuron  2021;109:947
  3. Neuronal morphologies built for reliable physiology in a rhythmic motor circuit.
    Authors: Otopalik Et al.
    Elife  2019;8
  4. Precise Temporal Regulation of Molecular Diffusion within Dendritic Spines by Actin Polymers during Structural Plasticity.
    Authors: Obashi Et al.
    Cell Rep  2019;27:1503
  5. Spike-timing-dependent plasticity rule for single, clustered and distributed dendritic spines.
    Authors: Tazerart Et al.
    Nat Commun  2019;11:4276
  6. Probing Single Synapses via the Photolytic Release of Neurotransmitters
    Authors: Mitchell Et al.
    Front Synaptic Neurosci  2019;11
  7. The CaMKII/NMDA receptor complex controls hippocampal synaptic transmission by kinase-dependent and independent mechanisms.
    Authors: Incontro
    Nat Commun  2018;9:2069
  8. OXT functions as a spatiotemporal filter for excitatory synaptic inputs to VTA DA neurons.
    Authors: Xiao Et al.
    Elife  2018;7
  9. Altered Excitability and Local Connectivity of mPFC-PAG Neurons in a Mouse Model of Neuropathic Pain.
    Authors: Cheriyan and Sheets
    J Neurosci  2018;38:4829
  10. Sub-populations of Spinal V3 Interneurons Form Focal Modules of Layered Pre-motor Microcircuits.
    Authors: Chopek Et al.
    Cell Rep  2018;25:146
  11. Neuronal Activity and Intracellular Calcium Levels Regulate Intracellular Transport of Newly Synthesized AMPAR.
    Authors: Hangen Et al.
    Cell Rep  2018;24:1001
  12. Slow AMPAR Synaptic Transmission Is Determined by Stargazin and Glutamate Transporters.
    Authors: Lu Et al.
    Neuron  2017;96:73
  13. CaMKII Autophosphorylation Is Necessary for Optimal Integration of Ca2+ Signals during LTP Induction, but Not Maintenance.
    Authors: Chang Et al.
    Neuron  2017;94:800
  14. Formation and Maintenance of Functional Spines in the Absence of Presynaptic Glutamate Release.
    Authors: Sigler Et al.
    Neuron  2017;94:304
  15. When complex neuronal structures may not matter.
    Authors: Otopalik Et al.
    Elife  2017;6
  16. Serotonin enhances excitability and gamma frequency temporal integration in mouse prefrontal fast-spiking interneurons.
    Authors: Athilingam Et al.
    Elife  2017;6
  17. Activity-dependent trafficking of lysosomes in dendrites and dendritic spines.
    Authors: Goo Et al.
    J Cell Biol  2017;216:2499
  18. A Presynaptic Glutamate Receptor Subunit Confers Robustness to Neurotransmission and Homeostatic Potentiation.
    Authors: Kiragasi Et al.
    Cell Rep  2017;19:2694
  19. Stereotyped initiation of retinal waves by bipolar cells via presynaptic NMDA autoreceptors.
    Authors: Zhang Et al.
    Nat.Commun.  2016;7:12650
  20. A family of photoswitchable NMDA receptors.
    Authors: Berlin Et al.
    Elife  2016;5
  21. 17β-OEAcutely Potentiates Glutamatergic Synaptic Transmission in the Hippocampus through Distinct Mechanisms in Males and Females.
    Authors: Oberlander
    J Neurosci  2016;36:2677
  22. The Shaping of Two Distinct Dendritic Spikes by A-Type Voltage-Gated K(+) Channels.
    Authors: Yang Et al.
    J Neurosci  2015;9:469
  23. 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
  24. Optical control of NMDA receptors with a diffusible photoswitch.
    Authors: Laprell Et al.
    PLoS One  2015;6:8076
  25. Distribution and function of HCN channels in the apical dendritic tuft of neocortical pyramidal neurons.
    Authors: Harnett Et al.
    PLoS One  2015;35:1024
  26. Melanoma brain colonization involves the emergence of a brain-adaptive phenotype.
    Authors: Nygaard Et al.
    J Neurosci  2015;1:82
  27. 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
  28. 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
  29. Spatially reciprocal inhibition of inhibition within a stimulus selection network in the avian midbrain.
    Authors: Goddard Et al.
    PLoS One  2014;9:e85865
  30. Input integration around the dendritic branches in hippocampal dentate granule cells.
    Authors: Kamijo Et al.
    Cogn Neurodyn  2014;8:267
  31. Adult neurogenesis modifies excitability of the dentate gyrus.
    Authors: Ikrar Et al.
    Front Neural Circuits  2014;7:204
  32. Plasticity of binocularity and visual acuity are differentially limited by nogo receptor.
    Authors: Stephany Et al.
    J Neurosci  2014;34:11631
  33. Directional summation in non-direction selective retinal ganglion cells.
    Authors: Abbas Et al.
    PLoS Comput Biol  2013;9:e1002969
  34. Four-dimensional multi-site photolysis of caged neurotransmitters.
    Authors: Go Et al.
    Front Cell Neurosci  2013;7:231
  35. Rapid, activity-independent turnover of vesicular transmitter content at a mixed glycine/GABA synapse.
    Authors: Apostolides and Trussell
    J Neurosci  2013;33:4768
  36. 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
  37. Intrinsic connections in the anterior part of the bed nucleus of the stria terminalis.
    Authors: Turesson Et al.
    J Neurophysiol  2013;109:2438
  38. 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
  39. Mechanism of inhibition of the glutamate transporter EAAC1 by the conformationally constrained glutamate analogue (+)-HIP-B.
    Authors: Callender Et al.
    Biochemistry  2012;51:5486
  40. Alteration of synaptic network dynamics by the intellectual disability protein PAK3.
    Authors: Dubos Et al.
    J Neurosci  2012;32:519
  41. 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
  42. Neural circuit mechanisms for pattern detection and feature combination in olfactory cortex.
    Authors: Davison and Ehlers
    Neuron  2011;70:82
  43. Oligodendrocytes as regulators of neuronal networks during early postnatal development.
    Authors: Doretto Et al.
    PLoS One  2011;6:e19849
  44. Water and urea permeation pathways of the human excitatory amino acid transporter EAAT1.
    Authors: Vandenberg Et al.
    Biochem J  2011;439:333
  45. NMDA receptor signaling in oligodendrocyte progenitors is not required for oligodendrogenesis and myelination.
    Authors: Biase Et al.
    Oncoscience  2011;31:12650
  46. Hetero-oligomerization of neuronal glutamate transporters.
    Authors: Nothmann Et al.
    J Neurosci  2011;286:3935
  47. 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
  48. 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
  49. 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
  50. 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
  51. SLM Microscopy: Scanless Two-Photon Imaging and Photostimulation with Spatial Light Modulators.
    Authors: Nikolenko Et al.
    Front Neural Circuits  2009;2:5
  52. Robust short-latency perisomatic inhibition onto neocortical pyramidal cells detected by laser-scanning photostimulation.
    Authors: Brill and Huguenard
    J Neurosci  2009;29:7413
  53. 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
  54. 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
  55. Sequential changes in AMPA receptor targeting in the developing neocortical excitatory circuit.
    Authors: Brill and Huguenard
    J Reprod Dev  2008;28:13918
  56. 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
  57. 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
  58. 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
  59. Dendritic spines linearize the summation of excitatory potentials.
    Authors: Araya Et al.
    Proc Natl Acad Sci U S A  2006;103:18799
  60. The spine neck filters membrane potentials.
    Authors: Araya Et al.
    J Neurosci  2006;103:17961
  61. 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

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.

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