An HPLC assay for the lipophilic camptothecin analog AR-67 carboxylate and lactone in human whole blood

Biomedical Chromatography

Volumn 24, Issue 10, 2010, Pages 1045-1051

  Tsakalozou, Eleftheria ^a   Horn, Jamie ^a   Leggas, Mark ^a  

^a University of Kentucky   (United States)

Author keywords

AR 67; HPLC; Validation; Whole blood

Indexed keywords

CARBOXYLATION; CYTOLOGY; ESTERS;

AR-67; BUTYLDIMETHYLSILYL; CAMPTOTHECIN ANALOGS; CLINICAL TRIAL; HPLC; HYDROXYCAMPTOTHECIN; LACTONE MOIETY; RED CELLS; VALIDATION; WHOLE BLOOD;

BLOOD;

7 TERT BUTYLDIMETHYLSILYL 10 HYDROXYCAMPTOTHECIN; ACETONITRILE; AR 67; CAMPTOTHECIN DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; DB 67; LACTONE; METHANOL; UNCLASSIFIED DRUG;

ACCURACY; ANALYTIC METHOD; ARTICLE; CENTRIFUGATION; CONTROLLED STUDY; CYTOLYSIS; FLUORESCENCE; HEMOLYSIS; HUMAN; HUMAN EXPERIMENT; HUMAN TISSUE; LIPOPHILICITY; NORMAL HUMAN; PRECIPITATION; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SENSITIVITY AND SPECIFICITY;

EID: 77957323817     PISSN: 02693879     EISSN: 10990801     Source Type: Journal    
DOI: 10.1002/bmc.1404     Document Type: Article

References (28)

