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
• Article Data: 4

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

General Description

L-LUCIFERIN is a bioluminescent molecule found in the bodies of certain organisms, such as fireflies and some types of jellyfish. It plays a crucial role in the process of bioluminescence, which is the production and emission of light by living organisms. L-LUCIFERIN is typically involved in a reaction with the enzyme luciferase, which catalyzes the oxidation of the molecule and produces light as a result. This unique chemical is widely used in scientific research for imaging and detection purposes, as well as in biotechnology applications such as bioluminescent assays and bioimaging techniques. Its ability to produce light without the need for an external light source makes L-LUCIFERIN a valuable tool in various fields, including medicine, molecular biology, and environmental monitoring.

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

• 1198094-60-8 6-allyloxybenzothiazole-2-carbonitrile 
• 52-90-4 L-Cysteine 
• 939-69-5 2-cyano-6-hydroxybenzothiazole 
• 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 
• 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 

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.