BQ123 | CAS#136553-81-6 | ETA endothelin receptor antagonist

MedKoo Cat#: 526685 | Name: BQ123

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Description:

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

BQ123 is a selective ETA endothelin receptor antagonist (Ki values are 1.4 and 1500 nM at ETA and ETB receptors respectively). BQ123 potentiates acetaminophen induced hypothermia and reduces infarction following focal cerebral ischemia in rats. BQ123 Stimulates Skeletal Muscle Antioxidant Defense via Nrf2 Activation in LPS-Treated Rats. BQ123 reduces pulmonary vascular resistance after surgical intervention for congenital heart disease. BQ123 protects against myocardial and endothelial reperfusion injury.

Chemical Structure

BQ123

CAS#136553-81-6

Theoretical Analysis

MedKoo Cat#: 526685

Name: BQ123

CAS#: 136553-81-6

Chemical Formula: C31H42N6O7

Exact Mass: 610.3115

Molecular Weight: 610.71

Elemental Analysis: C, 60.97; H, 6.93; N, 13.76; O, 18.34

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 315.00	2 Weeks
5mg	USD 850.00	2 Weeks

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Synonym

BQ123; BQ-123; BQ 123; Cyclo(D-trp-D-asp-pro-D-val-leu);

IUPAC/Chemical Name

2-((3R,6S,9R,12R,17aS)-9-((1H-indol-3-yl)methyl)-6-isobutyl-3-isopropyl-1,4,7,10,13-pentaoxohexadecahydro-1H-pyrrolo[1,2-a][1,4,7,10,13]pentaazacyclopentadecin-12-yl)acetic acid

InChi Key

VYCMAAOURFJIHD-PJNXIOHISA-N

InChi Code

InChI=1S/C31H42N6O7/c1-16(2)12-21-27(40)33-22(13-18-15-32-20-9-6-5-8-19(18)20)28(41)35-23(14-25(38)39)31(44)37-11-7-10-24(37)29(42)36-26(17(3)4)30(43)34-21/h5-6,8-9,15-17,21-24,26,32H,7,10-14H2,1-4H3,(H,33,40)(H,34,43)(H,35,41)(H,36,42)(H,38,39)/t21-,22+,23+,24-,26+/m0/s1

SMILES Code

O=C(O)C[C@H]1NC([C@@H](CC2=CNC3=C2C=CC=C3)NC([C@H](CC(C)C)NC([C@@H](C(C)C)NC([C@@](CCC4)([H])N4C1=O)=O)=O)=O)=O

Appearance

Solid powder

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, 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:

BQ-123 is a potent and selective endothelin A (ETA) receptor antagonist with an IC50 of 7.3 nM and a Ki of 25 nM.

In vitro activity:

BQ123 exhibited increased inhibition of PC-3M cells in a time-dependent manner, with inhibition rates of 22.32%, 44.88% and 64.47% at 24 h, 48 h and 72 h, respectively (P < 0.05). Reference: Zhonghua Nan Ke Xue. 2009 Apr;15(4):341-5. https://pubmed.ncbi.nlm.nih.gov/19472909/

In vivo activity:

Taken together, these results indicate that BQ123 can activate PMN-MDSCs but not M-MDSCs in mice, and that Arg1 is involved in BQ123-induced PMN-MDSC-mediated immunosuppression. Previous studies have reported that the effect of BQ123 on various diseases depends on the ET1-ETAR system (10–12, 14). To better understand the nature of the BQ123-derived PMN-MDSC, we performed additional experiments. Reference: Front Immunol. 2021; 12: 641874. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8019801/

	Solvent	mg/mL	mM
Solubility
	DMF	1.0	1.64
	DMSO	20.0	32.75
	DMSO:PBS (pH 7.2) (1:2)	0.3	0.54

