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Synthesis and in vitro evaluation of antiviral and cytostatic properties of novel 8-triazolyl acyclovir derivatives

Saftić, Dijana; Žinić, Biserka; Glavaš- Obrovac, Ljubica; Studzińska, Mirosława; Paradowska, Edyta; Leśnikowski, Zbigniew J. (2018) Synthesis and in vitro evaluation of antiviral and cytostatic properties of novel 8-triazolyl acyclovir derivatives. Nucleosides, Nucleotides and Nucleic Acids, 37 (7). pp. 397-414. ISSN 1525-7770

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Abstract

As a part of the research aimed on identification of new nucleobase derivatives with improved biological properties, a series of novel 8-substituted acyclovir derivatives were synthesized. The 8-azidoguanosine 4 and novel 8-azidoacyclovir 9 were synthesized from commercially available guanosine 1 and acyclovir 6 which were transformed into 8- bromopurine derivatives 2 and 7 and hydrazine derivatives 3 and 8, respectively. 8- Triazolylguanosine 5 and 8- triazolylacyclovir analogs 1012 were successfully synthesized via the Cu(I) catalyzed 1, 3-dipolar cycloaddition reaction of azides 4 and 9 with propargyl alcohol, 4-pentyn-1-ol and 5-hexyn-1-ol. The novel 1, 4-disubstituted 1, 2, 3-triazolyl compounds 5, 1012 were evaluated for antiviral activity against selected DNA and RNA viruses and cytostatic activity against normal Madine Darby canine kidney (MDCK I) cells, and seven tumor cell lines (HeLa, CaCo-2, NCI-H358, Jurkat, K562, Raji and HuT78). While tested compounds exerted no antiviral activity at nontoxic concentrations, the 8-triazolyl acyclovir derivative 10, with the shortest alkyl substituent at the C-4 of triazole ring, was found to be the most active against the CaCo-2 cell line.

Item Type: Article
Additional Information: The authors gratefully acknowledge financial support from the Ministry of Science, Education and Sport of Croatia (grants 098-0982914-2935, 219-0982914-2176); Croatian Science Foundation (grant HRZZ-1477); National Science Center, Poland (grant 2015/16/W/ST5/00413); J.J. Strossmayer University of Osijek supporting grant to Lj. Glavas-Obrovac (IZIP-2016) and VIF2015-MEFOS-2. Additionally, contributions from the Statutory Fund of IMB PAS are also gratefully acknowledged.
Uncontrolled Keywords: 8-triazolyl acyclovir ; 1, 4-disubstituted 1, 2, 3-triazole ; cytotoxic activity ; antiviral activity
Subjects: NATURAL SCIENCES > Chemistry
NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Projects:
Project titleProject leaderProject codeProject type
Višenamjensko očitavanje DNA / RNA sekundarne strukture molekularnim kemijskim senzorima-DNA/RNA-MolSenseIvo PiantanidaIP-2013-11-1477HRZZ
Sinteza novih biološki aktivnih derivata nukleobaza i nukleotida-Biserka Žinić098-0982914-2935MZOS
Mehanizam bioloških učinaka novih malih molekula na stanice tumora čovjeka-Ljubica Glavaš Obrovac219-0982914-2176MZOS
Depositing User: Dr. sc. Dijana Pavlović Saftić
Date Deposited: 11 Dec 2019 11:05
Last Modified: 11 Dec 2019 11:05
URI: http://fulir.irb.hr/id/eprint/5253
DOI: 10.1080/15257770.2018.1485932

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