Synthesis and Characterization of GHK Peptides and their Interactions with Copper Investigated by Mass Spectrometry
Disciplines
Analytical Chemistry | Medicinal-Pharmaceutical Chemistry
Abstract (300 words maximum)
Tripeptide, GHK, has been observed to interact with copper in human blood plasma and forms GHK-Cu complexes that occur naturally and allow for the transfer of nontoxic copper ions into cells. These GHK-Cu complexes present in plasma aid in a variety of biological functions related to healing including promotion of healing of wounds, attraction of immune cells, blood vessel growth, and antioxidant and anti-inflammatory effects. Synthetically derived GHK-Cu complexes are frequently used in cosmetics that address repairing and anti-aging effects in skin. Nitrogen present in the amino acids glycine and histidine are responsible for the binding of Copper within the GHK-Cu complex. In this study, three peptides including GHK, GHKGHK, and GHKGHKGHK were synthesized via Solid-Phase Peptide Synthesis (SPPS) using rink amide resin. To synthesize a peptide in SPPS, three key steps need to be fulfilled: i) resin swelling, (ii) deprotection of the protected group, and (iii) coupling reaction in order to form the amide bonds. After the synthesis, the peptide-resin complex needs to cleavage using high percentage of trifluoracetic acid. Subsequently, peptide was precipitated by addition cold ether and recovered as power by lyophilization under high vacuum. The synthesis of these three peptides were confirmed by mass spectrometry which agreed well with the theoretical masses. For GHK peptide, peaks observed at m/z 341 and 171 corresponds to [M+H]+ and [M+2H]2+ charge states. For GHKGHK and GHKGHKGHK peptides, peaks detected at m/z 662 and 984 corresponds to [M+H]+ charge state, respectively. Beside singly charge states, double charge states are also noticed for these peptides. Current studies are focusing to obtain the copper interactions with these peptides.
Academic department under which the project should be listed
CSM - Chemistry and Biochemistry
Primary Investigator (PI) Name
Mohammad A. Halim
Synthesis and Characterization of GHK Peptides and their Interactions with Copper Investigated by Mass Spectrometry
Tripeptide, GHK, has been observed to interact with copper in human blood plasma and forms GHK-Cu complexes that occur naturally and allow for the transfer of nontoxic copper ions into cells. These GHK-Cu complexes present in plasma aid in a variety of biological functions related to healing including promotion of healing of wounds, attraction of immune cells, blood vessel growth, and antioxidant and anti-inflammatory effects. Synthetically derived GHK-Cu complexes are frequently used in cosmetics that address repairing and anti-aging effects in skin. Nitrogen present in the amino acids glycine and histidine are responsible for the binding of Copper within the GHK-Cu complex. In this study, three peptides including GHK, GHKGHK, and GHKGHKGHK were synthesized via Solid-Phase Peptide Synthesis (SPPS) using rink amide resin. To synthesize a peptide in SPPS, three key steps need to be fulfilled: i) resin swelling, (ii) deprotection of the protected group, and (iii) coupling reaction in order to form the amide bonds. After the synthesis, the peptide-resin complex needs to cleavage using high percentage of trifluoracetic acid. Subsequently, peptide was precipitated by addition cold ether and recovered as power by lyophilization under high vacuum. The synthesis of these three peptides were confirmed by mass spectrometry which agreed well with the theoretical masses. For GHK peptide, peaks observed at m/z 341 and 171 corresponds to [M+H]+ and [M+2H]2+ charge states. For GHKGHK and GHKGHKGHK peptides, peaks detected at m/z 662 and 984 corresponds to [M+H]+ charge state, respectively. Beside singly charge states, double charge states are also noticed for these peptides. Current studies are focusing to obtain the copper interactions with these peptides.