Application of vibrational spectroscopy and nuclear magnetic resonance methods for drugs pharmacokinetics research
-
Vladimir V. Rafalskiy
Abstract
Objectives
The development of new methods for determining the concentration of drugs is an actual topic today. The article contains a detailed review on vibrational spectroscopy and nuclear magnetic resonance methods using for pharmacokinetic research. This study is devoted to the possibility of using vibrational spectroscopy and 1H nuclear magnetic resonance spectroscopy to determine the concentration of drugs and the use of these groups of techniques for therapeutic drug monitoring.
Content
The study was conducted by using scientific libraries (Scopus, Web of Science Core Collection, Medline, GoogleScholar, eLIBRARY, PubMed) and reference literature. A search was conducted for the period from 2011 to 2021 in Russian and English, by combinations of words: 1H nuclear magnetic resonance (1H NMR), vibrational spectroscopy, Surface-Enhanced Raman spectroscopy, drug concentration, therapeutic drug monitoring. These methods have a number of advantages and are devoid of some of the disadvantages of classical therapeutic drug monitoring (TDM) methods – high performance liquid chromatography and mass spectrometry. This review considers the possibility of using the methods of surface-enhanced Raman scattering (SERS) and 1H NMR-spectroscopy to assess the concentration of drugs in various biological media (blood, urine), as well as to study intracellular metabolism and the metabolism of ophthalmic drugs. 1Н NMR-spectroscopy can be chosen as a TDM method, since it allows analyzing the structure and identifying metabolites of various drugs. 1Н NMR-based metabolomics can provide information on the side effects of drugs, predict response to treatment, and provide key information on the mechanisms of action of known and new drug compounds.
Summary and outlook
SERS and 1Н NMR-spectroscopy have great potential for further study and the possibility of introducing them into clinical practice, including for evaluating the efficacy and safety of drugs.
-
Research funding: Part of the work devoted to the use of Raman scattering and SERS to determine the concentration of drugs was supported by the Russian Science Foundation grant No. 19-15-00132. Part of the work devoted to the application of the 1H NMR method for determining the concentration of drugs was supported by a grant from the Russian Foundation for Basic Research and the Government of the Kaliningrad Region, project No. 19-415-390001.
-
Author contributions: E.M. Moiseeva – writing the section “Introduction”, compiling sections: “Materials and methods”, “Using Raman scattering and giant Raman scattering to determine the concentration of drugs”, “Application of the 1H NMR method to determine the concentration of drugs”, “Conclusion”, compiling a bibliographic list. A.Yu. Zyubin – compiling sections: “The use of Raman scattering of light and giant Raman scattering of light to determine the concentration of drugs”, “Conclusion”, compiling a bibliographic list. G.S. Kupriyanova – compiling the section “Application of the 1H NMR method for determining the concentration of drugs”, “Conclusion”, compiling a bibliographic list. I.G. Mershiev – compiling the section “Application of the 1H NMR method for determining the concentration of drugs”, “Conclusion”, compiling a bibliographic list. V.V. Rafalskiy – compiling the “Introduction” section, compiling the sections: “Materials and Methods”, “Using Raman scattering and giant Raman scattering to determine the concentration of drugs”, “Application of the 1H NMR method to determine the concentration of drugs”, “Conclusion”, compiling a bibliographic list. N.O. Kryukova – compiling sections “Use of Raman scattering of light and giant Raman scattering of light to determine the concentration of drugs”, “Application of the 1H NMR method to determine the concentration of drugs”. I.I. Kon. – compiling figures “Model images of the electric field amplification of the SERS sensor in the case of a single particle and a surface formed from metal particles”. I.G. Samusev – compiling the section “Application of the 1H NMR method for determining the concentration of drugs”, “Conclusion”, compiling a bibliographic list. Y.D. Belousova – compiling the “Introduction” section, compiling the sections: “Materials and Methods”. S.A. Doktorova – compiling the “Introduction” section, compiling the sections: “Materials and Methods”. All authors have accepted responsibility for the entire content of this manuscript and approved its submission.
