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Investigation of Selectivity of Amino Functionalised Phases for Pharmaceutical Applications

  • Catherine Gaki
  • Catherine Georganta
  • Maria G. Kouskoura
  • Catherine K. MarkopoulouEmail author
Original
  • 27 Downloads

Abstract

Amino column is a special stationary phase with diverse applications on reversed and normal phase, as well as on hydrophilic interaction chromatography. The objective of the present research was to explore the retention mechanism of the amino column, which triggered the detailed study of the chromatographic behavior of 44 drugs (analytes) divided into eight groups. The analytes were studied at five different mobile phases and the retention times were interpreted on the basis of their physicochemical properties and structural features (expressed by 30 variables). The data were fed as input in the partial least squares software and were processed for the development of three different validated models which provided an overview of the behavior of the analytes on amino column. The results showed that the major factors responsible for the chromatographic behavior of the studied drugs on amino column were: the presence of carboxylic group(s), the ionization degree, the pKa values of their basic moieties, and the molar volume. On the contrary, it was observed that the presence of hydroxyl group(s) is indirectly related to the retention phenomenon. In few words, the amino column is attributed a mixed mode depending on the conditions, especially on the composition of the mobile phase. The information derived from such a research could provide a solid base to optimize the use of an amino column in drug analysis not only for research purposes, but also for its use in the pharmaceutical industry.

Keywords

High-performance liquid chromatography Amino column Pharmaceutical compounds Partial least squares 

Notes

Compliance with Ethical Standards

Conflict of interest

There is no conflict of interest.

Human and Animal Rights

This article does not contain any studies with human participants or animals performed by any of the authors.

Supplementary material

10337_2019_3833_MOESM1_ESM.docx (202 kb)
Supplementary material 1 (DOCX 284 kb)

