Iberin | CAS#505-44-2 | sulforaphane homolog | antioxidant

MedKoo Cat#: 540215 | Name: Iberin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Iberin is a sulforaphane homolog and antioxidant. It induces phase II enzyme activity and suppresses CDK expression, inducing apoptosis in cancer cells.

Chemical Structure

Iberin

CAS#505-44-2

Theoretical Analysis

MedKoo Cat#: 540215

Name: Iberin

CAS#: 505-44-2

Chemical Formula: C5H9NOS2

Exact Mass: 163.0126

Molecular Weight: 163.25

Elemental Analysis: C, 36.79; H, 5.56; N, 8.58; O, 9.80; S, 39.28

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks
10mg	USD 600.00	2 Weeks

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Synonym

1-Isothiocyanato-3-(methylsulfinyl)propane; 3-Methylsulfinylpropyl isothiocyanate; 3-Methylsulphinylpropylisothiocyanate; Iberin

IUPAC/Chemical Name

1-isothiocyanato-3-(methylsulfinyl)propane

InChi Key

LELAOEBVZLPXAZ-UHFFFAOYSA-N

InChi Code

InChI=1S/C5H9NOS2/c1-9(7)4-2-3-6-5-8/h2-4H2,1H3

SMILES Code

S=C=NCCCS(C)=O

Appearance

A solution in ethanol

Purity

>95% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Iberin (NSC 321801), a sulfoxide analogue of sulforaphane, is a naturally occurring member of isothiocyanate family. Iberin inhibits cell survival with an IC50 of 2.3 μM in HL60 cell. Iberin induces apoptosis.

In vitro activity:

As such, this study performed a slide biofilm assay in order to determine if iberin was able to reduce biofilm formation by P. aeruginosa through the downregulation of pel and psl. Figure 5 shows that the sample treated with 500 μM iberin had significantly less biofilm formation than the control sample in ABTGC. This suggests that iberin may be used not only as an antipathogenic agent but also as an antibiofilm agent. Reference: Antimicrob Agents Chemother. 2014 Nov;58(11):6648-59. https://pubmed.ncbi.nlm.nih.gov/25155599/

In vivo activity:

The in vivo tumorgenesis study further evidenced the protection of Iberin against OC development. Besides, Iberin displayed a synergistic effect on the enhancement of chemo-sensitivity in OC cells. In summary, this study demonstrates the anti-tumor effect of Iberin on OC and its potential as a therapeutic agent against OC in the future. Reference: Biomed Pharmacother. 2021 Oct;142:111533. https://pubmed.ncbi.nlm.nih.gov/34148735/

	Solvent	mg/mL	mM
Solubility
	DMF	16.0	98.01
	DMSO	163.0	998.45
	Ethanol	10.5	64.32
	PBS (pH 7.2)	10.0	61.25

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 163.25 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Tan SY, Liu Y, Chua SL, Vejborg RM, Jakobsen TH, Chew SC, Li Y, Nielsen TE, Tolker-Nielsen T, Yang L, Givskov M. Comparative systems biology analysis to study the mode of action of the isothiocyanate compound Iberin on Pseudomonas aeruginosa. Antimicrob Agents Chemother. 2014 Nov;58(11):6648-59. doi: 10.1128/AAC.02620-13. Epub 2014 Aug 25. PMID: 25155599; PMCID: PMC4249438. 2. Jakobsen TH, Bragason SK, Phipps RK, Christensen LD, van Gennip M, Alhede M, Skindersoe M, Larsen TO, Høiby N, Bjarnsholt T, Givskov M. Food as a source for quorum sensing inhibitors: iberin from horseradish revealed as a quorum sensing inhibitor of Pseudomonas aeruginosa. Appl Environ Microbiol. 2012 Apr;78(7):2410-21. doi: 10.1128/AEM.05992-11. Epub 2012 Jan 27. PMID: 22286987; PMCID: PMC3302586. 3. Gong TT, Guo Q, Li X, Zhang TN, Liu FH, He XH, Lin B, Wu QJ. Isothiocyanate Iberin inhibits cell proliferation and induces cell apoptosis in the progression of ovarian cancer by mediating ROS accumulation and GPX1 expression. Biomed Pharmacother. 2021 Oct;142:111533. doi: 10.1016/j.biopha.2021.111533. Epub 2021 Jun 17. PMID: 34148735. 4. Munday R, Munday CM. 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. doi: 10.1021/jf030549s. PMID: 15053522.