-
Competing interests: Authors state no conflict of interest.
-
Informed consent: Not applicable.
-
Ethical approval: Not applicable.
References
1. Cuker, A, Husseinzadeh, H, Lebedeva, T, Marturano, JE, Massefski, W, Lowery, TJ, et al.. Rapid evaluation of platelet function with T2 magnetic resonance. Am J Clin Pathol 2016;146:681–93. https://doi.org/10.1093/ajcp/aqw189.Search in Google Scholar PubMed PubMed Central
2. Pauwels, S, Allegaert, K. Therapeutic drug monitoring in neonates. Arch Dis Child 2016;101:377–81. https://doi.org/10.1136/archdischild-2013-305309.Search in Google Scholar PubMed
3. Eliasson, E, Lindh, JD, Malmstrom, RE, Beck, O, Dahl, ML. Therapeutic drug monitoring for tomorrow. Eur J Clin Pharmacol 2013;69(1 Suppl):25–32. https://doi.org/10.1007/s00228-013-1504-x.Search in Google Scholar PubMed
4. Zhang, Y, Zhang, R. Recent advances in analytical methods for the therapeutic drug monitoring of immunosuppressive drugs. Drug Test Anal 2018;10:81–94. https://doi.org/10.1002/dta.2290.Search in Google Scholar PubMed
5. Jaworska, A, Fornasaro, S, Sergo, V, Bonifacio, A. Potential of surface enhanced Raman spectroscopy (SERS) in therapeutic drug monitoring (TDM). A critical review. Biosensors 2016;6:47–64. https://doi.org/10.3390/bios6030047.Search in Google Scholar PubMed PubMed Central
6. Zyubin, A, Kon, I, Tcibulnikova, A, Matveeva, K, Khankaev, A, Myslitskaya, N, et al.. Numerical FDTD-based simulations and Raman experiments of femtosecond LIPSS. Opt Express 2021;29:4547–58. https://doi.org/10.1364/oe.413460.Search in Google Scholar PubMed
7. Xie, Y, Jiang, Y, Ben-Amotz, D. Detection of amino acid and peptide phosphate protonation using Raman spectroscopy. Anal Biochem 2005;343:223–30. https://doi.org/10.1016/j.ab.2005.05.038.Search in Google Scholar PubMed
8. Vítek, P, Osterrothová, K, Jehlička, J. Beta-carotene—a possible biomarker in the Martian evaporitic environment: Raman micro-spectroscopic study. Planet Space Sci 2009;57:454–9. https://doi.org/10.1016/j.pss.2008.06.001.Search in Google Scholar
9. Cals, FL, Schut, TCB, Hardillo, JA, de Jong, RJB, Koljenovic, S, Puppels, GJ. Investigation of the potential of Raman spectroscopy for oral cancer detection in surgical margins. Lab Invest 2015;95:1186–96. https://doi.org/10.1038/labinvest.2015.85.Search in Google Scholar PubMed
10. Huang, J, Zong, C, Shen, H, Liu, M, Chen, B, Ren, B, et al.. Mechanism of cellular uptake of graphene oxide studied by surface-enhanced Raman spectroscopy. Small 2012;8:2577–84. https://doi.org/10.1002/smll.201102743.Search in Google Scholar PubMed
11. Wang, Y, Lee, K, Irudayaraj, J. SERS aptasensor from nanorod-nanoparticle junction for protein detection. Chem Commun 2010;46:613–5. https://doi.org/10.1039/b919607b.Search in Google Scholar PubMed
12. Dina, NE, Colniță, A, Leopold, N, Haisch, C. Rapid single-cell detection and identification of bacteria by using surface-enhanced Raman spectroscopy. Proc Technol 2017;27:203–7. https://doi.org/10.1016/j.protcy.2017.04.086.Search in Google Scholar
13. Hamon, C, Liz-Marzan, LM. Colloidal design of plasmonic sensors based on surface enhanced Raman scattering. J Colloid Interface Sci 2018;512:834–43. https://doi.org/10.1016/j.jcis.2017.10.117.Search in Google Scholar PubMed
