D-Luciferin Firefly, free acid - Suitable for molecular biology, ≥99.9%(HPLC) , CAS No.103404-75-7

CAS: 103404-75-7 Cat. No.: D1375477 Molecular Weight: 302.3 EC Number: 600-430-4

GRADE & PURITY Suitable for molecular biology, ≥99.9%(HPLC)

Synonyms

5-Dihydro-2-(6-hydroxy-2-benzothiazolyl)-4-thiazolecarboxylic acid | (S)-2-(6-Hydroxy-2-benzothiazolyl)-2-thiazoline-4-carboxylic acid | 4,5-Dihydro-2-(6-hydroxy-2-benzothiazolyl)-4-thiazolecarboxylic acid | Firefly Luciferin | D-(-)-Luciferin | Beetle Lu

Storage

Protected from light,Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Application

ATP Assay, Bioluminescence, Cell Viability Assay, In Vivo Imaging, Reporter Gene Assay

Overview

  Luciferin is a common bioluminescent reporter used for in vivo imaging of the expression of luciferase. This substrate for the firefly luciferase enzyme utilizes ATP and Mg²⁺ as cofactors to emit a characteristic yellow-green emission in the presence of oxygen, which shifts to red light in vivo at 37°C. Through the utilization of ATP, the reaction can be further used to indicate the presence of energy or life in order to function as a life-death stain.

  Luciferin is a common reagent used throughout the biotechnology field and specifically for in vivo imaging. Luciferase labeled tumor cells, stem cells or infectious diseases are often inoculated into research animals such as rats or mice for investigation. The injection of luciferin allows for the real-time, noninvasive monitoring of disease progression and/or drug efficacy in these model systems through Bioluminescence Imaging (BLI).

  Luciferin is also commonly used for in vitro research, including luciferase and ATP assays, gene reporter assays, high throughput sequencing and various contamination assays.
APPLICATIONS
in vivo cellular imaging
luciferase and ATP assays
gene reporter assays
high throughput sequencing
contamination assays

Specifications

Synonyms

5-Dihydro-2-(6-hydroxy-2-benzothiazolyl)-4-thiazolecarboxylic acid | (S)-2-(6-Hydroxy-2-benzothiazolyl)-2-thiazoline-4-carboxylic acid | 4, 5-Dihydro-2-(6-hydroxy-2-benzothiazolyl)-4-thiazolecarboxylic acid | Firefly Luciferin | D-(-)-Luciferin | Beetle Lu

Specifications & Purity

Suitable for molecular biology, ≥99.9%(HPLC)

Stability And Storage

Store at -20℃ long term (5 years). Store in the dark. Desiccated.

Storage

Protected from light, Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Suitable for molecular biology

Purity

≥99.9%(HPLC)

Names and Identifiers

• Canonical Smiles: C1C(N=C(S1)C2=NC3=C(S2)C=C(C=C3)O)C(=O)[O-].[Na+]
• IUPAC Name: sodium;(4S)-2-(6-hydroxy-1,3-benzothiazol-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylate
• InChIKey: LILQLBIQROYWIA-OGFXRTJISA-M
• INCHI: 1S/C11H8N2O3S2.Na/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);/q;+1/p-1/t7-;/m1./s1
• Isomeric SMILES: C1[C@@H](N=C(S1)C2=NC3=C(S2)C=C(C=C3)O)C(=O)[O-].[Na+]
• WGK Germany: 3
• Molecular Weight: 302.3
• Reaxy-Rn: 62728073
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=62728073&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Cysteine and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: Cysteine and derivatives
• Alternative Parents: Benzothiazoles 1-hydroxy-2-unsubstituted benzenoids Imidothiolactones Thiazolines Thiazoles Heteroaromatic compounds Carboxylic acid salts Sulfenyl compounds Propargyl-type 1,3-dipolar organic compounds Organic alkali metal salts Monocarboxylic acids and derivatives Imidothioic acids and derivatives Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Cysteine or derivatives - 1,3-benzothiazole - 1-hydroxy-2-unsubstituted benzenoid - Imidothiolactone - Benzenoid - Heteroaromatic compound - Meta-thiazoline - Thiazole - Azole - Imidothioester - Carboxylic acid salt - Azacycle - Organic alkali metal salt - Organic metal salt - Organoheterocyclic compound - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Sulfenyl compound - Monocarboxylic acid or derivatives - Imidothioic acid or derivatives - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organic salt - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as cysteine and derivatives. These are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: No less than 50mg/mL in DMSO
• Molecular Weight: 280.300 g/mol
• XLogP3: 2.200
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 279.998 Da
• Monoisotopic Mass: 279.998 Da
• Topological Polar Surface Area: 136.000 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 390.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Xiao Kui, Zhang Niyuan, Li Feifei, Hou Dayong, Zhai Xiaoyi, Xu Wanhai, Wang Gelin, Wang Hao, Zhao Liang.  (2022)  Pro-oxidant response and accelerated ferroptosis caused by synergetic Au(I) release in hypercarbon-centered gold(I) cluster prodrugs.  Nature Communications,  13  (1): (1-13).  [PMID:35945240] [10.1038/s41467-022-32474-y]

2. Chao Chen, Hongxia Zhang, Lingling Qi, Haoqi Lei, Xuefei Feng, Yingjie Chen, Yuanyuan Cheng, Defeng Pang, Jufeng Wan, Haiying Xu, Shifeng Cao, Baofeng Yang, Yan Zhang, Xin Zhao.  (2025)  Obesity-driven oleoylcarnitine accumulation in tumor microenvironment promotes breast cancer metastasis-like phenotype.  Acta Pharmaceutica Sinica B,      [PMID:40486851] [10.1016/j.apsb.2025.02.026]

3. Song Zhengwei, Sun Quanwei, Yang Wenshuo, Li Yunlong, Hu Chaoyu, Chen Chen, Liu Kang, Shen Wei, Yang Ye, Yin Dengke.  (2025)  Inflammation-targeted nanomedicine prevents tumor metastasis following photodynamic therapy by reversing epithelial-mesenchymal transition and ROS-mediated immunosuppression.  JOURNAL OF NANOBIOTECHNOLOGY,  23  (1): (1-19).  [PMID:40186261] [10.1186/s12951-025-03332-y]

4. Dong-Ni Pei, Yang Song, Ying-Xia Zhou, Bo Shu, Shao-wei Huang, Fa-Zhao Li, Wei-Dong Dai, Bao-Ye Sun.  (2025)  Enhancing cDC1-mediated anti-tumor immunity limits tumor progression and potentiates anti-PD-1 therapy in intrahepatic cholangiocarcinoma.  Frontiers in Immunology,      [PMID:41459487] [10.3389/fimmu.2025.1708962]

5. Xianghua Zhong, Xinchao Liu, Jiajia Luo, Xinyang Liu, Xueting Wei, Xi Peng, Lu Wang, Huaimin Wang, Kunyu Zhang, Liming Bian, Peng Shi.  (2026)  Cell surface engineering with a pseudofibrotic ECM reprograms the antifibrotic activity of mesenchymal stromal cells.  Science Advances,  12  (3):   [PMID:41544160] [10.1126/sciadv.aea0998]