Probucol | CAS#23288-49-5

MedKoo Cat#: 318571 | Name: Probucol

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Description:

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

Probucol is a potent antioxidant that inhibits the oxidation of cholesterol in LDL, which prevents the formation of macrophage-derived foam cells that lead to atherosclerotic vascular lesions. Probucol inhibits up to 80% efflux of cholesterol from J774 macrophages by impairing the translocation of ATP-binding cassette transporter A1 from intracellular compartments to the plasma membrane.

Chemical Structure

Probucol

CAS#23288-49-5

Theoretical Analysis

MedKoo Cat#: 318571

Name: Probucol

CAS#: 23288-49-5

Chemical Formula: C31H48O2S2

Exact Mass: 516.3096

Molecular Weight: 516.84

Elemental Analysis: C, 72.04; H, 9.36; O, 6.19; S, 12.41

Price and Availability

Size	Price	Availability	Quantity
2g	USD 150.00
5g	USD 250.00
10g	USD 450.00
20g	USD 950.00
50g	USD 1,650.00

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Synonym

Probucol; Lorelco; Biphenabid; Bisphenabid; Lesterol; Lurselle; Superlipid; Biphenabid; DH 581; DH-581; DH581; Hoechst Brand of Probucol;

IUPAC/Chemical Name

2,6-ditert-butyl-4-[2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanylpropan-2-ylsulfanyl]phenol

InChi Key

FYPMFJGVHOHGLL-UHFFFAOYSA-N

InChi Code

InChI=1S/C31H48O2S2/c1-27(2,3)21-15-19(16-22(25(21)32)28(4,5)6)34-31(13,14)35-20-17-23(29(7,8)9)26(33)24(18-20)30(10,11)12/h15-18,32-33H,1-14H3

SMILES Code

CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)SC(C)(C)SC2=CC(=C(C(=C2)C(C)(C)C)O)C(C)(C)C

Appearance

Solid powder

Purity

>98% (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, not in water

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:

Probucol (DH-581) is an anti-hyperlipidemic agent by lowering the level of cholesterol in the bloodstream by increasing the rate of LDL catabolism.

In vitro activity:

Probucol inhibited cholesterol efflux up to 80% in J774 macrophages expressing ABCA1. Probucol inhibited cholesterol efflux from normal human skin fibroblasts but not from fibroblasts from a Tangier patient. Probucol also inhibited the formation of an ABCA1-linked cholesterol oxidase sensitive plasma membrane domain. Consistent with the inhibitory effect on ABCA1 translocation to the plasma membrane, probucol reduced cell surface-specific [125I]-labeled apolipoprotein-AI binding. Reference: Arterioscler Thromb Vasc Biol. 2004 Dec;24(12):2345-50. https://pubmed.ncbi.nlm.nih.gov/15514211/

In vivo activity:

The objective of the present study was to examine the effect of probucol on ischemia/reperfusion-induced cardiomyocyte apoptosis in rabbits. Probucol pretreatment apparently caused a decrease in the apoptotic index ((21.64 +/- 3.08) %, p < 0.01 versus the sham or control group) and serum MDA concentration (1.95 +/- 0.51 micromol/L, p < 0.01 versus the sham or control group), and increased the levels of serum SOD (162.61 +/- 16.13 microU/L, p < 0.01 versus the sham group; p < 0.05 versus the control group). The caspase-3 activation and mitochondrial cytochrome c release in the control group were also higher than those in the treated group (p < 0.01). The present study shows that probucol attenuates ischemia/reperfusion-induced cardiomyocyte apoptosis. The protective effect of probucol on the myocardium may be partly due to its antioxidant activity. Reference: Scand J Clin Lab Invest. 2006;66(7):549-58. https://pubmed.ncbi.nlm.nih.gov/17101546/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	58.04
	DMSO	74.3	143.82
	Ethanol	64.0	123.83
	Water	0.7	1.30

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 516.84 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. Favari E, Zanotti I, Zimetti F, Ronda N, Bernini F, Rothblat GH. Probucol inhibits ABCA1-mediated cellular lipid efflux. Arterioscler Thromb Vasc Biol. 2004 Dec;24(12):2345-50. doi: 10.1161/01.ATV.0000148706.15947.8a. Epub 2004 Oct 28. PMID: 15514211. 2. Wu CA, Tsujita M, Hayashi M, Yokoyama S. Probucol inactivates ABCA1 in the plasma membrane with respect to its mediation of apolipoprotein binding and high density lipoprotein assembly and to its proteolytic degradation. J Biol Chem. 2004 Jul 16;279(29):30168-74. doi: 10.1074/jbc.M403765200. Epub 2004 May 12. PMID: 15140889. 3. Wu BJ, Di Girolamo N, Beck K, Hanratty CG, Choy K, Hou JY, Ward MR, Stocker R. Probucol [4,4'-[(1-methylethylidene)bis(thio)]bis-[2,6-bis(1,1-dimethylethyl)phenol]] inhibits compensatory remodeling and promotes lumen loss associated with atherosclerosis in apolipoprotein E-deficient mice. J Pharmacol Exp Ther. 2007 May;321(2):477-84. doi: 10.1124/jpet.106.118612. Epub 2007 Feb 9. PMID: 17293560. 4. Ruixing Y, Al-Ghazali R, Wenwu L, Jinzhen W. Pretreatment with probucol attenuates cardiomyocyte apoptosis in a rabbit model of ischemia/reperfusion. Scand J Clin Lab Invest. 2006;66(7):549-58. doi: 10.1080/00365510600863820. PMID: 17101546.

