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A8851 Sigma-Aldrich

Apicidin

≥98% (HPLC), from microbial

Synonym: Cyclo[(2S)-2-amino-8-oxodecanoyl-1-methoxy-L-tryptophyl-L-isoleucyl-(2R)-2-piperidinexcarbonyl]

  • CAS Number 183506-66-3

  • Empirical Formula (Hill Notation) C34H49N5O6

  • Molecular Weight 623.78

  •  MDL number MFCD03452661

  •  PubChem Substance ID 329771019

  •  NACRES NA.77

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Properties

Related Categories AN-AZ, Antibiotics, Antibiotics A to Z, Antibiotics  A-F, Antitumor Agents,
Quality Level   200
biological source   microbial
assay   ≥98% (HPLC)
form   solid
solubility   DMSO: ~1 mg/mL
Mode of action   enzyme | inhibits
antibiotic activity spectrum   parasites
shipped in   wet ice
storage temp.   −20°C
SMILES string   [H][C@]12CCCCN1C(=O)[C@@H](NC(=O)[C@H](Cc3cn(OC)c4ccccc34)NC(=O)[C@H](CCCCCC(=O)CC)NC2=O)C(C)CC
InChI   1S/C34H49N5O6/c1-5-22(3)30-34(44)38-19-13-12-18-29(38)33(43)35-26(16-9-7-8-14-24(40)6-2)31(41)36-27(32(42)37-30)20-23-21-39(45-4)28-17-11-10-15-25(23)28/h10-11,15,17,21-22,26-27,29-30H,5-9,12-14,16,18-20H2,1-4H3,(H,35,43)(H,36,41)(H,37,42)/t22?,26-,27-,29+,30?/m0/s1
InChI key   JWOGUUIOCYMBPV-PYAAAQPJSA-N

Description

General description

Apicidin is a cyclic tetrapeptide fungal metabolite.

Application

Apicidin has been used as a histone deacetylase 2 (HDAC2) inhibitor to study its effects on 5-lipoxygenase (5-LO) mRNA expression in cell lines of Mono Mac6. It has also been used to study the effects of toll-like receptor 8 (TLR-8) stimulation and histone modification on the expression of an activator protein 1 [AP-1] family member(Fra-2) and tissue inhibitor of metalloproteinases 1 (TIMP-1) in monocytes.

Packaging

1, 5 mg in glass bottle

Biochem/physiol Actions

Apicidin is a potent inhibitor of histone deacetylase (HDAC). It particularlyinhibits histone deacetylase 1 and 3 (HDAC1 and HDAC3). Apicidin exhibits anti-protozoal activity against apicomplexan metabolite produced by parasites. It also possesses anti-proliferative activity against several cancer cell lines. Apicidin shows anti-cancer activity against human acute promyelocytic leukemia cell.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles

Articles

Balancing Histone/Protein Acetylation: Gene Regulation and Cancer Therapy

A highly sophisticated mechanism organizes the 2-meter long human genome within a 6-μm wide nucleus. Up to 10,000-fold of compaction of the chromatin is achieved during mitosis, allowing faithful seg...
Min-Hao Kuo
LSI Volume 7 Article 1
Keywords: Acetylations, Anaerobic, Apoptosis, Biochemistry, Cancer, Catalysis, Cell division, Cell proliferation, Chromatin immunoprecipitation, Clinical, DNA replication, Degradations, Environmental, Enzymology, Gene expression, Genetic, Genetics, Hormones, Immunoprecipitation, Indicators, Mass spectrometry, Metal organic frameworks, Methylations, Microarray Analysis, Molecular biology, Phase transitions, Phosphorylations, Recombination, Substitutions, Transcription

Carcinogenesis and Epigenetics

Cancer research has revealed that the classical model of carcinogenesis, a three step process consisting of initiation, promotion, and progression, is not complete. The expansion of the carcinogenesi...
Vicki Caligur
BioFiles 2008, 3.5, 18.
Keywords: Acetylations, Adhesion, Alkylations, Apoptosis, Biofiles, Cancer, Carcinogens, Cell division, Cell proliferation, Cell signaling, DNA microarrays, Drug discovery, Environmental, Epigenetics, Events, Gene expression, Genetic, Hormones, Metabolism, Methylations, Microarray Analysis, Mutagens, PAGE, Recombination, Reductions, Sequences, Transcription, Type, transformation

Discover Bioactive Small Molecules for Gene Regulation

The loss of regulation of gene expression is a key component to many human disease states, including neurodegenerative disorders, autoimmune conditions and, most prominently, cancers. Regulation of g...
Keywords: Acetylations, Epigenetics, Gene expression, Genomics, Methylations, PAGE, Post translational modifications, Transcription

Histone Modification and Chromatin Remodeling

Gene expression is governed by complex mechanisms including transcription factor binding to DNA and coordinated changes in chromatin structure. The primary protein components of chromatin are the his...
Savita Bagga, PhD.
BioFiles v7 n3, 2012, 10–16
Keywords: Acetylations, Amplification, Cancer, Cell culture, Chromatin immunoprecipitation, Cloning, DNA purification, Diseases, Epigenetics, Gene expression, Immunoprecipitation, Indicators, Methylations, Microarray Analysis, Polymerase chain reaction, Polymerase chain reaction - quantitative, Polymorphisms, Purification, Sequencing, Transcription, Whole genome amplification

Peer-Reviewed Papers
15

References

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