In vitro protocol:

In vivo protocol:

1. Gong TT, Guo Q, Li X, Zhang TN, Liu FH, He XH, Lin B, Wu QJ. Isothiocyanate Iberin inhibits cell proliferation and induces cell apoptosis in the progression of ovarian cancer by mediating ROS accumulation and GPX1 expression. Biomed Pharmacother. 2021 Oct;142:111533. doi: 10.1016/j.biopha.2021.111533. Epub 2021 Jun 17. PMID: 34148735. 2. Munday R, Munday CM. 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. doi: 10.1021/jf030549s. PMID: 15053522.

1: Tan SY, Liu Y, Chua SL, Vejborg RM, Jakobsen TH, Chew SC, Li Y, Nielsen TE, Tolker-Nielsen T, Yang L, Givskov M. Comparative systems biology analysis to study the mode of action of the isothiocyanate compound Iberin on Pseudomonas aeruginosa. Antimicrob Agents Chemother. 2014 Nov;58(11):6648-59. doi: 10.1128/AAC.02620-13. Epub 2014 Aug 25. PubMed PMID: 25155599; PubMed Central PMCID: PMC4249438. 2: Ernst IM, Palani K, Esatbeyoglu T, Schwarz K, Rimbach G. Synthesis and Nrf2-inducing activity of the isothiocyanates iberverin, iberin and cheirolin. Pharmacol Res. 2013 Apr;70(1):155-62. doi: 10.1016/j.phrs.2013.01.011. Epub 2013 Feb 9. PubMed PMID: 23403058. 3: Jakobsen TH, Bragason SK, Phipps RK, Christensen LD, van Gennip M, Alhede M, Skindersoe M, Larsen TO, Høiby N, Bjarnsholt T, Givskov M. Food as a source for quorum sensing inhibitors: iberin from horseradish revealed as a quorum sensing inhibitor of Pseudomonas aeruginosa. Appl Environ Microbiol. 2012 Apr;78(7):2410-21. doi: 10.1128/AEM.05992-11. Epub 2012 Jan 27. PubMed PMID: 22286987; PubMed Central PMCID: PMC3302586. 4: Traka MH, Chambers KF, Lund EK, Goodlad RA, Johnson IT, Mithen RF. Involvement of KLF4 in sulforaphane- and iberin-mediated induction of p21(waf1/cip1). Nutr Cancer. 2009;61(1):137-45. doi: 10.1080/01635580802348641. PubMed PMID: 19116884. 5: Jadhav U, Ezhilarasan R, Vaughn SF, Berhow MA, Mohanam S. Iberin induces cell cycle arrest and apoptosis in human neuroblastoma cells. Int J Mol Med. 2007 Mar;19(3):353-61. PubMed PMID: 17273780; PubMed Central PMCID: PMC2435066. 6: Jadhav U, Ezhilarasan R, Vaughn SF, Berhow MA, Mohanam S. Dietary isothiocyanate iberin inhibits growth and induces apoptosis in human glioblastoma cells. J Pharmacol Sci. 2007 Feb;103(2):247-51. PubMed PMID: 17310076. 7: Shibata T, Nakashima F, Honda K, Lu YJ, Kondo T, Ushida Y, Aizawa K, Suganuma H, Oe S, Tanaka H, Takahashi T, Uchida K. Toll-like receptors as a target of food-derived anti-inflammatory compounds. J Biol Chem. 2014 Nov 21;289(47):32757-72. doi: 10.1074/jbc.M114.585901. Epub 2014 Oct 7. PubMed PMID: 25294874; PubMed Central PMCID: PMC4239626. 8: Wang W, Wang S, Howie AF, Beckett GJ, Mithen R, Bao Y. Sulforaphane, erucin, and iberin up-regulate thioredoxin reductase 1 expression in human MCF-7 cells. J Agric Food Chem. 2005 Mar 9;53(5):1417-21. PubMed PMID: 15740016. 9: Chambers KF, Bacon JR, Kemsley EK, Mills RD, Ball RY, Mithen RF, Traka MH. Gene expression profile of primary prostate epithelial and stromal cells in response to sulforaphane or iberin exposure. Prostate. 2009 Sep 15;69(13):1411-21. doi: 10.1002/pros.20986. PubMed PMID: 19489030. 