alpha-MSH (11-13)/KPV peptide

alpha-MSH (11-13)/KPV peptide

• Handling and Storage of Synthetic Peptides
• Material Safety Data Sheets (MSDS)

Batch to batch variation of the purity

KPV

H-Lys-Pro-Val-OH

3

98.1%

C₁₆H₃₀N₄O₄

342.44

Synthetic

Powder

KPV is a C-terminal peptide fragment of α-MSH. It is highly hydrophilic and has poor skin penetration. KPV exhibits potent anti-inflammatory effects by binding to melanocortin receptors (MC-Rs) in the skin. The anti-inflammatory activity of α-MSH is mediated by the three terminal amino acids, Lysine-Proline-Valine (KPV). KPV lacks the entire sequence motif required for binding to the MC-Rs, but still retains full anti-inflammatory effect of the parent hormone. The inflammatory activity of KPV is suggested to be mediated via inhibition of interleukin (IL)-1β. Unlike α-MSH, KPV is free from the melanotropic effects and thus does not cause any pigmentation. Additionally, it is smaller in size and more chemically stable than α-MSH. Recently albumin based KPV nanoparticles were targeted to the colon with polysaccharide hydrogel reduce inflammatory bowel disease in a mouse model. It has also been reported that KPV suppresses NFkB signaling, inhibits p65RelA nuclear import and activates epithelial MC3Rs in the airway inflammation in lung disease. Hence KPV may be a suitable candidate for the treatment of inflammatory skin disorders.

Normally, this peptide will be delivered in lyophilized form and should be stored in a freezer at or below -20 °C. For more details, please refer to the manual: Handling and Storage of Synthetic Peptides

• S.J.Getting et al., J. Pharmacol. Exp. Ther., 306, 631 (2003)
• G.Dalmasso et al., Gastroenterology, 134, 166 (2008)
• Pawar K, Kolli CS, Rangari VK, Babu RJ. Transdermal Iontophoretic Delivery of Lysine-Proline-Valine (KPV) Peptide Across Microporated Human Skin. J Pharm Sci. 2017 Jul;106(7):1814-1820. doi: 10.1016/j.xphs.2017.03.017. Epub 2017 Mar 24. PMID: 28343991.

Trifluoroacetic acid (TFA) has a significant impact on peptides due to its role in the peptide synthesis process.

TFA is essential for the protonation of peptides that lack basic amino acids such as Arginine (Arg), Histidine (His), and Lysine (Lys), or ones that have blocked N-termini. As a result, peptides often contain TFA salts in the final product.

TFA residues, when present in custom peptides, can cause unpredictable fluctuations in experimental data. At a nanomolar (nM) level, TFA can influence cell experiments, hindering cell growth at low concentrations (as low as 10 nM) and promoting it at higher doses (0.5–7.0 mM). It can also serve as an allosteric regulator on the GlyR of glycine receptors, thereby increasing receptor activity at lower glycine concentrations.

In an in vivo setting, TFA can trifluoroacetylate amino groups in proteins and phospholipids, inducing potentially unwanted antibody responses. Moreover, TFA can impact structure studies as it affects spectrum absorption.