Radicicol

Names

[ Name ]:
Radicicol

[Synonym ]:
monorden
monorderne
[Biotinyl]-Radicicol
(1aR,2Z,4E,14R,15aR)-8-Chloro-9,11-dihydroxy-14-methyl-1a,14,15,15a-tetrahydro-6H-oxireno[e][2]benzoxacyclotetradecine-6,12(7H)-dione
Monorden/Radicicol
humicola fuscoatra
Radicicol from Diheterospora chlamydosporia
6H-Oxireno[e][2]benzoxacyclotetradecin-6,12(7H)-dione, 8-chloro-1a,14,15,15a-tetrahydro-9,11-dihydroxy-14-methyl-, (1aR,2Z,4E,14R,15aR)-
MFCD01709459
KF9-A
RADISICOL
Radicicol
[TAMRA]-Radicicol
MONORODENE
FO-4910

Biological Activity

[Description]:

Radicicol is an inhibitor of the ATPase/kinase with IC50 values of 1 μM, 100 μM and 400 μM, respectively for Hsp90, Topo VI and PDK3 [1]. Radicicol inhibits a wide variety of tumor cell lines by targeting Hsp90, binds to the ATPase domain of Hsp90 and prevents maturation of Hsp90 clients, leading to proteasomal degradation [2]. Radicicol is an antifungal antibiotic with antimalarial activity, impairs mitochondrial replication by targeting P. falciparum topoisomerase VIB[2]. Radicicol is an inhibitor of fat mass and obesity-associated protein (FTO), exhibits a dose-dependent inhibition of FTO demethylation activity with an IC50 value of 16.04 µM[3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Infection

Signaling Pathways >> Membrane Transporter/Ion Channel >> ATP Synthase

[Target]

IC50: of 1 μM (Hsp90), 100 μM (Topo VI) and 400 μM (PDK3)[1]

[References]

[1]. Kato M, et al. Distinct structural mechanisms for inhibition of pyruvate dehydrogenase kinase isoforms by AZD7545, dichloroacetate, and radicicol. Structure. 2007 Aug;15(8):992-1004. Epub 2007 Aug 2.

[2]. Chalapareddy S, et al. Radicicol confers mid-schizont arrest by inhibiting mitochondrial replication in Plasmodium falciparum. Antimicrob Agents Chemother. 2014 Aug;58(8):4341-52.

[3]. Wang R, et al. Identification of Natural Compound Radicicol as a Potent FTO Inhibitor. Mol Pharm. 2018 Sep 4;15(9):4092-4098.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
656.2±55.0 °C at 760 mmHg

[ Melting Point ]:
190-194ºC

[ Molecular Formula ]:
C₁₈H₁₇ClO₆

[ Molecular Weight ]:
364.777

[ Flash Point ]:
350.7±31.5 °C

[ Exact Mass ]:
364.071381

[ PSA ]:
96.36000

[ LogP ]:
1.53

[ Vapour Pressure ]:
0.0±2.0 mmHg at 25°C

[ Index of Refraction ]:
1.583

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RR1105000

CHEMICAL NAME :: 6H-Oxireno(e)(2)benzoxacyclotetradecin-6,12(7H)-dione , 8-chloro-1a,14,15,15a-tetrahydro-9, 11-dihydroxy-14-methyl-

CAS REGISTRY NUMBER :: 12772-57-5

LAST UPDATED :: 199609

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C18-H17-Cl-O6

MOLECULAR WEIGHT :: 364.80

WISWESSER LINE NOTATION :: T F3-14-6 BVO GO MV IU KUTT&J D1 PG QQ SQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 300 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 48,824,1995

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 175 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 2,448,1980

Safety Information

[ Symbol ]:

GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301-H340-H350

[ Precautionary Statements ]:
Missing Phrase - N15.00950417-P201-P280-P308 + P313

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
26

[ RIDADR ]:
UN 2811 6.1/PG 3

[ WGK Germany ]:
1

[ RTECS ]:
RR1105000

[ Hazard Class ]:
6.1

[ HS Code ]:
29322090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Screening for negative effects of candidate ascidian antifoulant compounds on a target aquaculture species, Perna canaliculus Gmelin.

Biofouling 29(1) , 29-37, (2013)

The natural chemical compounds radicicol, polygodial and ubiquinone-10 (Q10) have previously been identified as inhibitors of metamorphosis in ascidian larvae. Accordingly, they have potential as a sp...

[Thermosensitization of tumor cells with inhibitors of chaperone activity and expression].

Biomed. Khim. 58(6) , 662-72, (2012)

Effects of inhibitors of the heat shock protein 90 (HSP90) chaperone activity and inhibitors of the heat shock protein (HSP) expression on sensitivity of HeLa tumor cells to hyperthermia were studied....

Geldanamycin and its derivatives as Hsp90 inhibitors.

Front. Biosci. (Landmark Ed.) 17 , 2269-77, (2012)

The Hsp90 molecule, one of the most abundant heat shock proteins in mammalian cells, maintains homeostasis and prevents stress-induced cellular damage. Hsp90 is expressed under normal conditions at a ...