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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)
MDL number:
MFCD29917507
UNSPSC Code:
12352103
PubChem Substance ID:
329769097
NACRES:
NA.23
Pricing and availability is not currently available.

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

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF4957V
WXBF1494V
WXBF2794V
WXBD9469V
MKCR8975

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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)
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: 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.

TokeOni Analog - seMpai: Properties & Applications

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

TokeOni Analog - seMpai: Properties & Applications

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

TokeOni Analog - seMpai: Properties & Applications

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

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Questions

1–3 of 3 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

  3. Is the raw data for the Akalumine-HCl emission spectrum available to add into the Living Image software?

    Is the raw data for the Akalumine-HCl emission spectrum available to add into the Living Image software?

    1 answer

    1. Please refer to the spectrum available at https://www.sigmaaldrich.com/US/en/technical-documents/technical-article/research-and-disease-areas/cancer-research/tokeoni

      There are also a few articles that may be beneficial to review: https://pubchem.ncbi.nlm.nih.gov/compound/124203055 and https://pubmed.ncbi.nlm.nih.gov/34081790/

      Helpful?

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