10: Al Janobi AA, Mithen RF, Gasper AV, Shaw PN, Middleton RJ, Ortori CA, Barrett DA. Quantitative measurement of sulforaphane, iberin and their mercapturic acid pathway metabolites in human plasma and urine using liquid chromatography-tandem electrospray ionisation mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Dec 5;844(2):223-34. Epub 2006 Aug 23. PubMed PMID: 16931178. 11: Luang-In V, Narbad A, Nueno-Palop C, Mithen R, Bennett M, Rossiter JT. The metabolism of methylsulfinylalkyl- and methylthioalkyl-glucosinolates by a selection of human gut bacteria. Mol Nutr Food Res. 2014 Apr;58(4):875-83. doi: 10.1002/mnfr.201300377. Epub 2013 Oct 30. PubMed PMID: 24170324. 12: Jakubikova J, Bao Y, Bodo J, Sedlak J. Isothiocyanate iberin modulates phase II enzymes, posttranslational modification of histones and inhibits growth of Caco-2 cells by inducing apoptosis. Neoplasma. 2006;53(6):463-70. PubMed PMID: 17167713. 13: Wang N, Wang W, Liu C, Jin J, Shao B, Shen L. Inhibition of growth and induction of apoptosis in A549 cells by compounds from oxheart cabbage extract. J Sci Food Agric. 2016 Aug;96(11):3813-20. doi: 10.1002/jsfa.7575. Epub 2016 Feb 16. PubMed PMID: 26679410. 14: Oliviero T, Verkerk R, Vermeulen M, Dekker M. In vivo formation and bioavailability of isothiocyanates from glucosinolates in broccoli as affected by processing conditions. Mol Nutr Food Res. 2014 Jul;58(7):1447-56. doi: 10.1002/mnfr.201300894. Epub 2014 Mar 31. PubMed PMID: 24687744. 15: Slaby O, Sachlova M, Brezkova V, Hezova R, Kovarikova A, Bischofová S, Sevcikova S, Bienertova-Vasku J, Vasku A, Svoboda M, Vyzula R. Identification of microRNAs regulated by isothiocyanates and association of polymorphisms inside their target sites with risk of sporadic colorectal cancer. Nutr Cancer. 2013;65(2):247-54. doi: 10.1080/01635581.2013.756530. PubMed PMID: 23441612. 16: Wilson EA, Ennahar S, Marchioni E, Bergaentzlé M, Bindler F. Improvement in determination of isothiocyanates using high-temperature reversed-phase HPLC. J Sep Sci. 2012 Aug;35(16):2026-31. doi: 10.1002/jssc.201200071. Epub 2012 Jul 2. PubMed PMID: 22752995. 17: Ko MO, Kim MB, Lim SB. Relationship between Chemical Structure and Antimicrobial Activities of Isothiocyanates from Cruciferous Vegetables against Oral Pathogens. J Microbiol Biotechnol. 2016 Dec 28;26(12):2036-2042. doi: 10.4014/jmb.1606.06008. PubMed PMID: 27586534. 18: Steverding D, Michaels S, Read KD. In vitro and in vivo studies of trypanocidal activity of dietary isothiocyanates. Planta Med. 2014 Feb;80(2-3):183-6. doi: 10.1055/s-0033-1360262. Epub 2014 Jan 22. PubMed PMID: 24452460. 19: Barrera LN, Johnson IT, Bao Y, Cassidy A, Belshaw NJ. Colorectal cancer cells Caco-2 and HCT116 resist epigenetic effects of isothiocyanates and selenium in vitro. Eur J Nutr. 2013 Jun;52(4):1327-41. doi: 10.1007/s00394-012-0442-1. Epub 2012 Aug 26. PubMed PMID: 22923034. 20: Li D, Wu K, Howie AF, Beckett GJ, Wang W, Bao Y. Synergy between broccoli sprout extract and selenium in the upregulation of thioredoxin reductase in human hepatocytes. Food Chem. 2008 Sep 1;110(1):193-8. doi: 10.1016/j.foodchem.2008.01.032. Epub 2008 Feb 1. PubMed PMID: 26050183.