MNI-caged-L-glutamate

Name: MNI-caged-L-glutamate
Brand: Tocris Bioscience
SKU: 1490
Rating: 5 (0 reviews)

Tocris Bioscience a Bio-Techne Brand

Catalog # 1490

Citations (61)

(1)

COA / SDS

Catalog #

Availability

Size / Price

Qty

Key Product Details

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)
Molecular Weight:	323.3

View Full Technical Details for MNI-caged-L-glutamate

Complete Your Research

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
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.

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

Solubility for MNI-caged-L-glutamate

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
Solubility	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

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.

Mass

Concentration

Volume

M. Wt*

g/mol

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

Dilution Calculator

Calculate the dilution required to prepare a stock solution.

Concentration 1 (C1)

Volume 1 (V1)

Concentration 2 (C2)

Volume 2 (V2)

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.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

References for MNI-caged-L-glutamate

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

Ellis-Davies Two-Photon Uncaging of Glutamate Front Synaptic Neurosci. 2019 PMID: 30687075
Palma-Cerda New caged neurotransmitter analogs selective for glutamate receptor sub-types based on methoxynitroindoline and nitrophenylethoxycarbonyl caging groups. Neuropharmacology. 2012 PMID: 22609535
Maier Comparative analysis of inhibitory effects of caged ligands for the NMDA receptor. J.Neurosci.Methods 2005 PMID: 15652611
Canepari Photochemical and pharmacological evaluation of 7-nitroindolinyl- and 4-methoxy-7-nitroindolinyl-amino acids as novel, fast caged neurotransmitters. J.Neurosci.Methods 2001 PMID: 11640955
Matsuzaki Dendritic spine geometry is critical for AMPA receptor expression in hippocampal CA1 pyramidal neurons. Nat.Neurosci. 2001 PMID: 11687814
Papageorgiou and Corrie Effects of aromatic substitutions on the photocleavage of 1-acyl-7-nitroindolines. Tetrahedron

Citations for MNI-caged-L-glutamate (61)

Showing 1 - 10 of 61 citations Showing All

Search Title:

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

Wu et al. (2021) Ketamine Rapidly Enhances Glutamate-Evoked Dendritic Spinogenesis in Medial Prefrontal Cortex Through Dopaminergic Mechanisms Biol.Psychiatry. 89:1096
PMID: 33637303
Nuno-Perez (2021) Stress undermines reward-guided cognitive performance through synaptic depression in the lateral habenula Neuron. 109:947
PMID: 33535028
Otopalik et al. (2019) Neuronal morphologies built for reliable physiology in a rhythmic motor circuit. Elife. 8
PMID: 30657452
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
Tazerart et al. (2019) Spike-timing-dependent plasticity rule for single, clustered and distributed dendritic spines. Nat Commun. 11:4276
PMID: 32848151
Mitchell et al. (2019) Probing Single Synapses via the Photolytic Release of Neurotransmitters Front Synaptic Neurosci. 11
PMID: 31354469
Incontro (2018) The CaMKII/NMDA receptor complex controls hippocampal synaptic transmission by kinase-dependent and independent mechanisms. Nat Commun. 9:2069
PMID: 29802289
Xiao et al. (2018) OXT functions as a spatiotemporal filter for excitatory synaptic inputs to VTA DA neurons. Elife. 7
PMID: 29676731
Hangen et al. (2018) Neuronal Activity and Intracellular Calcium Levels Regulate Intracellular Transport of Newly Synthesized AMPAR. Cell Rep. 24:1001
PMID: 30044968
Chopek et al. (2018) Sub-populations of Spinal V3 Interneurons Form Focal Modules of Layered Pre-motor Microcircuits. Cell Rep. 25:146
PMID: 30282024
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
Kiragasi et al. (2017) A Presynaptic Glutamate Receptor Subunit Confers Robustness to Neurotransmission and Homeostatic Potentiation. Cell Rep. 19:2694
PMID: 28658618
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
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
Lu et al. (2017) Slow AMPAR Synaptic Transmission Is Determined by Stargazin and Glutamate Transporters. Neuron. 96:73
PMID: 28919175
Zhang et al. (2016) Stereotyped initiation of retinal waves by bipolar cells via presynaptic NMDA autoreceptors. Nat.Commun.. 7:12650
PMID: 27586999
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
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
Go et al. (2013) Four-dimensional multi-site photolysis of caged neurotransmitters. Front Cell Neurosci. 7:231
PMID: 24348330
Turesson et al. (2013) Intrinsic connections in the anterior part of the bed nucleus of the stria terminalis. J Neurophysiol. 109:2438
PMID: 23446692
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
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
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
Dubos et al. (2012) Alteration of synaptic network dynamics by the intellectual disability protein PAK3. J Neurosci. 32:519
PMID: 22238087
Doretto et al. (2011) Oligodendrocytes as regulators of neuronal networks during early postnatal development. PLoS One. 6:e19849
PMID: 21589880
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
Biase et al. (2011) NMDA receptor signaling in oligodendrocyte progenitors is not required for oligodendrogenesis and myelination. Oncoscience. 31:12650
PMID: 21880926
Nothmann et al. (2011) Hetero-oligomerization of neuronal glutamate transporters. J Neurosci. 286:3935
PMID: 21127051
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
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
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
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
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

There are no citations that match your criteria.

Showing 1 - 10 of 61 citations Showing All

Customer Reviews for MNI-caged-L-glutamate (1)

5 out of 5

1 customer rating

5 stars

100%

4 stars

3 stars

2 stars

1 star

Customer Images

Showing 1 - 1 of 1 review Showing All

Filter By:

Glutamate uncaging on dendritic spines

Name: Anonymous

Assay Type: In Vitro

Cell Line/Tissue: Organotypic Hippocampus Slices

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.

There are no reviews that match your criteria.