Bradykinin (1-5) | CAS#23815-89-6 | metabolite of bradykinin

Bradykinin (1-5)
featured

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

MedKoo CAT#: 597785

CAS#: 23815-89-6

Description: Bradykinin (1-5) is among the most stable of naturally occurring metabolites. It may be used as a marker for BK production in vivo. It is known that an intact Arg residue in the C-terminus is required for biological activities. BK 1-5 is the minimal peptide that inhibited α-thrombin-induced platelet aggregation and secretion and calcium mobilization. It also prevented α-thrombin from cleaving the thrombin receptor peptide, NATLDPRSFLLR, between arginine and serine. Such antithrombin activities of BK 1-5 may contribute to the cardioprotective nature of kinins.

Chemical Structure

Bradykinin (1-5)

CAS# 23815-89-6

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 597785
Name: Bradykinin (1-5)
CAS#: 23815-89-6
Chemical Formula: C27H40N8O6
Exact Mass: 572.31
Molecular Weight: 572.660
Elemental Analysis: C, 56.63; H, 7.04; N, 19.57; O, 16.76

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 240
5mg	USD 490
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Bradykinin (1-5); Arg-pro-pro-gly-phe;

IUPAC/Chemical Name: L-arginyl-L-prolyl-L-prolylglycyl-L-phenylalanine

InChi Key: USSUMSBPLJWFSZ-TUFLPTIASA-N

InChi Code: InChI=1S/C27H40N8O6/c28-18(9-4-12-31-27(29)30)24(38)35-14-6-11-21(35)25(39)34-13-5-10-20(34)23(37)32-16-22(36)33-19(26(40)41)15-17-7-2-1-3-8-17/h1-3,7-8,18-21H,4-6,9-16,28H2,(H,32,37)(H,33,36)(H,40,41)(H4,29,30,31)/t18-,19-,20-,21-/m0/s1

SMILES Code: O=C(O)[C@H](CC1=CC=CC=C1)NC(CNC([C@H]2N(C([C@H]3N(C([C@H](CCCNC(N)=N)N)=O)CCC3)=O)CCC2)=O)=O

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

Shelf Life: >3 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: 2934.99.03.00

More Info:

Product Data:

Product Data

Instruction:

View handling instruction

Biological target:	Bradykinin (1-5) is a major stable metabolite of Bradykinin, formed by the proteolytic action of angiotensin-converting enzyme (ACE).
In vitro activity:	Compared with the model group, the BK (bradykinin) and inhibitor groups significantly decreased in proliferation rate (P = 0.01) and protein expression levels of Col-1 (P = 0.01), TGF-β1 (P = 0.01), and p-Smad2 (P = 0.00). Also, they were significantly elevated in apoptosis rate (P = 0.02) and p-Smad7 protein expression (P = 0.02). BK regulates the proliferation, apoptosis, and the cycle of glomerular mesangial cells by inhibiting the TGF-β1/Smad signaling pathway. Reference: Turk J Biol. 2021 Feb 9;45(1):17-25. https://pubmed.ncbi.nlm.nih.gov/33597818/
In vivo activity:	Bradykinin treatment significantly improved the hind limb motor function of SCII rats and increased B2R expression, inhibiting COX-2, iNOS, and p-p65 expression in the spinal cord of SCII rats together with a decrease of the inflammatory mediators of IL-6, TNF-α, and MCP-1 levels. Bradykinin administration activated B2R in the spinal cord of SCII rats, which may improve hind limb locomotor recovery by regulating the NF-κB signaling pathway to inhibit the inflammatory response. Reference: ACS Chem Neurosci. 2021 Mar 17;12(6):1031-1038. https://pubmed.ncbi.nlm.nih.gov/33621043/

