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CID 9862773

HCID 9862773
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Grundinformationen

CAS
49557-75-7
Standard-SMILES
NCC(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N[C@@H](CCCC[NH3+])C(=O)[O-]
InChIKey
MVORZMQFXBLMHM-QWRGUYRKSA-N
Summenformel
C14H24N6O4
Durchschnittliche Molmasse
340,38 g/mol
Monoisotopische Masse
340,18590327

Überblick

Prezatide is a tripeptide consisting of glycine, histidine, and lysine which readily forms a complex with copper ions. Prezatide is used in cosmetic products for the skin and hair. It is known to aid wound healing and its potential applications in chronic obstructive pulmonary disease and metastatic colon cancer are currently being investigated.

Namen und Bezeichner

Bevorzugter Name
CID 9862773
IUPAC
(2S)-2-[[(2S)-2-[(2-aminoacetyl)amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-6-azaniumylhexanoate
Englischer Name
Copper Peptide
Summenformel
C14H24N6O4
Molmasse
340.38

Namen und Synonyme

Ahk-cuGHKCB0875341Glycyl-L-Histidyl-L-LysineTripeptide-1 CopperBlue copper peptideCooper PeptideGHK Cu Copper PeptideCu-GHKCopper Peptide AHK-Cu

Datenbank-Bezeichner

CAS
49557-75-7
PubChem CID
9862773

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-3,7
Polarare Oberfläche (TPSA)
181 Ų
H-Brücken-Donoren
5
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
10
Schwere Atome
24
Formalladung
0
Komplexität
428

Physikochemische Eigenschaften

Schmelzpunkt
144 °C · >144°C (dec.)
Siedepunkt
831 · 831.0±65.0 °C(Predicted)
Dichte
1.324 · 1.324
storage temp.
2 · under inert gas (nitrogen or Argon) at 2–8 °C
Löslichkeit
Aqueous Acid (Slightly), DMSO (Slightly)
Aggregatzustand
Solid
pka
3.11 · 3.11±0.10(Predicted)
Farbe
Off-White
Stabilität
Hygroscopic
InChIKey
MVORZMQFXBLMHM-QWRGUYRKSA-N
SMILES
C(O)(=O)[C@H](CCCCN)NC(=O)[C@H](CC1N=CNC=1)NC(=O)CN

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Sicherheitsdaten

Alarmwort
Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H317

Chemie und Industrie

Pharmakologische Informationen

Pharmacodynamics · 1 Eintrag

Prezatide in complex with copper improve skin elasticity, density, and firmness, reduces fine lines and wrinkles, reduces photodamage, increases keratinocyte proliferation. Prezatide also displays anti-oxidant and angiogenic effects and appears to modulate tissue remodeling in injury.

Mechanism of Action · 1 Eintrag

Prezatide in complex with copper increases the synthesis and deposition of type I collagen and glycosaminoglycan. It also increases the expression of matrix metalloproteinase-2 as well as tissue inhibitor of matrix metalloproteinases-1 and -2, suggesting that it plays a role in the modulation of tissue remodeling. It is thought that prezatide's antioxidant activity is due to its ability to supply copper for superoxide dismutase and its anti inflammatory ability due to the blockage the of iron (Fe2+) release during injury. Prezatide also increases angiogenesis to injury sites. The precise mechanisms of these effects are unknown. It is also unknown whether prezatide's effects are due to the action of the tripeptide itself or its ability to localize and transport copper. Prezatide is known to be bound by heparin and heparin sulfate

Biological Half-LifePrezatide is rapidly eliminated within minutes.
Metabolism/MetabolitesPrezatide is broken down to histidyl-lysine which is likely further degraded to other metabolites of proteolysis.
Absorption, Distribution and ExcretionPrezatide both free and in complex with copper can pass through the stratum corneum. Its absorption is pH dependent with the highest absorption occurring at physiological pH.
Anwendungen · 2 Einträge

BeschreibungCopper peptide GHK-Cu is a naturally occurring copper complex of the tripeptide glycyl-L-histidyl-L-lysine. The tripeptide has strong affinity for copper(II) and was first isolated from human plasma. It can be found also in saliva and urine.

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Verwendenanti-wrikle

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Fmoc-His(Trt)-OHN6-(tert-Butoxycarbonyl)-N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-lysinFmoc-Gly-OH

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Ergänzende Hinweise

DefinitionChEBI: Gly-His-Lys is a tripeptide composed of glycine, L-histidine and L-lysine residues joined in sequence. It has a role as a metabolite, a chelator, a vulnerary and a hepatoprotective agent.