34500-31-7

Basic information

• Product Name: L-LUCIFERIN
• Synonyms: L-LUCIFERIN;L-Luciferin free acid, 99%;(+)-2-(6-Hydroxy-2-benzothiazolyl)-2-thiazoline-4-carboxylic acid;(4R)-4,5-Dihydro-2-(6-hydroxy-2-benzothiazolyl)-4-thiazolecarboxylic acid;(R)-4,5-Dihydro-2-(6-hydroxy-2-benzothiazolyl)-4-thiazolecarboxylic acid
• CAS NO: 34500-31-7
• Molecular Formula: C₁₁H₈N₂O₃S₂
• Molecular Weight: 280.32
• Mol File: 34500-31-7.mol

Chemical Properties

• Boiling Point: 588℃
• Flash Point: 309℃
• Appearance: /
• Density: 1.81
• Vapor Pressure: 1.19E-14mmHg at 25°C
• Refractive Index: 1.864
• CAS DataBase Reference: L-LUCIFERIN(CAS DataBase Reference)
• NIST Chemistry Reference: L-LUCIFERIN(34500-31-7)
• EPA Substance Registry System: L-LUCIFERIN(34500-31-7)

Safety Data

• Hazardous Substances Data: 34500-31-7(Hazardous Substances Data)

Usage

Uses

Used in Scientific Research:
L-LUCIFERIN is used as a bioluminescent indicator for imaging and detection purposes in various scientific studies. Its ability to produce light upon reaction with luciferase makes it a preferred choice for visualizing biological processes in real-time.
Used in Biotechnology Applications:
In the biotechnology industry, L-LUCIFERIN is used as a key component in bioluminescent assays and bioimaging techniques. It facilitates the monitoring of gene expression, cell signaling, and other biological activities with high sensitivity and specificity.
Used in Medicine:
L-LUCIFERIN is employed as a diagnostic tool in medical research and clinical applications. Its use in imaging techniques allows for the non-invasive visualization of disease progression and the evaluation of therapeutic responses.
Used in Molecular Biology:
In molecular biology, L-LUCIFERIN is used as a reporter molecule to study gene expression and protein interactions. Its light-emitting properties enable researchers to track and quantify biological events at the molecular level.
Used in Environmental Monitoring:
L-LUCIFERIN is utilized in environmental studies as a means to detect and monitor the presence of specific organisms or pollutants. Its bioluminescent properties provide a sensitive and specific method for ecological assessments and environmental surveillance.

InChI:InChI=1/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-/m0/s1

Upstream product

• 52-90-4 L-Cysteine 
• 939-69-5 2-cyano-6-hydroxybenzothiazole 
• 1198094-60-8 6-allyloxybenzothiazole-2-carbonitrile 
• 884-22-0 6-methoxy-benzothiazole-2-carboxylic acid methyl ester 
• 946-13-4 6-methoxybenzo[d]thiazol-2-carboxylic acid 
• 946-12-3 6-methoxybenzothiazole-2-carboxamide 
• 943-03-3 2-cyano-6-methoxybenzothiazole 
• 91634-13-8 6-ethoxy-benzothiazole-2-carbonitrile 
• 18522-99-1 ethyl 4'-methoxyoxanilate 
• 452-35-7 6-ethoxybenzothiazole-2-sulfonamide 
• 131474-37-8 6-O-β-D-galactopyranosyl-luciferin 
• 601524-61-2 6-O-β-D-glucopyranosyl-luciferin 

Relevant articles and documents

Bioluminescence Imaging of Carbon Monoxide in Living Cells and Nude Mice Based on Pd0-Mediated Tsuji-Trost Reaction

Carbon monoxide (CO) is highly toxic and lethal to humans and animals because of its strong affinity for hemoglobin, while this silent killer is constantly generated in the body as a cell-signaling molecule of the gasotransmitter family in various pathological and physiological conditions. Up to now, designing fluorescent probes for real-time imaging of CO in living species is a continuous challenge due to background interference, light scattering, and photoactivation/photobleaching. Herein, a novel type of bioluminescence probe (allyl-luciferin) was synthesized and exploited to realize CO imaging with high signal-to-noise ratios. Based on Pd0-mediated Tsuji-Trost reaction, allyl-luciferin specifically reacted with CO to yield D-luciferin and thus generate a turn-on bioluminescence response, exhibiting high selectivity against bioactive small molecules such as reactive nitrogen, oxygen, and sulfur species. Furthermore, the new probe can be easily employed to detect exogenous CO in Huh7 cells and MDA-MB-231 cells, and CO production was enhanced greatly in these living cells after pretreatment with [Ru(CO)3Cl-(glycinate)] (CORM-3). Through the use of PdCl2-containing liposomes to improve poor membrane permeability of PdCl2, endogenous CO stimulated by heme was also seen clearly. In addition, the probe was successfully used to monitor exogenous and endogenous CO in nude mice. Overall, our data proved that the allyl-luciferin is a promising tool for exogenous and endogenous CO detection and imaging within living species. This is the first demonstration of bioluminescence imaging obtained by a probe for CO. We anticipate that the good imaging properties of allyl-luciferin presented in this study will provide a potentially powerful approach for illuminating CO functions in the future.

Luciferin and derivatives as a DYRK selective scaffold for the design of protein kinase inhibitors

D-Luciferin is widely used as a substrate in luciferase catalysed bioluminescence assays for in vitro studies. However, little is known about cross reactivity and potential interference of D-luciferin with other enzymes. We serendipitously found that firefly luciferin inhibited the CDK2/Cyclin A protein kinase. Inhibition profiling of D-luciferin over a 103-protein kinase panel showed significant inhibition of a small set of protein kinases, in particular the DYRK-family, but also other members of the CMGC-group, including ERK8 and CK2. Inhibition profiling on a 16-member focused library derived from D-luciferin confirms that D-luciferin represents a DYRK-selective chemotype of fragment-like molecular weight. Thus, observation of its inhibitory activity and the initial SAR information reported here promise to be useful for further design of protein kinase inhibitors with related scaffolds.

A simple bioluminescent method for measuring d-amino acid oxidase activity

d-Amino acid oxidase (DAO) plays important roles in regulating d-amino acid neurotransmitters and was recently identified as a key enzyme integral to hydrogen sulfide production from d-Cys. We report here the development of a simple biocompatible, bioluminescent method for measuring DAO activity based on the highly selective condensation of d-Cys with 6-hydroxy-2-cyanobenzothiazole (CBT-OH) to form d-luciferin. This journal is

Synthesis of luciferin glycosides as substrates for novel ultrasensitive enzyme assays

Condensation of 2-cyano-6-hydroxybenzothiazole with acetohalogeno derivatives of D-glucose, D-galactose, and 2-acetamido-2-deoxy-D-glucose gave the corresponding β-glycosides.Attempted basic deacetylation caused methanolysis of the nitrile group.Condensation of the first two acetylated glycosides with D-cysteine, followed by deacetylation, gave the firefly luciferin β-glycosides that were substrates for the corresponding glycohydrolases.The liberated luciferin was determined by fluorescence spectroscopy and, in one instance, by coupled-bioluminescence assay with firefly luciferase.The amount of luciferin released and determined by bioluminescence assay, was only ca. 65 percent of that determined by fluorescence spectroscopy, which suggested that the luciferin was partly racemised.Because of the great sensitivity of bioluminescence detection, these novel substrates provide potentially ultrasensitive assays for glycohydrolases, but their syntheses are more difficult than those of the corresponding fluorogenic substrates.