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palmitoyl pentapeptide

Yun Lim Choi, Eun Ji Park, Eunje Kim, Dong Hee Na, Young-Hee Shin
Collagen pentapeptide (Lys-Thr-Thr-Lys-Ser, KTTKS) and its palmitoylated derivative (pal-KTTKS) have received a great deal of attention as cosmeceutical ingredients for their anti-wrinkle effects. The objective of this study was to evaluate stability and permeability of KTTKS and pal-KTTKS in hairless mouse skin. In this study, a liquid chromatography-tandem mass spectrometric method was developed for the quantification of pal-KTTKS, and used for stability and permeability studies. Stability studies were performed using skin extracts and homogenates...
July 2014: Biomolecules & Therapeutics
Oforiwa A Gorleku, Anna-Marie Barns, Gerald R Prescott, Jennifer Greaves, Luke H Chamberlain
Intracellular palmitoylation dynamics are regulated by a family of 24 DHHC (aspartate-histidine-histidine-cysteine) palmitoyltransferases, which are localized in a compartment-specific manner. The majority of DHHC proteins localize to endoplasmic reticulum (ER) and Golgi membranes, and a small number target to post-Golgi membranes. To date, there are no reports of the fine mapping of sorting signals in mammalian DHHC proteins; thus, it is unclear how spatial distribution of the DHHC family is achieved. Here, we have identified and characterized lysine-based sorting signals that determine the restricted localization of DHHC4 and DHHC6 to ER membranes...
November 11, 2011: Journal of Biological Chemistry
Masakatsu Kamiya, Keisuke Oyauchi, Yoshinori Sato, Takuya Yokoyama, Mofei Wang, Tomoyasu Aizawa, Yasuhiro Kumaki, Mineyuki Mizuguchi, Kunio Imai, Makoto Demura, Koichi Suzuki, Keiichi Kawano
We previously reported that yamamarin, a pentapeptide with an amidated C-terminus (DILRG-NH(2)) isolated from larvae of the silkmoth, and its palmitoylated analog (C16-DILRG-NH(2)) suppressed proliferation of rat hepatoma (liver cancer) cells. In this study, we investigated the structure-activity relationship of yamamarin by in vitro assay and spectroscopic methods (CD and NMR) for various analogs. The in vitro assay results demonstrated that the chemical structure of the C-terminal part (-RG-NH(2)) of yamamarin is essential for its activity...
May 2010: Journal of Peptide Science: An Official Publication of the European Peptide Society
Yosinori Sato, Ping Yang, Ying An, Kazushige Matsukawa, Kikukatsu Ito, Shigeo Imanishi, Hirokazu Matsuda, Yusuke Uchiyama, Kunio Imai, Shigeki Ito, Yoji Ishida, Koichi Suzuki
A palmitoyl conjugate of an insect pentapeptide that occurs in diapausing insects causes a reversible cell-cycle arrest and suppresses mitochondrial respiration. This peptide compound also causes growth arrest in murine leukemic cell line expressing human gene Bcr/Abl and a farnesoyl peptide induces embryonic diapause in Bombyx mori. These results demonstrate that the insect peptide compounds can lead to the understanding of a common pathway in developmental arrest in animals and may provide a new peptidominetic analog in the development of biopharmaceuticals and pest management...
May 2010: Peptides
Raluca-Ioana Chirita, Patrick Chaimbault, Jean-Christophe Archambault, Isabelle Robert, Claire Elfakir
Palmitoyl peptides are anti-aging agents widely used in cosmetics. This article describes the development of a LC-MS/MS analytical procedure that allows, after a liquid-liquid extraction procedure, their unambiguous detection in cosmetic formulation. MS/MS detection is shown to be specific regarding placebo formulations. Limits of quantification, linearity, accuracy and precision of the method were estimated. The results presented show that palmitoyl peptides can be thus reliably assayed. The palmitoylated pentapeptide palmitoyl-lysyl-threonyl-threonyl-lysyl-serine (pal-KTTKS) was assayed in anti-wrinkle creams using palmitoyl-glycyl-histidyl-lysine (pal-GHK) as internal standard...
May 8, 2009: Analytica Chimica Acta
L R Robinson, N C Fitzgerald, D G Doughty, N C Dawes, C A Berge, D L Bissett
The palmitoyl pentapeptide palmitoyl-lysine-threonine-threonine-lysine-serine (pal-KTTKS) is a synthetic material that was designed as a topical agent to stimulate collagen production and thus provide a skin anti-wrinkle benefit. To determine if pal-KTTKS is effective, the clinical study reported here was conducted. Caucasian female subjects (n = 93, aged 35-55) participated in a 12-week, double-blind, placebo-controlled, split-face, left-right randomized clinical study assessing two topical products: moisturizer control product vs...
