Influence of the methyl substituents of a thiazole-containing lexitropsin on the mode of binding to DNA.
We have studied the DNA-binding properties of two thiazole-containing analogues of netropsin which differ by the absence (Thia-Nt) or presence (Methia-Nt) of methyl groups on the thiazole rings. The mode of binding to DNA of the two lexitropsins was investigated by circular dichroism, electric linear dichroism and viscosity measurements. The spectroscopic and hydrodynamic results indicate that the non-methylated lexitropsin binds to the minor groove of DNA, whereas the methylated analogue behaves as an intercalator. Our findings led to the notion that the methyl substituents on the thiazole rings might play a significant part in the intercalation process.
Plouvier
B
B
Institut de Chimie Pharmaceutique, Lille, France.
Houssin
R
R
Helbecque
N
N
Colson
P
P
Houssier
C
C
Hénichart
J P
JP
Bailly
C
C
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000378:metabolism*; D001665:Binding Sites; D002417:Cattle; D004247:DNA / Q000378:metabolism*; D007364:Intercalating Agents / Q000737:chemistry / Q000378:metabolism; D009429:Netropsin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D013057:Spectrum Analysis; D013844:Thiazoles / Q000378:metabolism*; D014783:Viscosity
D000970:Antineoplastic Agents; D007364:Intercalating Agents; D013844:Thiazoles; C053654:lexitropsin; D009429:Netropsin; D004247:DNA