Identification and characterization of impurities of tetracosactide by capillary electrophoresis and liquid chromatography coupled to time-of-flight mass spectrometry

Analytical and Bioanalytical Chemistry

Volumn 401, Issue 4, 2011, Pages 1365-1375

  Taichrib, Angelina ^a   Scriba, Gerhard K E ^b   Neusü, Christian ^a  

^a AALEN UNIVERSITY   (Germany)

^b FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

CE MS; Impurity identification; LC MS; Tetracosactide

Indexed keywords

ACCURATE MASS; ADRENAL CORTEX; ADRENOCORTICOTROPIC HORMONES; FRAGMENT IONS; IMPURITIES IN; LC/MS; MEDICAL USE; PROTECTING GROUP; QUADRUPOLES; SEMI-QUANTITATIVE; SYNTHETIC PEPTIDE; TETRACOSACTIDE; TIME OF FLIGHT MASS SPECTROMETRY; TIME-OF-FLIGHT MASS SPECTROMETERS;

AMINO ACIDS; CAPILLARY ELECTROPHORESIS; IMPURITIES; LIQUIDS; MASS SPECTROMETERS; MASS SPECTROMETRY; PEPTIDES;

LIQUID CHROMATOGRAPHY;

PEPTIDE; TETRACOSACTIDE;

ARTICLE; CAPILLARY ELECTROPHORESIS; CHEMISTRY; DRUG CONTAMINATION; HUMAN; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY;

CHROMATOGRAPHY, LIQUID; COSYNTROPIN; DRUG CONTAMINATION; ELECTROPHORESIS, CAPILLARY; HUMANS; MASS SPECTROMETRY; PEPTIDES;

EID: 80052585534     PISSN: 16182642     EISSN: 16182650     Source Type: Journal    
DOI: 10.1007/s00216-011-5183-0     Document Type: Article

References (41)