14. Zyubin, A, Rafalskiy, V, Tcibulnikova, A, Moiseeva, E, Matveeva, K, Tsapkova, A, et al.. Surface-enhanced Raman spectroscopy for antiplatelet therapy effectiveness assessment. Laser Phys Lett 2020;17:1–10. https://doi.org/10.1088/1612-202x/ab7be5.Search in Google Scholar
15. Schlucker, S. SERS microscopy: nanoparticle probes and biomedical applications. ChemPhysChem 2009;10:1344–54. https://doi.org/10.1002/cphc.200900119.Search in Google Scholar PubMed
16. Schlucker, S. Surface-enhanced Raman spectroscopy: concepts and chemical applications. Angew Chem Int Ed Engl 2014;53:4756–95. https://doi.org/10.1002/anie.201205748.Search in Google Scholar PubMed
17. Ma, Y, Liu, H, Mao, M, Meng, J, Yang, L, Liu, J. Surface-enhanced Raman spectroscopy on liquid interfacial nanoparticle arrays for multiplex detecting drugs in urine. Anal Chem 2016;88:8145–51. https://doi.org/10.1021/acs.analchem.6b01884.Search in Google Scholar PubMed
18. Tommasini, M, Zanchi, C, Lucotti, A, Bombelli, A, Villa, NS, Casazza, M, et al.. Laser-synthesized SERS substrates as sensors toward therapeutic drug monitoring. Nanomaterials 2019;9:677–92. https://doi.org/10.3390/nano9050677.Search in Google Scholar PubMed PubMed Central
19. Atkins, CG, Buckley, K, Blades, MW, Turner, RFB. Raman spectroscopy of blood and blood components. Appl Spectrosc 2017;71:767–93. https://doi.org/10.1177/0003702816686593.Search in Google Scholar PubMed
20. Bantz, KC, Meyer, AF, Wittenberg, NJ, Im, H, Kurtulus, O, Lee, SH, et al.. Recent progress in SERS biosensing. Phys Chem Chem Phys 2011;13:11551–67. https://doi.org/10.1039/c0cp01841d.Search in Google Scholar PubMed PubMed Central
21. Litti, L, Amendola, V, Toffoli, G, Meneghetti, M. Detection of low-quantity anticancer drugs by surface-enhanced Raman scattering. Anal Bioanal Chem 2016;408:2123–31. https://doi.org/10.1007/s00216-016-9315-4.Search in Google Scholar PubMed
22. Chen, C, Liu, W, Tian, S, Hong, T. Novel surface-enhanced Raman spectroscopy techniques for DNA, protein and drug detection. Sensors 2019;19:1712–33. https://doi.org/10.3390/s19071712.Search in Google Scholar PubMed PubMed Central
23. Fornasaro, S, Marta, SD, Rabusin, M, Bonifacio, A, Sergo, V. Toward SERS-based point-of-care approaches for therapeutic drug monitoring: the case of methotrexate. Faraday Discuss 2016;187:485–99. https://doi.org/10.1039/c5fd00173k.Search in Google Scholar PubMed
24. Roberts, JA, Norris, R, Paterson, DL, Martin, JH. Therapeutic drug monitoring of antimicrobials. Br J Clin Pharmacol 2012;73:27–36. https://doi.org/10.1111/j.1365-2125.2011.04080.x.Search in Google Scholar PubMed PubMed Central
25. Beumer, JH, Chu, E, Allegra, C, Tanigawara, Y, Milano, G, Diasio, R, et al.. Therapeutic drug monitoring in oncology: international association of therapeutic drug monitoring and clinical toxicology recommendations for 5-fluorouracil therapy. Clin Pharmacol Ther 2019;105:598–613. https://doi.org/10.1002/cpt.1124.Search in Google Scholar PubMed PubMed Central
26. El-Zahry, MR, Refaat, IH, Mohamed, HA, Lendl, B. Sequential SERS determination of aspirin and vitamin C using in situ laser-induced photochemical silver substrate synthesis in a moving flow cell. Anal Bioanal Chem 2016;408:4733–41. https://doi.org/10.1007/s00216-016-9562-4.Search in Google Scholar PubMed
