Diazo group electrophilicity in kinamycins and lomaiviticin A: potential insights into the molecular mechanism of antibacterial and antitumor activity.
Theoretical and chemical studies of the reactivity of isoprekinamycin, the kinamycins, and the lomaiviticins support the proposal that these natural products exhibit enhanced diazonium salt character and may owe their antitumor antibiotic properties to their ability to act as electrophilic azo-coupling agents in vivo.
Laufer
Radoslaw S
RS
Department of Chemistry, University of Waterloo, Waterloo, Ontario, Canada, N2L 3G1.
Dmitrienko
Gary I
GI
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D005449:Fluorenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D011809:Quinones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D000095602:Angucyclines and Angucyclinones
D000900:Anti-Bacterial Agents; D000903:Antibiotics, Antineoplastic; D005449:Fluorenes; D011809:Quinones; C433842:lomaiviticin A; D000095602:Angucyclines and Angucyclinones; C001507:kinamycin A; C041511:benzo(a)fluorene