Ac-DNLD-AMC

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Ac-DNLD-AMC

Ac-DNLD-AMC | 958001-92-8

Catalog Number A18-0040
Category Fluorescent Enzyme Substrates
Molecular Formula C30H38N6O12
Molecular Weight 674.7
Catalog Number Size Price Quantity

Product Introduction

Ac-DNLD-AMC is a fluorogenic substrate for caspase-3. It is cleaved by caspase-3 to release the fluorescent moiety 7-amino-4-methylcoumarin (AMC), which can be used to quantify caspase-3 activity.

Chemical Information

Synonyms N-Acetyl-Asp-Asn-Leu-Asp-7-amido-Methylcoumarin; N-acetyl-L-α-aspartyl-L-asparaginyl-L-leucyl-N-(4-methyl-2-oxo-2H-1-benzopyran-7-yl)-L-α-asparagine
Purity ≥95%
IUPAC Name (3S)-3-acetamido-4-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-3-carboxy-1-[(4-methyl-2-oxochromen-7-yl)amino]-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-4-oxobutanoic acid
Canonical SMILES CC1=CC(=O)OC2=C1C=CC(=C2)NC(=O)C(CC(=O)O)NC(=O)C(CC(C)C)NC(=O)C(CC(=O)N)NC(=O)C(CC(=O)O)NC(=O)C
InChI InChI=1S/C30H38N6O12/c1-13(2)7-18(34-29(46)19(10-23(31)38)35-30(47)20(11-24(39)40)32-15(4)37)28(45)36-21(12-25(41)42)27(44)33-16-5-6-17-14(3)8-26(43)48-22(17)9-16/h5-6,8-9,13,18-21H,7,10-12H2,1-4H3,(H2,31,38)(H,32,37)(H,33,44)(H,34,46)(H,35,47)(H,36,45)(H,39,40)(H,41,42)/t18-,19-,20-,21-/m0/s1
InChI Key IBRRXVTUFUKLDZ-TUFLPTIASA-N
  • Product Specification
  • Application
Storage Store at -20°C

Ac-DNLD-AMC is a synthetic fluorogenic substrate specifically designed for the enzyme caspase-3, an essential protease involved in the execution phase of cell apoptosis. The substrate is composed of the amino acid sequence Asp-Glu-Val-Asp (DEVD) linked to a 7-amino-4-methylcoumarin (AMC) moiety. When caspase-3 cleaves the amide bond between the DEVD peptide and AMC, the non-fluorescent substrate releases free AMC, a highly fluorescent compound. This fluorogenic reaction allows for the quantitative measurement of caspase-3 activity, as the level of fluorescence correlates directly with enzyme activity.

One of the primary applications of Ac-DNLD-AMC is in apoptosis research, where it serves as a reliable indicator of caspase-3 activity, a hallmark of programmed cell death. Researchers utilize this substrate in cell lysates and intact cells to monitor apoptotic processes and understand the molecular mechanisms underlying diseases characterized by excessive or insufficient apoptosis, such as cancer and neurodegenerative disorders. The ability to detect and quantify apoptosis provides crucial insights into the pathophysiology of these diseases and the effectiveness of therapeutic interventions.

Another key application of Ac-DNLD-AMC is in drug discovery and development, particularly for cancer therapies. Potential anti-cancer compounds can be screened for their pro-apoptotic effects by assessing their ability to activate caspase-3 in tumor cells. Ac-DNLD-AMC offers a high-throughput and sensitive method to evaluate the efficacy and potency of new drugs, as increased fluorescence indicates enhanced caspase-3 activation and apoptotic cell death. This application accelerates the identification of promising therapeutic candidates and optimizes lead compounds for clinical success.

Ac-DNLD-AMC is also employed in the study of neurodegenerative diseases, where altered apoptosis plays a critical role. Researchers can measure caspase-3 activity in neuronal models to investigate the contribution of apoptosis to disease progression and neuropathology in conditions such as Alzheimer’s and Parkinson’s diseases. By quantifying caspase-3 activity, scientists can better understand the cellular events leading to neuronal loss and evaluate potential neuroprotective agents that may inhibit apoptosis and preserve neuronal function.

Finally, Ac-DNLD-AMC is utilized in basic biological research to elucidate cellular signaling pathways involving caspase-3. By applying this substrate in various experimental conditions, scientists can dissect the regulatory networks that control apoptosis in different cell types and tissues. This fundamental knowledge advances our overall understanding of cell biology and informs the development of novel interventions targeting apoptotic pathways to treat a broad range of human diseases.

Computed Properties

XLogP3 -1.9
Hydrogen Bond Donor Count 8
Hydrogen Bond Acceptor Count 12
Rotatable Bond Count 17
Exact Mass 674.25477067 g/mol
Monoisotopic Mass 674.25477067 g/mol
Topological Polar Surface Area 290Ų
Heavy Atom Count 48
Formal Charge 0
Complexity 1330
Isotope Atom Count 0
Defined Atom Stereocenter Count 4
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
Covalently-Bonded Unit Count 1
Compound Is Canonicalized Yes
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