Citation: Ruifeng Bai, Dong Sun, Yuqin Shan, Zhiqiong Guo, Dafeng Chu, John Paul Fawcett, Jingkai Gu. Disposition and fate of polyoxyethylene glycerol ricinoleate as determined by LC-Q-TOF MS coupled with MS^ALL, SWATH and HR MS/MS techniques[J]. Chinese Chemical Letters, ;2021, 32(10): 3237-3240. doi: 10.1016/j.cclet.2021.04.031 shu

Disposition and fate of polyoxyethylene glycerol ricinoleate as determined by LC-Q-TOF MS coupled with MS^ALL, SWATH and HR MS/MS techniques

Center for Drug Metabolism Research, School of Life Sciences, Jilin University, Changchun 130012, China

gujk@jlu.edu.cn

Received Date: 2 February 2021
Revised Date: 13 March 2021
Accepted Date: 16 April 2021
Available Online: 22 April 2021

Figures(4)

Polyoxyethylene glycerol ricinoleate (PGR) serves as a solubilizer/emulsifier that is commonly used in pharmaceutical formulations despite being associated with severe anaphylactoid hypersensitivity reactions. Cremophor EL® (CrEL) is the most representative PGR produced from reacting ethylene oxide with castor oil. To help clarify the cause of side effects and potentially improve the safety of PGR-based drug delivery vehicle, we have developed separate but related analytical methods for the quantitation of CrEL and its main metabolites, glycerol ethoxylate (GE) and ricinoleic acid (RA). Since CrEL and GE are highly disperse mixtures of polymers that are not amenable to analysis by conventional liquid chromatography-tandem mass spectrometry (LC-MS/MS), we used liquid chromatography-triple-quadrupole-time-of-flight mass spectrometry (LC-Q-TOF MS) combined with product ion data acquisition by MS^ALL and sequential window acquisition of all theoretical fragments mass spectrometry (SWATH MS), respectively to perform the analysis. In contrast, RA is a single molecular entity that could be readily analyzed using conventional LC-HR MS/MS. Selection of specific fragment ions for CrEL, GE, RA and their internal standards enabled a precise quantitation of such a complex analytes system in rat plasma after a single and simple sample preparation method. Assay validation indicated linearity for CrEL, GE and RA over the concentration ranges 0.2~20.0 μg/mL, 0.1~10.0 μg/mL and 0.1~20.0 μg/mL, respectively with satisfactory results for other validation parameters. A subsequent pharmacokinetic study involving single intravenous 200 mg/kg injections of CrEL to rats showed the methods enable comprehensive and high throughput quantitation of CrEL and its metabolites in a biological matrix. Our combination of assays provides effective application in investigating the cause of the hypersensitivity reaction of PGR and potentially to improve its safety for using as a vehicle in drug formulations.
- Polyoxyethylene glycerol ricinoleate,
- Cremophor EL,
- LC-Q-TOF MS,
- Glycerol ethoxylate,
- Ricinoleic acid
1. [1]
  J. Szebeni, C.R. Alving, S. Savay, et al., Int. Immunopharmacol. 1(2001) 721-735. doi: 10.1016/S1567-5769(01)00006-6
2. [2]
  A. Nan, Miscellaneous drugs, materials, medical devices and techniques, in: S.D. Ray (Ed. ), Side Effects of Drugs Annual, Elsevier B.V., Amsterdam, 2016, pp. 523-532.
3. [3]
  M. Kongshaug, L.S. Cheng, J. Moan, C. Rimington, Int. J. Biochem. 23(1991) 473-478. doi: 10.1016/0020-711X(91)90176-N
4. [4]
  K. Woodburn, D. Kessel, J. Photochem. Photobiol. B 22(1994) 197-201. doi: 10.1016/1011-1344(93)06968-9
5. [5]
  P.C. de Groen, A.J. Aksamit, J. Rakela, G.S. Forbes, R.A. Krom, N. Engl. J. Med. 317(1987) 861-866. doi: 10.1056/NEJM198710013171404
6. [6]
  G.J. Lesser, S.A. Grossman, S. Eller, E.K. Rowinsky, Cancer Chemother. Pharmacol. 37(1995) 173-178.
7. [7]
  T. Shimomura, H. Fujiwara, S. Ikawa, J. Kigawa, N. Terakawa, Lancet 352(1998) 541-542.
