6-Amino-D-luciferin

SKU: A0306

Category: Fluorescent Detection

Synonyms: 4,5-dihydro-2[6-amino-2-benzthiazolyl]-4-thiazole carboxylic acid; 161055-47-6
CAS-Number: C₁₁H₉N₃O₂S₂
Molecular Formula: 279.34
Molecular Weight

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥99% (HPLC)
Identity: 1H-NMR
Appearance: Yellow powder

Properties

Solvents: water

Shipping: AMBIENT
Use / Stability: Stable for at least 2 years after receipt when stored at -20°C.
Handling Advice: Protect from light and moisture.
Long Term Storage: -20°C
Short Term Storage: +4°C

Description: Amino analog of the common D-luciferin substrate for use in measuring firefly luciferase activity. This cell permeable reagent can be used when considering design of proluminescent bioconjugates (peptidase substrates) of luciferin for ultrasensitive luminescent assays. In bioluminescent protease assays peptides or amino acids are conjugated to the luciferin analog 6-amino-D-luciferin. These substrates are useful for ultrasensitive analysis of a variety of protease enzymes including various caspases and cathepsins, chymotrypsin, trypsin, elastase, kallikrein, thrombin, ficin, bromoalain, plasmin, papain, ficin and many others or even for use in vivo tracing of luciferase transfected cells in living tissues. The resulting bioluminescence spectrum of reaction of 6-Amino-D-luciferin is very similar to that observed for the natural substrate D-luciferin. Peptidase assays using a bioluminogenic substrate can be easily adapted to 96-well formats for HTS-based assays. Using this principle, it is possible to design an assay to detect almost any peptidase or protease activity via bioluminescence by using a substrate with a suitable peptide sequence. Applications in pathogen detection, discovery of protease inhibitors, probing cell physiology and assessing protease activity in oncogenesis are possible at extraordinary sensitivity.
References: (1) R. Shinde, et al., Biochemistry 45, 11103 (2006) , (2) A. Dragulescu-Andrasi, et al., Bioconjugate Chem. 20, 1660 (2009) , (3) H. Takakura, et al., Chem. Asian J. 5, 2053 (2010) , (4) K.R. Harwood, et al., Chem. Biol. 18, 1649 (2011) , (5) S.J. Orcutt, et al., BBA Mol. Res. 1823, 2079 (2012) , (6) Z-S. Li, et al., J. Photochem. Photobiol. A: Chem. 243, 7 (2012) , (7) R. Kojima, et al., Angew. Chem. Int. Ed. 52, 1175 (2013) , (8) J. Li, et al., Anal. Chem. 86, 2747 (2014) , (9) V.R. Viviani, et al., Biochemistry 53, 5208 (2014) , (10) D.M. Mofford, et al., JACS 136, 13277 (2014) , (11) Y. Nam, et al., Chem. Commun. 52, 1128 (2016)
InChi Key: HKSJKXOOBAVPKR-SSDOTTSWSA-N
Smiles: C1C(N=C(S1)C2=NC3=C(S2)C=C(C=C3)N)C(=O)O

Amino analog of the common D-luciferin substrate for use in measuring firefly luciferase activity. This cell permeable reagent can be used when considering design of proluminescent bioconjugates (peptidase substrates) of luciferin for ultrasensitive luminescent assays. In bioluminescent protease assays peptides or amino acids are conjugated to the luciferin analog 6-amino-D-luciferin. These substrates are useful for ultrasensitive analysis of a variety of protease enzymes including various caspases and cathepsins, chymotrypsin, trypsin, elastase, kallikrein, thrombin, ficin, bromoalain, plasmin, papain, ficin and many others or even for use in vivo tracing of luciferase transfected cells in living tissues. The resulting bioluminescence spectrum of reaction of 6-Amino-D-luciferin is very similar to that observed for the natural substrate D-luciferin. Peptidase assays using a bioluminogenic substrate can be easily adapted to 96-well formats for HTS-based assays. Using this principle, it is possible to design an assay to detect almost any peptidase or protease activity via bioluminescence by using a substrate with a suitable peptide sequence. Applications in pathogen detection, discovery of protease inhibitors, probing cell physiology and assessing protease activity in oncogenesis are possible at extraordinary sensitivity.

SKU: A0306 Category: Fluorescent Detection

Additional information

Additional information

Synonyms	4,5-dihydro-2[6-amino-2-benzthiazolyl]-4-thiazole carboxylic acid
Purity	≥99% (HPLC)
Appearance	Yellow powder
CAS-Number	161055-47-6
Molecular Formula	C11H9N3O2S2
Molecular Weight	279.34
Identity	1H-NMR
Solvents	water
Smiles	C1C(N=C(S1)C2=NC3=C(S2)C=C(C=C3)N)C(=O)O
InChi Key	HKSJKXOOBAVPKR-SSDOTTSWSA-N
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at -20°C.
References	(1) R. Shinde, et al., Biochemistry 45, 11103 (2006), (2) A. Dragulescu-Andrasi, et al., Bioconjugate Chem. 20, 1660 (2009), (3) H. Takakura, et al., Chem. Asian J. 5, 2053 (2010), (4) K.R. Harwood, et al., Chem. Biol. 18, 1649 (2011), (5) S.J. Orcutt, et al., BBA Mol. Res. 1823, 2079 (2012), (6) Z-S. Li, et al., J. Photochem. Photobiol. A: Chem. 243, 7 (2012), (7) R. Kojima, et al., Angew. Chem. Int. Ed. 52, 1175 (2013), (8) J. Li, et al., Anal. Chem. 86, 2747 (2014), (9) V.R. Viviani, et al., Biochemistry 53, 5208 (2014), (10) D.M. Mofford, et al., JACS 136, 13277 (2014), (11) Y. Nam, et al., Chem. Commun. 52, 1128 (2016)
Quantity	1 mg, 5 mg, Bulk