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Pregled bibliografske jedinice broj: 853931

Design, synthesis and biological evaluation of novel primaquine-cinnamic acid conjugates of the amide and acylsemicarbazide type


Pavić, Kristina; Perković, Ivana; Gilja, Petra; Kozlina, Filip; Ester, Katja; Kralj, Marijeta; Schols, Dominique; Hadjipavlou- Litina, Dimitra; Pontiki, Eleni; Zorc, Branka
Design, synthesis and biological evaluation of novel primaquine-cinnamic acid conjugates of the amide and acylsemicarbazide type // Molecules, 21 (2016), 12; 1629, 24 doi:10.3390/molecules21121629 (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 853931 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Design, synthesis and biological evaluation of novel primaquine-cinnamic acid conjugates of the amide and acylsemicarbazide type

Autori
Pavić, Kristina ; Perković, Ivana ; Gilja, Petra ; Kozlina, Filip ; Ester, Katja ; Kralj, Marijeta ; Schols, Dominique ; Hadjipavlou- Litina, Dimitra ; Pontiki, Eleni ; Zorc, Branka

Izvornik
Molecules (1420-3049) 21 (2016), 12; 1629, 24

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

Ključne riječi
primaquine ; cinnamic acid derivative ; conjugate ; cytostatic activity ; antiviral activity ; antioxidative activity

Sažetak
In this paper design and synthesis of a scaffold comprising primaquine (PQ) motif and cinnamic acid derivatives (CADs) bound directly (compounds 3a–k) or via a spacer (compounds 7a– k) are reported. In the first series of compounds, PQ and various CADs were connected by amide bonds and in the second series by acylsemicarbazide functional groups built from the PQ amino group, CONHNH spacer and the carbonyl group originating from the CADs. PQ- CAD amides 3a–k were prepared by a simple one- step condensation reaction of PQ with a series of CAD chlorides (method A) or benzotriazolides 2 (method B). The synthesis of acylsemicarbazides 7a–k included activation of PQ with benzotriazole, preparation of PQ- semicarbazide 6 and its condensation with CAD chlorides 4. All synthesized PQ-CAD conjugates were evaluated for their anticancer, antiviral and antioxidative activities. Almost all compounds from series 3 were selective towards the MCF-7 cell line and active at micromolar concentrations. The o-fluoro derivative 3h showed high activity against HeLa, MCF-7 and in particular against the SW 620 cell line, while acylsemicarbazide 7f with a benzodioxole ring and 7c, 7g and especially 7j with methoxy-, chloro- or trifluoromethyl-substituents in the para position showed high selectivity and high inhibitory activity against MCF-7 cell line at micromolar (7c, 7f, 7g) and nanomolar (7j) levels. Acylsemicarbazide derivatives with trifluoromethyl group(s) 7i, 7j and 7k showed specific activity against human coronavirus (229E) at concentrations which did not alter the normal cell morphology. The same compounds exerted the most potent reducing activity in the DPPH test, together with 7d and 7g, while methoxy (compounds 7c–e), benzodioxole (7f), p- Cl (7g) and m-CF3 (7i) acylsemicarbazides and amide 3f presented the highest LP inhibition (83%–89%). The dimethoxy derivative 7d was the most potent LOX inhibitor (IC50 = 10 μΜ). The performed biological tests gave evidence of acylsemicarbazide functional group as superior binding group in PQ-CAD conjugates.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti, Farmacija



POVEZANOST RADA


Projekti:
IP-2013-11-5660 - Mulitidisciplinarni pristup otkriću lijekova s ciljanim djelovanjem na matične stanice tumora – uloga transporta kalija (MultiCaST) (Kralj, Marijeta, HRZZ - 2013-11) ( POIROT)
IP-2014-09-1501 - Dizajniranje, sinteza i evaluacija derivata primakina, vorinostata i sorafeniba kao potencijalnih citostatika (PVSderivatives) (HRZZ - 2014-09) ( POIROT)

Ustanove:
Farmaceutsko-biokemijski fakultet, Zagreb,
Institut "Ruđer Bošković", Zagreb

Profili:

Avatar Url Branka Zorc (autor)

Avatar Url Kristina Pavić (autor)

Avatar Url Marijeta Kralj (autor)

Avatar Url Katja Ester (autor)

Avatar Url Ivana Perković (autor)

Citiraj ovu publikaciju

Pavić, Kristina; Perković, Ivana; Gilja, Petra; Kozlina, Filip; Ester, Katja; Kralj, Marijeta; Schols, Dominique; Hadjipavlou- Litina, Dimitra; Pontiki, Eleni; Zorc, Branka
Design, synthesis and biological evaluation of novel primaquine-cinnamic acid conjugates of the amide and acylsemicarbazide type // Molecules, 21 (2016), 12; 1629, 24 doi:10.3390/molecules21121629 (međunarodna recenzija, članak, znanstveni)
Pavić, K., Perković, I., Gilja, P., Kozlina, F., Ester, K., Kralj, M., Schols, D., Hadjipavlou- Litina, D., Pontiki, E. & Zorc, B. (2016) Design, synthesis and biological evaluation of novel primaquine-cinnamic acid conjugates of the amide and acylsemicarbazide type. Molecules, 21 (12), 1629, 24 doi:10.3390/molecules21121629.
@article{article, year = {2016}, pages = {24}, DOI = {10.3390/molecules21121629}, chapter = {1629}, keywords = {primaquine, cinnamic acid derivative, conjugate, cytostatic activity, antiviral activity, antioxidative activity}, journal = {Molecules}, doi = {10.3390/molecules21121629}, volume = {21}, number = {12}, issn = {1420-3049}, title = {Design, synthesis and biological evaluation of novel primaquine-cinnamic acid conjugates of the amide and acylsemicarbazide type}, keyword = {primaquine, cinnamic acid derivative, conjugate, cytostatic activity, antiviral activity, antioxidative activity}, chapternumber = {1629} }
@article{article, year = {2016}, pages = {24}, DOI = {10.3390/molecules21121629}, chapter = {1629}, keywords = {primaquine, cinnamic acid derivative, conjugate, cytostatic activity, antiviral activity, antioxidative activity}, journal = {Molecules}, doi = {10.3390/molecules21121629}, volume = {21}, number = {12}, issn = {1420-3049}, title = {Design, synthesis and biological evaluation of novel primaquine-cinnamic acid conjugates of the amide and acylsemicarbazide type}, keyword = {primaquine, cinnamic acid derivative, conjugate, cytostatic activity, antiviral activity, antioxidative activity}, chapternumber = {1629} }

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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