In vitro protocol:

In vivo protocol:

1. Wu BJ, Di Girolamo N, Beck K, Hanratty CG, Choy K, Hou JY, Ward MR, Stocker R. Probucol [4,4'-[(1-methylethylidene)bis(thio)]bis-[2,6-bis(1,1-dimethylethyl)phenol]] inhibits compensatory remodeling and promotes lumen loss associated with atherosclerosis in apolipoprotein E-deficient mice. J Pharmacol Exp Ther. 2007 May;321(2):477-84. doi: 10.1124/jpet.106.118612. Epub 2007 Feb 9. PMID: 17293560. 2. Ruixing Y, Al-Ghazali R, Wenwu L, Jinzhen W. Pretreatment with probucol attenuates cardiomyocyte apoptosis in a rabbit model of ischemia/reperfusion. Scand J Clin Lab Invest. 2006;66(7):549-58. doi: 10.1080/00365510600863820. PMID: 17101546.

1: Wang YY, Li H, Wang XH, Yuan M, Li GP. Probucol inhibits MMP-9 expression through regulating miR-497 in HUVECs and apoE knockout mice. Thromb Res. 2016 Apr;140:51-8. doi: 10.1016/j.thromres.2016.02.012. Epub 2016 Feb 12. PubMed PMID: 26897284. 2: Wang YY, Li H, Wang XH, Yuan M, Li GP. Combination of rosuvastatin and probucol inhibits MMP-9 expression via upregulation of miR-497 in cultured HUVECs and apoE knockout mice. J Thromb Thrombolysis. 2016 May;41(4):592-605. doi: 10.1007/s11239-015-1291-6. PubMed PMID: 26502925. 3: Yakushiji E, Ayaori M, Nishida T, Shiotani K, Takiguchi S, Nakaya K, Uto-Kondo H, Ogura M, Sasaki M, Yogo M, Komatsu T, Lu R, Yokoyama S, Ikewaki K. Probucol-Oxidized Products, Spiroquinone and Diphenoquinone, Promote Reverse Cholesterol Transport in Mice. Arterioscler Thromb Vasc Biol. 2016 Apr;36(4):591-7. doi: 10.1161/ATVBAHA.115.306376. Epub 2016 Feb 4. PubMed PMID: 26848156. 4: Kufner S, Sorges J, Mehilli J, Cassese S, Repp J, Wiebe J, Lohaus R, Lahmann A, Rheude T, Ibrahim T, Massberg S, Laugwitz KL, Kastrati A, Byrne RA; ISAR-TEST 5 Investigators. Randomized Trial of Polymer-Free Sirolimus- and Probucol-Eluting Stents Versus Durable Polymer Zotarolimus-Eluting Stents: Five-Year Results of the ISAR-TEST 5 Trial. JACC Cardiovasc Interv. 2016 Mar 18. pii: S1936-8798(16)00039-X. doi: 10.1016/j.jcin.2016.01.009. [Epub ahead of print] PubMed PMID: 27017366. 5: Chai YL, Xu JZ, Zhang YL, Sheng GT. Effects of probucol on cultured human umbilical vein endothelial cells injured by hypoxia/reoxygenation. Genet Mol Res. 2016 Mar 4;15(1). doi: 10.4238/gmr.15016752. PubMed PMID: 26985931. 6: Shao Q, Korantzopoulos P, Fu H, Ye L, Liu E, Xu G, Li G, Liu T. Effects of probucol on left atrial remodeling in patients with paroxysmal atrial fibrillation. Int J Cardiol. 2016 Mar 15;207:117-9. doi: 10.1016/j.ijcard.2016.01.017. Epub 2016 Jan 6. PubMed PMID: 26800130. 7: Zhang KQ, Chen D, Sun DQ, Zhang H, Li B, Fu Q. Probucol Improves Erectile Function by Restoring Endothelial Function and Preventing Cavernous Fibrosis in Streptozotocin-induced Diabetic Rats. Urology. 2016 Feb 16. pii: S0090-4295(16)00133-3. doi: 10.1016/j.urology.2016.02.004. [Epub ahead of print] PubMed PMID: 26896732. 8: Liu G, Ji W, Huang J, Liu L, Wang Y. 4-HNE expression in diabetic rat kidneys and the protective effects of probucol. J Endocrinol Invest. 2016 Feb 1. [Epub ahead of print] PubMed PMID: 26830905. 9: Chen Y, Pandiri I, Joe Y, Kim HJ, Kim SK, Park J, Ryu J, Cho GJ, Park JW, Ryter SW, Chung HT. Synergistic Effects of Cilostazol and Probucol on ER Stress-Induced Hepatic Steatosis via Heme Oxygenase-1-Dependent Activation of Mitochondrial Biogenesis. Oxid Med Cell Longev. 2016;2016:3949813. Epub 2016 Jan 6. PubMed PMID: 27057275. 