Synthesis and cytogenetic effects of aminoquinone derivatives with a di- and a tripeptide.
Quinones are of significant interest due to their important role in specific cellular functions. Quinoproteins are a big class of oxyreductive agents occurring in bacteria and other organisms. In this investigation derivatives of 2-amino-1,4-benzoquinone, 2-amino-1,4-naphthoquinone and 2-amino-5,8-dihydroxy-1,4-naphthoquinone with a di- and a tripeptide were prepared for first time. The effect of the synthesized compounds on sister chomatid exchange (SCE) rates and human lymphocyte proliferation kinetics on a molar basis was studied. Among these coupled products the most effective in inducing SCEs and depressing proliferation rate indices is the coupling product of 2-amino-1,4-naphthoquinone with the tripeptide GHK (10). Next in order of magnitude in inducing cytogenetic effects is 2-amino-1,4-naphthoquinone (2) and its coupling products with glycine and serine (4 and 5), while the rest displayed marginal activity.
Pachatouridis
C
C
Department of Chemical Engineering, Section of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54006, Greece.
Iakovidou
Z
Z
Myoglou
E
E
Mourelatos
D
D
Pantazaki
A A
AA
Papageorgiou
V P
VP
Kotsis
A
A
Liakopoulou-Kyriakides
M
M
D016227:Benzoquinones / Q000138:chemical synthesis* / Q000494:pharmacology*; D004249:DNA Damage; D004260:DNA Repair; D006801:Humans; D008214:Lymphocytes / Q000648:ultrastructure; D008677:Metaphase / Q000187:drug effects; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000494:pharmacology*; D009842:Oligopeptides / Q000737:chemistry*; D012854:Sister Chromatid Exchange / Q000187:drug effects*
D016227:Benzoquinones; D009285:Naphthoquinones; D009842:Oligopeptides