Preparing Stock Solutions

The following data is based on the product molecular weight 572.66 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. Dong J, Ding L, Wang L, Yang Z, Wang Y, Zang Y, Cao X, Tang L. Effects of bradykinin on proliferation, apoptosis, and cycle of glomerular mesangial cells via the TGF-β1/Smad signaling pathway. Turk J Biol. 2021 Feb 9;45(1):17-25. doi: 10.3906/biy-2007-58. PMID: 33597818; PMCID: PMC7877713. 2. Bellis A, Sorriento D, Fiordelisi A, Izzo R, Sadoshima J, Mauro C, Cerasuolo F, Mancusi C, Barbato E, Pilato E, Trimarco B, Morisco C. Autocrine Bradykinin Release Promotes Ischemic Preconditioning-Induced Cytoprotection in Bovine Aortic Endothelial Cells. Int J Mol Sci. 2020 Apr 23;21(8):2965. doi: 10.3390/ijms21082965. PMID: 32340102; PMCID: PMC7215376. 3. Yang G, Yao P, Ma S, Zhang C. Bradykinin Activates the Bradykinin B2 Receptor to Ameliorate Neuronal Injury in a Rat Model of Spinal Cord Ischemia-Reperfusion Injury. ACS Chem Neurosci. 2021 Mar 17;12(6):1031-1038. doi: 10.1021/acschemneuro.1c00054. Epub 2021 Feb 23. PMID: 33621043. 4. Dal F, Küçük C, Talih T, Sözüer E, Topal U, Deniz K, Akyıldız H. Effects of bradykinin preconditioning in an experimental intestinal ischemia reperfusion model on rats. Acta Cir Bras. 2020 Jun 19;35(4):e202000402. doi: 10.1590/s0102-865020200040000002. PMID: 32578722; PMCID: PMC7307719.
In vitro protocol:	1. Dong J, Ding L, Wang L, Yang Z, Wang Y, Zang Y, Cao X, Tang L. Effects of bradykinin on proliferation, apoptosis, and cycle of glomerular mesangial cells via the TGF-β1/Smad signaling pathway. Turk J Biol. 2021 Feb 9;45(1):17-25. doi: 10.3906/biy-2007-58. PMID: 33597818; PMCID: PMC7877713. 2. Bellis A, Sorriento D, Fiordelisi A, Izzo R, Sadoshima J, Mauro C, Cerasuolo F, Mancusi C, Barbato E, Pilato E, Trimarco B, Morisco C. Autocrine Bradykinin Release Promotes Ischemic Preconditioning-Induced Cytoprotection in Bovine Aortic Endothelial Cells. Int J Mol Sci. 2020 Apr 23;21(8):2965. doi: 10.3390/ijms21082965. PMID: 32340102; PMCID: PMC7215376.
In vivo protocol:	1. Yang G, Yao P, Ma S, Zhang C. Bradykinin Activates the Bradykinin B2 Receptor to Ameliorate Neuronal Injury in a Rat Model of Spinal Cord Ischemia-Reperfusion Injury. ACS Chem Neurosci. 2021 Mar 17;12(6):1031-1038. doi: 10.1021/acschemneuro.1c00054. Epub 2021 Feb 23. PMID: 33621043. 2. Dal F, Küçük C, Talih T, Sözüer E, Topal U, Deniz K, Akyıldız H. Effects of bradykinin preconditioning in an experimental intestinal ischemia reperfusion model on rats. Acta Cir Bras. 2020 Jun 19;35(4):e202000402. doi: 10.1590/s0102-865020200040000002. PMID: 32578722; PMCID: PMC7307719.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.

Mass

Concentration

Volume

M. Wt* g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

Dilution Calculator

Calculate the dilution required to prepare a stock solution.

Concentration 1

Volume 1

Concentration 2

Volume 2

1: Voronina L, Masson A, Kamrath M, Schubert F, Clemmer D, Baldauf C, Rizzo T. Conformations of Prolyl-Peptide Bonds in the Bradykinin 1-5 Fragment in Solution and in the Gas Phase. J Am Chem Soc. 2016 Jul 27;138(29):9224-33. doi: 10.1021/jacs.6b04550. Epub 2016 Jul 18. PubMed PMID: 27366919.

2: Murphey LJ, Malave HA, Petro J, Biaggioni I, Byrne DW, Vaughan DE, Luther JM, Pretorius M, Brown NJ. Bradykinin and its metabolite bradykinin 1-5 inhibit thrombin-induced platelet aggregation in humans. J Pharmacol Exp Ther. 2006 Sep;318(3):1287-92. Epub 2006 Jun 13. PubMed PMID: 16772538.

3: Bujak-Giżycka B, Olszanecki R, Madej J, Suski M, Gębska A, Korbut R. Metabolism of bradykinin in aorta of hypertensive rats. Acta Biochim Pol. 2011;58(2):199-202. Epub 2011 May 27. PubMed PMID: 21623416.

4: Nieman MT, Pagan-Ramos E, Warnock M, Krijanovski Y, Hasan AA, Schmaier AH. Mapping the interaction of bradykinin 1-5 with the exodomain of human protease activated receptor 4. FEBS Lett. 2005 Jan 3;579(1):25-9. PubMed PMID: 15620686.

5: Shima C, Majima M, Katori M. A stable metabolite, Arg-Pro-Pro-Gly-Phe, of bradykinin in the degradation pathway in human plasma. Jpn J Pharmacol. 1992 Oct;60(2):111-9. PubMed PMID: 1479739.

6: Cugno M, Salerno F, Nussberger J, Bottasso B, Lorenzano E, Agostoni A. Bradykinin in the ascitic fluid of patients with liver cirrhosis. Clin Sci (Lond). 2001 Dec;101(6):651-7. PubMed PMID: 11724653.

