Synthesis and binding properties of conjugates between oligodeoxynucleotides and daunorubicin derivatives.
Conjugation of an anthracycline to a triplex-forming oligonucleotide (TFO) allows delivery of this drug to a specific DNA site, preserving the intercalation geometry of this class of anticancer agents. Conjugate 11, in which the TFO is linked via a hexamethylene bridge to the O-4 on the D ring of the anthraquinone moiety, affords the most stable triple helix, through intercalation of the planar chromophore between DNA bases and binding of both the TFO and the amino sugar to the major and the minor groove respectively.
Garbesi
A
A
I.Co.CEA-CNR, Via P.Gobetti 101, 40129 Bologna, Italy. garbesi@area.bo.cnr.it
Bonazzi
S
S
Zanella
S
S
Capobianco
M L
ML
Giannini
G
G
Arcamone
F
F
D000903:Antibiotics, Antineoplastic / Q000378:metabolism*; D004247:DNA / Q000378:metabolism; D003630:Daunorubicin / Q000031:analogs & derivatives* / Q000378:metabolism; D009690:Nucleic Acid Conformation; D009841:Oligonucleotides / Q000378:metabolism*; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet
D000903:Antibiotics, Antineoplastic; D009841:Oligonucleotides; D004247:DNA; D003630:Daunorubicin