Bradykinin

Base Information

• Chemical Name: Bradykinin
• CAS No.: 58-82-2
• Molecular Formula: C50H73 N15 O11
• Molecular Weight: 1060.22
• Mol file: 58-82-2.mol

Synonyms:Arginine,N2-[N-[1-[N-[N-[N-[1-(1-arginyl-L-prolyl)-L-prolyl]glycyl]-3-phenylalanyl]seryl]prolyl]-3-phenylalanyl]-(6CI); 1020: PN: EP2071336 PAGE: 73 unclaimed sequence; 1021: PN: WO2006091861SEQID: 1021 claimed protein; 107: PN: WO2006069765 SEQID: 107 claimed protein;10: PN: WO2008008766 SEQID: 124 unclaimed sequence; 111: PN: WO2008058016SEQID: 112 claimed protein; 115: PN: WO2008104000 TABLE: 4 unclaimed sequence;11: PN: US20040209344 SEQID: 7 unclaimed protein; 13: PN: WO0023092 SEQID: 13unclaimed protein; 147: PN: US20030119021 SEQID: 25 unclaimed protein; 14: PN:US20090088553 SEQID: 88 unclaimed protein; 14: PN: US6525021 SEQID: 13unclaimed protein; 153: PN: WO2006067198 SEQID: 165 claimed protein; 156: PN:WO2009126292 TABLE: 4 unclaimed sequence; 15: PN: US6258776 SEQID: 24 unclaimedprotein; 15: PN: WO2007058336 SEQID: 15 claimed sequence; 165: PN:US20050175581 SEQID: 165 unclaimed protein; 16: PN: WO2006079099 SEQID: 1unclaimed protein; 175: PN: WO2008008805 SEQID: 178 unclaimed protein; 187: PN:US20030176421 PAGE: 54-55 claimed protein; 18: PN: JP2006280210 SEQID: 18unclaimed protein; 19: PN: US20060223140 SEQID: 18 claimed protein; 19: PN:WO2007022248 SEQID: 19 claimed protein; 1: PN: CN101344527 PAGE: 6 claimedsequence; 1: PN: JP2005049164 SEQID: 1 claimed protein; 1: PN: US20040198666SEQID: 1 unclaimed protein; 1: PN: US20040220110 PAGE: 2 unclaimed protein; 1:PN: US20070015715 SEQID: 1 unclaimed sequence; 1: PN: US7605120 SEQID: 1unclaimed sequence; 1: PN: WO02102835 SEQID: 3 unclaimed protein; 1: PN:WO2006130718 SEQID: 1 unclaimed protein; 1: PN: WO2006134125 SEQID: 22 claimedprotein; 227: PN: WO2009118205 PAGE: 176 unclaimed sequence; 229: PN:US20090048431 SEQID: 227 claimed sequence; 24: PN: US20080226503 TABLE: 1unclaimed sequence; 2: PN: WO2005042027 SEQID: 1 unclaimed protein; 2: PN:WO2005057221 PAGE: 17 unclaimed protein; 360: PN: WO2009117524 SEQID: 5unclaimed sequence; 38: PN: WO2006017688 SEQID: 38 unclaimed protein;

Chemical Property of Bradykinin

Chemical Property:

• Melting Point: 170ºC
• Refractive Index: 1.6930 (estimate)
• Boiling Point: °Cat760mmHg
• PKA: 3.34±0.10(Predicted)
• Flash Point: °C
• PSA: 413.78000
• Density: 1.49 g/cm³
• LogP: 1.28130
• Storage Temp.: −20°C
• Solubility.: H2O: >40 mg/mL
• Water Solubility.: Soluble to 1 mg/ml in water.

