Truncated azinomycin analogues intercalate into DNA.
The design and synthesis of a potentially more therapeutically-viable azinomycin analogue 4 based upon 3 has been completed. It involved coupling of a piperidine mustard to the acid chloride of the azinomycin chromophore. Both the designed azinomycin analogue 4 and the natural product 3 bind to DNA and cause unwinding, supporting an intercalative mode of binding.
Casely-Hayford
Maxwell A
MA
Department of Pharmaceutical and Biological Chemistry, School of Pharmacy, University of London, 29-39 Brunswick Square, London WC1N 1AX, UK.
Pors
Klaus
K
Patterson
Laurence H
LH
Gerner
Clive
C
Neidle
Stephen
S
Searcey
Mark
M
D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000494:pharmacology; D053961:Azabicyclo Compounds; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D004247:DNA / Q000737:chemistry / Q000187:drug effects* / Q000378:metabolism; D004151:Dipeptides; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D006801:Humans; D007364:Intercalating Agents / Q000138:chemical synthesis*; D009691:Nucleic Acid Denaturation / Q000187:drug effects; D010880:Piperidines / Q000737:chemistry; D013329:Structure-Activity Relationship
D000903:Antibiotics, Antineoplastic; D053961:Azabicyclo Compounds; D004151:Dipeptides; D006020:Glycopeptides; D007364:Intercalating Agents; D010880:Piperidines; C051054:azinomycin A; C032727:piperidine; D004247:DNA