Synonym
D-Luciferin Sodium
IUPAC/Chemical Name
sodium (S)-2-(6-hydroxybenzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylate
InChi Key
LILQLBIQROYWIA-OGFXRTJISA-M
InChi Code
InChI=1S/C11H8N2O3S2.Na/c14-5-1-2-6-8(3-5)18-10(12-6)9-13-7(4-17-9)11(15)16;/h1-3,7,14H,4H2,(H,15,16);/q;+1/p-1/t7-;/m1./s1
SMILES Code
O=C([C@@H]1N=C(C2=NC3=CC=C(O)C=C3S2)SC1)[O-].[Na+]
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
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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
Biological target:
D-Luciferin (D-(-)-Luciferin) sodium is the substrate of luciferases that catalyze the production of light in bioluminescent insects.
In vitro activity:
This study describes a rapid and highly sensitive functional assay of OAT1 based on bioluminescence (BL) detection using D-luciferin as a substrate in living cells. The principle of measurement simply relies on the biochemical feature of D-luciferin to be recognized as a substrate of OAT1, and the BL intensity depending on intracellular D-luciferin level and luciferase activity, thereby allowing the quantitative analysis of OAT1-mediated D-luciferin transport. The present method is applicable to high-throughput screening to identify and avoid potential OAT1 inhibitors in drug development.
Reference: Methods Mol Biol. 2022;2524:119-126. https://pubmed.ncbi.nlm.nih.gov/35821467/
In vivo activity:
Bioluminescence signals were strongly observed from the region containing the mouse liver when using d-luciferin and TokeOni.
Reference: J Biochem. 2022 Oct 19;172(5):321-327. https://pubmed.ncbi.nlm.nih.gov/36047849/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
16.7 |
55.24 |
| DMSO |
45.1 |
149.05 |
| Ethanol |
0.3 |
0.83 |
| PBS (pH 7.2) |
10.0 |
0.33 |
| Water |
140.1 |
463.50 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
302.30
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 |
Formulation protocol:
1. Inoue K, Sugiyama K, Furuya T. A Simple and Rapid Bioluminescence-Based Functional Assay of Organic Anion Transporter 1 as a D-Luciferin Transporter. Methods Mol Biol. 2022;2524:119-126. doi: 10.1007/978-1-0716-2453-1_9. PMID: 35821467.
2. Niwa K, Kato DI. Biosynthesis-Inspired Deracemizative Production of D-Luciferin In Vitro by Combining Luciferase and Thioesterase. Methods Mol Biol. 2022;2524:53-58. doi: 10.1007/978-1-0716-2453-1_4. PMID: 35821462.
3. Fukuchi M, Mitazaki S, Saito-Moriya R, Kitada N, Maki SA, Izumi H, Mori H. Bioluminescence imaging using d-luciferin and its analogs for visualizing Bdnf expression in living mice; different patterns of bioluminescence signals using distinct luciferase substrates. J Biochem. 2022 Oct 19;172(5):321-327. doi: 10.1093/jb/mvac070. PMID: 36047849.
4. Inoue Y, Kiryu S, Watanabe M, Tojo A, Ohtomo K. Timing of imaging after d-luciferin injection affects the longitudinal assessment of tumor growth using in vivo bioluminescence imaging. Int J Biomed Imaging. 2010;2010:471408. doi: 10.1155/2010/471408. Epub 2010 Jul 5. PMID: 20671955; PMCID: PMC2910476.
In vitro protocol:
1. Inoue K, Sugiyama K, Furuya T. A Simple and Rapid Bioluminescence-Based Functional Assay of Organic Anion Transporter 1 as a D-Luciferin Transporter. Methods Mol Biol. 2022;2524:119-126. doi: 10.1007/978-1-0716-2453-1_9. PMID: 35821467.
2. Niwa K, Kato DI. Biosynthesis-Inspired Deracemizative Production of D-Luciferin In Vitro by Combining Luciferase and Thioesterase. Methods Mol Biol. 2022;2524:53-58. doi: 10.1007/978-1-0716-2453-1_4. PMID: 35821462.
In vivo protocol:
1. Fukuchi M, Mitazaki S, Saito-Moriya R, Kitada N, Maki SA, Izumi H, Mori H. Bioluminescence imaging using d-luciferin and its analogs for visualizing Bdnf expression in living mice; different patterns of bioluminescence signals using distinct luciferase substrates. J Biochem. 2022 Oct 19;172(5):321-327. doi: 10.1093/jb/mvac070. PMID: 36047849.
2. Inoue Y, Kiryu S, Watanabe M, Tojo A, Ohtomo K. Timing of imaging after d-luciferin injection affects the longitudinal assessment of tumor growth using in vivo bioluminescence imaging. Int J Biomed Imaging. 2010;2010:471408. doi: 10.1155/2010/471408. Epub 2010 Jul 5. PMID: 20671955; PMCID: PMC2910476.
1: Patrick PS, Lyons SK, Rodrigues TB, Brindle KM. Oatp1 enhances bioluminescence by acting as a plasma membrane transporter for D-luciferin. Mol Imaging Biol. 2014 Oct;16(5):626-34. doi: 10.1007/s11307-014-0741-4. PubMed PMID: 24798747; PubMed Central PMCID: PMC4161938.
2: Presiado I, Erez Y, Huppert D. Excited-state intermolecular proton transfer of firefly luciferin III. Proton transfer to a mild base. J Phys Chem A. 2010 Dec 30;114(51):13337-46. doi: 10.1021/jp107360d. Epub 2010 Dec 3. PubMed PMID: 21128619.
3: Schoellhammer CM, Lauwers GY, Goettel JA, Oberli MA, Cleveland C, Park JY, Minahan D, Chen Y, Anderson DG, Jaklenec A, Snapper SB, Langer R, Traverso G. Ultrasound-Mediated Delivery of RNA to Colonic Mucosa of Live Mice. Gastroenterology. 2017 Apr;152(5):1151-1160. doi: 10.1053/j.gastro.2017.01.002. Epub 2017 Jan 11. PubMed PMID: 28088460; PubMed Central PMCID: PMC5368009.
4: Ghosh M, Gambhir SS, De A, Nowels K, Goris M, Wapnir I. Bioluminescent monitoring of NIS-mediated (131)I ablative effects in MCF-7 xenografts. Mol Imaging. 2006 Apr-Jun;5(2):76-84. PubMed PMID: 16954021; PubMed Central PMCID: PMC4160082.
