233691-67-3

Basic information

• Product Name: BOC-LYS(AC)-AMC
• Synonyms: BOC-LYS(AC)-7-AMINO-4-METHYLCOUMARIN;BOC-LYS(AC)-AMC;BOC-LYSINE(AC)-AMC;BOC-N-EPSILON-ACETYL-L-LYSINE 7-AMIDO-4-METHYLCOUMARIN;HDAC SUBSTRATE (FLUOROMETRIC);HISTONE DEACETYLASE SUBSTRATE, FLUOROGENIC;HISTONE DEACETYLASE SUBSTRATE (FLUOROMETRIC);MAL
• CAS NO: 233691-67-3
• Molecular Formula: C₂₃H₃₁N₃O₆
• Molecular Weight: 445.51
• Mol File: 233691-67-3.mol

Chemical Properties

• Boiling Point: 732.6±60.0 °C(Predicted)
• Appearance: /
• Density: 1.209±0.06 g/cm3(Predicted)
• Storage Temp.: -15°C
• PKA: 11.23±0.46(Predicted)
• CAS DataBase Reference: BOC-LYS(AC)-AMC(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-LYS(AC)-AMC(233691-67-3)
• EPA Substance Registry System: BOC-LYS(AC)-AMC(233691-67-3)

Safety Data

• Hazardous Substances Data: 233691-67-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
BOC-LYS(AC)-AMC is used as a research tool for the investigation of histone deacetylase (HDAC) activity. It aids in understanding the role of HDACs in various cellular processes and their potential as therapeutic targets for the development of novel drugs.
Used in Drug Discovery and Development:
BOC-LYS(AC)-AMC is utilized as a screening agent in the drug discovery process to identify potential HDAC inhibitors. These inhibitors can be further developed into therapeutic agents for the treatment of diseases associated with HDAC dysregulation, such as cancer, neurological disorders, and cardiovascular diseases.
Used in Diagnostic Applications:
BOC-LYS(AC)-AMC serves as a diagnostic marker for the assessment of HDAC activity in various samples, including cell lysates and tissue extracts. This information can be valuable in the diagnosis and monitoring of diseases related to HDAC activity.
Used in Academic Research:
BOC-LYS(AC)-AMC is employed as an experimental reagent in academic research to study the molecular mechanisms underlying HDAC function and regulation. This knowledge can contribute to the advancement of our understanding of HDAC biology and its implications in health and disease.
Used in Biotechnology:
BOC-LYS(AC)-AMC is used as a component in the development of biosensors and analytical devices for the detection and quantification of HDAC activity. These devices can be applied in various fields, including drug development, diagnostics, and environmental monitoring.

Upstream product

• 26093-31-2 7-amino-4-methylcoumarin. 
• 6404-26-8 (S)-6-acetamido-2-((tertbutoxycarbonyl)amino)hexanoic acid 

Downstream Products

• 13734-28-6 Boc-Lys-OH 
• 26093-31-2 7-amino-4-methylcoumarin. 
• 116883-12-6 N-(4-methyl-7-coumarinyl)-N-α-(tert-butyloxycarbonyl)-lysinamide 
• 577969-56-3 ac-gak(ac)-amc 

Relevant articles and documents

A Genetically Encoded, Phage-Displayed Cyclic-Peptide Library

Superior to linear peptides in biological activities, cyclic peptides are considered to have great potential as therapeutic agents. To identify cyclic-peptide ligands for therapeutic targets, phage-displayed peptide libraries in which cyclization is achieved by the covalent conjugation of cysteines have been widely used. To resolve drawbacks related to cysteine conjugation, we have invented a phage-display technique in which its displayed peptides are cyclized through a proximity-driven Michael addition reaction between a cysteine and an amber-codon-encoded N?-acryloyl-lysine (AcrK). Using a randomized 6-mer library in which peptides were cyclized at two ends through a cysteine–AcrK linker, we demonstrated the successful selection of potent ligands for TEV protease and HDAC8. All selected cyclic peptide ligands showed 4- to 6-fold stronger affinity to their protein targets than their linear counterparts. We believe this approach will find broad applications in drug discovery.

