Skip to main content
Log in

Raman spectroscopic investigation of the antimalarial agent mefloquine

  • Original Paper
  • Published:
Analytical and Bioanalytical Chemistry Aims and scope Submit manuscript

Abstract

The antimalarial agent mefloquine was investigated using Fourier transform near-infrared (FT NIR) Raman and FT IR spectroscopy. The IR and Raman spectra were calculated with the help of density functional theory (DFT) and a very good agreement with the experimental spectra was achieved. These DFT calculations were applied to unambiguously assign the prominent features in the experimental vibrational spectra. The calculation of the potential energy distribution (PED) and the atomic displacements provide further valuable insight into the molecular vibrations. The most prominent NIR Raman bands at 1,363 cm−1 and 1,434 cm−1 are due to C=C stretching (in the quinoline part of mefloquine) and CH2 wagging vibrations, while the most intense IR peaks at 1,314 cm−1; 1,147 cm−1; and 1,109 cm−1 mainly consist of ring breathings and δCH (quinoline); C–F stretchings; and asymmetric ring breathings, C–O stretching as well as CH2 twisting/rockings located at the piperidine moiety. Since the active agent (mefloquine) is usually present in very low concentrations within the biological samples, UV resonance Raman spectra of physiological solutions of mefloquine were recorded. By employing the detailed non-resonant mode assignment it was also possible to unambiguously identify the resonantly enhanced modes at 1,619 cm−1, 1,603 cm−1 and 1,586 cm−1 in the UV Raman spectra as high symmetric C=C stretching vibrations in the quinoline part of mefloquine. These spectroscopic results are important for the interpretation of upcoming in vitro and in vivo mefloquine target interaction experiments.

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

Access this article

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. http://rbm.who.int/wmr2005

  2. Hastings IM, Bray PG, Ward SA (2002) Science 298:74–74

    Article  CAS  Google Scholar 

  3. Ridley RG (2002) Nature 415:686–693

    Article  CAS  Google Scholar 

  4. Constantinidis I, Satterlee JD (1988) J Am Chem Soc 110:927–932

    Article  CAS  Google Scholar 

  5. Constantinidis I, Satterlee JD (1988) J Am Chem Soc 110:4391–4395

    Article  CAS  Google Scholar 

  6. Pagola S, Stephens PW, Bohle DS, Kosar AD, Madsen SK (2000) Nature 404:307–310

    Article  CAS  Google Scholar 

  7. Buller R, Peterson ML, Almarsson Ö, Leisirowitz L (2002) Cryst Growth Des 2:(6) 553–562

    Article  CAS  Google Scholar 

  8. Frosch T, Schmitt M, Schenzel K, Faber JH, Bringmann G, Kiefer W, Popp J (2006) Biopolymers 82:295–300

    Article  CAS  Google Scholar 

  9. MJ Frisch, GW Trucks, HB Schlegel, GE Scuseria, MA Robb, JR Cheeseman, JA Montgomery Jr, T Vreven, KN Kudin, JC Burant, JM Millam, SS Iyengar, J Tomasi, V Barone, B Mennucci, M Cossi, G Scalmani, N Rega, GA Petersson, H Nakatsuji, M Hada, M Ehara, K Toyota, R Fukuda, J Hasegawa, M Ishida, T Nakajima, Y Honda, O Kitao, H Nakai, M Klene, X Li, JE Knox, HP Hratchian, JB Cross, C Adamo, J Jaramillo, R Gomperts, RE Stratmann, O Yazyev, AJ Austin, R Cammi, C Pomelli, JW Ochterski, PY Ayala, K Morokuma, GA Voth, P Salvador, J Dannenberg, VG Zakrzewski, S Dapprich, AD Daniels, MC Strain, O Farkas, DK Malick, AD Rabuck, K Raghavachari, JB Foresman, JV Ortiz, Q Cui, AG Baboul, S Clifford, J Cioslowski, BB Stefanov, G Liu, A Liashenko, P Piskorz, I Komaromi, RL Martin, DJ Fox, T Keith, MA Al-Laham, CY Peng, A Nanayakkara, M Challacombe, PM W Gill, B Johnson, W Chen, MW Wong, C Gonzalez, JA Pople (2004) Gaussian 03, Revision C 02. Gaussian, Wallingford CT,

  10. Petry R, Schmitt M Popp J (2003) ChemPhysChem 4:14–30 (and refs cited therein)

    Article  CAS  Google Scholar 

  11. McHale JL (2002) In: Chalmers JM, Griffiths PR (eds) Handbook of vibrational spectroscopy, vol 1. Wiley, Chichester (and refs cited therein)

  12. Becke AD (1992) J Chem Phys 97:9173; AD Beck (1993) J Chem Phys 98:5648

    Article  CAS  Google Scholar 

  13. Perdew JP, Wang Y (1992) Phys Rev B45:13244; Perdew, JP, Chevary JA, Vosko, SH Jackson, KA, Pederson MR, Singh DJ, Fiolhais C (1992) Phys Rev B46:6671