References

  1. 1.
    Cazes J (2009) Encyclopedia of chromatography, 3rd edn. CRC Press, USAGoogle Scholar
  2. 2.
    Jandera P (2011) Stationary and mobile phases in hydrophilic interaction chromatography: a review. Anal Chim Acta 692:1–25PubMedCrossRefGoogle Scholar
  3. 3.
    Alpert AJ (1990) Hydrophilic-interaction chromatography for the separation of peptides, nucleic acids and other polar compounds. J Chromatogr 499:177PubMedCrossRefGoogle Scholar
  4. 4.
    McCalley DV (2017) Understanding and manipulating the separation in hydrophilic interaction liquid chromatography. J Chromatogr A 1523:49–71PubMedCrossRefGoogle Scholar
  5. 5.
    Hemström P, Irgum K (2006) Ηydrophilic interaction chromatography. J Sep Sci 29:1784–1821PubMedCrossRefGoogle Scholar
  6. 6.
    Guo Y, Gaiki S (2011) Retention and selectivity of stationary phases for hydrophilic interaction chromatography. J Chromatogr A 1218:5920–5938PubMedCrossRefGoogle Scholar
  7. 7.
    Snyder LR, Kirkland JJ, Glajch JL (1997) Practical HPLC method development, 2nd edn. Wiley, USACrossRefGoogle Scholar
  8. 8.
    Martínez Montero C, Rodríguez Dodero MC, Guillén Sánchez DA, Barroso CG (2004) Analysis of low molecular weight carbohydrates in food and beverages: a review. Chromatographia 1–2:15–30Google Scholar
  9. 9.
    Buszewski B, Noga S (2012) Hydrophilic interaction liquid chromatography (HILIC)—a powerful separation technique. Anal Bioanal Chem 402(1):231–247PubMedCrossRefGoogle Scholar
  10. 10.
    Snyder LR, Kirkland JJ, Dolan JW (2010) Introduction to modern liquid chromatography, 3rd edn. Wiley, USAGoogle Scholar
  11. 11.
    Nikolov ZL, Meagher MM, Reilly PJ (1985) High-performance liquid chromatography of trisaccharides on amine-bonded silica columns. J Chromatogr A 321:393–399CrossRefGoogle Scholar
  12. 12.
    Endo T, Ueda H, Kobayashi S, Nagai T (1995) Isolation, purification and characterization of cyclomaltodecaose (ε-cyclodextrin). Carbohyd Res 269:369–373CrossRefGoogle Scholar
  13. 13.
    Chang KB, Lee J, Fu WR (2000) HPLC analysis of N-acetylchitooligosaccharides during the acid hydrolysis of chitin. J Food Drug Anal 8(1):75–83Google Scholar
  14. 14.
    Ko JH, Cheong WJ (2001) Bull Korean Chem Soc 22(1):123–126Google Scholar
  15. 15.
    Tanimoto T, Ikuta A, Sugiyama M, Koizumi M (2002) HPLC analysis of manno-ologosaccharides derived from Saccharomyces cerevisiae mannan using an amino column or a graphitized carbon column. Chem Pharm Bull 50(2):280–283PubMedCrossRefGoogle Scholar
  16. 16.
    Shao Y, Alluri R, Mummert M, Koetter U, Lech S (2004) A stability-indicating HPLC method for the determination of glucosamine in pharmaceutical formulations. J Pharm Biomed Anal 35(3):625–631PubMedCrossRefGoogle Scholar
  17. 17.
    Rahman NA, Hasan M, Hussain M, Jahim J (2008) Determination of glucose and fructose from glucose isomerization process by high performance liquid chromatography with UV detection. Mod Appl Sci 2(4):151–154CrossRefGoogle Scholar
  18. 18.
    Zhang TB, Yue RQ, Xu J, Ho JM, Ma DL, Leung CH, Chau SL, Zhao ZZ, Chen HB, Han QB (2015) Comprehensive quantitative analysis of Shuang-Huang-Lian oral liquid using UHPLC–Q-TOF–MS and HPLC–ELSD. J Pharm and Biomed Anal 102:1–8CrossRefGoogle Scholar
  19. 19.
    Fung HY, Lang Y, Ho HM, Wong TL, Ma DL, Leung CH, Han QB (2017) Comprehensive quantitative analysis of 32 chemical ingredients of a Chinese patented drug sanhuang tablet. Molecules 22(1):111–118PubMedCentralCrossRefPubMedGoogle Scholar
  20. 20.
    Chaisuwan P, Kongprasertsak T, Sangcakul A, Smith NW, Nachapricha D, Wilairat P, Uraisin K (2011) Direct injection of human serum and pharmaceutical formulations for glucosamine determination by CE-C(4)D method. J Chromatogr B 879(23):2185–2188CrossRefGoogle Scholar
  21. 21.
    Suo H, Xu K, Zhang H, Zheng X (2015) Determination of glucosamine and its derivatives released from photocrosslinked gelatin hydrogels using HPLC. Biomed Chromatogr 30(2):169–174PubMedCrossRefGoogle Scholar
  22. 22.
    Bushway R (1982) High-performance chromatographic separation of potato glycoalkaloids using a radially compressed amino column. J Chromatogr A 247(1):180–183CrossRefGoogle Scholar
  23. 23.
    Liu C, Li LS, Xu LL, Zhou ZM (2007) Separationa and identification of stevioside and rebaudioside A in stevia by HPLC. Chin J Anal Lab 26:23–26Google Scholar
  24. 24.
    Grizzle PL, Sablotny DM (1986) Automated liquid chromatographic compound class group-type separation of crude oils and bitumens using chemically bonded silica–NH2. Anal Chem 58(12):2389–2396CrossRefGoogle Scholar
  25. 25.
    Östman CE, Colmsjö A (1987) Backflush HPLC for the isolation of polycyclic aromatic compounds—a comparative study. Chromatographia 23(12):903–908CrossRefGoogle Scholar
  26. 26.