27. Markina, NE, Markin, AV. Application of aluminum hydroxide for improvement of label-free SERS detection of some cephalosporin antibiotics in urine. Biosensors 2019;9:91–103. https://doi.org/10.3390/bios9030091.Search in Google Scholar PubMed PubMed Central
28. McKeating, KS, Aube, A, Masson, JF. Biosensors and nanobiosensors for therapeutic drug and response monitoring. Analyst 2016;141:429–49. https://doi.org/10.1039/c5an01861g.Search in Google Scholar PubMed
29. Jager, NG, van Hest, RM, Lipman, J, Taccone, FS, Roberts, JA. Therapeutic drug monitoring of anti-infective agents in critically ill patients. Expet Rev Clin Pharmacol 2016;9:961–79. https://doi.org/10.1586/17512433.2016.1172209.Search in Google Scholar PubMed
30. McKeating, KS, Couture, M, Dinel, MP, Garneau-Tsodikova, S, Masson, JF. High throughput LSPR and SERS analysis of aminoglycoside antibiotics. Analyst 2016;141:5120–6. https://doi.org/10.1039/c6an00540c.Search in Google Scholar PubMed PubMed Central
31. Han, G, Liu, R, Han, MY, Jiang, C, Wang, J, Du, S, et al.. Label-free surface-enhanced Raman scattering imaging to monitor the metabolism of antitumor drug 6-mercaptopurine in living cells. Anal Chem 2014;86:11503–7. https://doi.org/10.1021/ac503539w.Search in Google Scholar PubMed
32. Yang, J, Tan, X, Shih, WC, Cheng, MM. A sandwich substrate for ultrasensitive and label-free SERS spectroscopic detection of folic acid/methotrexate. Biomed Microdevices 2014;16:673–9. https://doi.org/10.1007/s10544-014-9871-3.Search in Google Scholar PubMed
33. Dong, J, Chen, Q, Rong, C, Li, D, Rao, Y. Minimally invasive surface-enhanced Raman scattering detection with depth profiles based on a surface-enhanced Raman scattering-active acupuncture needle. Anal Chem 2011;83:6191–5. https://doi.org/10.1021/ac2007009.Search in Google Scholar PubMed
34. Yu, YP, Yan, XY, Yao, C, Xia, JL. Bioequivalence assessment of topical ophthalmic drugs using sparse sampling pharmacokinetics data. Biomed Environ Sci 2019;32:788–92.Search in Google Scholar
35. Chockalingam, A, Xu, L, Stewart, S, LeMerdy, M, Tsakalozou, E, Fan, J, et al.. Protocol for evaluation of topical ophthalmic drug products in different compartments of fresh eye tissues in a rabbit model. J Pharmacol Toxicol Methods 2019;96:9–14. https://doi.org/10.1016/j.vascn.2018.12.002.Search in Google Scholar PubMed
36. Elshout, M, Erckens, RJ, Webers, CA, Beckers, HJ, Berendschot, TT, de Brabander, J, et al.. Detection of Raman spectra in ocular drugs for potential in vivo application of Raman spectroscopy. J Ocul Pharmacol Therapeut 2011;27:445–51. https://doi.org/10.1089/jop.2011.0018.Search in Google Scholar PubMed
37. Serkova, NJ, Davis, DM, Steiner, J, Agarwal, R. Quantitative NMR-based metabolomics on tissue biomarkers and its translation into in vivo magnetic resonance spectroscopy. Methods Mol Biol 2019;1978:369–87.10.1007/978-1-4939-9236-2_23Search in Google Scholar PubMed
38. Emwas, AH, Roy, R, McKay, RT, Tenori, L, Saccenti, E, Gowda, GAN, et al.. NMR spectroscopy for metabolomics research. Metabolites 2019;9:123–62. https://doi.org/10.3390/metabo9070123.Search in Google Scholar PubMed PubMed Central
39. Amin, AM, Chin, LS, Teh, CH, Mostafa, H, Noor, DAM, Sk Kader, MAA, et al.. (1)H NMR based pharmacometabolomics analysis of urine identifies metabolic phenotype of clopidogrel high on treatment platelets reactivity in coronary artery disease patients. J Pharm Biomed Anal 2017;146:135–46. https://doi.org/10.1016/j.jpba.2017.08.018.Search in Google Scholar PubMed
