Skip to main content
SpringerLink
Log in

Spectrometric methods in pharmaceutical analysis of glycosaminoglycans: the state-of-the-art

  • Review
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

Glycosaminoglycans are important complex carbohydrates that are used in a number of pharmaceutical products. Because glycosaminoglycans are obtained by isolation from biological materials, their pharmaceutical analysis before therapeutic use is of paramount importance. Due to their versatility, wide applicability, non-destructiveness, and in particular the possibility of obtaining a “fingerprint” clearly proving the given chemical specie, spectrometric methods are one of the essential methods used for these analyzes. This review is focused on significant spectrometric methods used in the pharmaceutical analysis of glycosaminoglycans. The advantages and prospects of individual methods (NMR spectrometry, infrared and Raman spectrometry, UV/Vis spectrometry, spectrofluorimetry, chemiluminescence, and circular dichroism) used and methodological aspects of the analysis are discussed. The possibilities of further development and application of spectral methods in the discussed area are outlined.

Graphic abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

Similar content being viewed by others

References

  1. Gandhi NS, Mancera RL (2008) Chem Biol Drug Des 72:455

    CAS  PubMed  Google Scholar 

  2. Köwitsch A, Zhou G, Groth T (2018) J Tissue Eng Regen Med 12:e23

    PubMed  Google Scholar 

  3. van Dam JEG, van den Broek LAM, Boeriu CG (2017) Nat Prod Commun 12:821

    Google Scholar 

  4. Ahsan H (2019) J Carbohydr Chem 38:213

    CAS  Google Scholar 

  5. Rabenstein DL (2002) Nat Prod Rep 19:312

    CAS  PubMed  Google Scholar 

  6. Salwowska NM, Bebenek KA, Zadlo DA, Wcislo-Dziadecka DL (2016) J Cosmet Dermatol 15:520

    PubMed  Google Scholar 

  7. Sandri G, Rossi S, Bonferoni MC, Miele D, Faccendini A, Del Favero E, Di Cola E, Icaro Cornaglia A, Boselli C, Luxbacher T, Malavasi L, Cantu’ L, Ferrari F (2019) Carbohydr Polym 220:219

    CAS  PubMed  Google Scholar 

  8. Henrotin Y, Mobasheri A (2018) Curr Rheumatol Rep 20:72

    PubMed  Google Scholar 

  9. Pomin VH, Vignovich WP, Gonzales AV, Vasconcelos AA, Mulloy B (2019) Molecules 24:2803

    PubMed Central  Google Scholar 

  10. Volpi N (2007) J Pharm Sci 96:3168

    CAS  PubMed  Google Scholar 

  11. Volpi N (2019) Molecules 24:1447

    CAS  PubMed Central  Google Scholar 

  12. Burns DT, Walker MJ, Mussell C (2018) J AOAC Int 101:196

    CAS  PubMed  Google Scholar 

  13. Ramacciotti E, Clark M, Sadeghi N, Hoppensteadt D, Thethi I, Gomes M, Fareed J (2011) Clin Appl Thromb Hemost 17:126

    CAS  PubMed  Google Scholar 

  14. Rosania L (2010) Food Drug Law J 65:489

    PubMed  Google Scholar 

  15. Beni S, Limtiaco JFK, Larive CK (2011) Anal Bioanal Chem 399:527

    CAS  PubMed  Google Scholar 

  16. Szajek AY, Chess E, Johansen K, Gratzl G, Gray E, Keire D, Linhardt RJ, Liu J, Morris T, Mulloy B, Nasr M, Shriver Z, Torralba P, Viskov C, Williams R, Woodcock J, Workman W, Al-Hakim A (2016) Nat Biotechnol 34:625

