DNI-Glutamate

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DNI-Glutamate
DNI-Glutamate.png
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
3D model (JSmol)
ChemSpider
  • 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
  • COC1=C(C=C(C2=C1CCN2C(=O)CC[C@@H](C(=O)O)N)[N+](=O)[O-])[N+](=O)[O-]
Properties
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).
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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- (lexc = 360 nm) as well as two-photon irradiation (lexc = 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[edit]

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[edit]

  1. ^ 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 and 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.{{cite journal}}: CS1 maint: uses authors parameter (link)
  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.