Apicidin

AdipoGen Life Sciences
Product Code: AG-CN2-0087
CodeSizePrice
AG-CN2-0087-M0011 mg£60.00
Quantity:
AG-CN2-0087-M0055 mg£210.00
Quantity:
Prices exclude any Taxes / VAT

Overview

Regulatory Status: RUO
Shipping:
Ambient
Storage:
+4°C

Images

1 / 1
Chemical Structure

Chemical Structure

Further Information

Alternate Names/Synonyms:
cyclo-[L-(2-Amino-8-oxodecanoyl)-L-(N-methoxy-tryptophan)-L-isoleucyl-D-pipecolinyl]; OSI-2040
Appearance:
White to off-white solid.
CAS:
183506-66-3
Class:
6.1
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS06
Handling Advice:
Keep cool and dry.
Hazards:
H300, H310, H330
InChi:
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
InChiKey:
JWOGUUIOCYMBPV-LQJYRIKDSA-N
Long Description:
Chemical. CAS: 183506-66-3. Formula: C34H49N5O6. MW: 623.8. Isolated from fungus Fusarium sp. Antiprotozoal. Potent inhibitor of histone deacetylase (HDAC). Inhibits proliferation. Induces cell cycle arrest at the G1 phase. Induces hyperacetylation of histone H4. Apoptosis inducer. Potent anti-angiogenic compound. Decreases HIF-1alpha protein levels and transcriptional activity in human and mouse tumor cell lines. Autophagy inducer in oral squamous cell carcinoma (OSCC) cells. Promotes either self-renewal or differentiation of embryonic stem cells.
MDL:
MFCD26142628
Molecular Formula:
C34H49N5O6
Molecular Weight:
623.8
Package Type:
Vial
PG:
III
Precautions:
P260, P280, P301, P310, P304, P340
Product Description:
Antiprotozoal [1]. Potent inhibitor of histone deacetylase (HDAC) [1,2]. Inhibits proliferation [2,3]. Induces cell cycle arrest at the G1 phase [2]. Induces hyperacetylation of histone H4 [5]. Apoptosis inducer [4,8,9]. Potent anti-angiogenic compound [5-7]. Decreases HIF-1alpha protein levels and transcriptional activity in human and mouse tumor cell lines [3]. Autophagy inducer in oral squamous cell carcinoma (OSCC) cells [8]. Promotes either self-renewal or differentiation of embryonic stem cells [10].
Purity:
>98% (HPLC, TLC)
Signal word:
Danger
SMILES:
[H][C@]12CCCCN1C(=O)[C@@]([H])(NC(=O)[C@H](CC1=CN(OC)C3=C1C=CC=C3)NC(=O)[C@H](CCCCCC(=O)CC)NC2=O)C(C)CC
Solubility Chemicals:
Soluble in ethanol or DMSO.
Source / Host:
Isolated from fungus Fusarium sp.
Transportation:
Excepted Quantity
UN Nummer:
UN 2811
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 1 year after receipt when stored at -20°C. Stock solutions are stable for at least 3 months when stored at -20°C.

References

Apicidin: a novel antiprotozoal agent that inhibits parasite histone deacetylase: S.J. Darkin-Rattray, et al.; PNAS 93, 13143 (1996) | Apicidin, a histone deacetylase inhibitor, inhibits proliferation of tumor cells via induction of p21WAF1/Cip1 and gelsolin: J.W. Han, et al.; Cancer Res. 60, 6068 (2000) | Transcriptional activation of p21(WAF1/CIP1) by apicidin, a novel histone deacetylase inhibitor: J.S. Kim, et al.; BBRC 281, 866 (2001) | Apicidin, a histone deacetylase inhibitor, induces apoptosis and Fas/Fas ligand expression in human acute promyelocytic leukemia cells: S.H. Kwon, et al.; J. Biol. Chem. 277, 2073 (2002) | Apicidin, a histone deacetylase inhibitor, induces differentiation of HL-60 cells: J. Hong, et al.; Cancer Lett. 189, 197 (2003) | Regulation of the HIF-1alpha stability by histone deacetylases: S.H. Kim, et al.; Oncol. Rep. 17, 647 (2007) | Apicidin, a novel histone deacetylase inhibitor, has profound anti-growth activity in human endometrial and ovarian cancer cells: T. Ueda, et al.; Int. J. Mol. Med. 19, 301 (2007) | Apicidin, a histone deaceylase inhibitor, induces both apoptosis and autophagy in human oral squamous carcinoma cells: M.Y. Ahn, et al.; Oral. Oncol. 47, 1032 (2011) | Apicidin induces endoplasmic reticulum stress- and mitochondrial dysfunction-associated apoptosis via phospholipase Cgamma1- and Ca(2+)-dependent pathway in mouse Neuro-2a neuroblastoma cells: J.H. Choi, et al.; Apoptosis 17, 1340 (2012) | Histone Deacetylase Inhibitors in Cell Pluripotency, Differentiation, and Reprogramming: A. Kretsovali, et al.; Stem Cells Int. 2012, 1 (2012)

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