D-Luciferin sodium salt - 10mM in DMSO , CAS No.103404-75-7

CAS: 103404-75-7 Cat. No.: D420420 Peso molecular: 302.3 Número EC: 600-430-4

GRADE & PURITY 10mM in DMSO

Synonyms

103404-75-7|D-Luciferin sodium salt|Sodium (S)-2-(6-hydroxybenzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylate|D-Luciferin Sodium|D-Luciferin (sodium)|D-Luciferin sodium salt monohydrate|C11H7N2NaO3S2|(4S)-4,5-Dihydro-2-(6-hydroxy-2-benzothiazolyl)-4-

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Descripción general

D-Luciferin sodium salt is used as a substrate which, upon oxidation by the enzyme luciferase, produces bioluminescence. This system is employed as a reporter in plants, bacteria, and mammalian cells. Because chemiluminescent techniques are virtually background-free, this reporter gene system is ideal for detecting low-level gene expression.
A substrate that produces bioluminescence upon oxidation by the enzyme luciferase.Substrate for firefly luciferase with a Km of approx 2 μM.

Specifications

Sinónimos

103404-75-7 | D-Luciferin sodium salt | Sodium (S)-2-(6-hydroxybenzo[d]thiazol-2-yl)-4, 5-dihydrothiazole-4-carboxylate | D-Luciferin Sodium | D-Luciferin (sodium) | D-Luciferin sodium salt monohydrate | C11H7N2NaO3S2 | (4S)-4, 5-Dihydro-2-(6-hydroxy-2-benzothiazolyl)-4-

Especificaciones y pureza

10mM in DMSO

Mecanismos bioquímicos y fisiológicos

Chemiluminescent luciferase substrate. Water soluble derivative of D-Luciferin and analog of D-Luciferin potassium salt. Excitation is pH dependent (pH ex λ = 327 and 385 nm for pH 4 and pH 11 respectively)

Condiciones de almacenamiento de almacenamiento

Store at -80°C

Enviado en

Dry ice packs + Cold packs

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Nombres e identificadores

• Sonrisas canónicas: 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
• Isómeros SMILES: C1[C@@H](N=C(S1)C2=NC3=C(S2)C=C(C=C3)O)C(=O)[O-].[Na+]
• WGK Alemania: 3
• Peso molecular: 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
    • Clase 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
• Clase: 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
• Descripción: 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

Propiedades químicas y físicas

• Peso molecular: 302.300 g/mol
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 301.98 Da
• Monoisotopic Mass: 301.98 Da
• Topological Polar Surface Area: 139.000 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 396.000
• 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: 2

XLogP3

Referencias

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]