D-Luciferin - CAS 2591-17-5
Catalog number:
2591-17-5
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C11H8N2O3S2
Molecular Weight:
280.32
COA:
Inquire
Targets:
Others
Description:
D-Luciferin is a popular bioluminescent substrate of luciferase in the presence of ATP, used in luciferase-based bioluminescence imaging and cell-based high-throughput screening applications.
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Purity:
98%
Appearance:
Solid powder
Synonyms:
N-benzyl-4-chloro-N-cyclohexylbenzamide
Solubility:
DMSO,56mg/mL(199.77mM);Ethanol,1mg/mL(3.56mM);Water,<1mg/mL(<1mM)
Storage:
3 years -20℃powder;6 months-80℃in solvent
MSDS:
Inquire
Shelf Life:
2 years if stored properly
Canonical SMILES:
C1CCC(CC1)N(CC2=CC=CC=C2)C(=O)C3=CC=C(C=C3)Cl
1.Luciferin Amides Enable in Vivo Bioluminescence Detection of Endogenous Fatty Acid Amide Hydrolase Activity.
Mofford DM1, Adams ST Jr1, Reddy GS1, Reddy GR1, Miller SC1. J Am Chem Soc. 2015 Jul 15;137(27):8684-7. doi: 10.1021/jacs.5b04357. Epub 2015 Jul 2.
Firefly luciferase is homologous to fatty acyl-CoA synthetases. We hypothesized that the firefly luciferase substrate d-luciferin and its analogs are fatty acid mimics that are ideally suited to probe the chemistry of enzymes that release fatty acid products. Here, we synthesized luciferin amides and found that these molecules are hydrolyzed to substrates for firefly luciferase by the enzyme fatty acid amide hydrolase (FAAH). In the presence of luciferase, these molecules enable highly sensitive and selective bioluminescent detection of FAAH activity in vitro, in live cells, and in vivo. The potency and tissue distribution of FAAH inhibitors can be imaged in live mice, and luciferin amides serve as exemplary reagents for greatly improved bioluminescence imaging in FAAH-expressing tissues such as the brain.
2.In Vivo Imaging of Human MDR1 Transcription in the Brain and Spine of MDR1-Luciferase Reporter Mice.
Yasuda K1, Cline C1, Lin YS1, Scheib R1, Ganguly S1, Thirumaran RK1, Chaudhry A1, Kim RB1, Schuetz EG2. Drug Metab Dispos. 2015 Nov;43(11):1646-54. doi: 10.1124/dmd.115.065078. Epub 2015 Aug 17.
P-glycoprotein (Pgp) [the product of the MDR1 (ABCB1) gene] at the blood-brain barrier (BBB) limits central nervous system (CNS) entry of many prescribed drugs, contributing to the poor success rate of CNS drug candidates. Modulating Pgp expression could improve drug delivery into the brain; however, assays to predict regulation of human BBB Pgp are lacking. We developed a transgenic mouse model to monitor human MDR1 transcription in the brain and spinal cord in vivo. A reporter construct consisting of ∼10 kb of the human MDR1 promoter controlling the firefly luciferase gene was used to generate a transgenic mouse line (MDR1-luc). Fluorescence in situ hybridization localized the MDR1-luciferase transgene on chromosome 3. Reporter gene expression was monitored with an in vivo imaging system following D-luciferin injection. Basal expression was detectable in the brain, and treatment with activators of the constitutive androstane, pregnane X, and glucocorticoid receptors induced brain and spinal MDR1-luc transcription.
3.The Drug Excipient Cyclodextrin Interacts With d-Luciferin and Interferes With Bioluminescence Imaging.
Kumar JS1, Miller Jenkins LM1, Gottesman MM2, Hall MD3. Mol Imaging. 2016 Jan 27;15. pii: 1536012115625225. doi: 10.1177/1536012115625225. Print 2016.
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-β-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.
4.In vivo bioluminescence imaging for viable human neural stem cells incorporated within in situ gelatin hydrogels.
Hwang do W1, Park KM, Shim HK, Jin Y, Oh HJ, Oh SW, Lee S, Youn H, Joung YK, Lee HJ, Kim SU, Park KD, Lee DS. EJNMMI Res. 2014 Dec;4(1):61. doi: 10.1186/s13550-014-0061-3. Epub 2014 Nov 12.
BACKGROUND: Three-dimensional (3D) hydrogel-based stem cell therapies contribute to enhanced therapeutic efficacy in treating diseases, and determining the optimal mechanical strength of the hydrogel in vivo is important for therapeutic success. We evaluated the proliferation of human neural stem cells incorporated within in situ-forming hydrogels and compared the effect of hydrogels with different elastic properties in cell/hydrogel-xenografted mice.
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CAS 2591-17-5 D-Luciferin

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