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D-Luciferin

cell-permeable chemiluminescent luciferase substrate CAS# 2591-17-5

D-Luciferin

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Chemical structure

D-Luciferin

3D structure

Chemical Properties of D-Luciferin

Cas No. 2591-17-5 SDF Download SDF
PubChem ID 5459882 Appearance Powder
Formula C11H8N2O3S2 M.Wt 280.32
Type of Compound N/A Storage Desiccate at -20°C
Synonyms D-(-)-Luciferin; Firefly luciferin
Solubility >28mg/mL in DMSO
Chemical Name (2Z,4S)-2-(6-oxo-1,3-benzothiazol-2-ylidene)-1,3-thiazolidine-4-carboxylic acid
SMILES C1C(NC(=C2N=C3C=CC(=O)C=C3S2)S1)C(=O)O
Standard InChIKey IWJYWBVPCGUPLO-BFUDMSGGSA-N
Standard 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/h1-3,7,13H,4H2,(H,15,16)/b10-9-/t7-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of D-Luciferin

DescriptionD-luciferin is the natural substrate of luciferases that catalyze the production of light in bioluminescent insects.In Vitro:D-luciferin is the natural substrate of the enzyme luciferase (Luc), that catalyzes the production of the typical yellowgreen light of fireflies.The present review covers the synthesis of D-luciferin and derivatives or analogues that are substrates or inhibitors of the luciferase from the American firefly Photinus pyralis, the enzyme more frequently used in techniques of in vitro and optical imaging[1].In Vivo:Bioluminescence imaging (BLI) using the firefly luciferase (Fluc) as a reporter gene and D-luciferin as a substrate is currently the most widely employed technique. The total signal intensity is plotted against the time after D-luciferin injection to generate a time-intensity curve. In addition to the peak signal, the signals at fixed time points (5, 10, 15, and 20 min) after D-luciferin injection are determined as alternatives to the peak signal. The signal in a given time-intensity curve is normalized for the peak signal in the curve to represent the pattern of temporal changes after D-luciferin injection[2].

References:
[1]. Giuseppe Meroni, et al. D-Luciferin, derivatives and analogues: synthesis and in vitro/in vivo luciferase-catalyzed bioluminescent activity. ARKIVOC 2009 (i) 265-288. [2]. Inoue Y, et al. Timing of imaging after d-luciferin injection affects the longitudinal assessment of tumor growthusing in vivo bioluminescence imaging. Int J Biomed Imaging. 2010;2010:471408.

Protocol

Animal Administration [2]
Mice[2]In vivo BLI is performed using a cooled charge-coupled device camera system (IVIS Imaging System 100) 3, 5, 7, 10, 12, 14, 19, 21, 24, and 28 days after the inoculation of HCT116-Luc cells. Mice are injected with 75 mg/kg D-luciferin in 100 μL of phosphate-buffered saline subcutaneously near the scapula and were placed in the light-tight chamber of the imaging system under isoflurane anesthesia. Beginning 5 min after injection, dorsal luminescent images with an exposure time of 1 s are acquired sequentially at a rate of one image per min until 20 min after D-luciferin injection. Data acquisition is continued until 40 min postinjection on days 3 or 5 and until 25 min on day 7, because of the prolonged time course of light emission. Binning is 4 and the field of view is 15 cm.

References:
[1]. Giuseppe Meroni, et al. D-Luciferin, derivatives and analogues: synthesis and in vitro/in vivo luciferase-catalyzed bioluminescent activity. ARKIVOC 2009 (i) 265-288. [2]. Inoue Y, et al. Timing of imaging after d-luciferin injection affects the longitudinal assessment of tumor growthusing in vivo bioluminescence imaging. Int J Biomed Imaging. 2010;2010:471408.

D-Luciferin Dilution Calculator

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D-Luciferin Molarity Calculator

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Preparing Stock Solutions of D-Luciferin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.5674 mL 17.8368 mL 35.6735 mL 71.347 mL 89.1838 mL
5 mM 0.7135 mL 3.5674 mL 7.1347 mL 14.2694 mL 17.8368 mL
10 mM 0.3567 mL 1.7837 mL 3.5674 mL 7.1347 mL 8.9184 mL
50 mM 0.0713 mL 0.3567 mL 0.7135 mL 1.4269 mL 1.7837 mL
100 mM 0.0357 mL 0.1784 mL 0.3567 mL 0.7135 mL 0.8918 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on D-Luciferin

D-luciferin is a cell-permeable chemiluminescent luciferase substrate with a Km of approximately 2 μM. D-luciferin could emit lights upon oxidative decarboxylation in the presence of ATP. D-luciferin provides a bioluminescent signal for in vivo and in vitro detection of cellular ATP levels. D-Luciferin chould be used to assay the expression of the luciferase gene linked to a promoter of interest. Alternatively, D-luciferin and luciferase can be used to assess ATP availability in cellular or biochemical assays. D-luciferin could be administrated intravenously or intraperitonealy. In vivo and in vitro bioluminescence imaging (BLI) is a promising technique for non-invasive tumour imaging. The repeatability coefficients of intravenously and intraperitonealy was 80.2% and 95.0%, respectively. PEmax of IP was 5.6 times higher for IV. When compared with IP, IV administration showed better repeatability and better sensitivity. It would be more beneficial to evaluate the accurate tumor burden of the small tumors rather than the larger tumors [1].

