An octakis-intercalating molecule.
Herein we report the synthesis and characterization of a polyintercalator with eight potential intercalating l,4,5,8-naphthalenetetracarboxylic diimide (NDI) units linked in a head-to-tail arrangement via a peptide linker. UV spectroscopy and viscometry measurements indicated the molecule binds to double-stranded DNA with all eight NDI units intercalated simultaneously. Competition dialysis and DNAse 1 footprinting studies revealed a preference for GC-rich regions of DNA, and circular dichroism studies revealed significant distortion of B-form DNA upon binding. Our so-called "octamer" represents, to the best of our knowledge, the first intercalator that binds as an octakis-intercalator, capable of spanning at least 16 base pairs of DNA.
Murr
M M
MM
Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, TX 78712, USA.
Harting
M T
MT
Guelev
V
V
Ren
J
J
Chaires
J B
JB
Iverson
B L
BL
D000818:Animals; D020029:Base Pairing / Q000235:genetics / Q000502:physiology; D001665:Binding Sites / Q000502:physiology; D002417:Cattle; D002942:Circular Dichroism; D004247:DNA / Q000737:chemistry* / Q000378:metabolism; D018983:DNA Footprinting / Q000379:methods; D020862:GC Rich Sequence / Q000235:genetics / Q000502:physiology*; D007094:Imides / Q000737:chemistry* / Q000378:metabolism; D007364:Intercalating Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism*; D009281:Naphthalenes / Q000737:chemistry* / Q000378:metabolism; D010455:Peptides / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet / Q000379:methods; D014783:Viscosity
C429685:1,4,5,8-naphthalenetetracarboxylic diimide; D007094:Imides; D007364:Intercalating Agents; D009281:Naphthalenes; D010455:Peptides; D004247:DNA; C427203:calf thymus DNA