The effect of alkylamine additives on the sensitivity of detection for paclitaxel and docetaxel and analysis in plasma of paclitaxel by liquid chromatography-tandem mass spectrometry

Biomedical Chromatography

Volumn 20, Issue 8, 2006, Pages 683-695

  Gao, Songmei ^a,b   Zhang, Zong Ping ^b   Edinboro, L E ^a   Ngoka, Lambert C ^c   Karnes, H T ^a  

^a VIRGINIA COMMONWEALTH UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b Pharmaceutical Product Development   (United States)

^c VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

Author keywords

Adduct ions; Alkylamine; Docetaxel; LC MS MS; Paclitaxel; Quantitation

Indexed keywords

ADDITIVES; BINDING ENERGY; DRUG PRODUCTS; ION SOURCES; IONS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; SODIUM;

ADDUCT ION; ALKYLAMINE; ANALYTES; DOCETAXEL; LC-MS-MS; LC.MS/MS; MOLECULAR IONS; PACLITAXEL; QUANTITATION; SODIUM ADDUCTS;

BINDING SITES;

ALIPHATIC AMINE; ANTINEOPLASTIC AGENT; DOCETAXEL; DRUG ADDITIVE; ION; OCTYLAMINE; PACLITAXEL; SODIUM ION;

ACCURACY; ARTICLE; BINDING COMPETITION; BINDING SITE; CALIBRATION; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG DETERMINATION; DRUG STRUCTURE; EXPERIMENTAL STUDY; HUMAN; LIQUID CHROMATOGRAPHY; MOLECULAR INTERACTION; MOLECULAR STABILITY; QUANTITATIVE ASSAY; SAMPLE; SENSITIVITY ANALYSIS; SENSITIVITY AND SPECIFICITY; SURFACE PROPERTY; TANDEM MASS SPECTROMETRY; VALIDATION STUDY;

EID: 33746945413     PISSN: 02693879     EISSN: 10990801     Source Type: Journal    
DOI: 10.1002/bmc.582     Document Type: Article

References (44)

