APICIDIN

ChemicalBook > CAS DataBase List > APICIDIN

Product Name: APICIDIN
CAS No.: 183506-66-3
Chemical Name: APICIDIN
Synonyms: OSI 2040;APICIDIN;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
Formula Weight: 623.78
MOL File: 183506-66-3.mol

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APICIDIN Property

Melting point:: 188-190oC
Density: 1.27±0.1 g/cm3(Predicted)
storage temp.: −20°C
solubility: DMSO: ~1mg/mL
form: solid
pka: 13.09±0.70(Predicted)
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.

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Safety

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

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H300Fatal if swallowed

H310Fatal in contact with skin

H330Fatal if inhaled

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P284Wear respiratory protection.

P302+P350IF ON SKIN: Gently wash with plenty of soap and water.

P310Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: A8851
Product name: Apicidin
Purity: ≥98% (HPLC), from microbial
Packaging: 1mg
Price: $134
Updated: 2024/03/01

Sigma-Aldrich

Product number: A8851
Product name: Apicidin
Purity: ≥98% (HPLC), from microbial
Packaging: 5mg
Price: $466
Updated: 2024/03/01

Cayman Chemical

Product number: 10575
Product name: Apicidin
Purity: ≥90%
Packaging: 1mg
Price: $60
Updated: 2024/03/01

Cayman Chemical

Product number: 10575
Product name: Apicidin
Purity: ≥90%
Packaging: 5mg
Price: $230
Updated: 2024/03/01

Cayman Chemical

Product number: 10575
Product name: Apicidin
Purity: ≥90%
Packaging: 10mg
Price: $430
Updated: 2024/03/01

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APICIDIN Chemical Properties,Usage,Production

Description

Apicidin (183506-66-3) is a fungal toxin that is a potent, cell permeable inhibitor of histone deacetylases (HDAC’s).1?It also displays antitumor properties by inducing changes in p21WAF1/Cip1 and gelsolin gene expression causing cell cycle arrest in the G1?phase.2?Apicidin dramatically decreases HIF-1α protein levels and transcriptional activity in human and mouse tumor cell lines.3

Chemical Properties

Solid

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 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 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

References

1) Darkin-Rattray,?et al. (1996)?Apicidin: a novel antiprotozoal agent that inhibits parasite histone deacetylase; Proc. Nat. Acad. Sci. USA,?93?13143 2) Han?et al. (2000)?Apicidin, a histone deacetylase inhibitor, inhibits proliferation of tumor cells via induction of p21WAF1/Cip1 and gelsolin; Cancer Res.,?60?6068 3) Kim?et al. (2007)?Regulation of the HIF-1alpha stability by histone deacetylases; Oncol. Rep.?17?647

APICIDIN Preparation Products And Raw materials

Raw materials

Preparation Products

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APICIDIN Suppliers

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183506-66-3, APICIDINRelated Search:

Tubacin Entinostat HC TOXIN M344 Parthenolide Cyclen APICIDIN N-[(1-METHYL-2-PIPERIDINYL)METHYL]-1-PROPANAMINE N-[(1-BUTYL-2-PIPERIDINYL)METHYL]ETHANAMINE Apicidin, Fusarium sp. ETHYL[(1-PROPYLPIPERIDIN-2-YL)METHYL]AMINE BUTYL[(1-METHYLPIPERIDIN-2-YL)METHYL]AMINE N-[(1-BUTYL-2-PIPERIDINYL)METHYL]-1-PROPANAMINE BUTYL[(1-BUTYLPIPERIDIN-2-YL)METHYL]AMINE N-[(1-ETHYL-2-PIPERIDINYL)METHYL]-1-PROPANAMINE N-[(1-PROPYL-2-PIPERIDINYL)METHYL]-1-PROPANAMINE BUTYL[(1-PROPYLPIPERIDIN-2-YL)METHYL]AMINE BUTYL[(1-ETHYLPIPERIDIN-2-YL)METHYL]AMINE

Apicidin (OSI 2040)

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

CYCLO-[L-(2-AMINO-8-OXODECANOYL)-L-(N-METHOXYTRYPTOPHAN)-L-ISOLEUCYL-D-PIPECOLINYL

CYCLO[(2S)-2-AMINO-8-OXODECANOYL-1-METHOXY-L-TRYPTOPHYL-L-ISOLEUCYL-(2R)-2-PIPERIDINEXCARBONYL]

APICIDIN

(3S,6S,9S,15aR)-9-((S)-sec-Butyl)-6-((1-methoxy-1H-indol-3-yl)methyl)-3-(6-oxooctyl)octahydro-2H-pyrido[1,2-a][1,4,7,10]tetraazacyclododecine-1,4,7,10(3H,12H)-tetraone

Apicidin, HDAC inhibitor

183506-66-3

C34H49N5O6

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