Radicicol

Specifications / Handling

More Information
Product Details
Synonyms	Monorden; NSC 294404; RHI-12648
Product Type	Chemical
Properties
Formula	C₁₈H₁₇ClO₆
MW	364.8
Merck Index	14: 6253
CAS	12772-57-5
RTECS	RR1105000
Source/Host Chemicals	Isolated from Gilmaniella sp.
Purity Chemicals	≥99% (HPLC)
Appearance	White to slightly yellow solid.
Solubility	Soluble in DMSO, methanol, acetone, ethyl acetate or chloroform.
InChi Key	WYZWZEOGROVVHK-HAJNAQHISA-N
Smiles	[H][C@@]12C[C@@H](C)OC(=O)C3=C(O)C=C(O)C(Cl)=C3CC(=O)\C=C\C=C/[C@]1([H])O2
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Keep cool and dry. Protect from light.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C. Store solutions at -20°C in the dark.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

Antibiotic [1].
Protein tyrosine kinase inhibitor [1].
Has antifungal [4], antimalarial [6], antiangiogenic (in vivo) [2], anti-inflammatory [5] and antiviral activity.
Cyclooxygenase-2 (COX-2) expression inhibitor without affecting COX-1 expression in LPS-stimulated macrophages [3, 5].
Induces the differentiation of HL-60 cells into macrophages [4].
Potent HSP90 inhibitor [7, 9, 12].
Anticancer compound [7, 9, 12].
In vivo Rad/Raf interaction inhibitor [8].
Inhibitor of AP-1-, NF-κB- and serum response factor (SRF)-mediated transcription. Suppresses expression of iNOS (NOS II) [10].
Non-competitive inhibitor of ATP citrate lyase [11].
DNA topoisomerase VI and type II DNA topoisomerase inhibitor [13].
Protects against LPS/IFN-γ-induced neuronal cell death [14].
Apoptosis inducer [16].
Pyruvate dehydrogenase kinase 3 (PDK3) inhibitor, by binding directly to the ATP-binding pocket [15].

Product References

Potent and specific inhibition of p60v-src protein kinase both in vivo and in vitro by radicicol: H.J. Kwon, et al.; Cancer Res. 52, 6926 (1992)
Radicicol, a microbial cell differentiation modulator, inhibits in vivo angiogenesis: T. Oikawa, et al.; Eur. J. Pharmacol. 241, 221 (1993)
Radicicol, a protein tyrosine kinase inhibitor, suppresses the expression of mitogen-inducible cyclooxygenase in macrophages stimulated with lipopolysaccharide and in experimental glomerulonephritis: P. Chanmugam, et al.; J. Biol. Chem. 270, 5418 (1995)
Induction of differentiation of HL-60 cells by the anti-fungal antibiotic, radicicol: Y. Shimada, et al.; J. Antibiot. 48, 824 (1995)
Inhibitor of protein tyrosine kinase, radicicol, suppresses the expression of cyclooxygenase and pro-inflammatory cytokines in LPS-stimulated rat alveolar macrophage in part by accelerating degradation of mRNA: L. Feng, et al.; Adv. Exp. Med. Biol. 407, 281 (1997)
Antimalarial activity of radicicol, heptelidic acid and other fungal metabolites: Y. Tanaka, et al.; J. Antibiot. 51, 153 (1998)
Targeting of the protein chaperone, HSP90, by the transformation suppressing agent, radicicol: S.V. Sharma, et al.; Oncogene 16, 2369 (1998)
Identification of radicicol as an inhibitor of in vivo Ras/Raf interaction with the yeast two-hybrid screening system: S.W. Ki, et al.; J. Antibiot. 51, 936 (1998)
Structural basis for inhibition of the Hsp90 molecular chaperone by the antitumor antibiotics radicicol and geldanamycin: S.M. Roe, et al.; J. Med. Chem. 42, 260 (1999)
Radicicol suppresses expression of inducible nitric-oxide synthase by blocking p38 kinase and nuclear factor-kappaB/Rel in lipopolysaccharide-stimulated macrophages: Y.J. Jeon, et al.; J. Pharmacol. Exp. Ther. 294, 548 (2000)
Radicicol binds and inhibits mammalian ATP citrate lyase: S.W. Ki, et al.; J. Biol. Chem. 275, 39231 (2000)
Heat shock protein 90 (Hsp90) chaperone complex inhibitor, radicicol, potentiated radiation-induced cell killing in a hormone-sensitive prostate cancer cell line through degradation of the androgen receptor: K. Harashima, et al.; Int. J. Radiat. Biol. 81, 63 (2005)
The HSP90 and DNA topoisomerase VI inhibitor radicicol also inhibits human type II DNA topoisomerase: D. Gadelle, et al.; Biochem. Pharmacol. 72, 1207 (2006)
Protective effect of radicicol against LPS/IFN-gamma-induced neuronal cell death in rat cortical neuron-glia cultures: M.J. Sohn, et al.; Life Sci. 80, 1706 (2007)
Distinct Structural Mechanisms for Inhibition of Pyruvate Dehydrogenase Kinase Isoforms by AZD7545, Dichloroacetate, and Radicicol: M. Kato, et al.; Cell Structure 15, 992 (2007)
Radicicol, an inhibitor of Hsp90, enhances TRAIL-induced apoptosis in human epithelial ovarian carcinoma cells by promoting activation of apoptosis-related proteins: Y.J. Kim, et al.; Mol. Cell Biochem. 359, 33 (2012)

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