  14. Stephens PJ, Devlin FJ, Chabalowski CF, Frisch MJ (1994) J Phys Chem 98:11623

    Article  CAS  Google Scholar 

  15. Lee C, Yang W, Parr RG (1988) Phys Rev B37:785

    Google Scholar 

  16. Pople JA, Schlegel HB, Krishnan R, Defrees DJ, Binkley JS, Frisch MJ, Whitside RA (1981) Int J Quantum Chem Quant Chem Symp 15:269–278; MJ Frisch, JA Pople, JS Binkley (1984) J Chem Phys 80(7):3265–3269 (and refs therein); Hehre WJ, Stewart RF, Pople JA (1969) J Chem Phys 51(6):2657–2664 (and refs cited therein)

  17. Bright E, Wilson, JR (1941) J Chem Phys 9:76–84; Wilson E Jr (1939) J Chem Phys 7:1047–1052; Wilson EB, Decius JC, Cross PC (1955) Molecular vibrations. McGraw-Hill, New York

  18. Martin JML, Van Alsenoy C (1995) GAR2PED. University of Antwerp

  19. Frosch T, Küstner B, Schlücker S, Szeghalmi M, Schmitt W, Kiefer J, Popp J (2004) Raman Spectrosc 35:819–821

    Article  CAS  Google Scholar 

  20. Neugebauer J, Hess BA (2003) J Chem Phys 118 (16) 7215–7225

    Article  CAS  Google Scholar 

  21. Scott AP, Radom L (1996) J Phys Chem 100:16502–16513

    Article  CAS  Google Scholar 

  22. El-Azhary AA, Suter HU (1996) J Phys Chem 100:15056–15063

    Article  CAS  Google Scholar 

  23. Baker J, Jarzecki AA, Pulay P (1998) J Phys Chem A 102:1412–1424

    Article  CAS  Google Scholar 

  24. Rauhut G, Pulay P (1995) J Phys Chem 99:3093–3100

    Article  CAS  Google Scholar 

  25. Halls MD, Schlegel B (1998) J Chem Phys 109 (24):10587–10593

    Article  CAS  Google Scholar 

  26. Andersson MP, Uvdal P (2005) J Phys Chem A 109:2937–2941

    Article  CAS  Google Scholar 

  27. Boese AD, JML Martin (2003) J Chem Phys 119, 6:3005–3014

    Article  CAS  Google Scholar 

  28. Wiberg KB (2004) J Comput Chem 25:1342–1346

    Article  CAS  Google Scholar 

  29. Figgen D, Metz B, Stoll H, Rauhut G (2002) J Phys Chem A 106:6810–6816

    Article  CAS  Google Scholar 

  30. Liu R, Zhou X, Pulay P (1992) J Phys Chem 96:8336–8339

    Article  CAS  Google Scholar 

  31. Forgarais G, Zhou X, Taylor PW, Pulay P (1992) J Am Chem Soc 114:8191–8201

    Article  Google Scholar 

  32. Forgarasi G, Pulay P (1986) J Mol Struc 141:145–152

    Article  Google Scholar 

  33. Pulay P, Fogarasi G, Pongor G, Boggs JF, Vargha A (1983) J Am Chem Soc 105:7037–7047

    Article  CAS  Google Scholar 

  34. Pulay P, Fogarasi G, Pang F, Boggs JF (1979) J Am Chem Soc 101:10, 2550–2560

    Article  CAS  Google Scholar 

  35. Wong MW (1996) Chem Phys Lett 256:391–399

    Article  CAS  Google Scholar 

  36. Bauschlicher CW, Langhoff SR (1997) Spectrochim Acta Part A 53:1225–1240

    Article  Google Scholar 

  37. Halls MD, Velovski J, Schlegel HB (2001) Theor Chem Ac 105:43–421

    Google Scholar 

  38. Olivaro PL, Goldberg DE (1995) Parasit Today 11(8):294–297; Hawley SR, Bray PG, O’Neill PM, Park BK, Ward SA (1996) Biochem Pharmacol 52:723–733; Yayon A, Cabantchik ZI, Ginsburg H (1984) EMBO J 3(11):2695–2700 ; Ginsburg H, Geary TG (1987) Biochem Pharmacol 36(10):1567–1576

Download references

Acknowledgements

The authors gratefully acknowledge support from the Fonds der Chemischen Industrie and the Deutsche Forschungsgemeinschaft (Sonderforschungsbereich 630 “Recognition, Preparation, and Functional Analysis of Agents Against Infectious Diseases”, project C1). We thank Karla Schenzel for the possibility to use the FT NIR Raman spectrometer. Mefloquine was a kind gift from Roche Diagnostic GmbH.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jürgen Popp.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Frosch, T., Schmitt, M. & Popp, J. Raman spectroscopic investigation of the antimalarial agent mefloquine. Anal Bioanal Chem 387, 1749–1757 (2007). https://doi.org/10.1007/s00216-006-0754-1

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00216-006-0754-1

Keywords

Navigation