An innovative derivatization-free IC-MS/MS method for the detection of bisphosphonates in horse plasma.
IC-MS
SPE
bisphosphonates
horse doping control
plasma
Journal
Drug testing and analysis
ISSN: 1942-7611
Titre abrégé: Drug Test Anal
Pays: England
ID NLM: 101483449
Informations de publication
Date de publication:
Oct 2020
Oct 2020
Historique:
received:
15
05
2020
revised:
25
06
2020
accepted:
29
06
2020
pubmed:
3
7
2020
medline:
27
8
2021
entrez:
3
7
2020
Statut:
ppublish
Résumé
Bisphosphonates are prohibited drugs according to Article 6 of the International Agreement on Breeding, Racing and Wagering of the International Federation of Horseracing Authorities (IFHA) and the International Equestrian Federation (FEI). These compounds are used for the treatment of lameness, navicular and bone diseases in horses and are divided into two groups: non-nitrogen-containing bisphosphonate drugs (e.g. clodronic acid) and nitrogen-containing bisphosphonate drugs (e.g. zoledronic acid). Their hydrophilic properties and the high affinity for the bone matrix make the control of their use quite difficult. Current analytical strategies to detect such compounds often rely on a solid phase extraction (SPE) followed by detection by means of UHPLC-MS/MS after methylation with chemical reagents. To improve the analysis throughput and to eliminate the need for chemical derivatization, an innovative 96-well SPE followed by ion chromatography-mass spectrometry was developed. Analyses are conducted on an ICS-6000 HPIC system coupled to a TSQ Altis™ (Thermo Scientific™). The use of a 96-well SPE allowed 5-fold sample increase and a 6-fold throughput improvement. While preliminary results conducted on horse plasma exhibited similar performances to the method for the detection of non-nitrogen-containing bisphosphonates, the analytical performances of nitrogen-containing bisphosphonates were greatly improved.
Substances chimiques
Bone Density Conservation Agents
0
Diphosphonates
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
1452-1461Informations de copyright
© 2020 John Wiley & Sons, Ltd.
Références
Rogers MJ, Frith JC, Luckman SP, et al. Molecular mechanisms of action of bisphosphonates. Bone. 1999;24(5):73S-79S.
Zacharis CK, Tzanavaras PD. Determination of bisphosphonate active pharmaceutical ingredients in pharmaceuticals and biological material: a review of analytical methods. J Pharm Biomed Anal. 2008;48(3):483-496.
Fleisch H. Development of bisphosphonates. Breast Cancer Res. 2002;4(1):30-34.
Soto SA, Barbara AC. Bisphosphonates: pharmacology and clinical approach to their use in equine osteoarticular diseases. J Equine Vet Sci. 2014;34(6):727-737.
McGuigan MP, Cauvin E, Schramme MC, Pardoe CH, May SA, Wilson AM. A double-blind placebo-controlled trial of bisphosphonate in the treatment of navicular syndrome. Proc 39th Br Equine Vet Assoc Congr. 2000;207.
Nieto JE, Maher O, Stanley SD, Knych HK, Snyder JR. Pharmacokinetics, pharmacodynamics, and safety of zoledronic acid in horses. Am J Vet Res. 2013;74(4):550-556.
Popot MA, Garcia P, Hubert C, et al. HPLC/ESI-MS(n) method for non-amino bisphosphonates: application to the detection of tiludronate in equine plasma. J Chromatogr B. 2014;958:108-116.
Popot MA, Jacobs M, Garcia P, et al. Pharmacokinetics of tiludronate in horses: a field population study. Equine Vet J. 2018;50(4):488-492.
Article 6 of the International Agreement on Breeding, Racing and Wagering of the International Federation of Horseracing Authorities. Available at: https://www.ifhaonline.org/resources/ifAgreement.pdf. Accessed 15 May 2020.
2020 Equine Prohibited Substances List. Fédération Equestre Internationale. Available at: https://inside.fei.org/sites/default/files/2020%20Prohibited%20Substances%20List_0.pdf. Accessed 15 May 2020.
Fels JP, Guyonnet J, Berger Y, Cautreels W. Determination of (4-chlorophenyl)thiomethylene bisphosphonic acid, a new bisphosphonate, in biological fluids by high-performance liquid chromatography. J Chromatogr B. 1988;430(1):73-79.
Ptacek P, Klima J, Macek J. Determination of alendronate in human urine as 9-fluorenylmethyl derivative by high-performance liquid chromatography. J Chromatogr B. 2002;767(1):111-116.
Yun MH, Kwon KI. High-performance liquid chromatography method for determining alendronate sodium in human plasma by detecting fluorescence: application to a pharmacokinetic study in humans. J Pharm Biomed Anal. 2006;40(1):168-172.
Apostolou C, Dotsikas Y, Kousoulos C, et al. Application of a semi-automated 96-well format solid-phase extraction, column-switching, fluorescence detection protocol for the determination of alendronate in human urine samples obtained from a bioequivalence study. J Pharm Biomed Anal. 2007;43(3):1151-1155.