    CAS  PubMed  PubMed Central  Google Scholar 

  17. Vishenkova DA, Korotkova EI (2017) J Anal Chem 72:349

    CAS  Google Scholar 

  18. Volpi N, Maccari F, Suwan J, Linhardt RJ (2012) Electrophoresis 33:1531

    CAS  PubMed  PubMed Central  Google Scholar 

  19. Korir AK, Larive CK (2009) Anal Bioanal Chem 393:155

    CAS  PubMed  Google Scholar 

  20. Solakyildirim K (2019) Anal Bioanal Chem 411:3731

    CAS  PubMed  Google Scholar 

  21. Staples GO, Zaia J (2011) Curr Proteomics 8:325

    CAS  PubMed  PubMed Central  Google Scholar 

  22. Rudd TR, Macchi E, Gardini C, Muzi L, Guerrini M, Yates EA, Torri G (2012) Anal Chem 84:6841

    CAS  PubMed  Google Scholar 

  23. Devlin A, Mycroft-West CJ, Turnbull JE, Guerrini M, Yates EA, Skidmore MA (2019) bioRxiv. https://doi.org/10.1101/538074

  24. Sasisekharan R, Shriver Z (2009) Thromb Haemost 102:854

    CAS  PubMed  Google Scholar 

  25. Neville GA, Racey TJ, Rochon P, Rej RN, Perlin AS (1990) J Pharm Sci 79:425

    CAS  PubMed  Google Scholar 

  26. Beyer T, Diehl B, Randel G, Humpfer E, Schäfer H, Spraul M, Schollmayer C, Holzgrabe U (2008) J Pharm Biomed Anal 48:13

    CAS  PubMed  Google Scholar 

  27. Beyer T, Matz M, Brinz D, Rädler O, Wolf B, Norwig J, Baumann K, Alban S, Holzgrabe U (2010) Eur J Pharm Sci 40:297

    CAS  PubMed  Google Scholar 

  28. Beyer T, Diehl B, Holzgrabe U (2010) Bioanal Rev 2:1

    Google Scholar 

  29. Keire DA, Mans DJ, Ye H, Kolinski RE, Buhse LF (2010) J Pharm Biomed Anal 52:656

    CAS  PubMed  Google Scholar 

  30. Keire DA, Trehy ML, Reepmeyer JC, Kolinski RE, Ye W, Dunn J, Westenberger BJ, Buhse LF (2010) J Pharm Biomed Anal 51:921

    CAS  PubMed  Google Scholar 

  31. Zhang Z, Li B, Suwan J, Zhang F, Wang Z, Liu H, Mulloy B, Linhardt RJ (2009) J Pharm Sci 98:4017

    CAS  PubMed  Google Scholar 

  32. Pomin VH (2014) Anal Chem 86:65

    CAS  PubMed  Google Scholar 

  33. Monakhova YB, Diehl BWK (2018) J Pharm Biomed Anal 154:332

    CAS  PubMed  Google Scholar 

  34. Monakhova YB, Diehl BWK, Fareed J (2018) J Pharm Biomed Anal 149:114

    CAS  PubMed  Google Scholar 

  35. Monakhova YB, Rubtsova EM, Diehl BWK, Mushtakova SP (2019) J Anal Chem 74:945

    CAS  Google Scholar 

  36. Ruiz-Calero V, Saurina J, Galceran MT, Hernández-Cassou S, Puignou L (2000) Analyst 125:933

    CAS  PubMed  Google Scholar 

  37. The United States Pharmacopoeia 41, National Formulary 36 (2018) United States Pharmacopoeia Convention, Rockville

  38. Sakai S, Otake E, Toida T, Goda Y (2007) Chem Pharm Bull (Tokyo) 55:299

    CAS  Google Scholar 

  39. Langeslay DJ, Beni S, Larive CK (2012) J Magn Reson 216:169

    CAS  PubMed  Google Scholar 

  40. Langeslay DJ, Beecher CN, Naggi A, Guerrini M, Torri G, Larive CK (2013) Anal Chem 85:1247

    CAS  PubMed  Google Scholar 

  41. Guerrini M, Beccati D, Shriver Z, Naggi A, Viswanathan K, Bisio A, Capila I, Lansing JC, Guglieri S, Fraser B, Al-Hakim A, Gunay NS, Zhang Z, Robinson L, Buhse L, Nasr M, Woodcock J, Langer R, Venkataraman G, Linhardt RJ, Casu B, Torri G, Sasisekharan R (2008) Nat Biotechnol 26:669

