D-Luciferin | Firefly Luciferin | CAS#2591-17-5

MedKoo Cat#: 326665 | Name: D-Luciferin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

D-Luciferin, also known as Firefly Luciferin, is a light-emitting compound, found in many firefly (Lampyridae) species. It is the substrate of luciferase (EC 1.13.12.7), which is responsible for the characteristic yellow light emission from many firefly species. As with all other luciferins, oxygen is required to elicit light; however, it has also been found that adenosine triphosphate (ATP) and magnesium are required for light emission.

Chemical Structure

D-Luciferin

CAS#2591-17-5 (free acid)

Theoretical Analysis

MedKoo Cat#: 326665

Name: D-Luciferin

CAS#: 2591-17-5 (free acid)

Chemical Formula: C11H8N2O3S2

Exact Mass: 279.9976

Molecular Weight: 280.32

Elemental Analysis: C, 47.13; H, 2.88; N, 9.99; O, 17.12; S, 22.87

Price and Availability

Size	Price	Availability
10mg	USD 150.00	2 Weeks
25mg	USD 250.00	2 Weeks
50mg	USD 450.00	2 Weeks
100mg	USD 650.00	2 Weeks
200mg	USD 950.00	2 Weeks
500mg	USD 1,750.00	2 Weeks
1g	USD 2,950.00	2 Weeks

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Related CAS #

2591-17-5 (free acid) 115144-35-9 (potassium) 103404-75-7 (sodium)

Synonym

D-Luciferin; Firefly Luciferin; Luciferin;

IUPAC/Chemical Name

(4S)-2-(6-hydroxy-1,3-benzothiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid

InChi Key

BJGNCJDXODQBOB-SSDOTTSWSA-N

InChi Code

InChI=1S/C11H8N2O3S2/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)/t7-/m1/s1

SMILES Code

O=C([C@@H]1N=C(C2=NC3=CC=C(O)C=C3S2)SC1)O

Appearance

Solid powder

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, not in water

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

More Info

Crystal luciferin was found to be fluorescent, absorbing ultraviolet light with a peak at 327 nm and emitting light with a peak at 530 nm. Alkaline solutions caused a redshift of the absorption likely due to deprotonation of the hydroxyl group on the benzothiazole, but did not affect the fluorescence emission. It was found that the luciferyl adenylate (the AMP ester of luciferin) spontaneously emits light in solution. Different species of fireflies all use the same luciferin, however the color of the light emitted can differ greatly. The light from Photuris pennsylvanica was measured to be 552 nm (green-yellow) while Pyrophorus plagiophthalamus was measured to emit light at 582 nm (orange) in the ventral organ. Such differences are likely due to pH changes or differences in primary structure of the luciferase.

Product Data

Product Data

Instruction

View handling instruction

Biological target:

D-Luciferin (D-(-)-Luciferin) 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	30.0	107.02
	DMSO	35.3	126.05

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 280.32 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:

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: Zheng Z, Wang L, Tang W, Chen P, Zhu H, Yuan Y, Li G, Zhang H, Liang G. Hydrazide d-luciferin for in vitro selective detection and intratumoral imaging of Cu(2.). Biosens Bioelectron. 2016 Sep 15;83:200-4. doi: 10.1016/j.bios.2016.04.067. Epub 2016 Apr 22. PubMed PMID: 27131992. 2: Kumar JS, Miller Jenkins LM, Gottesman MM, Hall MD. The Drug Excipient Cyclodextrin Interacts With d-Luciferin and Interferes With Bioluminescence Imaging. Mol Imaging. 2016 Jan 27;15. pii: 1536012115625225. doi: 10.1177/1536012115625225. Print 2016. PubMed PMID: 27030398. 3: Zhu YQ, Zhang L, Guo JC. [Theoretical investigation on the structure and vibration spectrum of D-luciferin]. Guang Pu Xue Yu Guang Pu Fen Xi. 2014 Sep;34(9):2453-9. Chinese. PubMed PMID: 25532344. 4: Kuchlyan J, Banik D, Roy A, Kundu N, Sarkar N. Excited-state proton transfer dynamics of firefly's chromophore D-luciferin in DMSO-water binary mixture. J Phys Chem B. 2014 Dec 4;118(48):13946-53. doi: 10.1021/jp510389d. Epub 2014 Nov 21. PubMed PMID: 25415652. 5: Mofford DM, Reddy GR, Miller SC. Aminoluciferins extend firefly luciferase bioluminescence into the near-infrared and can be preferred substrates over D-luciferin. J Am Chem Soc. 2014 Sep 24;136(38):13277-82. doi: 10.1021/ja505795s. Epub 2014 Sep 11. PubMed PMID: 25208457; PubMed Central PMCID: PMC4183640. 6: Adams ST Jr, Miller SC. Beyond D-luciferin: expanding the scope of bioluminescence imaging in vivo. Curr Opin Chem Biol. 2014 Aug;21:112-20. doi: 10.1016/j.cbpa.2014.07.003. Epub 2014 Aug 1. Review. PubMed PMID: 25078002; PubMed Central PMCID: PMC4149945. 7: Viviani VR, Neves DR, Amaral DT, Prado RA, Matsuhashi T, Hirano T. Bioluminescence of beetle luciferases with 6'-amino-D-luciferin analogues reveals excited keto-oxyluciferin as the emitter and phenolate/luciferin binding site interactions modulate bioluminescence colors. Biochemistry. 2014 Aug 19;53(32):5208-20. doi: 10.1021/bi500160m. Epub 2014 Aug 4. PubMed PMID: 25025160. 8: 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. 9: Kuchlyan J, Banik D, Kundu N, Ghosh S, Banerjee C, Sarkar N. Effect of confinement on excited-state proton transfer of firefly's chromophore D-luciferin in AOT reverse micelles. J Phys Chem B. 2014 Mar 27;118(12):3401-8. doi: 10.1021/jp500210n. Epub 2014 Mar 13. PubMed PMID: 24624892. 10: Khalil AA, Jameson MJ, Broaddus WC, Chung TD, Golding SE, Dever SM, Rosenberg E, Valerie K. Subcutaneous administration of D-luciferin is an effective alternative to intraperitoneal injection in bioluminescence imaging of xenograft tumors in nude mice. ISRN Mol Imaging. 2013;2013. pii: 689279. PubMed PMID: 25392739; PubMed Central PMCID: PMC4226276. 11: Zhang Y, Pullambhatla M, Laterra J, Pomper MG. Influence of bioluminescence imaging dynamics by D-luciferin uptake and efflux mechanisms. Mol Imaging. 2012 Nov-Dec;11(6):499-506. PubMed PMID: 23084250; PubMed Central PMCID: PMC4332814. 12: Sun YQ, Liu J, Wang P, Zhang J, Guo W. D-luciferin analogues: a multicolor toolbox for bioluminescence imaging. Angew Chem Int Ed Engl. 2012 Aug 20;51(34):8428-30. doi: 10.1002/anie.201203565. Epub 2012 Jul 13. Erratum in: Angew Chem Int Ed Engl. 2012 Oct 22;51(43):10697. PubMed PMID: 22807027. 13: Erez Y, Presiado I, Gepshtein R, Pinto da Silva L, Esteves da Silva JC, Huppert D. Comparative study of the photoprotolytic reactions of D-luciferin and oxyluciferin. J Phys Chem A. 2012 Jul 19;116(28):7452-61. doi: 10.1021/jp301910p. Epub 2012 Jul 6. PubMed PMID: 22697799. 14: Hu H, Deng H, Fang Y. Label-free phenotypic profiling identified D-luciferin as a GPR35 agonist. PLoS One. 2012;7(4):e34934. doi: 10.1371/journal.pone.0034934. Epub 2012 Apr 12. PubMed PMID: 22511974; PubMed Central PMCID: PMC3325260. 15: Conley NR, Dragulescu-Andrasi A, Rao J, Moerner WE. A selenium analogue of firefly D-luciferin with red-shifted bioluminescence emission. Angew Chem Int Ed Engl. 2012 Apr 2;51(14):3350-3. doi: 10.1002/anie.201105653. Epub 2012 Feb 17. PubMed PMID: 22344705; PubMed Central PMCID: PMC3494413. 16: Theodossiou TA, Sideratou Z, Tsiourvas D, Paleos CM. A novel mitotropic oligolysine nanocarrier: Targeted delivery of covalently bound D-Luciferin to cell mitochondria. Mitochondrion. 2011 Nov;11(6):982-6. doi: 10.1016/j.mito.2011.08.004. Epub 2011 Aug 11. PubMed PMID: 21856448. 17: Huang R, Vider J, Serganova I, Blasberg RG. ATP-binding cassette transporters modulate both coelenterazine- and D-luciferin-based bioluminescence imaging. Mol Imaging. 2011 Jun;10(3):215-26. PubMed PMID: 21496450; PubMed Central PMCID: PMC4052835. 18: Presiado I, Erez Y, Huppert D. Excited-state intermolecular proton transfer of the firefly's chromophore D-luciferin. 2. Water-methanol mixtures. J Phys Chem A. 2010 Sep 9;114(35):9471-9. doi: 10.1021/jp1059837. PubMed PMID: 20704300. 19: Erez Y, Huppert D. Excited-state intermolecular proton transfer of the firefly's chromophore D-luciferin. J Phys Chem A. 2010 Aug 12;114(31):8075-82. doi: 10.1021/jp103264y. PubMed PMID: 20684579. 20: 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. PubMed PMID: 20671955; PubMed Central PMCID: PMC2910476.