Auriola S, Kostiainen R, Ylinen M, Mönkkönen J, Ylitalo P. Analysis of (dichloromethylene) bisphosphonate in urine by capillary gas chromatography-mass spectrometry. J Pharm Biomed Anal. 1989;7(12):1623-1629.
Sakiyama N, Kataoka H, Makita M. Gas chromatographic analysis of 3-amino-1-hydroxypropylidene-1,1-bisphosphonate and related bisphosphonate as their N-isobutoxycarbonyl methyl ester derivatives. J Chromatogr A. 1996;724(1-2):279-284.
Zhu LS, Lapko VN, Lee JW, et al. A general approach for the quantitative analysis of bisphosphonates in human serum and urine by high-performance liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom. 2006;20(22):3421-3426.
Tarcomnicu I, Silvestro L, Savu SR, Gherase A, Dulea C. Development and application of a high-performance liquid chromatography-mass spectrometry method to determine alendronate in human urine. J Chromatogr A. 2007;1160(1-2):21-33.
Tarcomnicu I, Gheorghe MC, Silvestro L, Savu SR, Boaru I, Tudoroniu A. High-throughput HPLC-MS/MS method to determine ibandronate in human plasma for pharmacokinetic applications. J Chromatogr B. 2009;877(27):3159-3168.
Wong ASY, Ho ENM, Wan TSM, Lam KKH, Stewart BD. Liquid chromatography-mass spectrometry analysis of five bisphosphonates in equine urine and plasma. J Chromatogr B. 2015;998:1-7.
Chester TL, Lewis EC, Benedict JJ, Sunberg RJ, Tettenhorst WC. Determination of (dichloromethylene) diphosphonate in physiological fluids by ion-exchange chromatography with phosphorus-selective detection. J Chromatogr. 1981;225(1):17-25.
Tsai EW, Ip DP, Brooks MA. Determination of alendronate in pharmaceutical dosage formulations by ion chromatography with conductivity detection. J Chromatogr. 1992;596(2):217-224.
Kovacevic M, Gartner A, Novic M. Determination of bisphosphonates by ion chromatography-inductively coupled plasma mass spectrometry. J Chromatogr A. 2004;1039(1-2):77-82.
Vallano PT, Shugarts SB, Kline WF, Woolf EJ, Matuszewski BK. Determination of risedronate in human urine by column-switching ion-pair high-performance liquid chromatography with ultraviolet detection. J Chromatogr B. 2003;794(1):23-33.
Xie Z, Jiang Y, Zhang DQ. Simple analysis of four bisphosphonates simultaneously by reverse phase liquid chromatography using N-amylamine as volatile ion-pairing agent. J Chromatogr A. 2006;1004(1-2):173-178.
Flesch G, Tominaga N, Degen P. Improved determination of the bisphosphonate pamidronate disodium in plasma and urine by pre-column derivatization with fluorescamine, high-performance liquid chromatography and fluorescence detection. J Chromatogr. 1991;568(1):261-266.
Wong JA, Renton KW, Crocker JF, O’Regan PA, Acott PD. Determination of pamidronate in human whole blood and urine by reversed-phase HPLC with fluorescence detection. Biomed Chromatogr. 2004;18(2):98-101.
Kudzin ZH, Gralak DK, Andrijewski G, Drabowicz J, Luczak J. Simultaneous analysis of biologically active aminoalkanephosphonic acids. J Chromatogr A. 2003;998(1-2):183-199.
Buchberger WW, Haddad PR. Advances in detection techniques for ion chromatography. J Chromatogr A. 1997;789(1-2):67-83.
Wang LJ, Schnute WC. Quantitative determination of bisphosphonate pharmaceuticals and excipients by capillary IC-MS. application note 1001. Thermo Scientific. 2012;1-7.
Association of Official Racing Chemists (AORC). Guidelines for the Minimum Criteria for Identification by Chromatography and Mass Spectrometry. Available at: http://www.aorc-online.org/documents/aorc-ms-criteria-modified-23-aug-16/ Accessed 15 May 2020.
Hardouin J, Guénin E, Malosse C, Caron M, Lecouvey M. Electrospray tandem mass spectrometry of alendronate analogues: fingerprints for characterization of new potential prodrugs. Rapid Commun Mass Spectrom. 2008;22(15):2287-2300.
Qu Z, Chen X, Qu C, et al. Fragmentation pathways of eight nitrogen-containing bisphosphonates (BPs) investigated by ESI-MSn in negative ion mode. Int J Mass Spectrom. 2010;295(1-2):85-93.
Huikko K, Kotiaho T, Yli-Kauhaluoma J, Kostiainen R. Electrospray ionization mass spectrometry and tandem mass spectrometry of clodronate and related bisphosphonate and phosphonate compounds. J Mass Spectrom. 2002;37(2):197-208.