40. De Castro, F, Benedetti, M, Del Coco, L, Fanizzi, FP. NMR-based metabolomics in metal-based drug research. Molecules 2019;24:2240–54. https://doi.org/10.3390/molecules24122240.Search in Google Scholar PubMed PubMed Central
41. Jiang, L, Lee, SC, Ng, TC. Pharmacometabonomics analysis reveals serum formate and acetate potentially associated with varying response to gemcitabine-carboplatin chemotherapy in metastatic breast cancer patients. J Proteome Res 2018;17:1248–57. https://doi.org/10.1021/acs.jproteome.7b00859.Search in Google Scholar PubMed
42. Xu, S, Zhou, Y, Geng, H, Song, D, Tang, J, Zhu, X, et al.. Serum metabolic profile Alteration reveals response to platinum-based combination chemotherapy for lung cancer: sensitive patients distinguished from insensitive ones. Sci Rep 2017;7:17524. https://doi.org/10.1038/s41598-017-16085-y.Search in Google Scholar PubMed PubMed Central
43. Espina, R, Yu, L, Wang, J, Tong, Z, Vashishtha, S, Talaat, R, et al.. Nuclear magnetic resonance spectroscopy as a quantitative tool to determine the concentrations of biologically produced metabolites: implications in metabolites in safety testing. Chem Res Toxicol 2009;22:299–310. https://doi.org/10.1021/tx800251p.Search in Google Scholar PubMed
44. Bawadikji, AA, Teh, CH, Kader, M, Sulaiman, SAS, Ibrahim, B. Pharmacometabonomics technique to identify warfarin response using nuclear magnetic resonance spectroscopy. Curr Pharmaceut Biotechnol 2017;18:740–7. https://doi.org/10.2174/1389201018666171103141828.Search in Google Scholar PubMed
45. Ge, Y, Chen, X, Godevac, D, Bueno, PCP, Abarca, LFS, Jang, YP, et al.. Metabolic profiling of saponin-rich ophiopogon japonicus roots based on 1H NMR and HPTLC platforms. Planta Med 2019;85:917–24. https://doi.org/10.1055/a-0947-5797.Search in Google Scholar PubMed
46. Takeuchi, K, Baskaran, K, Arthanari, H. Structure determination using solution NMR: is it worth the effort? J Magn Reson 2019;306:195–201. https://doi.org/10.1016/j.jmr.2019.07.045.Search in Google Scholar PubMed
47. Wyss, DF, Wang, YS, Eaton, HL, Strickland, C, Voigt, JH, Zhu, Z, et al.. Combining NMR and X-ray crystallography in fragment-based drug discovery: discovery of highly potent and selective BACE-1 inhibitors. Top Curr Chem 2012;317:83–114.10.1007/128_2011_183Search in Google Scholar PubMed
48. Jadeja, Y, Chomal, B, Patel, M, Jebaliya, H, Khunt, R, Shah, A. Method development and validation: quantitation of telmisartan bulk drug and its tablet formulation by (1) H NMR spectroscopy. Magn Reson Chem 2017;55:634–8. https://doi.org/10.1002/mrc.4565.Search in Google Scholar PubMed
49. Soulsby, D. Band-selective excitation NMR spectroscopy and quantitative time-domain analysis using Complete Reduction to Amplitude-Frequency Table (CRAFT) to determine distribution coefficients during drug development. Magn Reson Chem 2019;57:953–60. https://doi.org/10.1002/mrc.4888.Search in Google Scholar PubMed
50. Manzoor, S, Bilal, A, Khan, S, Ullah, R, Iftikhar, S, Emwas, AH, et al.. Identification and characterization of SSE15206, a microtubule depolymerizing agent that overcomes multidrug resistance. Sci Rep 2018;8:3305. https://doi.org/10.1038/s41598-018-21642-0.Search in Google Scholar PubMed PubMed Central
