APICIDIN
- CAS No.
- 183506-66-3
- Chemical Name:
- APICIDIN
- Synonyms
- APICIDIN;OSI 2040;Ccris 9163;Apicidin Ia;Apicidin (OSI 2040);Apicidin, HDAC inhibitor;APICIDIN, FUSARIUM SPECIES;CYCLO-[L-(2-AMINO-8-OXODECANOYL)-L-(N-METHOXYTRYPTOPHAN)-L-ISOLEUCYL-D-PIPECOLINYL;CYCLO-L-(2-AMINO-8-OXODEACANOYL)-L-(N-METHOXY-TRYPTOPHAN)-L-ISOLEUCYL-D-PIPECOLINYL;Cyclo(8-oxo-L-2-aMinodecanoyl-1-Methoxy-L-tryptophyl-L-isoleucyl- D-2-piperidinecarbonyl)
- CBNumber:
- CB4482789
- Molecular Formula:
- C34H49N5O6
- Molecular Weight:
- 623.78
- MDL Number:
- MFCD26142628
- MOL File:
- 183506-66-3.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| Melting point | 188-190oC |
|---|---|
| Density | 1.27±0.1 g/cm3(Predicted) |
| storage temp. | −20°C |
| solubility | DMSO: ~1mg/mL |
| pka | 13.09±0.70(Predicted) |
| form | solid |
| color | White |
| biological source | microbial |
| Stability | Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months. Compound is prone to oxidation. Protect from exposure to air. |
| InChIKey | JWOGUUIOCYMBPV-PYAAAQPJSA-N |
| SMILES | [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 |
| FDA UNII | ND0S9TY2E8 |
| UNSPSC Code | 12352200 |
| NACRES | NA.77 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS06 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H300-H310-H330 | |||||||||
| Precautionary statements | P260-P264-P280-P284-P302+P350-P310 | |||||||||
| PPE | Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges | |||||||||
| Hazard Codes | T+ | |||||||||
| Risk Statements | 26/27/28 | |||||||||
| Safety Statements | 22-26-36/37/39-45 | |||||||||
| RIDADR | UN 2811 6.1/PG 2 | |||||||||
| WGK Germany | 3 | |||||||||
| HS Code | 29419090 | |||||||||
| Storage Class | 11 - Combustible Solids | |||||||||
| NFPA 704 |
|
APICIDIN price More Price(44)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | A8851 | Apicidin ≥98% (HPLC), from microbial | 183506-66-3 | 1mg | $148 | 2026-04-30 | Buy |
| Sigma-Aldrich | A8851 | Apicidin ≥98% (HPLC), from microbial | 183506-66-3 | 5mg | $513 | 2026-04-30 | Buy |
| Cayman Chemical | 10575 | Apicidin ≥90% | 183506-66-3 | 1mg | $66 | 2026-04-30 | Buy |
| Cayman Chemical | 10575 | Apicidin ≥90% | 183506-66-3 | 5mg | $253 | 2026-04-30 | Buy |
| Cayman Chemical | 10575 | Apicidin ≥90% | 183506-66-3 | 10mg | $473 | 2026-04-30 | Buy |
APICIDIN Chemical Properties, Uses, Production
Description
Apicidin (183506-66-3) is a fungal toxin that is a potent, cell permeable inhibitor of histone deacetylases (HDAC’s).1It also displays antitumor properties by inducing changes in p21WAF1/Cip1 and gelsolin gene expression causing cell cycle arrest in the G1phase.2Apicidin dramatically decreases HIF-1α protein levels and transcriptional activity in human and mouse tumor cell lines.3
Chemical Properties
Solid
Uses
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.
Uses
Apicidin is a potent (nM) cell permeable inhibitor of histone deacetylase. Also, Apicidin exhibits antiprotozoal and potential antimalarial properties. Apicidin has antiproliferative activity on HeLa cells accompanied by cell arrest at the G1 phase. Apicidin induces selective changes in the expression of p21 and gelsolin.
Uses
Apicidin is a cyclic peptide antibiotic with broad spectrum antiparasitic and antiprotozoan activity. Apicidin, a histone deacetylase inhibitor, is anti-angiogenic and induces apoptosis.
General Description
Apicidin is a cyclic tetrapeptide fungal metabolite.
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.
Enzyme inhibitor
This fungal metabolite and potential oral chemotherapeutic agent (FW = 623.79 g/mol; CAS 183506-66-3), also known as [cyclo(N-O-methyl-L- tryptophanyl-L-isoleucinyl-D-pipecolinyl-L-2-amino-8-oxodecanoyl)], is an antiprotozoal agent. It is cell permeable and is a strong inhibitor of histone deacetylase (IC50 = 0.7 nM). Apicidin also inhibits proliferation of tumor cells via induction of p21WAF1/Cip1 and gelsolin. Apicidin’s low bioavailability of apicidin is mainly due to the P-gycoprotein-mediated efflux.
storage
-20°C
Background
Apicidin is a fungal metabolite, broad-spectrum antiprotozoal agent. This small molecule inhibits histone deacetylases, known to moderate histone acetylation and chromatin folding during gene expression. Apicidin has been shown to irreversibly prevent the development of intracellular Apicomplexan parasites in vitro through HDAC inhibition. Research indicates that Apicidin inhibits tumor cell proliferation through gene expression changes of p21WAF1/Cip1 and gelsolin, and can cause cell cycle arrest in the G1 phase. Apicidin also decreases HIF-1α protein levels in human and mouse cell lines. HDAC2 has been recognized as a host immune response to the influenza A virus and several other viruses, making HDAC inhibitors important compounds to study in relation to viral diseases.
References
[1] S J DARKIN-RATTRAY. Apicidin: a novel antiprotozoal agent that inhibits parasite histone deacetylase.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1996, 93 23: 13143-13147. DOI:10.1073/pnas.93.23.13143
[2] J W HAN. Apicidin, a histone deacetylase inhibitor, inhibits proliferation of tumor cells via induction of p21WAF1/Cip1 and gelsolin.[J]. Cancer research, 2000, 60 21: 6068-6074.
[3] SE-HEE KIM. Regulation of the HIF-1alpha stability by histone deacetylases.[J]. Oncology reports, 2007, 17 3: 647-651.
APICIDIN Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| J & K SCIENTIFIC LTD. | 18210857532 18210857532 | jkinfo@jkchemical.com | China | 96815 | 76 |
| Chemsky (shanghai) International Co.,Ltd | 021-50135380 | shchemsky@sina.com | China | 15350 | 60 |
| T&W GROUP | 021-61551611 13296011611 | contact@trustwe.com | China | 9884 | 58 |
| S.Z. PhyStandard Bio-Tech. Co., Ltd. | 0755-83725681-603 | China | 4484 | 50 | |
| Guangzhou Isun Pharmaceutical Co., Ltd | 020-39119399 18927568969 | isunpharm@qq.com | China | 4773 | 55 |
| AdooQ BioScience, LLC | +1 (866) 930-6790 | info@adooq.com | United States | 2774 | 58 |
| TargetMol Chemicals Inc. | 021-021-33632979 15002134094 | marketing@targetmol.com | China | 7993 | 58 |
| Jinan Mingya Medical Technology Co., Ltd. | 0531-85828981 | 864598798@qq.com | China | 587 | 58 |
| Shanghai JONLN Reagent Co., Ltd. | 400-0066400 13621662912 | 422131432@qq.com | China | 9970 | 55 |
| Bide Pharmatech Ltd. | 400-164-7117 18317119277 | product02@bidepharm.com | China | 40000 | 60 |
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