    CAS  PubMed  PubMed Central  Google Scholar 

  42. Guerrini M, Zhang Z, Shriver Z, Naggi A, Masuko S, Langer R, Casu B, Linhardt RJ, Torri G, Sasisekharan R (2009) Proc Natl Acad Sci USA 106:16956

    CAS  PubMed  Google Scholar 

  43. Bigler P, Brenneisen R (2009) J Pharm Biomed Anal 49:1060

    CAS  PubMed  Google Scholar 

  44. Mucci A, Schenetti L, Volpi N (2000) Carbohydr Polym 41:37

    CAS  Google Scholar 

  45. D’Arcy SMT, Carney SL, Howe TJ (1994) Carbohydr Res 255:41

    PubMed  Google Scholar 

  46. Bednarek E, Sitkowski J, Bocian W, Mulloy B, Kozerski L (2010) J Pharm Biomed Anal 53:302

    CAS  PubMed  Google Scholar 

  47. Sitkowski J, Bednarek E, Bocian W, Kozerski L (2008) J Med Chem 51:7663

    CAS  PubMed  Google Scholar 

  48. Kellenbach E, Burgering M, Kaspersen F (1999) Org Process Res Dev 3:141

    CAS  Google Scholar 

  49. Mainreck N, Brezillon S, Sockalingum GD, Maquart FX, Manfait M, Wegrowski Y (2011) J Pharm Sci 100:441

    CAS  PubMed  Google Scholar 

  50. Longas MO, Breitweiser KO (1991) Anal Biochem 192:193

    CAS  PubMed  Google Scholar 

  51. Garnjanagoonchorn W, Wongekalak L, Engkagul A (2007) Chem Eng Process 46:465

    CAS  Google Scholar 

  52. El-Gindy A, Attia KAS, Nassar MW, Seda HHA, Shoeib MAS (2012) J AOAC Int 95:1035

    CAS  PubMed  Google Scholar 

  53. El-Gindy A, Attia KAS, Nassar MW, El-Abasawy NMA, Shoeib MAS (2012) J AOAC Int 95:724

    CAS  PubMed  Google Scholar 

  54. Sun C, Zang H, Liu X, Dong Q, Li L, Wang F, Sui L (2010) J Pharm Biomed Anal 51:1060

    CAS  PubMed  Google Scholar 

  55. Spencer JA, Kauffman JF, Reepmeyer JC, Gryniewicz CM, Ye W, Toler DY, Buhse LF, Westenberger BJ (2009) J Pharm Sci 98:3540

