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- Apicidin
-
- $299.00
-
2026-05-11
- CAS:183506-66-3
- Purity: 99.93%
- Supply Ability: 10g
- Apicidin
-
- $299.00
-
2026-04-20
- CAS:183506-66-3
- Purity: 99.93%
- Supply Ability: 10g
|
| Product Name: | APICIDIN | | Synonyms: | APICIDIN, FUSARIUM SPECIES;Ccris 9163;Apicidin Ia;Cyclo(8-oxo-L-2-aMinodecanoyl-1-Methoxy-L-tryptophyl-L-isoleucyl-
D-2-piperidinecarbonyl);Cyclo[(2S)-2-aMino-8-oxodecanoyl-1-Methoxy-L-tryptophyl-L-isoleucyl-(2R)-2-piperidinecarbonyl];OSI 2040;Apicidin Cyclo[(2S)-2-amino-8-oxodecanoyl-1-methoxy-L-tryptophyl-L-isoleucyl-(2R)-2-piperidinecarbonyl];CYCLO-L-(2-AMINO-8-OXODEACANOYL)-L-(N-METHOXY-TRYPTOPHAN)-L-ISOLEUCYL-D-PIPECOLINYL | | CAS: | 183506-66-3 | | MF: | C34H49N5O6 | | MW: | 623.78 | | EINECS: | | | Product Categories: | antibiotic | | Mol File: | 183506-66-3.mol |  |
| | APICIDIN Chemical Properties |
| 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 |
| 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 |
| | APICIDIN Usage And Synthesis |
| 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 |
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