Umfang:
Online-Ressource
ISSN:
1521-4109
Inhalt:
Abstract: Electrochemical DNA‐based biosensors are used as screening devices for a rapid evaluation of chemical compounds interacting with double helix of the nucleic acid. Pentamidine is one of minor groove binding chemotherapeutics clinically used as anti‐PCP agent. Therefore, we designed, synthesized and tested some pentamidine analogues with diethyl ether linker and 1,2‐diazine (pyridazine) or 1,3,5‐triazine derivatives with cyanophenoxy substituent, precursors of amidine groups to establish if they can be more efficacious DNA interacting compounds than the original pentamidine drug. The tested compounds were: 1,5‐bis (4‐amidinophenoxy) pentane isethionate‐pentamidine (1) used as template, 6‐chloro‐3‐(4‐cyanophenoxy) pyridazine (2), 4,6‐dichloro‐2‐(4‐cyanophenoxy)‐1,3,5‐triazine (3), 4‐amidinophenol dihydrate (4), 1,5‐bis (4‐amidinophenoxy)‐3‐oxapentane dihydrochloride‐γ‐oxapentamidine (5), 1,5‐bis (N‐cyclohexyl‐4‐amidinophenoxy)‐3‐oxapentane dihydrochloride (6). The results show that none of the tested analogues binds dsDNA more strongly than the original drug pentamidine (1). Compound 2 with pyridazine group interacts with the nucleic acid in a different way than the one with triazine (3) – the signals obtained using DNA‐based biosensor had opposite features. Close derivatives 5 and 6 of the main drug pentamidine (1) showed a weak influence on the double‐stranded nucleic acid which proves that even small changes in the structure of a molecule can strongly affect the character and properties of the above mentioned compounds in the presence of DNA. In this context atomic charge distribution in the studied molecules is also discussed.
In:
volume:18
In:
number:13‐14
In:
year:2006
In:
pages:1422-1430
In:
extent:9
In:
Electroanalysis, Weinheim : Wiley-VCH-Verl., 1989-, 18, Heft 13‐14 (2006), 1422-1430 (gesamt 9), 1521-4109
Sprache:
Englisch
DOI:
10.1002/elan.200603554
URN:
urn:nbn:de:101:1-2023091004505300001627
URL:
https://doi.org/10.1002/elan.200603554
URL:
https://nbn-resolving.org/urn:nbn:de:101:1-2023091004505300001627
URL:
https://d-nb.info/1302056522/34
URL:
https://doi.org/10.1002/elan.200603554
