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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% (HPLC)
Citations (61)
Literature (4)

Biological Activity for MNI-caged-L-glutamate

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.

Licensing Information

Sold under license from the Medical Research Council

Technical Data for MNI-caged-L-glutamate

M. Wt 323.3
Formula C14H17N3O6
Storage Store at -20°C
Purity ≥99% (HPLC)
CAS Number 295325-62-1
PubChem ID 6604871
Smiles O=C(CC[C@H](N)C(O)=O)N2C1=C([N+]([O-])=O)C=CC(OC)=C1CC2

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.

Solubility Data for MNI-caged-L-glutamate

Solvent Max Conc. mg/mL Max Conc. mM
water 16.16 50

Preparing Stock Solutions for MNI-caged-L-glutamate

The following data is based on the product molecular weight 323.3. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
0.5 mM 6.19 mL 30.93 mL 61.86 mL
2.5 mM 1.24 mL 6.19 mL 12.37 mL
5 mM 0.62 mL 3.09 mL 6.19 mL
25 mM 0.12 mL 0.62 mL 1.24 mL

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Product Datasheets for MNI-caged-L-glutamate

Certificate of Analysis / Product Datasheet
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References for MNI-caged-L-glutamate

References are publications that support the biological activity of the product.

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

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

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

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

Ellis-Davies (2019) Two-Photon Uncaging of Glutamate Front Synaptic Neurosci. 10 48 PMID: 30687075

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

Keywords: MNI-caged-L-glutamate, MNI-caged-L-glutamate supplier, Stable, photoreleaser, L-glutamate, Caged, Compounds, Glutamate, mGlur, Receptors, Metabotropic, Non-Selective, iGlur, Ionotropic, agonists, MNI, glutamate, MNI-Glutamate, 4-Methoxy-7-nitroindolinyl-caged-L-glutamate, Miscellaneous, Non-selective, mGlu, 1490, Tocris Bioscience

61 Citations for MNI-caged-L-glutamate

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

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

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

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

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

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

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

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

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

Lu et al (2017) Slow AMPAR Synaptic Transmission Is Determined by Stargazin and Glutamate Transporters. Neuron 96 73 PMID: 28919175

Chang et al (2017) CaMKII Autophosphorylation Is Necessary for Optimal Integration of Ca2+ Signals during LTP Induction, but Not Maintenance. Neuron 94 800 PMID: 28521133

Goo et al (2017) Activity-dependent trafficking of lysosomes in dendrites and dendritic spines. J Cell Biol 216 2499 PMID: 28630145

Athilingam et al (2017) Serotonin enhances excitability and gamma frequency temporal integration in mouse prefrontal fast-spiking interneurons. Elife 6 PMID: 29206101

Sigler et al (2017) Formation and Maintenance of Functional Spines in the Absence of Presynaptic Glutamate Release. Neuron 94 304 PMID: 28426965

Otopalik et al (2017) When complex neuronal structures may not matter. Elife 6 PMID: 28165322

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

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

Xiao et al (2018) OXT functions as a spatiotemporal filter for excitatory synaptic inputs to VTA DA neurons. Elife 7 PMID: 29676731

Chopek et al (2018) Sub-populations of Spinal V3 Interneurons Form Focal Modules of Layered Pre-motor Microcircuits. Cell Rep 25 146 PMID: 30282024

Hangen et al (2018) Neuronal Activity and Intracellular Calcium Levels Regulate Intracellular Transport of Newly Synthesized AMPAR. Cell Rep 24 1001 PMID: 30044968

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

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

Otopalik et al (2019) Neuronal morphologies built for reliable physiology in a rhythmic motor circuit. Elife 8 PMID: 30657452

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

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

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

Nuno-Perez (2021) Stress undermines reward-guided cognitive performance through synaptic depression in the lateral habenula Neuron 109 947 PMID: 33535028

Wu et al (2021) Ketamine Rapidly Enhances Glutamate-Evoked Dendritic Spinogenesis in Medial Prefrontal Cortex Through Dopaminergic Mechanisms Biol.Psychiatry 89 1096 PMID: 33637303

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

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

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

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

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

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

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

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

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

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

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

Kiragasi et al (2017) A Presynaptic Glutamate Receptor Subunit Confers Robustness to Neurotransmission and Homeostatic Potentiation. Cell Rep 19 2694 PMID: 28658618

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

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

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

Obashi et al (2019) Precise Temporal Regulation of Molecular Diffusion within Dendritic Spines by Actin Polymers during Structural Plasticity. Cell Rep 27 1503 PMID: 31042476

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

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

Mitchell et al (2019) Probing Single Synapses via the Photolytic Release of Neurotransmitters Front Synaptic Neurosci 11 PMID: 31354469

Tazerart et al (2019) Spike-timing-dependent plasticity rule for single, clustered and distributed dendritic spines. Nat Commun 11 4276 PMID: 32848151

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

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

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

Incontro (2018) The CaMKII/NMDA receptor complex controls hippocampal synaptic transmission by kinase-dependent and independent mechanisms. Nat Commun 9 2069 PMID: 29802289

Cheriyan and Sheets (2018) Altered Excitability and Local Connectivity of mPFC-PAG Neurons in a Mouse Model of Neuropathic Pain. J Neurosci 38 4829 PMID: 29695413

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

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

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

Berlin et al (2016) A family of photoswitchable NMDA receptors. Elife 5 PMID: 26929991

Oberlander (2016) 17β-OEAcutely Potentiates Glutamatergic Synaptic Transmission in the Hippocampus through Distinct Mechanisms in Males and Females. J Neurosci 36 2677 PMID: 26937008

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