1. Arnold S, Rinehart J, Tsakalozou E, Eckardt J, Fields S, Shelton B, DeSimone P, Kee B, Moscow J and Leggas M. A phase I study of 7-t-butyldimethylsilyl- 10-hydroxycamptothecin in adult patients with refractory or metastatic solid malignancies. Clinical Cancer Research 2010; 16: 673-680.
2. Bom D, Curran DP, Chavan AJ, Kruszewski S, Zimmer SG, Fraley KA and Burke TG. Novel A,B,E-ring-modified camptothecins displaying high lipophilicity and markedly improved human blood stabilities. Journal of Medicinal Chemistry 1999; 42: 3018-3022.
3. Bom D, Curran DP, Zhang J, Zimmer SG, Bevins R, Kruszewski S, Howe JN, Bingcang A, Latus LJ and Burke TG. The highly lipophilic DNA topoisomerase I inhibitor DB-67 displays elevated lactone levels in human blood and potent anticancer activity. Journal of Controlled Release 2001; 74: 325-333.
4. Burke TG and Mi Z. Preferential binding of the carboxylate form of camptothecin by human serum albumin. Analytical Biochemistry 1993; 212: 285-287.
5. Burke TG and Mi Z. The structural basis of camptothecin interactions with human serum albumin: impact on drug stability. Journal of Medicinal Chemistry 1994; 37: 40-46.
6. Crews KR, Stewart CF, Jones-Wallace D, Thompson SJ, Houghton PJ, Heideman RL, Fouladi M, Bowers DC, Chintagumpala MM and Gajjar A. Altered irinotecan pharmacokinetics in pediatric high-grade glioma patients receiving enzyme-inducing anticonvulsant therapy. Clinical Cancer Research 2002; 8: 2202-2209.
7. De Cesare M, Pratesi G, Veneroni S, Bergottini R and Zunino F. Efficacy of the novel camptothecin gimatecan against orthotopic and metastatic human tumor xenograft models. Clinical Cancer Research 2004; 10: 7357-7364.
8. de Jong FA, Mathijssen RH, de Bruijn P, Loos WJ, Verweij J and Sparreboom A. Determination of irinotecan (CPT-11) and SN-38 in human whole blood and red blood cells by liquid chromatography with fluorescence detection. Journal of Chromatography B: Analytical Technology in Biomedicine and Life Sciences 2003; 795: 383-388.
9. FDA. Guidance for Industry Bioanalytical Method Validation. US Food and Drug Administration Center for Evaluation and Research, 2001. Available from: URL: http://www.fda.gov/cder/guidance/index.htm. Accessed 13 September 2004.
10. Gallo JM, Laub PB, Rowinsky EK, Grochow LB and Baker SD. Population Pharmacokinetic Model for Topotecan Derived From Phase I Clinical Trials. Journal of Clinical Oncology 2000; 18: 2459-2467.
11. Giovanella BC, Harris N, Mendoza J, Cao Z, Liehr J and Stehlin JS. Dependence of anticancer activity of camptothecins on maintaining their lactone function. Annals of the New York Academy of Science 2000; 922: 27-35.
12. Hertzberg RP, Caranfa MJ, Holden KG, Jakas DR, Gallagher G, Mattern MR, Mong SM, Bartus JO, Johnson RK and Kingsbury WD. Modification of the hydroxy lactone ring of camptothecin: inhibition of mammalian topoisomerase I and biological activity. Journal of Medicinal Chemistry 1989; 32: 715-720.
13. Horn J, Jordan SL, Song L, Roberts MJ, Anderson BD and Leggas M. Validation of an HPLC method for analysis of DB-67 and its water soluble prodrug in mouse plasma. Journal of Chromatography B: Analytical Technology in Biomedicine and Life Sciences 2006; 844: 15-22.
14. Hsiang YH, Liu LF, Wall ME, Wani MC, Nicholas AW, Manikumar G, Kirschenbaum S, Silber R and Potmesil M. DNA topoisomerase I-mediated DNA cleavage and cytotoxicity of camptothecin analogues. Cancer Research 1989; 49: 4385-4389.
15. Hubbard KE, Schaiquevich P, Bai F, Fraga CH, Miller L, Panetta JC and Stewart CF. Application of a highly specific and sensitive fluorescent HPLC method for topotecan lactone in whole blood. Biomedical Chromatography 2009; 23: 707-713.
16. Jaxel C, Kohn KW, Wani MC, Wall ME and Pommier Y. Structure-activity study of the actions of camptothecin derivatives on mammalian topoisomerase I: evidence for a specific receptor site and a relation to antitumor activity. Cancer Research 1989; 49: 1465-1469.
17. Keir ST, Hausheer F, Lawless AA, Bigner DD and Friedman HS. Therapeutic activity of 7-[(2-trimethylsilyl)ethyl]-20 (S)-camptothecin against central nervous system tumor-derived xenografts in athymic mice. Cancer Chemotherapy and Pharmacology 2001; 48: 83-87.
18. Li QY, Zu YG, Shi RZ and Yao LP. Review camptothecin: current perspectives. Current Medicinal Chemistry 2006; 13: 2021-2039.
19. Loos WJ, Verweij J, Gelderblom HJ, de Jonge MJ, Brouwer E, Dallaire BK and Sparreboom A. Role of erythrocytes and serum proteins in the kinetic profile of total 9-amino-20(S)-camptothecin in humans. Anticancer Drugs 1999; 10: 705-710.
20. Loos WJ, Gelderblom H, Verweij J, van Boven-van Zomeren DM, Nooter K, Stoter G and Sparreboom A. Red blood cells: a neglected compartment in topotecan pharmacokinetic analysis. Anticancer Drugs 2003; 14: 227-232.
21. Mi Z and Burke TG. Differential interactions of camptothecin lactone and carboxylate forms with human blood components. Biochemistry 1994; 33: 10325-10336.
22. Mi Z, Malak H and Burke TG. Reduced albumin binding promotes the stability and activity of topotecan in human blood. Biochemistry 1995; 34: 13722-13728.
23. Oguma T. Antitumor drugs possessing topoisomerase I inhibition: applicable separation methods. Journal of Chromatography B: Biomedical Sciences and Applications 2001; 764: 49-58.
24. Peck CC, Barr WH, Benet LZ, Collins J, Desjardins RE, Furst DE, Harter JG, Levy G, Ludden T, Rodman JH et al. Opportunities for integration of pharmacokinetics, pharmacodynamics, and toxicokinetics in rational drug development. Pharmaceutical Research 1992; 9: 826-833.
25. Rothenberg ML, Kuhn JG, Schaaf LJ, Drengler RL, Eckhardt SG, Villalona- Calero MA, Hammond L, Miller LL, Petit RG, Rowinsky EK and Von Hoff DD. Alternative dosing schedules for irinotecan. Oncology (Williston Park) 1998; 12: 68-71.
26. Sessa C, Cresta S, Cerny T, Baselga J, Rota Caremoli E, Malossi A, Hess D, Trigo J, Zucchetti M, D'Incalci M, Zaniboni A, Capri G, Gatti B, Carminati P, Zanna C, Marsoni S and Gianni L. Concerted escalation of dose and dosing duration in a phase I study of the oral camptothecin gimatecan (ST1481) in patients with advanced solid tumors. Annals of Oncology 2007; 18: 561-568.
27. van Riel JMGH, van Groeningen CJ, Kedde MA, Gall H, Leisink JMA, Gruia G, Pinedo HM, van der Vijgh WJF and Giaccone G. Continuous administration of irinotecan by hepatic arterial infusion: a phase I and pharmacokinetic study. Clinical Cancer Research 2002; 8: 405-412.
28. Zamboni WC, Bowman LC, Tan M, Santana VM, Houghton PJ, Meyer WH, Pratt CB, Heideman RL, Gajjar AJ, Pappo AS and Stewart CF. Interpatient variability in bioavailability of the intravenous formulation of topotecan given orally to children with recurrent solid tumors. Cancer Chemotherapy and Pharmacology 1999; 43: 454-460.