d[Cha4]-AVP

Product Name:d[Cha4]-AVP

CAS No:500170-27-4

Purity:95%

Molar Mass:1094.31

Chemical Formula:C50H71N13O11S2

Storage:Store at -20 degrees Celsius

Sequence:XYFXNCPRG

Target:human vasopressin V1B

Application:

d[Cha4]-AVP is a synthetic analog of arginine vasopressin (AVP), where the fourth amino acid, phenylalanine, is replaced by cyclohexylalanine (Cha). This modification alters the peptide’s binding affinity and selectivity for vasopressin receptors, particularly the V1a receptor subtype. d[Cha4]-AVP is commonly used in pharmacological studies to investigate vasopressin receptor function and to understand its role in regulating blood pressure, kidney function, and social behavior. Due to its receptor specificity, this analog is valuable for research on cardiovascular diseases, water retention disorders, and the development of drugs targeting vasopressin-related pathways.

Current Research:

[d-Cha⁴]-Arg⁸-Vasopressin, commonly referred to as [d-Cha⁴]-AVP, is a synthetic analog of the neuropeptide arginine vasopressin (AVP). This analog is characterized by the substitution of the fourth amino acid residue with d-cyclohexylalanine (d-Cha), resulting in a peptide sequence of Cys-Tyr-d-Cha-Gln-Asn-Cys-Pro-Arg-Gly-NH₂. This modification significantly alters the peptide's receptor binding profile and biological activity.

Structural Modification and Receptor Selectivity

The incorporation of d-Cha at position four enhances the peptide's stability against enzymatic degradation and confers increased selectivity towards specific vasopressin receptor subtypes. Notably, [d-Cha⁴]-AVP exhibits high affinity for the V₁a receptor, which is predominantly expressed in vascular smooth muscle cells and mediates vasoconstriction. Conversely, this analog demonstrates reduced affinity for the V₂ receptor, associated with antidiuretic effects in renal collecting ducts.

Pharmacological Profile

Due to its selective V₁a receptor agonism, [d-Cha⁴]-AVP induces potent vasoconstrictive responses without significantly affecting renal water reabsorption. This profile makes it a valuable tool for dissecting the distinct physiological roles of vasopressin receptor subtypes. Additionally, its resistance to metabolic breakdown prolongs its duration of action, facilitating sustained receptor activation in experimental settings.

Research Applications

In cardiovascular research, [d-Cha⁴]-AVP is employed to study the mechanisms underlying vasopressin-induced vasoconstriction and its implications in conditions such as hypertension and heart failure. Its receptor selectivity allows for the delineation of V₁a-mediated effects from those mediated by V₂ receptors, providing insights into receptor-specific signaling pathways.

Furthermore, [d-Cha⁴]-AVP serves as a reference compound in the development of novel therapeutics targeting vasopressin receptors. By understanding its interaction with V₁a receptors, researchers can design more selective and efficacious agents for treating disorders involving dysregulated vasopressin signaling.

Conclusion

[d-Cha⁴]-AVP is a synthetic vasopressin analog with enhanced stability and selective V₁a receptor agonism. Its unique pharmacological properties make it an indispensable tool in the investigation of vasopressin receptor functions and the development of targeted therapeutic strategies.

Reference:

Griffante, C., Green, A., Curcuruto, O., Haslam, C. P., Dickinson, B. A., & Arban, R. (2005). Selectivity of d [Cha4] AVP and SSR149415 at human vasopressin and oxytocin receptors: evidence that SSR149415 is a mixed vasopressin V1b/oxytocin receptor antagonist. British journal of pharmacology, 146(5), 744-751.