DNI-Glutamate

DNI-Glutamate
Names
	IUPAC name 2-amino-5-(4-methoxy-5,7-dinitroindolin-1-yl)-5-oxopentanoic acid
	Other names DNI-Glu; Dinitroindoline-glutamate; DMNI-Glu
Identifiers
CAS Number	864085-92-7;
3D model (JSmol)	Interactive image;
ChemSpider	29321113;
PubChem CID	124221751;
CompTox Dashboard (EPA)	DTXSID401336452 ;
	InChI InChI=1S/C14H16N4O8/c1-26-13-7-4-5-16(11(19)3-2-8(15)14(20)21)12(7)9(17(22)23)6-10(13)18(24)25/h6,8H,2-5,15H2,1H3,(H,20,21)/t8-/m0/s1 Key: SYNWQVVPBORTQE-QMMMGPOBSA-N;
	SMILES COC1=C(C=C(C2=C1CCN2C(=O)CC[C@@H](C(=O)O)N)[N+](=O)[O-])[N+](=O)[O-];
Properties
Chemical formula	C14H16N4O8
Molar mass	368.302 g·mol−1
Appearance	White crystals
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

DNI-Glutamate ((S)-α-Amino-2,3-dihydro-4-methoxy-5,7-dinitro-δ-oxo-1H-indole-1-pentanoic acid) is a caged form of the glutamate neurotransmitter, which is photocleavable by one- (l_exc = 360 nm) as well as two-photon irradiation (l_exc = 720 nm). Upon photocleaveage, the bioactive glutamate is released instantly and behaves as a neurotransmitter, which provides information about receptor distribution, channel kinetics and network circuitry of the neuronal network.^[1] DNI-Glu is an analogue of the common MNI-Glu compound, but it exhibits cca. 7-10 times larger efficiency in terms of quantum yields compared to the MNI compound. DNI-Glu has low biotoxicity and high water-solubility as well (at physiologic pH).^[1] Due to these properties, currently DNI-Glu is thought to be the most advanced caged-glutamate compound for neuroscientific research.

Discovery

DNI-Glu, the molecule itself was first discovered by George Papageorgiou in 2005,^[2] but its practical implementation was not mentioned in his publications. Later, in 2009, the compound was reinvestigated in neurophysiological studies and its high efficacy and beneficial properties were reported. The product is commercially available as a trifluoroacetate salt of the compound which was proved to be much more stable and less hygroscopic.^[1]

References

^ ^a ^b ^c Dénes Pálfi; Balázs Chiovini; Gergely Szalay; Attila Kaszás; Gergely F. Turi; Gergely Katona; Péter Ábrányi-Balogh; Milán Szőri; Attila Potor; Orsolya Frigyesi; Csilla Lukácsné Haveland; Zoltán Szadai; Miklós Madarász; Anikó Vasanits-Zsigrai; Ibolya Molnár-Perl; Béla Viskolcz; Imre G. Csizmadia; Zoltán Mucsi; Balázs Rózsa (2018). "High efficiency two-photon uncaging coupled by the correction of spontaneous hydrolysis". Org. Biomol. Chem. 16 (11): 1958–1970. doi:10.1039/C8OB00025E. PMID 29497727.
^ Papageorgiou, George (2005). "Synthetic and photochemical studies of substituted 1-acyl-7-nitroindolines". Photochem. Photobiol. Sci. 4 (11): 887–896. doi:10.1039/b508756b. PMID 16252044.

[:0-1] Dénes Pálfi; Balázs Chiovini; Gergely Szalay; Attila Kaszás; Gergely F. Turi; Gergely Katona; Péter Ábrányi-Balogh; Milán Szőri; Attila Potor; Orsolya Frigyesi; Csilla Lukácsné Haveland; Zoltán Szadai; Miklós Madarász; Anikó Vasanits-Zsigrai; Ibolya Molnár-Perl; Béla Viskolcz; Imre G. Csizmadia; Zoltán Mucsi; Balázs Rózsa (2018). "High efficiency two-photon uncaging coupled by the correction of spontaneous hydrolysis". Org. Biomol. Chem. 16 (11): 1958–1970. doi:10.1039/C8OB00025E. PMID 29497727.

[2] Papageorgiou, George (2005). "Synthetic and photochemical studies of substituted 1-acyl-7-nitroindolines". Photochem. Photobiol. Sci. 4 (11): 887–896. doi:10.1039/b508756b. PMID 16252044.

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