L-Cystine bis-4-nitroanilide
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L-Cystine bis-4-nitroanilide

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A substrate for measuring cystyl-aminopeptidase.

Category
L-Amino Acids
Catalog number
BAT-003973
CAS number
34199-07-0
Molecular Formula
C18H20N6O6S2
Molecular Weight
480.50
L-Cystine bis-4-nitroanilide
IUPAC Name
(2R)-2-amino-3-[[(2R)-2-amino-3-(4-nitroanilino)-3-oxopropyl]disulfanyl]-N-(4-nitrophenyl)propanamide
Synonyms
(H-L-Cys-pNA)2; L-CYSTINE BIS-P-NITROANILIDE; cystine-bis-4-nitroanilide; L-CYSTINYL-BIS-4-NITROANILIDE
Purity
95%
Density
1.553 g/cm3
Boiling Point
807.2 °C at 760 mmHg
Storage
Store at -20 °C
InChI
InChI=1S/C18H20N6O6S2/c19-15(17(25)21-11-1-5-13(6-2-11)23(27)28)9-31-32-10-16(20)18(26)22-12-3-7-14(8-4-12)24(29)30/h1-8,15-16H,9-10,19-20H2,(H,21,25)(H,22,26)/t15-,16-/m0/s1
InChI Key
UDNQCHDHUMEZRM-HOTGVXAUSA-N
Canonical SMILES
C1=CC(=CC=C1NC(=O)C(CSSCC(C(=O)NC2=CC=C(C=C2)[N+](=O)[O-])N)N)[N+](=O)[O-]

L-Cystine bis-4-nitroanilide, a widely utilized chromogenic substrate in biochemical research, finds diverse applications. Here are four key uses:

Enzyme Activity Assays: Serving as a cornerstone in enzyme activity measurements, L-Cystine bis-4-nitroanilide is integral for evaluating cysteine protease activity. Upon hydrolysis by these enzymes, it yields a yellow-colored product detectable by spectrophotometry, enabling real-time monitoring of enzymatic reactions and the collection of kinetic data for insightful analysis.

Protein Engineering: In the intricate realm of protein engineering, L-Cystine bis-4-nitroanilide plays a critical role in assessing the functional modifications of engineered proteases. By offering a clear and quantifiable response upon cleavage, this substrate aids scientists in gauging the success of enzyme modifications. Such evaluations are imperative for crafting proteases with enhanced or novel activities, essential for diverse industrial and therapeutic applications requiring tailored enzymatic functions.

Diagnostics: Unveiling its significance in diagnostic assays, L-Cystine bis-4-nitroanilide facilitates the detection of specific proteases serving as biomarkers for various diseases. Its utility extends to aiding in the diagnosis of conditions linked to aberrant protease activity, such as certain cancers and inflammatory disorders. The straightforward colorimetric detection method renders it suitable for high-throughput diagnostic screening, expediting disease identification and management.

High-Throughput Screening: Empowering drug discovery endeavors, L-Cystine bis-4-nitroanilide is harnessed in high-throughput screening platforms to uncover potential inhibitors of cysteine proteases. By subjecting numerous compounds to tests assessing their ability to impede substrate cleavage, researchers can pinpoint promising candidates with therapeutic potential. This accelerates the development of novel drugs targeting diseases associated with protease dysregulation, driving advancements in targeted therapeutic interventions.

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