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New anticancer active and selective phenylene-bisbenzothiazoles : Synthesis, Antiproliferative Evaluation and DNA binding


Racané, Livio; Kraljević Pavelić, Sandra; Nhili, Raja; Depauw, Sabine; Paul-Constant, Charles; Ratkaj, Ivana; David-Cordonnier, Marie-Helene; Pavelić, Krešimir; Tralić-Kulenović, Vesna; Karminski-Zamola, Grace
New anticancer active and selective phenylene-bisbenzothiazoles : Synthesis, Antiproliferative Evaluation and DNA binding // European journal of medicinal chemistry, 63 (2013), 882-891 doi:10.1016/j.ejmech.2013.02.026 (međunarodna recenzija, članak, znanstveni)


Naslov
New anticancer active and selective phenylene-bisbenzothiazoles : Synthesis, Antiproliferative Evaluation and DNA binding

Autori
Racané, Livio ; Kraljević Pavelić, Sandra ; Nhili, Raja ; Depauw, Sabine ; Paul-Constant, Charles ; Ratkaj, Ivana ; David-Cordonnier, Marie-Helene ; Pavelić, Krešimir ; Tralić-Kulenović, Vesna ; Karminski-Zamola, Grace

Izvornik
European journal of medicinal chemistry (0223-5234) 63 (2013); 882-891

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

Ključne riječi
Amdino-substituted phenylene-bisbenzothiazoles; antitumor evaluation; DNA-binding; apoptosis

Sažetak
Novel amidino- derivatives of phenylene-bisbenzothiazoles were synthesized and tested for their antiproliferative activity against several human cancer cell lines, as well as DNA-binding properties. The synthetic approach used for preparation of isomeric amidino substituted-phenylene-bis-benzothyazoles 3a-3f was achieved by condensation reaction of isophthaloyl dichloride 1a and terephthaloyl dichloride 1b or with phthalic acid 1c with 5-amidinium-2-aminobenzothiolate 2a and 5-(imidazolinium-2-yl)-2-aminobenzothiolate 2b in good yields. The targeted compounds were converted in the desired water soluble dihydrochloride salts by reaction of appropriate free base with concd HCl in ethanol or acetic acid. All tested compounds (3a-3f) showed antiproliferative effects on tumour cells in a concentration-dependent manner. The strongest activity and cytotoxicity was observed for diimidazolinyl substituted phenylene-bisbenzothiazole compound 3b. These effects were shown to be related to DNA-binding properties, topoisomerase I and II poisoning effects and apoptosis induction. The highest tested selectivity towards tumor cells was observed for the imidazolyl substituted phenylene-benzothiazole 3d that showed no cytotoxic effects on normal fibroblasts making it an excellent candidate for further chemical optimization and preclinical evaluation.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Biologija



POVEZANOST RADA


Projekt / tema
0982464-1356
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, )
335-0982464-239

Ustanove
Tekstilno-tehnološki fakultet, Zagreb,
Fakultet kemijskog inženjerstva i tehnologije, Zagreb,
Sveučilište u Rijeci - Odjel za biotehnologiju

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


Uključenost u ostale bibliografske baze podataka:


  • Chemoreception Abstracts


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