7: Sawyer HA, Marini JT, Stone EG, Ruotolo BT, Gillig KJ, Russell DH. The structure of gas-phase bradykinin fragment 1-5 (RPPGF) ions: an ion mobility spectrometry and H/D exchange ion-molecule reaction chemistry study. J Am Soc Mass Spectrom. 2005 Jun;16(6):893-905. PubMed PMID: 15878286.

8: Murphey LJ, Hachey DL, Vaughan DE, Brown NJ, Morrow JD. Quantification of BK1-5, the stable bradykinin plasma metabolite in humans, by a highly accurate liquid-chromatographic tandem mass spectrometric assay. Anal Biochem. 2001 May 1;292(1):87-93. PubMed PMID: 11319821.

9: Doggrell SA. A daughter of bradykinin that protects against septicaemia. Expert Opin Investig Drugs. 2001 Aug;10(8):1567-9. PubMed PMID: 11785456.

10: Murphey LJ, Gainer JV, Vaughan DE, Brown NJ. Angiotensin-converting enzyme insertion/deletion polymorphism modulates the human in vivo metabolism of bradykinin. Circulation. 2000 Aug 22;102(8):829-32. PubMed PMID: 10952948.

11: Hirata M, Hayashi I, Yoshimura K, Ishii K, Soma K, Ohwada T, Kakita A, Majima M. Blockade of bradykinin B(2) receptor suppresses acute pancreatitis induced by obstruction of the pancreaticobiliary duct in rats. Br J Pharmacol. 2002 Jan;135(1):29-36. PubMed PMID: 11786477; PubMed Central PMCID: PMC1573123.

12: Prieto AR, Ma H, Huang R, Khan G, Schwartz KA, Hage-Korban EE, Schmaier AH, Davis JM, Hasan AA, Abela GS. Thrombostatin, a bradykinin metabolite, reduces platelet activation in a model of arterial wall injury. Cardiovasc Res. 2002 Mar;53(4):984-92. PubMed PMID: 11922908.

13: Hasan AA, Amenta S, Schmaier AH. Bradykinin and its metabolite, Arg-Pro-Pro-Gly-Phe, are selective inhibitors of alpha-thrombin-induced platelet activation. Circulation. 1996 Aug 1;94(3):517-28. Erratum in: Circulation 1996 Oct 1;94(7):1794. PubMed PMID: 8759097.

14: Marmarou A, Guy M, Murphey L, Roy F, Layani L, Combal JP, Marquer C; American Brain Injury Consortium. A single dose, three-arm, placebo-controlled, phase I study of the bradykinin B2 receptor antagonist Anatibant (LF16-0687Ms) in patients with severe traumatic brain injury. J Neurotrauma. 2005 Dec;22(12):1444-55. PubMed PMID: 16379582.

15: Griswold JA, Baker CR Jr, Little DT, Little GH, Behal FJ. Bradykinin metabolism in rat hind limbs. Shock. 1998 Aug;10(2):146-52. PubMed PMID: 9721983.

16: Morinelli TA, Meier GP, Webb JG, Jaffa AA, Privitera PJ, Margolius HS. Utilization of a radioimmunoassay to detect the generation of Arg-Pro-Pro-Gly-Phe, a stable endproduct of bradykinin metabolism (from cultured rat aortic smooth muscle cells exposed to bradykinin). Int Immunopharmacol. 2002 Dec;2(13-14):1995-2003. PubMed PMID: 12489813.

17: Morinelli TA, Webb JG, Jaffa AA, Privitera PJ, Margolius HS. A metabolic fragment of bradykinin, Arg-Pro-Pro-Gly-Phe, protects against the deleterious effects of lipopolysaccharide in rats. J Pharmacol Exp Ther. 2001 Jan;296(1):71-6. PubMed PMID: 11123364.

18: Nieman MT, Warnock M, Hasan AA, Mahdi F, Lucchesi BR, Brown NJ, Murphey LJ, Schmaier AH. The preparation and characterization of novel peptide antagonists to thrombin and factor VIIa and activation of protease-activated receptor 1. J Pharmacol Exp Ther. 2004 Nov;311(2):492-501. Epub 2004 Jun 21. PubMed PMID: 15210836.

19: Nieman MT, LaRusch G, Fang C, Zhou Y, Schmaier AH. Oral thrombostatin FM19 inhibits prostate cancer. Thromb Haemost. 2010 Nov;104(5):1044-8. doi: 10.1160/TH09-08-0570. Epub 2010 Sep 30. PubMed PMID: 20886199; PubMed Central PMCID: PMC3552554.

20: Sugimoto K, Hirata M, Majima M, Katori M, Ohwada T. Evidence for a role of kallikrein-P6nin system in patients with shock after blunt trauma. Am J Physiol. 1998 Jun;274(6 Pt 2):R1556-60. PubMed PMID: 9608008.

Your view history

Bradykinin (1-5) featured