kallidin, des-Arg(10)- - 71800-36-7

kallidin, des-Arg(10)-

Catalog Number: EVT-242163
CAS Number: 71800-36-7
Molecular Formula: C50H73N13O11
Molecular Weight: 1032.2 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.

Product Introduction

Description

Kinins, such as bradykinin and kallidin, are oligopeptides that play a significant role in various physiological and pathological processes, including inflammation and the pathogenesis of bronchial asthma. These peptides exert their effects by interacting with specific cell surface receptors, known as B1 and B2 receptors. Kallidin and its derivative, des-Arg^10-kallidin, have been studied for their potential roles in mediating bronchoconstriction in asthmatic subjects and enhancing leukocyte adhesion, which is a critical step in the inflammatory response1 2.

Applications in Various Fields

The research on kallidin and des-Arg^10-kallidin has significant implications in the field of respiratory medicine, particularly in understanding and managing bronchial asthma. The ability of these kinins to induce bronchoconstriction can help in identifying new therapeutic targets for asthma treatment. Moreover, the observed cross-tachyphylaxis could provide insights into the development of resistance to certain asthma medications1.

In the field of immunology and inflammation, the role of des-Arg^10-kallidin in enhancing leukocyte adhesion opens up potential avenues for therapeutic intervention in inflammatory diseases. By modulating leukocyte adhesion, it may be possible to control the extent of leukocyte infiltration and thus the severity of the inflammatory response. This could be particularly beneficial in conditions characterized by excessive or chronic inflammation2.

Properties

CAS Number

71800-36-7

Product Name

kallidin, des-Arg(10)-

IUPAC Name

(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[2-[[(2S)-1-[(2S)-1-[(2S)-2-[[(2S)-2,6-diaminohexanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-3-hydroxypropanoyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoic acid

Molecular Formula

C50H73N13O11

Molecular Weight

1032.2 g/mol

InChI

InChI=1S/C50H73N13O11/c51-22-8-7-17-33(52)42(66)58-34(18-9-23-55-50(53)54)46(70)63-26-12-21-40(63)48(72)62-25-10-19-38(62)44(68)56-29-41(65)57-35(27-31-13-3-1-4-14-31)43(67)60-37(30-64)47(71)61-24-11-20-39(61)45(69)59-36(49(73)74)28-32-15-5-2-6-16-32/h1-6,13-16,33-40,64H,7-12,17-30,51-52H2,(H,56,68)(H,57,65)(H,58,66)(H,59,69)(H,60,67)(H,73,74)(H4,53,54,55)/t33-,34-,35-,36-,37-,38-,39-,40-/m0/s1

InChI Key

AILVBOHFGXNHCC-TZPCGENMSA-N

SMILES

C1CC(N(C1)C(=O)C2CCCN2C(=O)C(CCCN=C(N)N)NC(=O)C(CCCCN)N)C(=O)NCC(=O)NC(CC3=CC=CC=C3)C(=O)NC(CO)C(=O)N4CCCC4C(=O)NC(CC5=CC=CC=C5)C(=O)O

Synonyms

10-de-Arg-kallidin
bradykinin, Lys-D-Phe(8)-des-Arg(9)
bradykinin, Lys-desArg(9)
bradykinin, lysyl-des-arginine(9)
des-Arg(10)-kallidin
kallidin, des-Arg(10)-
kallidin, des-arginine(10)-
LDBk peptide
LYS-ARG-PRO-PRO-GLY-PHE-SER-PRO-PHE
Lys-des-Arg(9)-BK
LysdesArg(9)BK

Canonical SMILES

C1CC(N(C1)C(=O)C2CCCN2C(=O)C(CCCN=C(N)N)NC(=O)C(CCCCN)N)C(=O)NCC(=O)NC(CC3=CC=CC=C3)C(=O)NC(CO)C(=O)N4CCCC4C(=O)NC(CC5=CC=CC=C5)C(=O)O

Isomeric SMILES

C1C[C@H](N(C1)C(=O)[C@@H]2CCCN2C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCCCN)N)C(=O)NCC(=O)N[C@@H](CC3=CC=CC=C3)C(=O)N[C@@H](CO)C(=O)N4CCC[C@H]4C(=O)N[C@@H](CC5=CC=CC=C5)C(=O)O
Mechanism of Action

The mechanism of action of kallidin and des-Arg^10-kallidin involves their interaction with B2 receptors, which are implicated in the bronchoconstrictive response observed in asthmatic patients. Studies have shown that inhalation of bradykinin and kallidin, but not their des-Arg^9 or des-Arg^10 metabolites, can provoke potent bronchoconstriction. This suggests that the B2 receptor is specifically stimulated by these kinins. Cross-tachyphylactic studies have demonstrated that repeated exposure to these kinins can lead to a reduced bronchospastic response, indicating a possible development of tachyphylaxis. Surprisingly, even though des-Arg^9-bradykinin does not cause bronchoconstriction, it can reduce the airway response to bradykinin, suggesting a complex interplay between these kinins and their receptors1.