10: Yamashita S, Masuda D, Ohama T, Arai H, Bujo H, Kagimura T, Kita T, Matsuzaki M, Saito Y, Fukushima M, Matsuzawa Y; PROSPECTIVE Study Group. Rationale and Design of the PROSPECTIVE Trial: Probucol Trial for Secondary Prevention of Atherosclerotic Events in Patients with Prior Coronary Heart Disease. J Atheroscler Thromb. 2016 Jan 22. [Epub ahead of print] PubMed PMID: 26803913. 11: Lin M, Dai H, Zhao S. Long-term atorvastatin-ezetimibe-probucol triple therapy for homozygous familial hypercholesterolaemia from early childhood. Cardiol Young. 2016 Jan;26(1):197-201. doi: 10.1017/S1047951115000591. Epub 2015 Apr 24. PubMed PMID: 25907359. 12: Ma J, Zhao S, Gao G, Chang H, Ma P, Jin B. Probucol Protects Against Asymmetric Dimethylarginine-Induced Apoptosis in the Cultured Human Brain Microvascular Endothelial Cells. J Mol Neurosci. 2015 Dec;57(4):546-53. doi: 10.1007/s12031-015-0635-1. Epub 2015 Aug 9. PubMed PMID: 26254912. 13: Mooranian A, Negrulj R, Arfuso F, Al-Salami H. The effect of a tertiary bile acid, taurocholic acid, on the morphology and physical characteristics of microencapsulated probucol: potential applications in diabetes: a characterization study. Drug Deliv Transl Res. 2015 Oct;5(5):511-22. doi: 10.1007/s13346-015-0248-9. PubMed PMID: 26242686. 14: Zhu H, Chen X, Cai G, Zheng Y, Liu M, Liu W, Yao H, Wang Y, Li W, Wu H, Lun L, Zhang J, Guan X, Yin S, Zhuang X, Li J, Liu Y, Zhou C. Telmisartan combined with probucol effectively reduces urinary protein in patients with Type 2 diabetes: A randomized, double-blind, placebo-controlled, multi-center clinical study. J Diabetes. 2015 Oct 12. doi: 10.1111/1753-0407.12347. [Epub ahead of print] PubMed PMID: 26458146. 15: Mooranian A, Negrulj R, Arfuso F, Al-Salami H. Multicompartmental, multilayered probucol microcapsules for diabetes mellitus: Formulation characterization and effects on production of insulin and inflammation in a pancreatic β-cell line. Artif Cells Nanomed Biotechnol. 2015 Sep 17:1-12. [Epub ahead of print] PubMed PMID: 26377035. 16: Wang R, Wei RB, Yang Y, Wang N, Huang MJ, Cao CM, Wang ZC, Cai GY, Chen XM. Effect of probucol on insulin resistance in patients with non-diabetic chronic kidney disease. J Geriatr Cardiol. 2015 Sep;12(5):521-7. doi: 10.11909/j.issn.1671-5411.2015.05.020. PubMed PMID: 26512244; PubMed Central PMCID: PMC4605948. 17: Wang N, Wei RB, Li QP, Yang X, Li P, Huang MJ, Wang R, Cai GY, Chen XM. Renal Protective Effect of Probucol in Rats with Contrast-Induced Nephropathy and its Underlying Mechanism. Med Sci Monit. 2015 Sep 26;21:2886-92. doi: 10.12659/MSM.895543. PubMed PMID: 26408630; PubMed Central PMCID: PMC4588667. 18: Higashi K, Seo A, Egami K, Otsuka N, Limwikrant W, Yamamoto K, Moribe K. Mechanistic insight into the dramatic improvement of probucol dissolution in neutral solutions by solid dispersion in Eudragit E PO with saccharin. J Pharm Pharmacol. 2015 Aug 14. doi: 10.1111/jphp.12469. [Epub ahead of print] PubMed PMID: 26272472. 19: Yamashita S, Masuda D, Matsuzawa Y. Did we abandon probucol too soon? Curr Opin Lipidol. 2015 Aug;26(4):304-16. doi: 10.1097/MOL.0000000000000199. Review. PubMed PMID: 26125504. 20: Egami K, Higashi K, Yamamoto K, Moribe K. Crystallization of Probucol in Nanoparticles Revealed by AFM Analysis in Aqueous Solution. Mol Pharm. 2015 Aug 3;12(8):2972-80. doi: 10.1021/acs.molpharmaceut.5b00236. Epub 2015 Jul 7. PubMed PMID: 26106951.