1. R Schwyzer H Kappeler 1963 Synthese eines Tetracosapeptides mit hoher corticotroper Wirksamkeit: β1-24-Corticotropin Helvetica Chimica Acta 46 5 1550 1572 10.1002/hlca.19630460510 1:CAS:528:DyaF3sXksFGnu7s%3D
2. A Toft W Irvine 1974 Hormonal Effects of Synthetic ACTH Analogues Proc R Soc Med 67 749 750 1:STN:280:DyaE2M%2FjtVajuw%3D%3D
3. M Vogeser R Zachoval K Jacob 2001 Serum cortisol/cortisone ratio after Synacthen stimulation Clin Biochem 34 5 421 425 10.1016/S0009-9120(01)00251-X 1:CAS:528:DC%2BD3MXnsFSrsL0%3D (Pubitemid 32777853)
4. NA Bridges PC Hindmarsh PJ Pringle JW Honour CGD Brook 1998 Cortisol, Androstenedione (A4), Dehydroepiandrosterone Sulphate (DHEAS) and 17 Hydroxyprogesterone (17OHP) Responses to Low Doses of (1-24)ACTH J Clin Endocrinol Metab 83 10 3750 3753 10.1210/jc.83.10.3750 1:CAS:528: DyaK1cXmsFOjtLo%3D (Pubitemid 28500921)
5. H Otto C Minneker R Spaethe 1966 Synacthen-Kurztest zur Beurteilung der Nebennierenrindenfunktion (Intravenous injection of corticotropin β1-24 in the rapid diagnosis of adrenal cortical function) Dtsch Med Wochenschr 91 20 934 939 10.1055/s-0028-1110678 1:CAS:528:DyaF28XktlagsLg%3D
6. S Crowley PC Hindmarsh P Holownia JW Honour CGD Brook 1991 The use of low doses of ACTH in the investigation of adrenal function in man J Endocrinol 130 3 475 479 10.1677/joe.0.1300475 1:CAS:528:DyaK3MXlsFWisbc%3D
7. JC Agwu H Spoudeas PC Hindmarsh PJ Pringle CGD Brook 1999 Tests of adrenal insufficiency Arch Dis Child 80 4 330 333 10.1136/adc.80.4.330 1:STN:280:DyaK1Mzos1GlsA%3D%3D (Pubitemid 29164755)
8. P Alía C Villabona O Giménez E Sospedra J Soler MA Navarro 2006 Profile, mean residence time of ACTH and cortisol responses after low and standard ACTH tests in healthy volunteers Clin Endocrinol 65 3 346 351 10.1111/j.1365-2265.2006.02602.x
9. K Collomp A Arlettaz H Portier A-M Lecoq B Le Panse N Rieth J De Ceaurriz 2008 Short-term glucocorticoid intake combined with intense training on performance and hormonal responses Br J Sports Med 42 12 983 988 10.1136/bjsm.2007.043083 1:STN:280:DC%2BD1M%2FhtlOmsw%3D%3D
10. E Soetens J Hueting K Meirleir 1995 No influence of ACTH on maximal performance Psychopharmacology 118 3 260 266 10.1007/BF02245953 1:CAS:528:DyaK2MXls1OgsbY%3D
11. N Baume G Steel T Edwards E Thorstensen B Miller 2008 No variation of physical performance and perceived exertion after adrenal gland stimulation by synthetic ACTH (Synacthen®) in cyclists Eur J Appl Physiol 104 4 589 600 10.1007/s00421-008-0802-y 1:CAS:528:DC%2BD1cXhsVSjtrvJ
12. WADA (2011) The 2011 Prohibited List. http://www.wada-ama.org/Documents/ World-Anti-Doping-Program/WADP-Prohibited-list/To-be-effective/ WADA-Prohibited-List-2011-EN.pdf. Accessed Jan 18 2011
13. WJ Jeffcoate C Phenekos JG Ratcliffe S Williams L Rees GM Besser 1977 Comparison of the pharmacokinetics in man of two synthetic ACTH analogues: a1-24 and substituted β1-18 ACTH Clin Endocrinol 7 1 1 11 10.1111/j.1365-2265. 1977.tb02935.x 1:CAS:528:DyaE2sXlsVKisb8%3D (Pubitemid 8147534)
14. M Thevis M Bredehöft H Geyer M Kamber P Delahaut W Schänzer 2006 Determination of Synacthen in human plasma using immunoaffinity purification and liquid chromatography/tandem mass spectrometry Rapid Commun Mass Spectrom 20 23 3551 3556 10.1002/rcm.2774 1:CAS:528:DC%2BD28XhtlWqs7jE (Pubitemid 44871311)
15. A Thomas M Kohler W Schänzer M Kamber P Delahaut M Thevis 2009 Determination of Synacthen in urine for sports drug testing by means of nano-ultra-performance liquid chromatography/tandem mass spectrometry Rapid Commun Mass Spectrom 23 17 2669 2674 10.1002/rcm.4176 1:CAS:528: DC%2BD1MXpslyqu74%3D
16. A Chaabo J de Ceaurriz C Buisson J-C Tabet F Lasne 2011 Simultaneous quantification and qualification of synacthen in plasma Anal Bioanal Chem 399 5 1835 1843 10.1007/s00216-010-4565-z 1:CAS:528:DC%2BC3cXhsF2murnM
17. Tetracosactide (2011) In: European Pharmacopoeia. 7th edn. European Directorate of The Quality of Medicines, Strasbourg, p monograph 0644
18. (2011) https://extranet.edqu.eu/4DLink1/pdfs/chromatos/0644.pdf. Accessed April 20
19. V Kasicka 2010 Recent advances in CE and CEC of peptides (2007-2009) Electrophoresis 31 1 122 146 10.1002/elps.200900442 1:CAS:528:DC%2BC3cXjvVKm
20. Kates SA, Albericio F (eds) (2000) Solid-Phase Synthesis: A Practical Guide. Marcel Dekker, Inc., New York
21. Chan WC, White PD (eds) (2000) Fmoc Solid Phase Peptide Synthesis - A Practical Approach. Oxford University Press, Oxford
22. RB Merrifield 1963 Solid Phase Peptide Synthesis. I. The Synthesis of a Tetrapeptide J Am Chem Soc 85 14 2149 2154 10.1021/ja00897a025 1:CAS:528:DyaF3sXksVajsLg%3D
23. A Cifuentes H Poppe 1997 Behavior of peptides in capillary electrophoresis: Effect of peptide charge, mass and structure Electrophoresis 18 12-13 2362 2376 10.1002/elps.1150181227 1:CAS:528:DyaK1cXis1WlsA%3D%3D (Pubitemid 28020597)
24. NJ Adamson EC Reynolds 1997 Rules relating electrophoretic mobility, charge and molecular size of peptides and proteins J Chromatogr B Biomed Sci Appl 699 1-2 133 147 10.1016/S0378-4347(97)00202-8 1:CAS:528:DyaK2sXmvFWiur4%3D (Pubitemid 27473709)
