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

Acta Pharmaceutica

Volumn 60, Issue 3, 2010, Pages 325-337

  Rajić, Zrinka ^a   Končić, Marijana ^a   Miloloža, Kristina ^a   Perković, Ivana ^a   Butula, Ivan ^a   Bucar, Franz ^b   Zorc, Branka ^a  

^a UNIVERSITY OF ZAGREB   (Croatia)

^b Bereich Pharmakognosie Graz   (Austria)

Author keywords

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

Indexed keywords

1 (4 CHLOROBENZOYL) 2 METHYL 5 METHOXY N (4 (6 METHOXYQUINOLIN 8 YLAMINO)PENTYL) 1H INDOLE 3 ACETAMIDE; 2 [2 (2,6 DICHLOROPHENYLAMINO)PHENYL] N [4 (6 METHOXYQUINOLIN 8 YLAMINO)PENTYL]ACETAMIDE; ANTIBIOTIC AGENT; ANTINEOPLASTIC AGENT; ANTIOXIDANT; BENZOTRIAZOLIDE DERIVATIVE; BETA CAROTENE; CARBENE; DICLOFENAC; FENOPROFEN; IBUPROFEN; INDOMETACIN; IRON CHELATING AGENT; KETOPROFEN; N [4 (6 METHOXYQUINOLIN 8 YLAMINO)PENTYL] 2 (3 BENZOYLPHENYL)PROPANAMIDE; N [4 (6 METHOXYQUINOLIN 8 YLAMINO)PENTYL] 2 (3 BENZYLPHENYL)PROPANAMIDE; N [4 (6 METHOXYQUINOLIN 8 YLAMINO)PENTYL] 2 (3 PHENOXYPHENYL)PROPANAMIDE; N [4 (6 METHOXYQUINOLIN 8 YLAMINO)PENTYL] 2 (4 ISOBUTYLPHENYL)PROPANAMIDE; N [4 (6 METHOXYQUINOLIN-8 YLAMINO)PENTYL] 2 [3 (HYDROXY(PHENYL)METHYL)PHENYL]PROPAN AMIDE; NONSTEROID ANTIINFLAMMATORY AGENT; PRIMAQUINE; SCAVENGER; UNCLASSIFIED DRUG; [3 [1 (4 (6 METHOXYQUINOLIN 8 YLAMINO)PENTYLCARBAMOYL)ETHYL]PHENYL][(PHENYL)METHYL 4 (6 METHOXYQUINOLIN 8 YLAMINO)PENTYLCARBAMATE];

ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG EFFECT; DRUG SYNTHESIS; HUMAN; HUMAN CELL; NONHUMAN;

EID: 78650113042     PISSN: 13300075     EISSN: 18469558     Source Type: Journal    
DOI: 10.2478/v10007-010-0024-9     Document Type: Article

References (16)

1. A. Paboón, J. Carmona, L. C. Burgos, S. Blair Oxidative stress in patients with non-complicated malaria Clin. Biochem. 36 (2003) 71-78; DOI: 10.1016/S0009-9120(02)00423-X.
2. D. V. Ratnam, D. D. Ankola, V. Bhardwaj, D. K. Sahana and M. N. V. Ravi Kumar, Role of anti-oxidants in prophylaxis and therapy: A pharmaceutical perspective, J. Control. Rel. 113 (2006) 189-207; DOI: 10.1016/j.jconrel.2006. 04.015.
3. O. M. Akanbi, A. B. Odaibo, R. Olatoregun and A. B. Ademowo, Role of malaria induced oxida-tive stress on anaemia in pregnancy, Asian Pac. J. Trop. Med. 3 (2010) 211-214.
4. L. M. Veggi, L. Pretto, E. J. Ochoa, V. A. Catania, M. G. Luquita, D. R. Taborda, E. J. Sánchez Pozzi, S. Ikushiro, M. D. Coleman, M. G. Roma and A. D. Mottino, Dapsone induces oxidative stress and impairs antioxidant defenses in rat liver, Life Sci. 83 (2008) 155-163; DOI: 10.1016/j.lfs.2008.05.016.
5. N. Vale, R. Moreira and P. Gomes, Primaquine revisited six decades after its discovery, Eur. J. Med. Chem. 44 (2009) 937-953; DOI: 10.1016/j.ejmech.2008. 08.011.
6. M. Jain, S. Vangapandu, S. Sachdeva and R. Jain, Synthesis and blood-schizontocidal antimala-rial activities of 2-substituted/2,5- disubstituted-8-quinolinamines and some of their amino acid conjugates, Bioorg. Med. Chem. 12 (2004) 1003-1010; DOI: 10.1016/j.bmc.2003.12.029.
7. M. Šimunović, I. Perković, B. Zorc, K. Ester, M. Kralj, D. Hadjipavlou-Litina and E. Pontiki, Urea and carbamate derivatives of primaquine: Synthesis, cytostatic and antioxidant activities, Bioorg. Med. Chem. 17 (2009) 5605-5613; DOI: 10.1016/j.bmc.2009.06.030.
8. M. Zovko Konćić, Z. Rajić, N. Petrić and B. Zorc, Antioxidant activity of NSAID hydroxamic acids, Acta Pharm. 59 (2009) 235-242; DOI: 10.2478/v10007-009-0017-8.
9. G. F. Mabeza, M. Loyevsky, V. R. Gordeuk and G. Weiss, Iron chelation therapy for malaria: A review, Pharmacol. Ther. 81 (1999) 53-75.
10. M. J. Thun, S. J. Henley and C. Patrono, Nonsteroidal anti-inflammatory drugs as anticancer agents: mechanistic, pharmacologic, and clinical issues, J. Natl. Cancer Inst. 94 (2002) 252-266; DOI: 10.1093/jnci/94.4.267.
11. B. Zorc, S. Antolić and I. Butula, Macromolecular prodrugs. I. Synthesis of some non-steroidal anti-inflammatory drug esters, Acta Pharm. 43 (1993) 127-133.
12. Z. Rají, D. Hadjipavlou-Litina, E. Pontiki, M. Kralj, L. Žuman and B. Zorc, The novel keto-profen amides-Synthesis and biological evaluation as antioxidants, lipoxygenase inhibitors and cytostatic agents, Chem. Biol. Drug Des. 75 (2010) 641-652; DOI: 10.1111/j.1747-0285.2010. 00963.x.
13. G. C. Yen and H. Y. Chen, Antioxidant activity of various tea extracts in relation to their anti-mutagenicity, J. Agric. Food Chem. 43 (1995) 27-32; DOI: 10.1021/jf00049a007.
14. R. Amarowicz, R. B. Pegg, P. Rahimi-Moghaddam, B. Barl and J. A. Weil, Free-radical scavenging capacity and antioxidant activity of selected plant species from the Canadian prairies, Food Chem. 84 (2004) 551-562; DOI: 10.1016/S0308-8146(03)00278-4.
15. M. S. Al-Saikhan, L. R. Howard and J. C. Miller, Jr., Antioxidant activity and total phenolics in different genotypes of potato (Solanum tuberosum, L.), J. Food Sci. 60 (1995) 341-343.
16. E. A. Decker and B. Welch, Role of ferritin as lipid oxidation catalyst in muscle food, J. Agric. Food Chem. 38 (1990) 674-677; DOI: 10.1021/jf00093a018.