Quantification of dihydroartemisinin, artesunate and artemisinin in human blood: Overcoming the technical challenge of protecting the peroxide bridge

Bioanalysis

Volumn 3, Issue 14, 2011, Pages 1613-1624

  Lindegardh, Niklas ^a,b   Hanpithakpong, Warunee ^a   Kamanikom, Benjamas ^a   Pattayaso, Janhom ^a   Singhasivanon, Pratap ^a   White, Nicholas J ^a,b   Day, Nicholas P J ^a,b  

^a MAHIDOL UNIVERSITY   (Thailand)

^b UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ARTEMISININ; ARTESUNATE; DIHYDROARTEMISININ;

ANALYTIC METHOD; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DENATURATION; DRUG STRUCTURE; ENVIRONMENTAL TEMPERATURE; FLOW RATE; HEMOLYSIS; HUMAN; HUMAN EXPERIMENT; ISOTOPE LABELING; LIMIT OF QUANTITATION; LIQUID CHROMATOGRAPHY; MALE; NORMAL HUMAN; OXIDATION; PILOT STUDY; QUALITY CONTROL; SOLID PHASE EXTRACTION; TANDEM MASS SPECTROMETRY; THERMOSTABILITY; VALIDATION PROCESS;

ANTIMALARIALS; ARTEMISININS; CHROMATOGRAPHY, LIQUID; DRUG STABILITY; ERYTHROCYTES; FERROUS COMPOUNDS; HEMOGLOBINS; HUMANS; MALE; MASS SPECTROMETRY; REPRODUCIBILITY OF RESULTS;

EID: 79960553046     PISSN: 17576180     EISSN: 17576199     Source Type: Journal    
DOI: 10.4155/bio.11.158     Document Type: Article

References (41)

