MNI-caged-L-glutamate

Pricing Availability Delivery Time Qty
Cat.No. 1490 - MNI-caged-L-glutamate | C14H17N3O6 | CAS No. 295325-62-1
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% (HPLC)
Datasheet
Citations (41)
Literature

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

M. Wt 323.3
Formula C14H17N3O6
Storage Store at -20°C
Purity ≥98% (HPLC)
CAS Number 295325-62-1
PubChem ID 6604871
InChI Key GXIDBZKXGUNITQ-VIFPVBQESA-N
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.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
phosphate buffered saline 16.16 50
ethanol 32.33 100
water 16.16 50mM with gentle warming

Preparing Stock Solutions

The following data is based on the product molecular weight 323.3. Batch specific molecular weights may vary from batch to batch due to solvent 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
1 mM 3.09 mL 15.47 mL 30.93 mL
5 mM 0.62 mL 3.09 mL 6.19 mL
10 mM 0.31 mL 1.55 mL 3.09 mL
50 mM 0.06 mL 0.31 mL 0.62 mL

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

Product Datasheets

Certificate of Analysis / Product Datasheet
Select another batch:
Safety Datasheet

References

References are publications that support the products' biological activity.

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 PMID:

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


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

Keywords: 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 MNI glutamate Miscellaneous Glutamate

41 Citations for MNI-caged-L-glutamate

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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


Do you know of a great paper that uses MNI-caged-L-glutamate from Tocris? If so please let us know.

Commented out for usability testing

Reviews

TODO: Add Reviews

Literature in this Area

Pain

Pain Research Product Guide

A collection of over 250 products for pain research, the guide includes research tools for the study of:

  • Nociception
  • Ion Channels
  • G-Protein-Coupled Receptors
  • Intracellular Signaling
Metabotropic Glutamate Receptors

Metabotropic Glutamate Receptors Scientific Review

Written by Francine Acher, this review discusses the pharmacology and therapeutic potential of mGlu receptors, and the compounds acting upon them; compounds available from Tocris are listed.

Depression

Depression Poster

Major depressive disorder is characterized by depressed mood and a loss of interest and/or pleasure. Updated in 2015 this poster highlights presynaptic and postsynaptic targets for the potential treatment of major depressive disorder, as well as outlining the pharmacology of currently approved antidepressant drugs.

Learning & Memory

Learning & Memory Poster

Recognition memory enables us to make judgements about whether or not we have encountered a particular stimulus before. This poster outlines the cellular mechanisms underlying recognition memory and its links to long-term depression, as well as the use of pharmacological intervention to assess the role of neurotransmitters in recognition memory.

Parkinson's

Parkinson's Poster

Parkinson's disease (PD) causes chronic disability and is the second most common neurodegenerative condition. This poster outlines the neurobiology of the disease, as well as highlighting current therapeutic treatments for symptomatic PD, and emerging therapeutic strategies to delay PD onset and progression.

Pathways for MNI-caged-L-glutamate

Protocols

TODO: Add Protocols