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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)
UNSPSC Code:
12352103
PubChem Substance ID:
329769097
NACRES:
NA.23

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

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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.
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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

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