A GENETICALLY ENCODED, PHAGE-DISPLAYED CYCLIC PEPTIDE LIBRARY AND METHODS OF MAKING THE SAME

Embodiments of the present disclosure pertain to methods of selecting cyclic peptides that bind to a target by transforming a phage display library with a plurality of nucleic acids into bacterial host cells, where the nucleic acids include phage coat protein genes with a combinatorial region that encodes at least one cysteine and at least one non-canonical amino acid. The transformation results in the production of phage particles with phage coat proteins where the cysteine and the non-canonical amino acid couple to one another to form a cyclic peptide library. Phage particles are then screened against the desired target to select bound cyclic peptides. Amino acid sequences of the selected cyclic peptides are then identified. Additional embodiments pertain to methods of constructing a phage display library that encodes the cyclic peptides. Further embodiments of the present disclosure pertain to the produced cyclic peptides, phage display libraries and phage particles.

COMBINATION OF A SELECTIVE HISTONE DEACETYLASE 3 (HDAC3) INHIBITOR AND AN IMMUNOTHERAPY AGENT FOR THE TREATMENT OF CANCER

Aspects of the disclosure relate to compositions, kits, and methods for the treatment of cancer that utilize a selective histonc deacetylase 3 (HDAC3) inhibitor. In some aspects, the compositions, kits, and methods relate to use of a selective HDAC3 inhibitor in combination with an immunotherapy agent (e.g., an immune checkpoint inhibitor).

Design and Synthesis of Simplified Largazole Analogues as Isoform-Selective Human Lysine Deacetylase Inhibitors

Selective inhibition of KDAC isoforms while maintaining potency remains a challenge. Using the largazole macrocyclic depsipeptide structure as a starting point for developing new KDACIs with increased selectivity, a combination of four different simplified largazole analogue (SLA) scaffolds with diverse zinc-binding groups (for a total of 60 compounds) were designed, synthesized, and evaluated against class I KDACs 1, 3, and 8, and class II KDAC6. Experimental evidence as well as molecular docking poses converged to establish the cyclic tetrapeptides (CTPs) as the primary determinant of both potency and selectivity by influencing the correct alignment of the zinc-binding group in the KDAC active site, providing a further basis for developing new KDACIs of higher isoform selectivity and potency.

ISOFORM-SELECTIVE LYSINE DEACETYLASE INHIBITORS

Isoform-selective lysine deacetylase inhibitors are described. Inhibitors of the lysine deacetylase enzyme are useful as antitumor drugs and for treating addiction, asthma, cardio-vascular disease, immunosuppression, neurodegenerative diseases, sepsis, sickle-cell disease, uveal melanoma and termination of viral latency, particularly HIV-1 latency.

Inhibitors of histone deacetylase

The present invention relates to compounds of formula (I): or a pharmaceutically acceptable salt, hydrate, solvate, or prodrug thereof, wherein U, J, V, X, R2a, R2b, R2c, R5 and t are as described herein. The present invention relates generally to inhibitors of histone deacetylase and to methods of making and using them. These compounds are useful for promoting cognitive function and enhancing learning and memory formation. In addition, these compounds are useful for treating, alleviating, and/or preventing various conditions, including for example, neurological disorders, memory and cognitive function disorders/impairments, extinction learning disorders, fungal diseases and infections, inflammatory diseases, hematological diseases, and neoplastic diseases in humans and animals.

INHIBITORS OF HISTONE DEACETYLASE

The present invention relates to compounds of formula (I) or a pharmaceutically acceptable salt, hydrate, solvate, or prodrug thereof, wherein X1, X2, X3, X4, X5, W1, W2, W3, and W4 are as described. The present invention relates generally to inhibitors of histone deacetylase and to methods of making and using them. In one aspect, the invention relates to selective HDAC3 inhibitors useful for protecting β-cells and improving insulin resistence. The selective HDAC3 inhibitors are also useful for promoting cognitive function and enhancing learning and memory formation. Compounds of the invention are useful for treating, alleviating, and/or preventing various conditions, including for example, a metabolic disorder such as type 1 or type 2 diabetes, dyslipidemias, lipodystrophies, liver disease associated with metabolic syndrome, polycystic ovarian syndrome, or obesity; inflammatory disease; neurological disorder; a memory or cognitive function disorder/impairment; an extinction learning disorder; fungal disease or infection; viral disease or infection such as HIV; hematological disease; liver disease; lysosomal storage disease; or neoplastic disease in humans or animals.

First non-radioactive assay for in vitro screening of histone deacetylase inhibitors

Inhibitors of histone deacetylase (HD) are of great potential as new drugs due to their ability to influence transcriptional regulation and to induce apoptosis or differentiation in cancer cells. So far only radioactive enzyme activity assays or in vivo a