1. Akashi S, Osawa R and Nishimura Y. Evaluation of protein-DNA binding affinity by electrospray ionization mass spectrometry. Journal of the American Society for Mass Spectrometry 2005; 16: 116-125.
2. Arai S, Ishihara S, Takeoka S, Ohkawa H, Shibue T and Nishide H. Stability of porphyrincalix[4]arene complexes analyzed by electrospray ionization mass spectrometry. Rapid Communications in Mass Spectrometry 2004; 18: 2065-2068.
3. Basileo G, Breda M, Fonte G, Pisano R and James CA. Quantitative determination of paclitaxel in human plasma using semi-automated liquid-liquid extraction in conjunction with liquid chromatography/ tandem mass spectrometry. Journal of Pharmaceutical and Biomedical Analysis 2003; 32: 591-600.
4. Blaghen M, Lahlou N, Dzairi FZ, Moutaouakkil A and Talbi M. Complexation and ionophoric properties of taxol and colchicine: complex formation and transport of sodium, potassium, magnesium and calcium ions across a liquid membrane. Natural Toxins 1999; 7: 179-185.
5. Cole RB. Electrospray Ionization Mass Spectrometry: Fundamentals, Instrumentation, and Applications. Wiley: New York, 1997, 33.
6. Cuyckens F and Claeys M. Optimization of a liquid chromatography method based on simultaneous electrospray ionization mass spectrometric and ultraviolet photodiode array detection for analysis of flavonoid glycosides. Rapid Communications in Mass Spectrometry 2002; 16: 2341-2348.
7. David WM and Brodbelt JS. Threshold dissociation energies of protonated amine/polyether complexes in a quadrupole ion trap. Journal of the American Society for Mass Spectrometry 2003; 14: 383-392.
8. Davidson WR, Sunner J and Kebarle P. Hydrogen bonding of water to onium ions hydration of substituted pyridinium ions and related systems. Journal of the American Chemical Society 1979; 101: 1675-1680.
9. Enke CG. A predictive model for matrix and analyte effects in electrospray ionization of singly-charged ionic analytes. Analytical Chemistry 1997; 69: 4885-4893.
10. Forastiere AA. Use of paclitaxel (Taxol) in squamous cell carcinoma of the head and neck. Seminars in Oncology 1993; 20: 56-60.
11. Guan F, Uboh C, Soma L, Hess A, Luo Y and Tsang DS. Sensitive liquid chromatographic/tandem mass spectrometric method for the determination of beclomethasone dipropionate and its metabolites in equine plasma and urine. Journal of Mass. Spectrometry 2003; 38: 823-838.
12. Guo P, Ma J, Li S and Gallo JM. Determination of paclitaxel in mouse plasma and brain tissue by liquid chromatography-mass spectrometry. Journal of Chromatography B 2003; 798: 79-86.
13. Holmes FA, Walters RS, Theriault RL, Forman AD, Newton LK, Raber MN, Buzdar AU, Frye DK and Hortogagyi GN. Phase II trial of taxol, an active drug in the treatment of metastatic breast cancer. Journal of the National Cancer Institute 1991; 83: 1797-1805.
14. + affinities of organic and small biological molecules in the gas phase. Journal of the American Chemical Society 1999; 121: 8864-8875.
15. Hunter EP and Lias SG. NIST standard reference database 69. http://webbook.nist.gov, 1998.
16. Kamel AM, Brown PR and Munson B. Effects of mobile-phase additives, solution pH, ionization constant, and analyte concentration on the sensitivities and electrospray ionization mass spectra of nucleoside antiviral agents. Analytical Chemistry 1999; 71: 5481-5492.
17. Karlsson K-E. Cationization in electrospray microcolumn liquid chromatography-mass spectrometry. Journal of Chromatography A 1998; 794: 359-366.
18. Li XF, Ma MS, Scherban K and Tam YK. Liquid chromatography-electrospray mass spectrometric studies of ginkgolides and bilobalide using simultaneous monitoring of proton, ammonium, and sodium adducts. Analyst 2002; 127: 641-646.
19. Loo JA. Observation of large subunit protein complexes by electrospray ionization mass spectrometry. Journal of Mass Spectrometry 1995; 30: 180-183.
20. Lorenz SA, Maziarz III EP and Wood TD. Using solution phase hydrogen/ deuterium (H/D) exchange to determine the origin of non-covalent complexes observed by electrospray ionization mass spectrometry: in solution or in vacuo. Journal of the American Society for Mass Spectrometry 2001; 12: 795-804.
21. Lorenz SA, Bigwarfe PM, JR, Balasubramanian SV, Fetterly GJ, Straubinger RM and Wood TD. Noncovalent dimerization of paclitaxel in solution: evidence from electrospray ionization mass spectrometry. Journal of Pharmaceutical Sciences 2002; 91: 2057-2066.
