Cat. No. 1490

MNI-caged-L-glutamate C14H17N3O6 [295325-62-1]

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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

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.

Licensing Information

Sold under license from the Medical Research Council

Technical Data

Soluble to 50 mM in water with gentle warming
>98 %
Store at -20°C

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.

Certificate of Analysis / Product Datasheet / Safety Datasheet

Certificate of Analysis / Product Datasheet
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References are publications that support the products' biological activity.

Palma-Cerda et al (2012) New caged neurotransmitter analogs selective for glutamate receptor sub-types based on methoxynitroindoline and nitrophenylethoxycarbonyl caging groups. Neuropharmacology. 63 624. PMID: 22609535.

Maier et al (2005) Comparative analysis of inhibitory effects of caged ligands for the NMDA receptor. J.Neurosci.Methods 142 1. PMID: 15652611.

Canepari et al (2001) Photochemical and pharmacological evaluation of 7-nitroindolinyl- and 4-methoxy-7-nitroindolinyl-amino acids as novel, fast caged neurotransmitters. J.Neurosci.Methods 112 29. PMID: 11640955.

Matsuzaki et al (2001) Dendritic spine geometry is critical for AMPA receptor expression in hippocampal CA1 pyramidal neurons. Nat.Neurosci. 4 1086. PMID: 11687814.

Papageorgiou and Corrie (2000) Effects of aromatic substitutions on the photocleavage of 1-acyl-7-nitroindolines. Tetrahedron 56 8197.

If you know of a relevant reference for MNI-caged-L-glutamate please let us know.

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

Zhang et al (2016) Stereotyped initiation of retinal waves by bipolar cells via presynaptic NMDA autoreceptors. Nat.Commun. 7 12650. PMID: 27586999.

Erlandson et al (2015) The Functional Organization of Neocortical Networks Investigated in Slices with Local Field Recordings and Laser Scanning Photostimulation. Front Cell Neurosci 10 e0132008. PMID: 26134668.

Ferreira et al (2015) Highly differentiated cellular and circuit properties of infralimbic pyramidal neurons projecting to the periaqueductal gray and amygdala. Nat Commun 9 161. PMID: 25972785.

Harnett et al (2015) Distribution and function of HCN channels in the apical dendritic tuft of neocortical pyramidal neurons. PLoS One 35 1024. PMID: 25609619.

Laprell et al (2015) Optical control of NMDA receptors with a diffusible photoswitch. PLoS One 6 8076. PMID: 26311290.

Nygaard et al (2015) Melanoma brain colonization involves the emergence of a brain-adaptive phenotype. J Neurosci 1 82. PMID: 25593989.

Otmakhov et al (2015) Fast Decay of CaMKII FRET Sensor Signal in Spines after LTP Induction Is Not Due to Its Dephosphorylation. Front Cell Neurosci 10 e0130457. PMID: 26086939.

Yang et al (2015) The Shaping of Two Distinct Dendritic Spikes by A-Type Voltage-Gated K(+) Channels. J Neurosci 9 469. PMID: 26696828.

Goddard et al (2014) Spatially reciprocal inhibition of inhibition within a stimulus selection network in the avian midbrain. PLoS One 9 e85865. PMID: 24465755.

Ikrar et al (2014) Adult neurogenesis modifies excitability of the dentate gyrus. Front Neural Circuits 7 204. PMID: 24421758.

Kamijo et al (2014) Input integration around the dendritic branches in hippocampal dentate granule cells. Cogn Neurodyn 8 267. PMID: 25009669.

Stephany et al (2014) Plasticity of binocularity and visual acuity are differentially limited by nogo receptor. J Neurosci 34 11631. PMID: 25164659.

Abbas et al (2013) Directional summation in non-direction selective retinal ganglion cells. PLoS Comput Biol 9 e1002969. PMID: 23516351.

Apostolides and Trussell (2013) Rapid, activity-independent turnover of vesicular transmitter content at a mixed glycine/GABA synapse. J Neurosci 33 4768. PMID: 23486948.

Go et al (2013) Four-dimensional multi-site photolysis of caged neurotransmitters. Front Cell Neurosci 7 231. PMID: 24348330.

Li et al (2013) Molecular layer perforant path-associated cells contribute to feed-forward inhibition in the adult dentate gyrus. Proc Natl Acad Sci U S A 110 9106. PMID: 23671081.

Turesson et al (2013) Intrinsic connections in the anterior part of the bed nucleus of the stria terminalis. J Neurophysiol 109 2438. PMID: 23446692.