In the context of inflammation, des-Arg^10-kallidin has been found to enhance the adhesion of polymorphonuclear leukocytes (PMNs) to extracellular matrix proteins and endothelial cells. This effect is crucial for leukocyte recruitment to inflammatory sites. The kinin peptides can also modulate the expression of Mac-1 integrin on the PMN surface, further influencing the adhesion process. These findings highlight the regulatory role of kinins in leukocyte adhesion and infiltration into inflamed tissues2.

Method of Synthesis or Extraction
Kallidin, des-Arg(10)- can be synthesized by solid-phase peptide synthesis or extracted from biological fluids. Solid-phase peptide synthesis involves the stepwise addition of amino acids to a growing peptide chain anchored to a solid support. The yield and efficiency of this method depend on the purity of the starting materials, the quality of the reagents, and the expertise of the chemist. The environmental and safety considerations of this method include the disposal of hazardous waste and the use of toxic solvents.
Kallidin, des-Arg(10)- can also be extracted from biological fluids, such as plasma and urine, by various methods, including immunoaffinity chromatography, high-performance liquid chromatography, and enzyme-linked immunosorbent assay. The efficiency and yield of these methods depend on the specificity and sensitivity of the antibodies or enzymes used for the extraction. The environmental and safety considerations of these methods include the use of animal-derived antibodies and the disposal of biological waste.
Chemical Structure and Biological Activity
Kallidin, des-Arg(10)- is a nonapeptide with the chemical formula C50H73N15O11. It consists of nine amino acids, including arginine, proline, and phenylalanine. The biological activity of kallidin, des-Arg(10)- is mediated by its interaction with two G protein-coupled receptors, B1 and B2. B2 receptors are constitutively expressed in various tissues, while B1 receptors are induced under inflammatory conditions.
Kallidin, des-Arg(10)- binds to B2 receptors with high affinity and activates a signaling cascade that leads to the release of nitric oxide, prostaglandins, and other inflammatory mediators. This results in vasodilation, increased vascular permeability, and pain. Kallidin, des-Arg(10)- also binds to B1 receptors with lower affinity and induces a similar response under inflammatory conditions.
Biological Effects
Kallidin, des-Arg(10)- has various biological effects on cell function and signal transduction. It plays a crucial role in the regulation of blood pressure by inducing vasodilation and increasing vascular permeability. It also contributes to the pathogenesis of various inflammatory diseases, such as asthma, arthritis, and sepsis, by inducing pain, edema, and leukocyte infiltration.
Kallidin, des-Arg(10)- has potential therapeutic and toxic effects. It has been used as a diagnostic tool for the assessment of renal function and as a therapeutic agent for the treatment of hypertension, heart failure, and angioedema. However, its use is limited by its short half-life, rapid degradation, and potential side effects, such as hypotension, bronchoconstriction, and allergic reactions.
Future Perspectives and Challenges
The current limitations in the use and study of kallidin, des-Arg(10)- include its short half-life, rapid degradation, and potential side effects. Possible solutions and improvements include the development of stable analogs, the use of targeted drug delivery systems, and the identification of novel therapeutic targets.
Future trends and prospects in the application of kallidin, des-Arg(10)- in scientific research include the development of personalized medicine based on the individual's genetic makeup and the use of artificial intelligence and machine learning to predict drug efficacy and toxicity. The challenges in the application of kallidin, des-Arg(10)- in scientific research include the ethical considerations of animal testing and the regulatory requirements for drug approval and commercialization.
Conclusion:
Kallidin, des-Arg(10)- is a peptide hormone that plays a crucial role in various physiological processes, including inflammation, pain, and blood pressure regulation. It can be synthesized by solid-phase peptide synthesis or extracted from biological fluids. Its biological activity is mediated by its interaction with two G protein-coupled receptors, B1 and B2. It has various biological effects on cell function and signal transduction and has potential therapeutic and toxic effects. It has various applications in medical, environmental, and industrial research. The current limitations in the use and study of kallidin, des-Arg(10)- include its short half-life, rapid degradation, and potential side effects. Possible solutions and improvements include the development of stable analogs, the use of targeted drug delivery systems, and the identification of novel therapeutic targets.

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