Synonym
Infraluciferin; Infra-luciferin; Infra luciferin; iLH2; iLH 2; iLH-2;
IUPAC/Chemical Name
(S,E)-2-(2-(6-hydroxybenzo[d]thiazol-2-yl)vinyl)-4,5-dihydrothiazole-4-carboxylic acid
InChi Key
NYOZDHLDCWALEQ-CDAZIORVSA-N
InChi Code
InChI=1S/C13H10N2O3S2/c16-7-1-2-8-10(5-7)20-12(14-8)4-3-11-15-9(6-19-11)13(17)18/h1-5,9,16H,6H2,(H,17,18)/b4-3+/t9-/m1/s1
SMILES Code
O=C([C@@H]1N=C(/C=C/C2=NC3=CC=C(O)C=C3S2)SC1)O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
306.35
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Stowe CL, Burley TA, Allan H, Vinci M, Kramer-Marek G, Ciobota DM, Parkinson GN, Southworth TL, Agliardi G, Hotblack A, Lythgoe MF, Branchini BR, Kalber TL, Anderson JC, Pule MA. Near-infrared dual bioluminescence imaging in mouse models of cancer using infraluciferin. Elife. 2019 Oct 15;8:e45801. doi: 10.7554/eLife.45801. PMID: 31610848; PMCID: PMC6828332.
2: Halliwell LM, Jathoul AP, Bate JP, Worthy HL, Anderson JC, Jones DD, Murray JAH. ΔFlucs: Brighter Photinus pyralis firefly luciferases identified by surveying consecutive single amino acid deletion mutations in a thermostable variant. Biotechnol Bioeng. 2018 Jan;115(1):50-59. doi: 10.1002/bit.26451. Epub 2017 Oct 23. PMID: 28921549.
3: Woodhouse JL, Assmann M, Parkes MA, Grounds H, Pacman SJ, Anderson JC, Worth GA, Fielding HH. Photoelectron spectroscopy of isolated luciferin and infraluciferin anions in vacuo: competing photodetachment, photofragmentation and internal conversion. Phys Chem Chem Phys. 2017 Aug 30;19(34):22711-22720. doi: 10.1039/c7cp04815g. PMID: 28820195.
4: Anderson JC, Grounds H, Jathoul AP, Murray JAH, Pacman SJ, Tisi L. Convergent synthesis and optical properties of near-infrared emitting bioluminescent infra- luciferins. RSC Adv. 2017 Jan 16;7(7):3975-3982. doi: 10.1039/c6ra19541e. PMID: 28496975; PMCID: PMC5361108.