1. Wongsrichanalai C, Meshnick SR. Declining artesunate-mefloquine efficacy against Falciparum malaria on the Cambodia- Thailand border. Emerg. Infect. Dis. 14(5), 716-719 (2008). (Pubitemid 351838633)
2. Alker AP, Lim P, Sem R et al. Pfmdr 1 and in vivo resistance to artesunate-mefloquine in falciparum malaria on the Cambodian-Thai border. Am. J. Trop. Med. Hyg. 76(4), 641-647 (2007). (Pubitemid 351627700)
3. No authors listed. Resistance to artemisinin derivatives along the Thai-Cambodian border. Wkly Epidemiol. Rec. 82(41), 360 (2007).
4. Jansen FH, Soomro SA. Chemical instability determines the biological action of the artemisinins. Curr. Med. Chem. 14(30), 3243-3259 (2007).
5. Krishna S, Woodrow Cj, Staines HM, Haynes RK, Mercereau-Puijalon O. Re-evaluation of how artemisinins work in light of emerging evidence of in vitro resistance. Trends Mol. Med. 12(5), 200-205 (2006). (Pubitemid 43728412)
6. Eckstein-Ludwig U, Webb RJ, Van Goethem ID et al. Artemisinins target the serca of plasmodium falciparum. Nature 424(6951), 957-961 (2003). (Pubitemid 37051688)
7. Klayman DL. Qinghaosu (artemisinin): an antimalarial drug from china. Science 228(4703), 1049-1055 (1985). (Pubitemid 15227365)
8. Ding XC, Beck Hp, Raso G. Plasmodium sensitivity to artemisinins: MAGIC bullets hit elusive targets. Trends Parasitol. 27(2), 73-81 (2011).
9. Haynes RK, Cheu KW, Tang MM et al. Reactions of antimalarial peroxides with each of leucomethylene blue and dihydroflavins: flavin reductase and the cofactor model exemplified. Chem. Med. Chem. 6(2), 279-291 (2011).
10. Haynes RK, Chan Wc, Wong HN et al. Facile oxidation of leucomethylene blue and dihydroflavins by artemisinins: relationship with flavoenzyme function and antimalarial mechanism of action. ChemMedChem 5(8), 1282-1299 (2010).
11. Dondorp A, Nosten F, Stepniewska K, Day N, White N. Artesunate versus quinine for treatment of severe Falciparum malaria: a randomised trial. Lancet 366(9487), 717-725 (2005 (Pubitemid 41207233)
12. Dondorp AM, Fanello CI, Hendriksen IC et al. Artesunate versus quinine in the treatment of severe falciparum malaria in african children (aquamat): an open-label, randomised trial. Lancet 376(9753), 1647-1657 (2010).
13. Dondorp AM, Nosten F, Yi P et al. Artemisinin resistance in plasmodium Falciparum malaria. N. Engl. J. Med. 361(5), 455-467 (2009
14. Edlund PO, Westerlund D, Carlqvist J, Wu BL, Jin YH. Determination of artesunate and dihydroartemisinine in plasma by liquid chromatography with post-column derivatization and uv-detection. Acta Pharm. Suec. 21, 223-234 (1984).
15. Gordi T, Nielsen E, Yu Z, Westerlund D, Ashton M. Direct analysis of artemisinin in plasma and saliva using coupled-column high-performance liquid chromatography with a restricted-access material pre-column. J. Chromatogr. B 742, 155-162 (2000). (Pubitemid 30330933)
16. Batty KT, Davis TM, Thu LT, Binh TQ, Anh TK, Ilett KF. Selective high-performance liquid chromatographic determination of artesunate and a- and b-dihydroartemisinin in patients with falciparum malaria. J. Chromatogr. 677(2), 345-350 (1996). (Pubitemid 26106005)
17. Lai CS, Nair NK, Mansor SM, Olliaro PL, Navaratnam V. An analytical method with a single extraction procedure and two separate high performance liquid chromatographic systems for the determination of artesunate, dihydroartemisinin and mefloquine in human plasma for application in clinical pharmacological studies of the drug combination. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 857(2), 308-314 (2007). (Pubitemid 47444589)
18. Na-Bangchang K, Congpuong K, Hung Ln, Molunto P, Karbwang J. Simple high-performance liquid chromatographic method with electrochemical detection for the simultaneous determination of artesunate and dihydroartemisinin in biological fluids. J. Chromatogr. B 708, 201-207 (1998). (Pubitemid 28239905)
19. Navaratnam V, Mordi MN, Mansor SM. Simultaneous determination of artesunic acid and dihydroartemisinin in blood plasma by high-performance liquid chromatography for application in clinical pharmacological studies. J. Chromatogr. B 669, 157-162 (1997). (Pubitemid 27208477)
