808350

Sigma-Aldrich

TokeOni

Synonym(s):
Soluble NIR emission luciferin, 2-[(1E,3E)-4-[4-(Dimethylamino)phenyl]-1,3-butadien-1-yl]-4,5-dihydro-(4S)-4-thiazolecarboxylic acid hydrochloride salt, AkaLumine-HCl
Empirical Formula (Hill Notation):
C16H19ClN2O2S · xHCl
Molecular Weight:
338.85 (free base basis)
PubChem Substance ID:
NACRES:
NA.23

form

powder

Quality Level

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

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.

Packaging

5, 25 mg in poly bottle

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

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)
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)
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Articles
Overall results suggest that seMpai is a suitable substrate of near-infrared BLI for many biological experiments. Its high solubility in neutral buffer conditions further extends the bioluminescent application of TokeOni derivatives.
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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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