June 2005: International Journal of Cosmetic Science
Alison L Clarke, Steven Petrou, John V Walsh, Joshua J Singer
Fatty acids and other negatively charged single-chain lipids increase large-conductance Ca(2+)-activated K(+) (BK(Ca)) channel activity, whereas sphingosine and other positively charged single-chain lipids suppress activity. Because these molecules are effective on both inside-out and outside-out patches and because they can flip across the bilayer, the location of their site of action is unclear. To identify the site of action of charged lipids on this channel, we used two compounds that are unlikely to flip across the lipid bilayer...
March 2003: American Journal of Physiology. Cell Physiology
F Delie, P Couvreur, D Nisato, J B Michel, F Puisieux, Y Letourneux
A diglyceride derivative of a pentapeptide renin inhibitor, the 1,3-dipalmitoyl-[Iva-Phe-Nle-Sta-Ala-Sta-acetyl]-glycerol was synthesized and tested in vitro as a potential prodrug for oral administration. The ability of the diglyceride analog to inhibit the renin activity was equivalent to that of the parent peptide after predigestion with pancreatic lipase. Furthermore, the presence of the palmitoyl groups was found to induce, in vitro, an efficient protection of the peptide from gastric and intestinal hydrolysis...
August 1994: Pharmaceutical Research
R B Johnson, S Köhl, K Wiesmüller, G Jung, W G Bessler
Two analogues of the N-terminal part of bacterial lipoprotein, S-[2,3-bis(palmitoyloxy)-(2RS)propyl]-N-palmitoyl-(R)-cysteine methyl ester ("tripalmitoyl cysteine") and S [-2,3-bis(palmitoyloxy)-(2RS)-propyl]-N-palmitoyl-(R)-cysteinyl-(S)-seryl-(S)-seryl-(S)-asparaginyl-(S)-alanine ("tripalmitoyl pentapeptide") were synthesized and tested for mitogenic activity. The compounds were potent mitogens towards mouse spleen cell cultures, as measured by 3H-thymidine incorporation and by hemolytic plaque assays. This activity was not dependent on the presence of serum...
July 1983: Immunobiology
K H Wiesmüller, W Bessler, G Jung
The N-terminal pentapeptide of the lipoprotein from the outer membrane of Escherichia coli was obtained by coupling S-[2,3-bis(palmitoyloxy)-(2RS)-propyl]-N-palmitoyl-(R)-cysteine to O-tert-butylseryl-O-tert-butyl-seryl-asparaginyl-alanine tert-butyl ester followed by deprotection with trifluoroacetic acid. The tetrapeptide was built up from alanine tert-butyl ester with N-9-fluorenylmethyloxycarbonyl protected amino acids. S-[2,3-Bis(palmitoyloxy)propyl]-N-palmitoylcysteine was obtained from N,N'-dipalmitoylcystine di-tert-butyl ester via reduction to the thiol, and S-alkylation with racemic 3-bromo-1,2-propanediol followed by esterification with palmitic acid in the presence of dicyclohexylcarbodiimide/dimethylaminopyridine and deprotection with trifluoroacetic acid...
May 1983: Hoppe-Seyler's Zeitschrift Für Physiologische Chemie
L Biesert, W Scheuer, W G Bessler
Lipoprotein from the outer membrane of Escherichia coli constitutes a potent mitogen and polyclonal activator for B lymphocytes of different species. The binding of lipoprotein to murine spleen cells was investigated using water-soluble 125I-labelled citraconylated lipoprotein from E. coli B/r. Our results indicate that the binding of this B-cell mitogen to splenocytes is a saturable, time- and dose-dependent, reversible process; about 9.7 X 10(8) lipoprotein molecules were bound to each cell. The mechanism of the binding of lipoprotein to lymphocytes was investigated by using the synthetic analogue of its N-terminal part, S-[2,3-bis(palmitoyloxy)-(2RS)-propyl]-N-palmitoyl-(R)-cysteinyl-( S)-seryl- (S)-seryl-(S)-asparaginyl-(S)-alanine (tripalmitoyl pentapeptide)...
February 2, 1987: European Journal of Biochemistry
A Lex, K H Wiesmüller, G Jung, W G Bessler
Lipoprotein from the outer membrane of Escherichia coli and other Enterobacteriaceae constitutes a potent B lymphocyte mitogen and polyclonal activator in various species. Tripalmitoyl pentapeptide (S-(2,3-bis-(palmitoyloxy)-(2RS)-propyl)-N-palmitoyl-(R)-cysteinyl -(S)-seryl-(S)-seryl-(S)-asparaginyl-(S)-alanine) is a synthetic analogue of the N-terminal part of lipoprotein and has, in all assays tested, a biologic activity similar to native lipoprotein. It also exhibits a strong adjuvant activity in vitro: In the presence of 3...
October 15, 1986: Journal of Immunology: Official Journal of the American Association of Immunologists
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