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Novel Diamidino-Substituted Derivatives of Phenyl-Benzothiazolyl- and Dibenzothiazolyl-Furans and Thiophenes : Synthesis, Antiproliferative and DNA binding Properties


Racané, Livio; Tralić-Kulenović, Vesna; Kraljević Pavelić, Sandra; Ratkaj, Ivana; Peixoto, Paul; Nhili, Raja; Depauw, Sabine; Hildebrand, Marie-Paule; David-Cordonnier, Marie-Hélène; Pavelić, Krešimir; Karminski-Zamola, Grace
Novel Diamidino-Substituted Derivatives of Phenyl-Benzothiazolyl- and Dibenzothiazolyl-Furans and Thiophenes : Synthesis, Antiproliferative and DNA binding Properties // Journal of medicinal chemistry, 53 (2010), 5; 2418-2432 doi:10.1021/jm901441b (međunarodna recenzija, članak, znanstveni)


Naslov
Novel Diamidino-Substituted Derivatives of Phenyl-Benzothiazolyl- and Dibenzothiazolyl-Furans and Thiophenes : Synthesis, Antiproliferative and DNA binding Properties

Autori
Racané, Livio ; Tralić-Kulenović, Vesna ; Kraljević Pavelić, Sandra ; Ratkaj, Ivana ; Peixoto, Paul ; Nhili, Raja ; Depauw, Sabine ; Hildebrand, Marie-Paule ; David-Cordonnier, Marie-Hélène ; Pavelić, Krešimir ; Karminski-Zamola, Grace

Izvornik
Journal of medicinal chemistry (0022-2623) 53 (2010), 5; 2418-2432

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Diamidines ; furans ; thieophenes ; antitumor activizy ; DNA binding ; sequence-selectivity ; celllular distribuction ; spectroscopic identification

Sažetak
A series of new diamidino, diisopropylamidino and diimidazolinyl substituted derivatives of phenyl-benzothiazolyl- and dibenzothiazolyl-furans and -thiophenes were successfully prepared and evaluated for their antiproliferative activity on tumour cell lines in vitro, DNA binding propensity and sequence-selectivity as well as cellular distribution. A strong antiproliferative effect of the tested compounds was observed on all tested cell lines in a concentration-dependent response pattern. In general, imidazolinyl-substituded derivatives and/or the thiophene core were in correlation with increased antiproliferative activity. Two compounds (2b and 3b) were chosen for biological studies due to their differential antiproliferative properties. The DNA binding properties of this new series of compounds were assessed and evidenced their efficient minor groove binding properties with preferential interaction at AT-rich sites. Both compounds also present nuclear sub-cellular localization, suggesting that their cellular mode of action implies localization in the DNA compartment and direct inhibition of DNA replication and induction of apoptosis.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Biologija



POVEZANOST RADA


Projekt / tema
117-0000000-3283 - Istraživanje novih višenamjenskih bojila i optičkih bjelila (Livio Racane, )
125-0982464-1356 - Novi heterocikli kao antitumorski i antivirusni ("pametni") lijekovi (Marijana Hranjec, )
335-0000000-3532 - Uloga IGF2 i signalni putovi nizvodno u karcinomima pluća čovjeka (Sandra Kraljević Pavelić, )
335-0982464-2393 - Molekularna obilježja miofibroblasta Dupuytrenove bolesti (Krešimir Pavelić, )

Ustanove
Institut "Ruđer Bošković", Zagreb,
Tekstilno-tehnološki fakultet, Zagreb,
Fakultet kemijskog inženjerstva i tehnologije, Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE


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