Purity/Quality:

99% ^*data from raw suppliers

BK ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Bradykinin is used to lower blood pressure, increase bradykinin (by inhibiting its degradation) further lowering blood pressure. Bradykinin dilates blood vessels via the release of prostacyclin, nitric oxide, and endothelium-derived hyperpolarizing factor. Leucine Enkephalin acetate salt hydrate has been used in the calibration of the Q-Tof Micro hybrid, triple quadrupole-orthogonal acceleration time of flight (TOF) instrument in single-stage TOF mode. It has also been used to perform the calibration of mass spectrometry. It has also been used in liquid chromatography-mass spectrometry (LCMS)/MS for calibration of the system and for relative correction of the spectra.
• Biological Functions: The kallikrein–kinin system is an enzymatic pathway giving rise to two predominant vasoactive peptides, kallidin and bradykinin. Kallikrein, the enzyme responsible for the formation of these peptides, exists in plasma and tissues. However, circulating levels of the end products, kallidin and bradykinin, are quite low because the kallikrein enzymes are present largely in inactive forms. In addition, the short half-life of these peptides (15 seconds) also contributes to low plasma levels. In general, the kinins produce relaxation of vascular smooth muscle and vasodilation. Bradykinin causes vascular smooth muscle relaxation by stimulating the endothelium to release prostacyclin and nitric oxide. Blood flow to the brain, heart, viscera, skeletal muscle, and glands is increased. In nonvascular smooth muscle, bradykinin will produce a contractile response. Other actions of kinins include activation of clotting factors simultaneously with the production of bradykinin. In the kidney, bradykinin production results in an increase in renal papillary blood flow, with a secondary inhibition of sodium reabsorption in the distal tubule. In the peripheral nervous system, bradykinin is important for the initiation of pain signals. It is also associated with the edema, erythema, and fever of inflammation. Bradykinin exerts its physiological effects via two receptors, the B1 and B2 receptors, with most of its physiological effects being mediated by the B2 receptor. The precise function of the B1 receptor is unclear; however, some of the chronic inflammatory responses to bradykinin may be mediated through actions at this receptor. Bradykinin antagonists of the B2 receptor are currently in development and may find utility in the treatment of pain associated with burns and such chronic inflammatory disorders as arthritis, asthma, and chronic pain.
• Clinical Use: 9-peptide, produced in response to tissue damage, inflammation, viral infections, etc. Produces pain, increased vascular permeability, and synthesis of prostaglandins.

Technology Process of Bradykinin

There total 9 articles about Bradykinin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 69.0%

Fmoc-Pro-OH (71989-31-6) + N-Fmoc L-Phe (35661-40-6) + N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5) + Fmoc-L-Arg-OH (91000-69-0,130752-32-8) → bradykinin (58-82-2)

Guidance literature:

Multistep reaction;

DOI:10.1007/BF02759162

Reference yield:

Z-(NO2)Arg-Pro-Pro-Gly-Phe-(OBzl)Ser-Pro-Phe-(NO2)Arg-PNB → bradykinin (58-82-2)

Guidance literature:

With hydrogenchloride; hydrogen; palladium; In acetic acid; for 48h; Ambient temperature;

Reference yield:

ortho-aminobenzoic acid-MISLMKRPPGFSPFRSSRI-NH2 → bradykinin (58-82-2) + methionyl-lysyl-bradykinin (550-19-6) + Lys-bradykinin (342-10-9)

Guidance literature:

With falcipain-2; water; 1,4-Dithioerythritol; In aq. acetate buffer; at 37 ℃; pH=5.5; Reagent/catalyst; Enzymatic reaction;

DOI:10.1016/j.molbiopara.2013.01.002

upstream raw materials:

Fmoc-Pro-OH

N-Fmoc L-Phe

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine

Fmoc-L-Arg-OH

Downstream raw materials:

C₅₂H₇₄BrN₁₅O₁₂

Refernces

• 1、 Malavolta, Luciana,Nakaie, Clóvis R.. "Peptide dissociation in solution or bound to a polymer: Comparative solvent effect". . p. 9417 - 9424. Retrieved 2004.
• 2、 Cotrin, Simone S.,Gouvêa, Iuri E.,Melo, Pollyana M.S.,Bagnaresi, Piero,Assis, Diego M.,Araújo, Mariana S.,Juliano, Maria Aparecida,Gazarini, Marcos L.,Rosenthal, Philip J.,Juliano, Luiz,Carmona, Adriana K.. "Substrate specificity studies of the cysteine peptidases falcipain-2 and falcipain-3 from Plasmodium falciparum and demonstration of their kininogenase activity". . p. 111 - 116. Retrieved 2013/04/24.