25. V Sanz-Nebot F Benavente I Toro J Barbosa 2003 Evaluation of chromatographic versus electrophoretic behaviour of a series of therapeutical peptide hormones J Chromatogr A 985 1-2 411 423 10.1016/S0021-9673(02)01902-7 1:CAS:528:DC%2BD3sXpsVWgtQ%3D%3D (Pubitemid 36164831)
26. DJ Winzor 2003 Classical approach to interpretation of the charge-dependence of peptide mobilities obtained by capillary zone electrophoresis J Chromatogr A 1015 1-2 199 204 10.1016/S0021-9673(03)01212-3 1:CAS:528:DC%2BD3sXnsVKmsb0%3D (Pubitemid 37163517)
27. B Tessier F Blanchard R Vanderesse C Harscoat I Marc 2004 Applicability of predictive models to the peptide mobility analysis by capillary electrophoresis-electrospray mass spectrometry J Chromatogr A 1024 1-2 255 266 10.1016/j.chroma.2003.10.050 1:CAS:528:DC%2BD3sXps1Omtbo%3D (Pubitemid 37532552)
28. M Jalali-Heravi Y Shen M Hassanisadi MG Khaledi 2005 Prediction of electrophoretic mobilities of peptides in capillary zone electrophoresis by quantitative structure-mobility relationships using the offord model and artificial neural networks Electrophoresis 26 10 1874 1885 10.1002/elps. 200410308 1:CAS:528:DC%2BD2MXkvF2ku70%3D (Pubitemid 40796652)
29. JL Meek 1980 Prediction of peptide retention times in high-pressure liquid chromatography on the basis of amino acid composition Proc Natl Acad Sci USA 77 3 1632 1636 10.1073/pnas.77.3.1632 1:CAS:528:DyaL3cXitFWisLk%3D
30. D Guo CT Mant AK Taneja JMR Parker RS Rodges 1986 Prediction of peptide retention times in reversed-phase high-performance liquid chromatography I. Determination of retention coefficients of amino acid residues of model synthetic peptides J Chromatogr A 359 499 518 10.1016/0021-9673(86)80102-9 1:CAS:528:DyaL28XkvFertLk%3D
31. CT Mant TWL Burke JA Black RS Hodges 1988 Effect of peptide chain length on peptide retention behaviour in reversed-phase chromatogrphy J Chromatogr A 458 193 205 10.1016/S0021-9673(00)90564-8 1:CAS:528:DyaL1MXksV2lt78%3D
32. K Petritis LJ Kangas B Yan ME Monroe EF Strittmatter W-J Qian JN Adkins RJ Moore Y Xu MS Lipton DG Camp RD Smith 2006 Improved Peptide Elution Time Prediction for Reversed-Phase Liquid Chromatography-MS by Incorporating Peptide Sequence Information Anal Chem 78 14 5026 5039 10.1021/ac060143p 1:CAS:528:DC%2BD28XlsFaksbg%3D (Pubitemid 44121117)
33. V Spicer M Grigoryan A Gotfrid KG Standing OV Krokhin 2010 Predicting Retention Time Shifts Associated with Variation of the Gradient Slope in Peptide RP-HPLC Anal Chem 82 23 9678 9685 10.1021/ac102228a 1:CAS:528: DC%2BC3cXhtlOrsLfK
34. XJ Tang P Thibault RK Boyd 1993 Fragmentation reactions of multiply-protonated peptides and implications for sequencing by tandem mass spectrometry with low-energy collision-induced dissociation Anal Chem 65 20 2824 2834 10.1021/ac00068a020 1:CAS:528:DyaK3sXlslKqtro%3D
35. P Roepstorff J Fohlman 1984 Letter to the editors: Proposal for a common nomenclature for sequence ions in mass spectra of peptides Biol Mass Spectrom 11 11 601-601 10.1002/bms.1200111109
36. V Sanz-Nebot I Toro A Castillo J Barbosa 2001 Investigation of synthetic peptide hormones by liquid chromatography coupled to pneumatically assisted electrospray ionization mass spectrometry: analysis of a synthesis crude of peptide triptorelin Rapid Commun Mass Spectrom 15 13 1031 1039 10.1002/rcm.343 1:CAS:528:DC%2BD3MXltVKitrw%3D (Pubitemid 32606948)
37. V Sanz-Nebot I Toro A Garcés J Barbosa 1999 Separation and identification of peptide mixtures in a synthesis crude of carbetocin by liquid chromatography/electrospray ionization mass spectrometry Rapid Commun Mass Spectrom 13 23 2341 2347 10.1002/(SICI)1097-0231(19991215)13:23<2341::AID- RCM795>3.0.CO;2-9 1:CAS:528:DyaK1MXnslOms70%3D
38. V Sanz-Nebot F Benavente J Barbosa 2000 Separation and characterization of multicomponent peptide mixtures by liquid chromatography-electrospray ionization mass spectrometry: Application to crude products of the synthesis of leuprolide J Chromatogr A 870 1-2 315 334 10.1016/S0021-9673(99)01088-2 1:CAS:528:DC%2BD3cXpsFKntg%3D%3D (Pubitemid 30077435)
39. V Sanz-Nebot F Benavente I Toro J Barbosa 2004 Separation and characterization of complex crude mixtures produced in the synthesis of therapeutic peptide hormones by liquid chromatography coupled to electrospray mass spectrometry (LC-ES-MS) Anal Chim Acta 521 1 25 36 10.1016/j.aca.2004.05. 041 1:CAS:528:DC%2BD2cXms1ylt7s%3D (Pubitemid 39092874)
40. JR Litowski PD Semchuk CT Mant RS Hodges 1999 Hydrophilic interaction/cation-exchange chromatography for the purification of synthetic peptides from closely related impurities: serine side-chain acetylated peptides J Pept Res 54 1 1 11 10.1034/j.1399-3011.1999.00066.x 1:CAS:528: DyaK1MXkslGhtbk%3D (Pubitemid 29334082)
41. E Bayer 1991 Auf dem Weg zur chemischen Synthese von Proteinen Angewandte Chemie 103 2 117 133 10.1002/ange.19911030204 1:CAS:528:DyaK3MXitVOksrg%3D