8. [8]
  A.J. Windebank, M.D. Blexrud, P.C. de Groen, J. Pharmacol. Exp. Ther. 268(1994) 1051-1056.
9. [9]
  D.J. Brat, A.J. Windebank, S. Brimijoin, J. Pharmacol. Exp. Ther. 261(1992) 803-810.
10. [10]
  D.M. Woodcock, S. Jefferson, M.E. Linsenmeyer, et al., Cancer Res. 50(1990) 4199-4203.
11. [11]
  G.J. Schuurhuis, H.J. Broxterman, H.M. Pinedo, et al., Br. J. Cancer 62(1990) 591-594. doi: 10.1038/bjc.1990.335
12. [12]
  D.S. Chervinsky, M.L. Brecher, M.J. Hoelcle, Anticancer Res. 13(1993) 93-96.
13. [13]
  L. Webster, M. Linsenmeyer, M. Millward, et al., J. Natl. Cancer Inst. 85(1993) 1685-1690. doi: 10.1093/jnci/85.20.1685
14. [14]
  E. Friche, P.B. Jensen, M. Sehested, E.J. Demant, N.N. Nissen, Cancer Commun. 2(1990) 297-303.
15. [15]
  M. Martin-Facklam, J. Burhenne, R. Ding, et al., Br. J. Clin. Pharmacol. 53(2002) 576-581. doi: 10.1046/j.1365-2125.2002.01595.x
16. [16]
  K. Singh, Polyoxyethylene castor oil derivatives, in: R.C. Rowe, P.J. Sheskey, M.E. Quinn (Eds. ), Handbook of Pharmaceutical Excipients Sixth edition, Pharmaceutical Press, London, 2009, pp. 542-549.
17. [17]
  A. Sparreboom, W.J. Loos, J. Verweij, et al., Anal. Biochem. 255(1998) 171-175. doi: 10.1006/abio.1997.2467
18. [18]
  E. Brouwer, J. Verweij, B. Hauns, et al., Anal. Biochem. 261(1998) 198-202. doi: 10.1006/abio.1998.2746
19. [19]
  M. Kunkel, T. Meyer, J. Bohler, E. Keller, A.W. Frahm, J. Pharm. Biomed. Anal. 21(1999) 911-922. doi: 10.1016/S0731-7085(99)00212-5
20. [20]
  A. Sparreboom, O. van Tellingen, M.T. Huizing, W.J. Nooijen, J.H. Beijnen, J. Chromatogr. B Biomed. Appl. 681(1996) 355-362. doi: 10.1016/0378-4347(95)00544-7
21. [21]
  A. Ghassempour, M.R. Nabid, M. Talebi, A.A. Entezami, Talanta 59(2003) 435-441. doi: 10.1016/S0039-9140(02)00466-6
22. [22]
  V. Vijaya Bhaskar, A. Middha, Int. J. Anal. Chem. 2013(2013) 135613.
23. [23]
  J. Gong, X. Gu, W.E. Achanzar, et al., Anal. Chem. 86(2014) 7642-7649. doi: 10.1021/ac501507g
24. [24]
  R. Epping, U. Panne, J. Falkenhagen, Anal. Chem. 90(2018) 3467-3474. doi: 10.1021/acs.analchem.7b05214
25. [25]
  A. Nasioudis, J.W. van Velde, R.M. Heeren, O.F. van den Brink, J. Chromatogr. A 1218(2011) 7166-7172. doi: 10.1016/j.chroma.2011.08.032
26. [26]
  T. Wang, Y. Guo, Y. He, et al., Acta Pharm. Sin. B 10(2020) 2002-2009. doi: 10.1016/j.apsb.2020.02.001
27. [27]
  R. Bade, J.M. White, C. Gerber, Anal. Bioanal. Chem. 410(2018) 529-542. doi: 10.1007/s00216-017-0747-2
28. [28]
  H.E. Sidjabat, J. Gien, D. Kvaskoff, et al., Sci. Rep. 8(2018) 3871. doi: 10.1038/s41598-018-21984-9
29. [29]
  R. Alvarez-Ruiz, Y. Pico, J. Chromatogr. A 1595(2019) 81-90. doi: 10.1016/j.chroma.2019.02.041
30. [30]
  C. Ludwig, L. Gillet, G. Rosenberger, et al., Mol. Syst. Biol. 14(2018) e8126.
31. [31]
  G. Groeneveld, M.N. Dunkle, M. Rinken, et al., J. Chromatogr. A 1569(2018) 128-138. doi: 10.1016/j.chroma.2018.07.054
32. [32]
  H.E. Spinnler, C. Ginies, J.A. Khan, E.N. Vulfson, Proc. Natl. Acad. Sci. U. S. A. 93(1996) 3373-3376. doi: 10.1073/pnas.93.8.3373
33. [33]
  B.A. Black, C. Sun, Y.Y. Zhao, M.G. Ganzle, J.M. Curtis, J. Agric. Food. Chem. 61(2013) 5338-5346. doi: 10.1021/jf400932g
34. [34]
  L. van Zuylen, L. Gianni, J. Verweij, et al., Anticancer Drugs 11(2000) 331-337. doi: 10.1097/00001813-200006000-00003
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沈阳化工大学材料科学与工程学院沈阳 110142

Disposition and fate of polyoxyethylene glycerol ricinoleate as determined by LC-Q-TOF MS coupled with MSALL, SWATH and HR MS/MS techniques

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通讯作者: 陈斌, bchen63@163.com

Disposition and fate of polyoxyethylene glycerol ricinoleate as determined by LC-Q-TOF MS coupled with MS^ALL, SWATH and HR MS/MS techniques