51. Dias, DA, Jones, OA, Beale, DJ, Boughton, BA, Benheim, D, Kouremenos, KA, et al.. Current and future perspectives on the structural identification of small molecules in biological systems. Metabolites 2016;6:46–75. https://doi.org/10.3390/metabo6040046.Search in Google Scholar PubMed PubMed Central
52. Duchardt-Ferner, E, Wohnert, J. NMR experiments for the rapid identification of P=O…H-X type hydrogen bonds in nucleic acids. J Biomol NMR 2017;69:101–10. https://doi.org/10.1007/s10858-017-0140-7.Search in Google Scholar PubMed
53. Lee, HM, Kim, CS, Jang, YM, Kwon, SW, Lee, BJ. Separation and structural elucidation of a novel analogue of vardenafil included as an adulterant in a dietary supplement by liquid chromatography-electrospray ionization mass spectrometry, infrared spectroscopy and nuclear magnetic resonance spectroscopy. J Pharm Biomed Anal 2011;54:491–6. https://doi.org/10.1016/j.jpba.2010.09.022.Search in Google Scholar PubMed
54. Lu, X, Skomski, D, Thompson, KC, McNevin, MJ, Xu, W, Su, Y. Three-dimensional NMR spectroscopy of fluorinated pharmaceutical solids under ultrafast magic angle spinning. Anal Chem 2019;91:6217–24. https://doi.org/10.1021/acs.analchem.9b00884.Search in Google Scholar PubMed
55. Pauli, GF, Chen, SN, Lankin, DC, Bisson, J, Case, RJ, Chadwick, LR, et al.. Essential parameters for structural analysis and dereplication by (1)H NMR spectroscopy. J Nat Prod 2014;77:1473–87. https://doi.org/10.1021/np5002384.Search in Google Scholar PubMed PubMed Central
56. Fordwour, OB, Wolthers, KR. Active site arginine controls the stereochemistry of hydride transfer in cyclohexanone monooxygenase. Arch Biochem Biophys 2018;659:47–56. https://doi.org/10.1016/j.abb.2018.09.025.Search in Google Scholar PubMed
57. Jeziorowski, S, Thiele, CM. Poly-gamma-p-Biphenylmethyl-Glutamate as enantiodifferentiating alignment medium for NMR spectroscopy with temperature-tunable properties. Chemistry 2018;24:15631–7. https://doi.org/10.1002/chem.201802921.Search in Google Scholar PubMed
58. Li, P, Deng, J, Xiao, N, Cai, X, Wu, Q, Lu, Z, et al.. Identification of polyunsaturated triacylglycerols and CC location isomers in sacha inchi oil by photochemical reaction mass spectrometry combined with nuclear magnetic resonance spectroscopy. Food Chem 2020;307:125568. https://doi.org/10.1016/j.foodchem.2019.125568.Search in Google Scholar PubMed
59. Sousa, FF, Luzardo-Alvarez, A, Blanco-Mendez, J, Otero-Espinar, FJ, Martin-Pastor, M, Macho, IS. Use of 1H NMR STD, waterLOGSY, and Langmuir monolayer techniques for characterization of drug-zein protein complexes. Eur J Pharm Biopharm 2013;85:790–8. https://doi.org/10.1016/j.ejpb.2013.07.008.Search in Google Scholar PubMed
60. Choi, HW, Tian, M, Song, F, Venereau, E, Preti, A, Park, SW, et al.. Aspirin’s active metabolite salicylic acid targets high mobility group box 1 to modulate inflammatory responses. Mol Med 2015;21:526–35. https://doi.org/10.2119/molmed.2015.00148.Search in Google Scholar PubMed PubMed Central
61. Chen, C, Gao, J, Wang, TS, Guo, C, Yan, YJ, Mao, CY, et al.. NMR-Based metabolomic techniques identify the toxicity of emodin in HepG2 cells. Sci Rep 2018;8:9379. https://doi.org/10.1038/s41598-018-27359-4.Search in Google Scholar PubMed PubMed Central
