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MilliporeSigma

808350

Sigma-Aldrich

TokeOni

Synonym(s):

2-[(1E,3E)-4-[4-(Dimethylamino)phenyl]-1,3-butadien-1-yl]-4,5-dihydro-(4S)-4-thiazolecarboxylic acid hydrochloride salt, AkaLumine-HCl, Soluble NIR emission luciferin

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About This Item

Empirical Formula (Hill Notation):
C16H19ClN2O2S · xHCl
Molecular Weight:
338.85 (free base basis)
MDL number:
MFCD29917507
UNSPSC Code:
12352103
PubChem Substance ID:
329769097
NACRES:
NA.23

Key Documents

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form

powder

Quality Level

100

storage temp.

−20°C

SMILES string

CN(C)C1=CC=C(/C=C/C=C/C2=N[C@@H](C(O)=O)CS2)C=C1.[H]Cl

InChI

1S/C16H18N2O2S.ClH/c1-18(2)13-9-7-12(8-10-13)5-3-4-6-15-17-14(11-21-15)16(19)20;/h3-10,14H,11H2,1-2H3,(H,19,20);1H/b5-3+,6-4+;/t14-;/m1./s1

InChI key

PZCNKVAGZCXXHX-SSRSOBHISA-N

Related Categories

General description

  • Luciferin is a generic term for the light-emitting compound found in organisms that generate bioluminescence.
  • TokeOni is a new NIR emission luciferin analogue having luminescence peak at 670 ~ 680 nm with a peak range in the near-infrared (NIR) region.
  • TokeOni has the enhanced solubility of >10 mg/mL compared to HCl free (0.2 mg/mL).

Application

  • Bioimaging.
  • in vivo imaging.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ4657
MKCQ4660
MKCP6720
MKCN1137
MKCN1136

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Synthesis and luminescence properties of biphenyl-type firefly luciferin analogs with a new, near-infrared light-emitting bioluminophore.
Chihiro M, et al.
Tetrahedron, 69(46), 9726-9734 (2013)
Development of simple firefly luciferin analogs emitting blue, green, red and near-infrared biological window light.
Satoshi I, et al.
Tetrahedron, 69(19), 3847-3856 (2013)
Gi Bum Kim et al.
Cell, 179(1), 251-267 (2019-09-21)
In situ transgenesis methods such as viruses and electroporation can rapidly create somatic transgenic mice but lack control over copy number, zygosity, and locus specificity. Here we establish mosaic analysis by dual recombinase-mediated cassette exchange (MADR), which permits stable labeling

Articles

TokeOni Analog - seMpai: Properties & Applications

seMpai substrate is suitable for near-infrared BLI in biological experiments, offering high solubility for extended bioluminescent applications.

Synthesis and Applications of Graphene Nanoribbons Synthesized

Graphene nanoribbons (GNRs) are quasi-one-dimensional narrow strips of graphene comprised of sp2-hybridized carbon atoms arranged into hexagonal honeycomb lattice configurations.

TokeOni: Properties and Applications

Bioluminescence imaging (BLI) systems allows for high-sensitive and noninvasive monitoring of cell proliferation, activity of signaling pathways and protein-protein interactions in living tissues.

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