Original scientific paper

https://doi.org/10.2478/v10007-010-0024-9

Primaquine-NSAID twin drugs: Synthesis, radical scavenging, antioxidant and Fe2+ chelating activity

ZRINKA RAJIĆ ; Faculty of Pharmacy and Biochemistry, University of Zagreb, Zagreb, Croatia
MARIJANA ZOVKO KONČIĆ ; Faculty of Pharmacy and Biochemistry, University of Zagreb, Zagreb, Croatia
KRISTINA MILOLOŽA ; Faculty of Pharmacy and Biochemistry, University of Zagreb, Zagreb, Croatia
IVANA PERKOVIĆ ; Faculty of Pharmacy and Biochemistry, University of Zagreb, Zagreb, Croatia
IVAN BUTULA ; Faculty of Pharmacy and Biochemistry, University of Zagreb, Zagreb, Croatia
FRANZ BUCAR ; Institut für Pharmazeutische Wissenschaften, Bereich Pharmakognosie, Graz, Austria
BRANKA ZORC orcid.org/0000-0003-4355-8816 ; Faculty of Pharmacy and Biochemistry, University of Zagreb, Zagreb, Croatia

Abstract

Novel primaquine conjugates with non-steroidal anti-inflammatory drugs (PQ-NSAIDs, 4a-h) were prepared, fully chemically characterized and screened for radical scavenging and antioxidant activities. The synthetic procedure leading to twin drugs 4a-h involved two steps: i) preparation of NSAID benzotriazolides 3a-h from the corresponding NSAID (ibuprofen, ketoprofen, fenoprofen, ketoprofen hydroxy and methylene analogues, diclofenac or indomethacin) and benzotriazole carboxylic acid chloride (BtCOCl, 1), ii) reaction of intermediates 3a-h with PQ. The prepared PQ-NSAIDs exerted moderate activities in the DPPH free radical test and -carotene-linoleic acid assay. Moreover, ketoprofen derivatives 4d and 4b demonstrated a notable Fe2+ chelating ability as well. On the other hand, negligible antiproliferative and antituberculotic effects of conjugates 4a-h were observed.

Keywords

primaquine; NSAID; twin drug; conjugate; radical scavenging; antioxidant activity; chelating ability

Hrčak ID:

53494

URI

https://hrcak.srce.hr/53494

Publication date:

1.9.2010.

Article data in other languages: croatian

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