62. Xu, C, Rezeng, C, Li, J, Zhang, L, Yan, Y, Gao, J, et al.. (1)H NMR-based metabolomics study of the toxicological effects in rats induced by “renqing mangjue” pill, a traditional Tibetan medicine. Front Pharmacol 2017;8:602. https://doi.org/10.3389/fphar.2017.00602.Search in Google Scholar PubMed PubMed Central
63. Dallons, M, Schepkens, C, Dupuis, A, Tagliatti, V, Colet, JM. New insights about doxorubicin-induced toxicity to cardiomyoblast-derived H9C2 cells and dexrazoxane cytoprotective effect: contribut ion of in vitro (1)H-NMR metabonomics. Front Pharmacol 2020;11:79. https://doi.org/10.3389/fphar.2020.00079.Search in Google Scholar PubMed PubMed Central
64. Kyriakides, M, Maitre, L, Stamper, BD, Mohar, I, Kavanagh, TJ, Foster, J, et al.. Comparative metabonomic analysis of hepatotoxicity induced by acetaminophen and its less toxic meta-isomer. Arch Toxicol 2016;90:3073–85. https://doi.org/10.1007/s00204-015-1655-x.Search in Google Scholar PubMed PubMed Central
65. Al-Talla, ZA, Akrawi, SH, Tolley, LT, Sioud, SH, Zaater, MF, Emwas, AH. Bioequivalence assessment of two formulations of ibuprofen. Drug Des Devel Ther 2011;5:427–33. https://doi.org/10.2147/dddt.s24504.Search in Google Scholar PubMed PubMed Central
66. Portilla, D, Li, S, Nagothu, KK, Megyesi, J, Kaissling, B, Schnackenberg, L, et al.. Metabolomic study of cisplatin-induced nephrotoxicity. Kidney Int 2006;69:2194–204. https://doi.org/10.1038/sj.ki.5000433.Search in Google Scholar PubMed
67. Al-Talla, ZA, Akrawi, SH, Emwas, AH. Solid state NMR and bioequivalence comparison of the pharmacokinetic parameters of two formulations of clindamycin. Int J Clin Pharmacol Ther 2011;49:469–76. https://doi.org/10.5414/cp201478.Search in Google Scholar PubMed
68. Cullen, CH, Ray, GJ, Szabo, CM. A comparison of quantitative nuclear magnetic resonance methods: internal, external, and electronic referencing. Magn Reson Chem 2013;51:705–13. https://doi.org/10.1002/mrc.4004.Search in Google Scholar PubMed
69. Simmler, C, Napolitano, JG, McAlpine, JB, Chen, SN, Pauli, GF. Universal quantitative NMR analysis of complex natural samples. Curr Opin Biotechnol 2014;25:51–9. https://doi.org/10.1016/j.copbio.2013.08.004.Search in Google Scholar PubMed PubMed Central
70. Singh, S, Roy, R. The application of absolute quantitative (1)H NMR spectroscopy in drug discovery and development. Expet Opin Drug Discov 2016;11:695–706. https://doi.org/10.1080/17460441.2016.1189899.Search in Google Scholar PubMed
71. Sun, S, Jin, M, Zhou, X, Ni, J, Jin, X, Liu, H, et al.. The application of quantitative (1)H-NMR for the determination of orlistat in tablets. Molecules 2017;22:1517–27. https://doi.org/10.3390/molecules22091517.Search in Google Scholar PubMed PubMed Central
72. Walker, GS, Bauman, JN, Ryder, TF, Smith, EB, Spracklin, DK, Obach, RS. Biosynthesis of drug metabolites and quantitation using NMR spectroscopy for use in pharmacologic and drug metabolism studies. Drug Metab Dispos 2014;42:1627–39. https://doi.org/10.1124/dmd.114.059204.Search in Google Scholar PubMed
73. Alvares, RD, Hasabnis, A, Prosser, RS, Macdonald, PM. Quantitative detection of PEGylated biomacromolecules in biological fluids by NMR. Anal Chem 2016;88:3730–8. https://doi.org/10.1021/acs.analchem.5b04565.Search in Google Scholar PubMed