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 610.71 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. Xu S, Zhou WQ, Zhang ZY, Ge JP, Gao JP. [Effects of endothelin A receptor antagonist BQ123 on the proliferation and apoptosis of prostate cancer cell line PC-3M]. Zhonghua Nan Ke Xue. 2009 Apr;15(4):341-5. Chinese. PMID: 19472909. 2. Chen Z, Zhang X, Lv S, Xing Z, Shi M, Li X, Chen M, Zuo S, Tao Y, Xiao G, Liu J, He Y. Treatment With Endothelin-A Receptor Antagonist BQ123 Attenuates Acute Inflammation in Mice Through T-Cell-Dependent Polymorphonuclear Myeloid-Derived Suppressor Cell Activation. Front Immunol. 2021 Mar 22;12:641874. doi: 10.3389/fimmu.2021.641874. PMID: 33828553; PMCID: PMC8019801. 3. Zhang B, Wang H, Jin K, Jiang T, Shen S, Luo Z, Tuo Y, Jiang X, Liu X, Hu Y, Pang Z. BQ123 selectively improved tumor perfusion and enhanced nanomedicine delivery for glioblastomas treatment. Pharmacol Res. 2018 Jun;132:211-219. doi: 10.1016/j.phrs.2017.12.017. Epub 2017 Dec 22. PMID: 29274786.

In vitro protocol:

In vivo protocol:

1. Chen Z, Zhang X, Lv S, Xing Z, Shi M, Li X, Chen M, Zuo S, Tao Y, Xiao G, Liu J, He Y. Treatment With Endothelin-A Receptor Antagonist BQ123 Attenuates Acute Inflammation in Mice Through T-Cell-Dependent Polymorphonuclear Myeloid-Derived Suppressor Cell Activation. Front Immunol. 2021 Mar 22;12:641874. doi: 10.3389/fimmu.2021.641874. PMID: 33828553; PMCID: PMC8019801. 2. Zhang B, Wang H, Jin K, Jiang T, Shen S, Luo Z, Tuo Y, Jiang X, Liu X, Hu Y, Pang Z. BQ123 selectively improved tumor perfusion and enhanced nanomedicine delivery for glioblastomas treatment. Pharmacol Res. 2018 Jun;132:211-219. doi: 10.1016/j.phrs.2017.12.017. Epub 2017 Dec 22. PMID: 29274786.