Callender et al (2012) Mechanism of inhibition of the glutamate transporter EAAC1 by the conformationally constrained glutamate analogue (+)-HIP-B. Biochemistry 51 5486. PMID: 22703277.

Dubos et al (2012) Alteration of synaptic network dynamics by the intellectual disability protein PAK3. J Neurosci 32 519. PMID: 22238087.

Ferrario et al (2012) Withdrawal from cocaine self-administration alters NMDA receptor-mediated Ca2+ entry in nucleus accumbens dendritic spines. PLoS One 7 e40898. PMID: 22870207.

Zhang et al (2012) Increased excitatory synaptic input to granule cells from hilar and CA3 regions in a rat model of temporal lobe epilepsy. J Neurosci 32 1183. PMID: 22279204.

Biase et al (2011) NMDA receptor signaling in oligodendrocyte progenitors is not required for oligodendrogenesis and myelination. Oncoscience 31 12650. PMID: 21880926.

Davison and Ehlers (2011) Neural circuit mechanisms for pattern detection and feature combination in olfactory cortex. Neuron 70 82. PMID: 21482358.

Doretto et al (2011) Oligodendrocytes as regulators of neuronal networks during early postnatal development. PLoS One 6 e19849. PMID: 21589880.

Nothmann et al (2011) Hetero-oligomerization of neuronal glutamate transporters. J Neurosci 286 3935. PMID: 21127051.

Vandenberg et al (2011) Water and urea permeation pathways of the human excitatory amino acid transporter EAAT1. Biochem J 439 333. PMID: 21732909.

Earls et al (2010) Dysregulation of presynaptic calcium and synaptic plasticity in a mouse model of 22q11 deletion syndrome. J Biol Chem 30 15843. PMID: 21106823.

Hammond et al (2010) Discovery of a Novel Chemical Class of mGlu(5) Allosteric Ligands with Distinct Modes of Pharmacology. ACS Chem Neurosci 1 702. PMID: 20981342.

Tao et al (2010) Mechanism of cation binding to the glutamate transporter EAAC1 probed with mutation of the conserved amino acid residue Thr101. J Biol Chem 285 17725. PMID: 20378543.

Xu et al (2010) High precision and fast functional mapping of cortical circuitry through a novel combination of voltage sensitive dye imaging and laser scanning photostimulation. J Neurophysiol 103 2301. PMID: 20130040.

Brill and Huguenard (2009) Robust short-latency perisomatic inhibition onto neocortical pyramidal cells detected by laser-scanning photostimulation. J Neurosci 29 7413. PMID: 19515909.

Holbro et al (2009) Differential distribution of endoplasmic reticulum controls metabotropic signaling and plasticity at hippocampal synapses. Proc Natl Acad Sci U S A 106 15055. PMID: 19706463.

Nikolenko et al (2009) SLM Microscopy: Scanless Two-Photon Imaging and Photostimulation with Spatial Light Modulators. Front Neural Circuits 2 5. PMID: 19129923.

Wood et al (2009) Synaptic circuit abnormalities of motor-frontal layer 2/3 pyramidal neurons in an RNA interference model of methyl-CpG-binding protein 2 deficiency. Proc Natl Acad Sci U S A 29 12440. PMID: 19812320.

Brill and Huguenard (2008) Sequential changes in AMPA receptor targeting in the developing neocortical excitatory circuit. J Reprod Dev 28 13918. PMID: 19091980.

Shankar et al (2007) Natural oligomers of the Alzheimer amyloid-beta protein induce reversible synapse loss by modulating an NMDA-type glutamate receptor-dependent signaling pathway. J Neurosci 27 2866. PMID: 17360908.

Araya et al (2006) Dendritic spines linearize the summation of excitatory potentials. Proc Natl Acad Sci U S A 103 18799. PMID: 17132736.

Araya et al (2006) The spine neck filters membrane potentials. J Neurosci 103 17961. PMID: 17093040.

El-Kouhen et al (2006) 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. Br J Pharmacol 149 761. PMID: 17016515.

Tao et al (2006) 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. J Biol Chem 281 10263. PMID: 16478724.

Huang et al (2004) Astrocyte glutamate transporters regulate metabotropic glutamate receptor-mediated excitation of hippocampal interneurons. J Neurosci 24 4551. PMID: 15140926.

Do you know of a great paper that uses MNI-caged-L-glutamate from Tocris? If so please let us all ▼show less ▲

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