D-Luciferin

• CAT Number: I006506
• CAS Number: 2591-17-5
• Molecular Formula: C11H8N2O3S2
• Molecular Weight: 280.32
• Purity: ≥95%
• Solubility: Soluble in DMSO, not in water
• Storage: -20°C
• IUPAC Name: (4S)-2-(6-hydroxy-1,3-benzothiazol-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid
• InChI: 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
• InChIKey: BJGNCJDXODQBOB-SSDOTTSWSA-N
• SMILES: C1C(N=C(S1)C2=NC3=C(S2)C=C(C=C3)O)C(=O)O

D-Luciferin（Cat No.:I006506）, commonly known as Firefly Luciferin, is a luminescent compound found in firefly species. It serves as the substrate for the enzyme luciferase (EC 1.13.12.7), which is responsible for the emission of yellow light in fireflies. Light emission requires the presence of oxygen, as well as adenosine triphosphate (ATP) and magnesium. These co-factors are essential for the chemical reaction that produces light. D-Luciferin and luciferase are widely used in bioluminescence imaging and other research applications for their ability to generate visible light in a controlled manner.

Reference

1:Biosynthesis-inspired deracemizative production of d-luciferin by combining luciferase and thioesterase. Maeda J, Kato DI, Okuda M, Takeo M, Negoro S, Arima K, Ito Y, Niwa K.Biochim Biophys Acta. 2017 Apr 25. pii: S0304-4165(17)30135-6. doi: 10.1016/j.bbagen.2017.04.010. [Epub ahead of print] PMID: 28454735 2:Label-Free Cell Phenotypic Identification of D-Luciferin as an Agonist for GPR35. Hu H, Deng H, Fang Y.Methods Mol Biol. 2016;1461:3-17. doi: 10.1007/978-1-4939-3813-1_1. PMID: 27424891 3:Intracellular Self-Assembly of Cyclic d-Luciferin Nanoparticles for Persistent Bioluminescence Imaging of Fatty Acid Amide Hydrolase. Yuan Y, Wang F, Tang W, Ding Z, Wang L, Liang L, Zheng Z, Zhang H, Liang G.ACS Nano. 2016 Jul 26;10(7):7147-53. doi: 10.1021/acsnano.6b03412. Epub 2016 Jun 29. PMID: 27348334 4:Hydrazide d-luciferin for in vitro selective detection and intratumoral imaging of Cu(2.). Zheng Z, Wang L, Tang W, Chen P, Zhu H, Yuan Y, Li G, Zhang H, Liang G.Biosens Bioelectron. 2016 Sep 15;83:200-4. doi: 10.1016/j.bios.2016.04.067. Epub 2016 Apr 22. PMID: 27131992 5:The Drug Excipient Cyclodextrin Interacts With d-Luciferin and Interferes With Bioluminescence Imaging. Kumar JS, Miller Jenkins LM, Gottesman MM, Hall MD.Mol Imaging. 2016 Jan 27;15. pii: 1536012115625225. doi: 10.1177/1536012115625225. Print 2016. PMID: 27030398 Free PMC Article6:[Theoretical investigation on the structure and vibration spectrum of D-luciferin]. Zhu YQ, Zhang L, Guo JC.Guang Pu Xue Yu Guang Pu Fen Xi. 2014 Sep;34(9):2453-9. Chinese. PMID: 25532344 7:Excited-state proton transfer dynamics of firefly/’s chromophore D-luciferin in DMSO-water binary mixture. Kuchlyan J, Banik D, Roy A, Kundu N, Sarkar N.J Phys Chem B. 2014 Dec 4;118(48):13946-53. doi: 10.1021/jp510389d. Epub 2014 Nov 21. PMID: 25415652 8:Aminoluciferins extend firefly luciferase bioluminescence into the near-infrared and can be preferred substrates over D-luciferin. Mofford DM, Reddy GR, Miller SC.J Am Chem Soc. 2014 Sep 24;136(38):13277-82. doi: 10.1021/ja505795s. Epub 2014 Sep 11. PMID: 25208457 Free PMC Article9:Beyond D-luciferin: expanding the scope of bioluminescence imaging in vivo. Adams ST Jr, Miller SC.Curr Opin Chem Biol. 2014 Aug;21:112-20. doi: 10.1016/j.cbpa.2014.07.003. Epub 2014 Aug 1. Review. PMID: 25078002 Free PMC Article10: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. Viviani VR, Neves DR, Amaral DT, Prado RA, Matsuhashi T, Hirano T.Biochemistry. 2014 Aug 19;53(32):5208-20. doi: 10.1021/bi500160m. Epub 2014 Aug 4. PMID: 25025160