    Caceres A, Ysambertt F, Lopez J, Marquez N (1996) Analysis of photostabilizer in high density polyethylene by reverse- and normal-phase HPLC. Sep Sci Technol 31(16):2287–2298CrossRefGoogle Scholar
  27. 27.
    Doner LW, Hicks KB (1981) High-performance liquid chromatographic separation of ascorbic acid, erythobic acid, dehydroerythobic acid and diketogulonic acid. Anal Biochem 115(1):225–230PubMedCrossRefGoogle Scholar
  28. 28.
    Lopez PG, Pereira GF, Santoro MI, Kedor-Hackman ER, Vilchez Quero JL, Navalón Montón AL, Crovetto Montoya G, Aguilera Cabrera M (2011) Determination of vecuronium bromide in pharmaceuticals: development, validation and comparative study of HPLC and CZE analytical methods. Chromatographia 73(7–8):799–805Google Scholar
  29. 29.
    Kim JH, Shinn HK, Seo CS (2014) Development of a quantitative analysis method for the 12 marker compounds in Palmijihwang-hwan, a herbal formula, using a reversed-phase C18 column and an amino column by HPLC. Anal Methods 6(11):3763–3771CrossRefGoogle Scholar
  30. 30.
    Perlman S, Kirschbaum J (1981) High-performance liquid chromatographic analyses of the antihypertensive drug cartopril. J Chromatogr A 206(2):311–317CrossRefGoogle Scholar
  31. 31.
    Doner LW, Hsu AF (1982) High-performance liquid chromatographic separation of alkaloids from Papaver somniferum on a Zorbax NH2 analytical column. J Chromatogr A 253:120–123CrossRefGoogle Scholar
  32. 32.
    Xu CJ, Lin JT (1985) Comparison of silica, CIS-, and NH2-HPLC columns for the separation of neutral steroid saponins from Dioscorea plants. J Liq Chromatogr 8(2):361–368CrossRefGoogle Scholar
  33. 33.
    Hosotsubo H (1989) Rapid and specific method for the determination of vancomycin in plasma by high-performance liquid chromatographicy on an aminopropyl column. J Chromatogr B 487(2):421–427CrossRefGoogle Scholar
  34. 34.
    Lee C, Porziemsky J, Aubert M, Krstulovic A (1991) Liquid and high-pressure carbon dioxide chromatography of β-blockers: resolution of the enantiomers of nadolol. J Chromatogr A 539(1):55–69CrossRefGoogle Scholar
  35. 35.
    Ascalone V, Dal Bò L (1983) Determination of ceftriaxone, a novel cephalosporin, in plasma, urine and saliva by high-performance liquid chromatography on an NH2 bonded-phase column. J Chromatogr B 273(2):357–366CrossRefGoogle Scholar
  36. 36.
    Gagliardi L, de Orsi D, Cavazzutti G, Tonelli D, Zappoli S (1994) HPLC determination of oxiracetam, its impurities, and piracetam in pharmaceutical formulations. Anal Lett 27(5):879–885CrossRefGoogle Scholar
  37. 37.
    Olsen BA (2001) Hydrophilic interaction chromatography using amino and silica columns for the determination of polar pharmaceuticals and impurities. J Chromatogr A 913(1–2):113–122PubMedCrossRefGoogle Scholar
  38. 38.
    Sha DX, Zhang ML (2005) Determination of notoginsenoside R1, gingenoside Rg1 and Rb1in radix Notoginseng and its preparation by HPLC-ELSD. J Chin Mater Med 30(2):112–115Google Scholar
  39. 39.
    Popović G, Vučićević M, Vladimirov S, Agbaba D (2007) Comparison of HPTLC and HPLC for deteremination of econazole nitrate in topical dosage forms. J Planar Chromatogr Mod TLC 17(2):109–112CrossRefGoogle Scholar
  40. 40.
    López PG, Pereira Gomes F, Santoro MI, Kedor-Hackmann ER (2008) Validation of an HPLC analytical method for determination of pancuronium bromide in pharmaceutical injections. Anal Lett 41(10):1895–1908CrossRefGoogle Scholar
  41. 41.
    Tian J, Wang W, Gao H, Wang Z (2007) Determination of matrine, sophoridine and oxymatrine in Compound Kushen Injection by HPLC. J Chin Mater Med 32(3):222–224Google Scholar
  42. 42.
    Kouskoura MG, Hadjipavlou-Litina D, Markopoulou CK (2014) Elucidation of the retention mechanism on cyano column using PLS and QSAR models. J Sep Sci 37(15):1919–1929PubMedCrossRefGoogle Scholar
  43. 43.
    Kouskoura MG, Mitani CV, Markopoulou CK (2015) Study and development of reverse phase HPLC systems for the simultaneous determination of 2-imidazolines combined with preservatives in pharmaceutical preparations. J AOAC Int 98(5):1462–1470PubMedCrossRefGoogle Scholar
  44. 44.
    Kouskoura MG, Kachrimanis KG, Markopoulou CK (2014) Modelling the drugs’ passive transfer in the body based on their HPLC behavior. J Pharm Biomed Anal 4(100):94–102CrossRefGoogle Scholar
  45. 45.
    SimCa-P 9, User Guide and Tutorial, 2001Google Scholar
  46. 46.
  47. 47.
  48. 48.
  49. 49.
    Haaland DM, Thomas EV (1988) Partial least-squares methods for spectral analyses. 1. Relation to other quantitative calibration methods and the extraction of qualitative information. Anal Chem 60:193–1202CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Laboratory of Pharmaceutical Analysis, School of PharmacyAristotle UniversityThessalonikiGreece

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