74. Khandelwal, P, Zhang, L, Chimalakonda, A, Caceres-Cortes, J, Huang, C, Marathe, P, et al.. Pharmacokinetics of 40 kDa PEG in rodents using high-field NMR spectroscopy. J Pharm Biomed Anal 2019;171:30–4. https://doi.org/10.1016/j.jpba.2019.03.066.Search in Google Scholar PubMed
75. Kupriyanova, G, Rafalskiy, V, Mershiev, I, Moiseeva, E. NMR spectroscopy reveals acetylsalicylic acid metabolites in the human urine for drug compliance monitoring. PLoS One 2021;16:e0247102. https://doi.org/10.1371/journal.pone.0247102.Search in Google Scholar PubMed PubMed Central
© 2022 Walter de Gruyter GmbH, Berlin/Boston
Articles in the same Issue
- Frontmatter
- Editorial
- News in DMPT: Leaders in Pharmacogenetics Section
- Reviews
- Application of vibrational spectroscopy and nuclear magnetic resonance methods for drugs pharmacokinetics research
- A metabolic blueprint of COVID-19 and long-term vaccine efficacy
- Concept of Unani Jali (detergents/cleansers) drugs and its scientific validation: scope for new opportunities in dermatological pharmacotherapeutics
- Original Articles
- Post-treatment symptomatic improvement of the eastern Indian ADHD probands is influenced by CYP2D6 genetic variations
- CTH G1208T and MTHFR A1298C polymorphisms are associated with a higher risk of a first myocardial infarction with fatal outcome among women
- Evaluation of pharmacogenomic evidence for drugs related to ADME genes in CPIC database
- Therapeutic drug monitoring of teriflunomide: do plasma concentrations predict response to leflunomide in patients with rheumatoid arthritis?
- The investigation of the complex population-drug-drug interaction between ritonavir-boosted lopinavir and chloroquine or ivermectin using physiologically-based pharmacokinetic modeling
- Phytochemical investigation, antioxidant and anticancer activities of various Unani drugs
- The efficacy and safety of dry cupping in cervical spondylosis with optimization of cup application time – a randomized clinical trial
Articles in the same Issue
- Frontmatter
- Editorial
- News in DMPT: Leaders in Pharmacogenetics Section
- Reviews
- Application of vibrational spectroscopy and nuclear magnetic resonance methods for drugs pharmacokinetics research
- A metabolic blueprint of COVID-19 and long-term vaccine efficacy
- Concept of Unani Jali (detergents/cleansers) drugs and its scientific validation: scope for new opportunities in dermatological pharmacotherapeutics
- Original Articles
- Post-treatment symptomatic improvement of the eastern Indian ADHD probands is influenced by CYP2D6 genetic variations
- CTH G1208T and MTHFR A1298C polymorphisms are associated with a higher risk of a first myocardial infarction with fatal outcome among women
- Evaluation of pharmacogenomic evidence for drugs related to ADME genes in CPIC database
- Therapeutic drug monitoring of teriflunomide: do plasma concentrations predict response to leflunomide in patients with rheumatoid arthritis?
- The investigation of the complex population-drug-drug interaction between ritonavir-boosted lopinavir and chloroquine or ivermectin using physiologically-based pharmacokinetic modeling
- Phytochemical investigation, antioxidant and anticancer activities of various Unani drugs
- The efficacy and safety of dry cupping in cervical spondylosis with optimization of cup application time – a randomized clinical trial