Synthesis, DNA Interactions and Anticancer Evaluation of Novel Diamidine Derivatives of 3,4-Ethylenedioxythiophene

Stolić, Ivana; Avdičević, Monika; Bregović, Nikola; Piantanida, Ivo; Glavaš-Obrovac, Ljubica; Bajić, Miroslav (2012) Synthesis, DNA Interactions and Anticancer Evaluation of Novel Diamidine Derivatives of 3,4-Ethylenedioxythiophene. Croatica Chemica Acta, 85 (4). pp. 457-467. ISSN 0011-1643

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Abstract

Eight novel diamidino 3, 4-ethylenedioxythiophene-2, 5-dicarboxanilides (5a–h), obtained by condensation reaction of 3, 4-ethylenedioxythiophene-2, 5-dicarbonyl chloride and corresponding 3- or 4-aminobenzamidines, were evaluated for interactions with double-stranded DNA and RNA, and their cytotoxicity was assayed against the panel of human cancer cell lines. All compounds preferentially bind into the minor groove of DNA and had higher affinity for DNA than for RNA. Compounds 5a–h showed a moderate antiproliferative effect toward the panel of seven carcinoma cells line, whereby the highest inhibitory potential was displayed by compound 5a with unsubstituted amidino moieties in para position.

Item Type:	Article
Uncontrolled Keywords:	amide-amidines; 3,4-ethylenedioxythiophene; diarylamidine; DNA/RNA binding; antitumor activity; minor-groove binders; multidrug-resistance; aromatic diamidines; binding-properties; gastric-cancer; agents; pentamidine; antitumor; analogs; bisbenzamidines
Subjects:	NATURAL SCIENCES > Chemistry
Divisions:	Division of Organic Chemistry and Biochemistry
Projects:	Project title Project leader Project code Project type Elektroliti i koordinacijske reakcije u otopini [187592] Vladislav Tomišić 119-1191342-2960 MZOS Dizajn, sinteza i ispitivanje interakcija malih molekula s DNA, RNA i proteinima [202026] Ivo Piantanida 098-0982914-2918 MZOS Uloga malih zaštitinih TFF proteina u zdravlju i bolesti [222563] Mirela Baus Lončar 219-0982914-2179 MZOS Mehanizam bioloških učinaka novih malih molekula na stanice tumora čovjeka [162671] Ljubica Glavaš Obrovac 219-0982914-2176 MZOS Dizajn i sinteza bisamidina sa protutumorskim djelovanjem [1543] Miroslav Bajić 053-0982914-2965 MZOS
Depositing User:	Ivo Piantanida
Date Deposited:	10 Oct 2013 12:37
URI:	http://fulir.irb.hr/id/eprint/765
DOI:	10.5562/cca2141

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