    CAS  PubMed  Google Scholar 

  56. Zang H, Li L, Wang F, Yi Q, Dong Q, Sun C, Wang J (2012) J Pharm Biomed Anal 61:224

    CAS  PubMed  Google Scholar 

  57. Levine A, Schubert M (1952) J Am Chem Soc 74:91

    CAS  Google Scholar 

  58. Zhang S, Li N, Zhao F, Li K, Tong S (2002) Spectrochim Acta Part A 58:273

    Google Scholar 

  59. Farndale RW, Buttle DJ, Barrett AJ (1986) Biochim Biophys Acta 883:173

    CAS  PubMed  Google Scholar 

  60. Zhang S, Zhao F, Li N, Li K, Tong S (2002) Spectrochim Acta Part A 58:2613

    Google Scholar 

  61. Liang Z, Bonneville C, Senez T, Henderson T (2002) J Pharm Biomed Anal 28:245

    CAS  PubMed  Google Scholar 

  62. Frazier SB, Roodhouse KA, Hourcade DE, Zhang L (2008) Open Glycosci 1:31

    CAS  PubMed  PubMed Central  Google Scholar 

  63. Luo HQ, Liu SP, Liu ZF, Liu Q, Li NB (2001) Anal Chim Acta 449:261

    CAS  Google Scholar 

  64. Cui Z, Hu X, Liu S, Liu Z (2011) Spectrochim Acta Part A 83:1

    CAS  Google Scholar 

  65. Li T, Liu S, Liu Z, Hu X (2005) Arch Pharm (Weinh) 338:427

    CAS  Google Scholar 

  66. Wu LP, Huang CZ, Yang X, He J, Li LL, Liu H, Zhao HW (2013) Anal Methods 5:2511

    CAS  Google Scholar 

  67. Němcová I, Rychlovský P, Havelcová M, Brabcová M (1999) Anal Chim Acta 401:223

    Google Scholar 

  68. Pospíchal R, Nesměrák K, Rychlovský P, Němcová I (2007) Anal Lett 40:1167

    Google Scholar 

  69. Kradtap-Hartwell S, Sripaoraya W, Grudpan K (2011) J Anal Chem 66:135

    CAS  Google Scholar 

  70. Huang CZ, Pang XB, Li YF (2005) Anal Lett 38:317

    Google Scholar 

  71. Sommers CD, Mans DJ, Mecker LC, Keire DA (2011) Anal Chem 83:3422

    CAS  PubMed  Google Scholar 

  72. Sommers CD, Keire DA (2011) Anal Chem 83:7102

    CAS  PubMed  Google Scholar 

  73. Fu X, Chen L, Li J, Lin M, You H, Wang W (2012) Biosens Bioelectron 34:227

    CAS  PubMed  Google Scholar 

  74. Lima MA, Rudd TR, de Farias EHC, Ebner LF, Gesteira TF, de Souza LM, Mendes A, Córdula CR, Martins JRM, Hoppensteadt D, Fareed J, Sassaki GL, Yates EA, Tersariol ILS, Nader HB (2011) PLoS ONE 6:e15970

    CAS  PubMed  PubMed Central  Google Scholar 

  75. O’Brien JF, Emmerling ME (1978) Anal Biochem 85:377

    PubMed  Google Scholar 

  76. Diakun GP, Edwards HE, Allen JC, Phillips GO, Cundall RB (1979) Anal Biochem 94:378

    CAS  PubMed  Google Scholar 

  77. Manzoori JL, Jouyban A, Amjadi M, Ramezani AM (2013) J Appl Spectrosc 80:104

    CAS  Google Scholar 

  78. Zhu X, Wang X, Jiang C (2005) Anal Biochem 341:299

    CAS  PubMed  Google Scholar 

  79. Patil SR, Mote US, Patil SR, Kolekar GB (2009) Bull Korean Chem Soc 30:3034

    CAS  Google Scholar 

  80. Lühn S, Schrader T, Sun W, Alban S (2010) J Pharm Biomed Anal 52:1

    PubMed  Google Scholar 

  81. Lühn S, Schiemann S, Alban S (2011) Anal Bioanal Chem 399:673

    PubMed  Google Scholar 

  82. Alban S, Lühn S, Schiemann S (2011) Anal Bioanal Chem 399:681

    CAS  PubMed  Google Scholar 

  83. Qi Y, He J, Xiu FR, Yu X, Li Y, Lu Y, Gao X, Song Z, Li B (2019) Spectrochim Acta Part A 216:310

    CAS  Google Scholar 

  84. Stanley FE, Stalcup AM (2011) Anal Bioanal Chem 399:701

    CAS  PubMed  Google Scholar 

Download references

Acknowledgements

The financial support by the project Progress Q46 of Charles University is gratefully acknowledged.

Author information

Authors and Affiliations

  1. Department of Analytical Chemistry, Faculty of Science, Charles University, Prague, Czech Republic

    Karel Nesměrák & Rudolf Pospíchal

Authors
  1. Karel Nesměrák
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Rudolf Pospíchal
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Karel Nesměrák.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Nesměrák, K., Pospíchal, R. Spectrometric methods in pharmaceutical analysis of glycosaminoglycans: the state-of-the-art. Monatsh Chem 151, 1185–1192 (2020). https://doi.org/10.1007/s00706-020-02632-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-020-02632-3

Keywords

Search

Navigation