[D-Trp8]-γ-MSH

Product Name:[D-Trp8]-γ-MSH

CAS No:321351-81-9

Purity:95%

Molar Mass:1570.79

Chemical Formula:C74H99N21O16S

Storage:Store at -20 degrees Celsius

Sequence:YVMGHFRWDRFG

Target:melanocortin 3

Application:

[D-Trp8]-γ-MSH is a synthetic analog of the melanocyte-stimulating hormone (MSH) that features a substitution of D-tryptophan at position 8. This modification enhances the peptide’s stability and resistance to enzymatic degradation. γ-MSH is part of the melanocortin family and plays a key role in regulating inflammation, energy homeostasis, and cardiovascular functions by interacting with melanocortin receptors (MC-Rs). [D-Trp8]-γ-MSH is commonly used in research to study the effects of MSH on melanocortin receptors, particularly in models of obesity, hypertension, and inflammatory diseases, making it a valuable tool for investigating therapeutic applications related to these pathways.

Current Research:

[D-Trp⁸]-γ-Melanocyte-Stimulating Hormone ([D-Trp⁸]-γ-MSH) is a synthetic analog of the endogenous γ-MSH peptide, distinguished by the substitution of the eighth amino acid with D-tryptophan. This modification enhances its stability and alters its receptor binding profile, making it a valuable tool in neuroendocrine research.

Structural Characteristics

The native γ-MSH is a 12-amino acid peptide with the sequence Tyr¹-Val²-Met³-Gly⁴-His⁵-Phe⁶-Arg⁷-Trp⁸-Gly⁹-Ser¹⁰-Pro¹¹-Pro¹². In [D-Trp⁸]-γ-MSH, the L-tryptophan at position 8 is replaced with its D-isomer, resulting in the sequence Tyr¹-Val²-Met³-Gly⁴-His⁵-Phe⁶-Arg⁷-D-Trp⁸-Gly⁹-Ser¹⁰-Pro¹¹-Pro¹². This stereochemical alteration confers increased resistance to enzymatic degradation, thereby prolonging the peptide's half-life in biological systems.

Receptor Binding and Selectivity

γ-MSH primarily interacts with melanocortin receptors MC3R and MC4R, which are implicated in energy homeostasis and feeding behavior. The incorporation of D-Trp at position 8 in [D-Trp⁸]-γ-MSH enhances its binding affinity and selectivity for these receptors. This modification has been shown to increase the peptide's potency in activating MC3R and MC4R, leading to more pronounced physiological effects.

Physiological Implications

The melanocortin system, through receptors such as MC3R and MC4R, plays a crucial role in regulating energy balance, appetite, and body weight. By modulating these receptors, [D-Trp⁸]-γ-MSH can influence feeding behavior and energy expenditure. Studies have demonstrated that administration of [D-Trp⁸]-γ-MSH results in reduced food intake and increased energy expenditure in animal models, highlighting its potential therapeutic applications in obesity and metabolic disorders.

Research Applications

[D-Trp⁸]-γ-MSH serves as a potent agonist in studies investigating the melanocortin system's role in energy homeostasis and feeding behavior. Its enhanced stability and receptor selectivity make it a valuable tool for elucidating the physiological functions of MC3R and MC4R. Additionally, [D-Trp⁸]-γ-MSH is utilized in the development of therapeutic agents targeting metabolic disorders, providing insights into potential treatment strategies for conditions such as obesity and cachexia.

Conclusion

The development of [D-Trp⁸]-γ-MSH has significantly advanced our understanding of the melanocortin system's role in energy balance and feeding behavior. Its unique properties continue to facilitate research into metabolic regulation and the development of novel therapeutic interventions for metabolic diseases.

Reference:

Getting, S. J., Lam, C. W., Leoni, G., Gavins, F. N., Grieco, P., & Perretti, M. (2006). [D-Trp8]-γ-melanocyte-stimulating hormone exhibits anti-inflammatory efficacy in mice bearing a nonfunctional MC1R (recessive yellow e/e mouse). Molecular pharmacology, 70(6), 1850-1855.