505-44-2

505-44-2 structure

Name: Iberin
Chemical Name: 1-isothiocyanato-3-methylsulfinylpropane
CAS Number: 505-44-2
Molecular Formula: C₅H₉NOS₂
Molecular Weight: 163.261
Catalog: Signaling Pathways Apoptosis Apoptosis
Create Date: 2017-05-27 03:05:16
Modify Date: 2024-01-14 20:10:21
Iberin, a sulfoxide analogue of sulforaphane, is a naturally occurring member of isothiocyanate family. It inhibits cell survival with an IC50 of 2.3 μM in HL60 cell.

Name	1-isothiocyanato-3-methylsulfinylpropane
Synonyms	sulfpraphane 3-isothiocyanatopropyl methyl sulfoxide METHYLSULFINYLPROPYLISOTHIOCYANATE Propane, 1-isothiocyanato-3-(methylsulfinyl)- 3-Methylsulfinylpropyl isothiocyanate Iberin 1-Isothiocyanato-3-(methylsulfinyl)propane C5H9NOS2 3-Methylsulphinylpropylisothiocyanate

Description	Iberin, a sulfoxide analogue of sulforaphane, is a naturally occurring member of isothiocyanate family. It inhibits cell survival with an IC50 of 2.3 μM in HL60 cell.
Related Catalog	Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer Natural Products >> Others
Target	Human Endogenous Metabolite
In Vitro	Iberin inhibits the growth of neuroblastoma cells in a dose- and time-dependent manner. The iberin-induced cell cycle arrest in neuroblastoma cells is associated with inhibition of expression of cyclin-dependent kinase Cdk2, Cdk4, and Cdk6 proteins. There is an increase in apoptotic cell death in iberin treated cells as compared with control cells. The iberin-induced apoptosis is found to be associated with activation of caspase-9, caspase-3, and PARP[2]. Iberin inhibits growth of human glioblastoma cells in cell proliferation assays, enhances cytotoxicity, and induces apoptosis by activation of caspase-3 and caspase-9[3].
In Vivo	Iberin is tested in an in vivo foreign-body infection mouse model, and the results show no significantly difference in bacterial clearance between treated and nontreated miced[4]. Iberin increases tissue levels of the phase II detoxification enzymes quinone reductase and glutathione S-transferase in a variety of rat tissues[5].
Cell Assay	Cells are plated at a density of 1×105 cells/well in microtiter plates and treated with different concentrations of iberin (1, 2.5, 10 and 25 μM). Then 20 μL of 5 mg/mL MTT in PBS, is added to each well and allowed to incubate for a further 4 h. After 4 h of incubation, 100 μL of DMSO is added to each well to dissolve the formazan crystals. Absorbance values at 550 nm are measured with a microplate reader[2].
Animal Admin	Rats: Groups of five rats are dosed by oral intubation with the test compounds, as solutions in soybean oil, each day for 5 days. This doses used are 4.0 mg/kg/day for AITC, 5.9 mg/kg/day for iberverin, 6.5 mg/kg/day for iberin, 6.4 mg/kg/day for erucin, 7.1 mg/kg/day for sulforaphane, and 7.2 mg/kg/day for cheirolin. The volume of solution administered is 2 mL/kg in all cases. Ten control rats are dosed with soybean oil alone[5]. Mice: Iberin is diluted in 96% ethanol to a concentration of 32 mg/mL followed by a 40x dilution in 0.9% NaCl. The mice are injected with 0.2 mL of the final solution, corresponding to 8 μg/g of body weight. The placebo group is injected with a 2.4% ethanol solution (96% ethanol–0.9% NaCl) corresponding to the amount of ethanol that the iberin-treated group received. Mice are treated every 12 h from day 2 preinsertion to day 2 postinsertion, and treatment is continued until 12 h before the mice are euthanized[4].
References	[1]. Jakubikova J, et al. Isothiocyanates induce cell cycle arrest, apoptosis and mitochondrial potential depolarization in HL-60 and multidrug-resistant cell lines. Anticancer Res. 2005 Sep-Oct;25(5):3375-86. [2]. Jadhav U, et al. Iberin induces cell cycle arrest and apoptosis in human neuroblastoma cells. [3]. Jadhav U, et al. Dietary isothiocyanate iberin inhibits growth and induces apoptosis in human glioblastoma cells. J Pharmacol Sci. 2007 Feb;103(2):247-51. [4]. Jakobsen TH, et al. Food as a source for quorum sensing inhibitors: iberin from horseradish revealed as a quorumsensing inhibitor of Pseudomonas aeruginosa. Appl Environ Microbiol. 2012 Apr;78(7):2410-21. [5]. Munday R, et al. Induction of phase II detoxification enzymes in rats by plant-derived isothiocyanates: comparison of allyl isothiocyanate with sulforaphane and related compounds. J Agric Food Chem. 2004 Apr 7;52(7):1867-71.

Density	1.2±0.1 g/cm3
Boiling Point	362.4±25.0 °C at 760 mmHg
Molecular Formula	C₅H₉NOS₂
Molecular Weight	163.261
Flash Point	173.0±23.2 °C
Exact Mass	163.012558
PSA	80.73000
LogP	-0.05
Vapour Pressure	0.0±0.8 mmHg at 25°C
Index of Refraction	1.577
Storage condition	2-8℃

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NX8950000

CHEMICAL NAME :: Isothiocyanic acid, 3-(methylsulfinyl)propyl ester

CAS REGISTRY NUMBER :: 505-44-2

LAST UPDATED :: 199206

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C5-H9-N-O-S2

MOLECULAR WEIGHT :: 163.27

WISWESSER LINE NOTATION :: SCN3SO&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 90 mg/kg

TOXIC EFFECTS :: Behavioral - coma

REFERENCE :: FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 18,159,1980 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 100 mg/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

REFERENCE :: FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 18,159,1980

463-71-8

196200-06-3

~50%

505-44-2

Literature: Moon, Joon-Kwan; Kim, Jun-Ran; Ahn, Young-Joon; Shibamoto, Takayuki Journal of Agricultural and Food Chemistry, 2010 , vol. 58, # 11 p. 6672 - 6677

75-15-0

15813-61-3

505-44-2

Literature: Karrer et al. Helvetica Chimica Acta, 1950 , vol. 33, p. 1237,1240,1241

196200-06-3

505-44-2

Literature: Karrer et al. Helvetica Chimica Acta, 1950 , vol. 33, p. 1237,1240,1241

Precursor 3
463-71-8 196200-06-3 75-15-0
DownStream 0

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