1: Kowalczyk A, Jeleń A, Żebrowska M, Balcerczak E, Gorąca A. BQ123 Stimulates Skeletal Muscle Antioxidant Defense via Nrf2 Activation in LPS-Treated Rats. Oxid Med Cell Longev. 2016;2016:2356853. doi: 10.1155/2016/2356853. Epub 2015 Dec 28. PubMed PMID: 26823945; PubMed Central PMCID: PMC4707360. 2: Veurink M, Mangioris G, Kaufmann B, Asmus L, Hennig M, Heiligenhaus A, Gurny R, Möller M, Pournaras CJ. Development of an intravitreal peptide (BQ123) sustained release system based on poly(2-hydroxyoctanoic acid) aiming at a retinal vasodilator response. J Ocul Pharmacol Ther. 2014 Aug;30(6):517-23. doi: 10.1089/jop.2013.0117. Epub 2014 May 19. PubMed PMID: 24978907. 3: Piechota A, Polańczyk A, Goraca A. Protective effects of endothelin-A receptor antagonist BQ123 against LPS-induced oxidative stress in lungs. Pharmacol Rep. 2011;63(2):494-500. PubMed PMID: 21602605. 4: Briyal S, Gulati A. Endothelin-A receptor antagonist BQ123 potentiates acetaminophen induced hypothermia and reduces infarction following focal cerebral ischemia in rats. Eur J Pharmacol. 2010 Oct 10;644(1-3):73-9. doi: 10.1016/j.ejphar.2010.06.071. Epub 2010 Jul 16. PubMed PMID: 20638381. 5: Xu S, Zhou WQ, Zhang ZY, Ge JP, Gao JP. [Effects of endothelin A receptor antagonist BQ123 on the proliferation and apoptosis of prostate cancer cell line PC-3M]. Zhonghua Nan Ke Xue. 2009 Apr;15(4):341-5. Chinese. PubMed PMID: 19472909. 6: Yang Y, Qiao J, Wu Z, Chen Y, Gao M, Ou D, Wang H. Endothelin-1 receptor antagonist BQ123 prevents pulmonary artery hypertension induced by low ambient temperature in broilers. Biol Pharm Bull. 2005 Dec;28(12):2201-5. PubMed PMID: 16327149. 7: Liss P, Carlsson PO, Nygren A, Palm F, Hansell P. Et-A receptor antagonist BQ123 prevents radiocontrast media-induced renal medullary hypoxia. Acta Radiol. 2003 Jan;44(1):111-7. PubMed PMID: 12631011. 8: Bhalla S, Matwyshyn G, Gulati A. Potentiation of morphine analgesia by BQ123, an endothelin antagonist. Peptides. 2002 Oct;23(10):1837-45. PubMed PMID: 12383872. 9: Schulze-Neick I, Li J, Reader JA, Shekerdemian L, Redington AN, Penny DJ. The endothelin antagonist BQ123 reduces pulmonary vascular resistance after surgical intervention for congenital heart disease. J Thorac Cardiovasc Surg. 2002 Sep;124(3):435-41. PubMed PMID: 12202858. 10: Polak K, Petternel V, Luksch A, Krohn J, Findl O, Polska E, Schmetterer L. Effect of endothelin and BQ123 on ocular blood flow parameters in healthy subjects. Invest Ophthalmol Vis Sci. 2001 Nov;42(12):2949-56. PubMed PMID: 11687541. 11: Doi M, Asano A, Ishida T, Katsuya Y, Mezaki Y, Sasaki M, Terashima A, Taniguchi T, Hasegawa H, Shiono M. Caged and clustered structures of endothelin inhibitor BQ123, cyclo(-D-Trp-D-Asp--Pro-D-Val-Leu-)-Na+, forming five and six coordination bonds between sodium ions and peptides. Acta Crystallogr D Biol Crystallogr. 2001 May;57(Pt 5):628-34. Epub 2001 Apr 24. PubMed PMID: 11320303. 12: Szabó G, Bährle S, Fazekas L, MacDonald D, Stumpf N, Vahl CF, Hagl S. Endothelin-A receptor antagonist BQ123 protects against myocardial and endothelial reperfusion injury. Thorac Cardiovasc Surg. 1998 Aug;46(4):232-6. PubMed PMID: 9776499. 13: Curzen NP, Mitchell JA, Jourdan KB, Griffiths MJ, Evans TW. Endothelin-1-induced contraction of pulmonary arteries from endotoxemic rats is attenuated by the endothelin-A receptor antagonist, BQ123. Crit Care Med. 1996 Dec;24(12):2007-13. PubMed PMID: 8968269. 14: Maguire JJ, Kuc RE, Rous BA, Davenport AP. Failure of BQ123, a more potent antagonist of sarafotoxin 6b than of endothelin-1, to distinguish between these agonists in binding experiments. Br J Pharmacol. 1996 May;118(2):335-42. PubMed PMID: 8735635; PubMed Central PMCID: PMC1909647. 15: Peter MG, Davenport AP. Characterization of the endothelin receptor selective agonist, BQ3020 and antagonists BQ123, FR139317, BQ788, 50235, Ro462005 and bosentan in the heart. Br J Pharmacol. 1996 Feb;117(3):455-462. PubMed PMID: 8821534; PubMed Central PMCID: PMC1909322. 16: Peishoff CE, Janes RW, Wallace BA. Comparison of the structures of the endothelin A receptor antagonists BQ123 and N-methyl leucine BQ123 with the crystal structure of the C-terminal tail of endothelin-1. FEBS Lett. 1995 Nov 6;374(3):379-83. PubMed PMID: 7589575. 17: Takeoka M, Ishizaki T, Sakai A, Chang SW, Shigemori K, Higashi T, Ueda G. Effect of BQ123 on vasoconstriction as a result of either hypoxia or endothelin-1 in perfused rat lungs. Acta Physiol Scand. 1995 Sep;155(1):53-60. PubMed PMID: 8553877. 18: Garjani A, Wainwright CL, Zeitlin IJ, Wilson C, Slee SJ. Effects of endothelin-1 and the ETA-receptor antagonist, BQ123, on ischemic arrhythmias in anesthetized rats. J Cardiovasc Pharmacol. 1995 Apr;25(4):634-42. PubMed PMID: 7596133. 19: Han H, Neubauer S, Braeker B, Ertl G. Endothelin-1 contributes to ischemia/reperfusion injury in isolated rat heart-attenuation of ischemic injury by the endothelin-1 antagonists BQ123 and BQ610. J Mol Cell Cardiol. 1995 Feb;27(2):761-6. PubMed PMID: 7776381. 20: Bacon CR, Morrison JJ, O'Reilly G, Cameron IT, Davenport AP. ETA and ETB endothelin receptors in human myometrium characterized by the subtype selective ligands BQ123, BQ3020, FR139317 and PD151242. J Endocrinol. 1995 Jan;144(1):127-34. PubMed PMID: 7891013.