20. Xing J, Yan H, Zhang S, Ren G, Gao Y. A high-performance liquid chromatography/ tandem mass spectrometry method for the determination of artemisinin in rat plasma. Rapid Commun. Mass Spectrom. 20(9), 1463-1468 (2006).
21. Lindegardh N, Hanpithakpong W, Kamanikom B et al. Major pitfalls in the measurement of artemisinin derivatives in plasma in clinical studies. J. Chromatog. 876(1), 54-60 (2008).
22. Hanpithakpong H, Kamanikom B, Singhasivanon P, White NJ, Day NPJ, Lindegardh N. A liquid chromatographic- tandem mass spectrometric method for determination of artemether and its metabolite dihydroartemisinin in human plasma. Bioanalysis 1(1), 37-46 (2009).
23. Hanpithakpong W, Kamanikom B, Dondorp AM et al. A liquid chromatographic- tandem mass spectrometric method for determination of artesunate and its metabolite dihydroartemisinin in human plasma. J. Chromatog. 876(1), 61-68 (2008).
24. Lindegardh N, Tarning J, Toi PV et al. Quantification of artemisinin in human plasma using liquid chromatography coupled to tandem mass spectrometry. J. Pharm. Biomed. Anal. 49(3), 768-773 (2009).
25. Creek DJ, Ryan E, Charman WN et al. Stability of peroxide antimalarials in the presence of human hemoglobin. Antimicrob. Agents Chemotherapy 53(8), 3496-3500 (2009).
26. Creek DJ, Chiu FC, Prankerd RJ, Charman SA, Charman WN. Kinetics of iron-mediated artemisinin degradation: effect of solvent composition and iron salt. J. Pharm. Sci. 94(8), 1820-1829 (2005). (Pubitemid 41360875)
27. Zhang S, Gerhard GS. Heme activates artemisinin more efficiently than hemin, inorganic iron, or hemoglobin. Bioorganic Med. Chem. 16, 7853-7861 (2008).
28. Rehman HU. Methemoglobinemia. West J. Med. 175(3), 193-196 (2001). (Pubitemid 32923966)
29. Bradberry SM. Occupational methemoglobinaemia. Mechanisms of production, features, diagnosis and management including the use of methylene blue. Toxicol. Rev. 22(1), 13-27 (2003). (Pubitemid 37270709)
30. Charman SA, Perry CS, Chiu FC, Mcintosh KA, Prankerd RJ, Charman WN. Alteration of the intravenous pharmacokinetics of a synthetic ozonide antimalarial in the presence of a modified cyclodextrin. J. Pharma. Sci. 95(2), 256-267 (2006). (Pubitemid 43241969)
31. Kanias T, Acker JP. Biopreservation of red blood cells - the struggle with hemoglobin oxidation. FEBS J. 277(2), 343-356 (2010).
32. Gower JD, Healing G, Green CJ. Determination of desferrioxamine - available iron in biological tissues by high-pressure liquid chromatography. Anal. Biochem. 180(1), 126-130 (1989). (Pubitemid 19200573)
33. Pashynska VA, Van Den Heuvel H, Claeys M, Kosevich MV. Characterization of noncovalent complexes of antimalarial agents of the artemisinin-type and Fe(iii)-heme by electrospray mass spectrometry and collisional activation tandem mass spectrometry. J. Am. Soc. Mass Spectrom. 15(8), 1181-1190 (2004). (Pubitemid 38970062)
34. Keberle H. The biochemistry of desferrioxamine and its relation to iron metabolism. Ann. NY Acad. Sci. 119, 758-768 (1964).
35. Helmer OM, Emerson CP. The iron content of the whole blood of normal individuals. J. Biol. Chem. 104, 157-161 (1934).
36. Niihara Y, Ge J, Shalev O, Wu H, Tu A, Tanaka KR. Desferrioxamine decreases nad redox potential of intact red blood cells: evidence for desferrioxamine as an inducer of oxidant stress in red blood cells. BMC Clin. Pharmacol. 2, 8 (2002).
37. Viswanathan CT, Bansal S, Booth B et al. Quantitative bioanalytical methods validation and implementation: best practices for chromatographic and ligand binding assays. Pharma. Res. 24(10), 1962-1973 (2007). (Pubitemid 47389236)
38. Gu HM, Warhurst DC, Peters W. Uptake of [3h] dihydroartemisinine by erythrocytes infected with plasmodium falciparum in vitro. Trans. R. Soc. Trop. Med. Hyg. 78(2), 265-270 (1984). (Pubitemid 14143736)
39. Pooley S, Fatih FA, Krishna S et al. Artemisone uptake in plasmodium falciparum-infected erythrocytes. Antimicrob. Agents Chemother. 55(2), 550-556 (2011).
40. Vyas N, Avery BA, Avery MA, Wyandt CM. Carrier-mediated partitioning of artemisinin into plasmodium falciparum-infected erythrocytes. Antimicrob. Agents Chemother. 46(1), 105-109 (2002). (Pubitemid 34031610)
41. Colussi D, Parisot C, Legay F, Lefevre G. Binding of artemether and lumefantrine to plasma proteins and erythrocytes. Eur. J. Pharm. Sci. 9(1), 9-16 (1999). (Pubitemid 29430187)