22. Lyer SS, Gao S, Zhang Z, Kellogg GE and Karnes HT. A molecular model to explain paclitaxel and docetaxel sensitivity changes through adduct formation with primary amines in electrospray ionization mass spectrometry. Rapid Communications in Mass Spectrometry 2005; 19: 1221-1226
23. Ma Y and Kim H. Determination of steroids by liquid chromatography/mass spectrometry. Journal of the American Society for Mass Spectrometry 1997; 8: 1010-1020.
24. Madhusudanan KP, Chattopadhyay SK, Saha GC, Kulshrestha M, Sharma RP and Kumar S. Fast atom bombardment mass spectrometry for the characterization of taxanes. Journal of Mass Spectrometry 1997; 32: 216-224.
25. Makowiecki J, Tolonen A, Uusitalo J and Jalonen J. Cone voltage and collision cell collision-induced dissociation study of triphenylethylenes of pharmaceutical interest. Rapid Communications in Mass Spectrometry 2001; 15: 1506-1513.
26. Matuszewski BK, Constanzer ML and Chavez-Eng CM. Strategies for the assessment of matrix effect in quantitative bioanalytical methods based on HPLC-MS/MS. Analytical Chemistry 2003; 75: 3019-3030.
27. Meng CK and Fenn JB. Formation of charged clusters during electrospray ionization of organic solute species. Organic Mass Spectrometry 1991; 26: 542-549.
28. Miao X, March RE and Metcalfe CD. Fragmentation study of salinomycin and monensin a antibiotics using electrospray quadruple time-of-flight mass spectrometry. Rapid Communications in Mass Spectrometry 2003; 17: 149-154.
29. Morisaki N, Kobayashi H, Yamamura Y, Morisaki M, Nagasawa K and Hashimoto Y. Coordination of sodium cation to an oxygen function and olefinic double bond to form molecular adduct ion in fast atom bombardment mass spectrometry. Chemical and Pharmaceutical Bulletin 2002; 50: 935-940.
30. Mortier KA, Zhang GF, van Peteghem CH and Lambert WE. Adduct formation in quantitative bioanalysis: effect of ionization conditions on paclitaxel. Journal of the American Society for Mass Spectrometry 2004; 15: 585-592.
31. Nabuchi Y, Asoh Y and Takayama M. Folding analysis of hormonal polypeptide calcitonins and the oxidized calcitonins using electrospray ionization mass spectrometry combined with H/D exchange. Journal of the American Society for Mass Spectrometry 2004; 15: 1556-1564.
32. Ngoka LCM, Gross ML and Toogood PL. Sodium-directed selective cleavage of lactones: a method for structure determination of cyclodepsipeptides. International Journal of Mass Spectrometry 1999; 183: 289-298.
33. Niessen WMA. Liquid Chromatography-Mass Spectrometry, 2nd edn, Revised and Expanded. Marcel Dekker: New York, 1999; 249.
34. Parise RA, Ramanathan RK, Zamboni WC and Egorin MJ. Sensitive liquid chromatography-mass spectrometry assay quantitation of docetaxel and paclitaxel in human plasma. Journal of Chromatography B 2003; 783: 231-236.
35. Pine SH. Organic Chemistry, 5th edn. McGraw-Hill: New York, 1987; 69.
36. Schug K. Pseudo-molecular ion formation by aromatic acids in negative ionization mode electrospray ionization mass spectrometry. Dissertation of Virginia Polytechnic Institute and State University 2002; 26.
37. Schug K and McNair HM. Adduct formation in electrospray ionization mass spectrometry II. Benzoic acid derivatives. Journal of Chromatography A 2003; 985: 531-539.
38. Sherman CL and Brodbelt JS. An equilibrium partitioning model for predicting response to host-guest complexation in electrospray ionization mass spectrometry. Analytical Chemistry 2003; 75: 1828-1836.
39. Steed JW and Atwood JL. Supramolecular Chemistry. Wiley: New York, 2000; 88-97.
40. Stefansson M, Sjöberg Per JR and Markides KE. Regulation of multimer formation in electrospray mass spectrometry. Analytical Chemistry 1996; 68: 1792-1797.
41. Teshima K, Kondo T, Maeda C, Oda T, Hagimoto T, Tsukuda R and Yoshimura Y. Application of 1-alkylamines to a liquid chromatographic/turbo ionspray tandem mass spectrometric method for quantifying metabolites of a new bone anabolic agent, TAK-778, in human serum. Journal of Mass Spectrometry 2002; 37: 631-638.
42. Wani M, Taylor HL, Wall ME, Coggon P and Mcphail AT. Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. Journal of the American Chemical Society 1971; 93: 2325-2327.
43. Zhao JJ, Yang AY and Rogers JD. Effects of liquid chromatography mobile phase buffer contents on the ionization and fragmentation of analytes in liquid chromatographic/ionspray tandem mass spectrometric determination. Journal of Mass Spectrometry 2002; 37: 421-433.
44. Zhu MM, Rempel DL and Gross ML. Modeling data from titration, amide H/D exchange, and mass spectrometry to obtain protein-ligand binding constants. Journal of the American Society for Mass Spectrometry 2004; 15: 388-397.