Reference:
Keyaerts M, Verschueren J, Bos T J, et al.  Dynamic bioluminescence imaging for quantitative tumour burden assessment using IV or IP administration of D-luciferin: effect on intensity, time kinetics and repeatability of photon emission[J]. European journal of nuclear medicine and molecular imaging, 2008, 35(5): 999-1007.

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References on D-Luciferin

The Drug Excipient Cyclodextrin Interacts With d-Luciferin and Interferes With Bioluminescence Imaging.[Pubmed:27030398]

Mol Imaging. 2016 Jan 27;15. pii: 15/0/1536012115625225.

Cyclodextrins are well-characterized, barrel-shaped molecules that can solubilize organic small molecules in aqueous solution via host-guest interactions. As such, cyclodextrins are used as excipients for experimental therapeutics in vivo. We observed unanticipated modifications to bioluminescence imaging (BLI) signal intensity when 2-hydroxy-propyl-beta-cyclodextrin (HPCD) was coinjected as an excipient. We hypothesized that HPCD bindsD-Luciferin and interferes with the BLI signal. Using luciferase-expressing cell lines, we showed that HPCD lowers the BLI signal in a concentration-dependent manner. Flow cytometry revealed that HPCD resulted in reduced cellular accumulation ofD-Luciferin, and mass spectrometry revealedD-Luciferin HPCD species, confirming a direct interaction. In vivo imaging using a luciferase mouse model demonstrated that HPCD reduced luciferin-mediated BLI compared to luciferin alone. The implications of using HPCD as an excipient in BLI studies are discussed.

Hydrazide d-luciferin for in vitro selective detection and intratumoral imaging of Cu(2.).[Pubmed:27131992]

Biosens Bioelectron. 2016 Sep 15;83:200-4.

Copper is an essential micronutrient involved in fundamental life processes but using a bioluminescence (BL) probe to selectively sense Cu(2+)in vitro or image Cu(2+)in vivo is still unavailable. Herein, a latent BL probe hydrazide D-Luciferin (1) was rationally designed and successfully applied it for selective detection of Cu(2+)in vitro and imaging Cu(2+) in living cells and in tumors. Upon the catalysis of Cu(2+), 1 was converted to D-Luciferin and turned on the BL in the presence of firefly luciferase (fLuc). In vitro tests indicated that 1 could be applied for highly selective sensing Cu(2+) within the range of 0-80muM with a limit of detection (LOD) of 39.0nM. Cell and animal experiments indicated that 1 could be applied for specific BL imaging of Cu(2+) in living cells and tumors and the BL signal of 1 was more stable and longer than that of D-Luciferin. We envision that this unique probe 1 might serve as an elucidative tool for further exploration of the biological roles of Cu(2+) in physiological and pathological processes in the near future.

Intracellular Self-Assembly of Cyclic d-Luciferin Nanoparticles for Persistent Bioluminescence Imaging of Fatty Acid Amide Hydrolase.[Pubmed:27348334]

ACS Nano. 2016 Jul 26;10(7):7147-53.

Fatty acid amide hydrolase (FAAH) overexpression induces several disorder symptoms in nerve systems, and therefore long-term tracing of FAAH activity in vivo is of high importance but remains challenging. Current bioluminescence (BL) methods are limited in detecting FAAH activity within 5 h. Herein, by rational design of a latent BL probe (d-Cys-Lys-CBT)2 (1), we developed a "smart" method of intracellular reduction-controlled self-assembly and FAAH-directed disassembly of its cyclic D-Luciferin-based nanoparticles (i.e., 1-NPs) for persistent BL imaging of FAAH activity in vitro, in cells, and in vivo. Using aminoluciferin methyl amide (AMA), Lys-amino-D-Luciferin (Lys-Luc), and amino-D-Luciferin (NH2-Luc) as control BL probes, we validated that the persistent BL of 1 from luciferase-expressing cells or tumors was controlled by the activity of intracellular FAAH. With the property of long-term tracing of FAAH activity in vivo of 1, we envision that our BL precursor 1 could probably be applied for in vivo screening of FAAH inhibitors and the diagnosis of their related diseases (or disorders) in the future.

Label-Free Cell Phenotypic Identification of D-Luciferin as an Agonist for GPR35.[Pubmed:27424891]

Methods Mol Biol. 2016;1461:3-17.

D-Luciferin (also known as beetle or firefly luciferin) is one of the most widely used bioluminescent reporters for monitoring in vitro or in vivo luciferase activity. The identification of several natural phenols and thieno[3,2-b]thiophene-2-carboxylic acid derivatives as agonists for GPR35, an orphan G protein-coupled receptor, had motivated us to examine the pharmacological activity of D-Luciferin, given that it also contains phenol and carboxylic acid moieties. Here, we describe label-free cell phenotypic assays that ascertain D-Luciferin as a partial agonist for GPR35. The agonistic activity of D-Luciferin at the GPR35 shall evoke careful interpretation of biological data when D-Luciferin or its analogues are used as probes.

Description

D-luciferin is the natural substrate of luciferases that catalyze the production of light in bioluminescent insects.

Keywords:

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