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Extraction

Development of a magnetic solid phase extraction method for gemcitabine from rat plasma by using magnetic graphene oxide calix[6]arene composite and its application to pharmacokinetics

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Pages 1596-1606 | Received 16 Sep 2022, Accepted 03 Apr 2023, Published online: 18 Apr 2023

References

  • Jemal, A.; Murray, T.; Ward, E.; Samuels, A.; Tiwari, R. C.; Ghafoor, A., and Thun, M. J. Cancer Statistics. CA Cancer J. Clin. 2005, 55(1), 10–30. DOI: 10.3322/canjclin.55.1.10.
  • Coleman, M. P.; Gatta, G.; Verdecchia, A.; Esteve, J.; Sant, M.; Storm, H. Allemani, C., Ciccolallo, L., Santaquilani, M., Berrino, F. et al. EUROCARE-3 Summary: Cancer Survival in Europe at the End of the 20th Century. Ann. Oncol. 2003, 14, v128–149. DOI: 10.1093/annonc/mdg756.
  • FDA Expands Access to Gemcitabine for Pancreatic Cancer. Am. J. Heal. Pharm. 1995, 52(9), 931. DOI: 10.1093/ajhp/52.9.931.
  • Blomstrand, H.; Scheibling, U.; Bratthäll, C.; Green, H.; Elander, N. O. Real World Evidence on Gemcitabine and Nab-Paclitaxel Combination Chemotherapy in Advanced Pancreatic Cancer. BMC. Cancer. 2019, 19(1), 1–9. DOI: 10.1186/s12885-018-5244-2.
  • Amrutkar, M.; Aasrum, M.; Verbeke, C. S.; Gladhaug, I. P. Secretion of Fibronectin by Human Pancreatic Stellate Cells Promotes Chemoresistance to Gemcitabine in Pancreatic Cancer Cells. BMC. Cancer. 2019, 19(1), 1–16. DOI: 10.1186/s12885-019-5803-1.
  • Adachi, K.; Okuwaki, K.; Nishiyama, R.; Kida, M.; Imaizumi, H.; Iwai, T. Koizumi, W.; Kaneko, T.; Hasegawa, R.; Miyata, E. et al. A Case of Extrahepatic Bile Duct Cancer with Distant Metastases Showing Pathological Complete Response to Treatment Combining Gemcitabine and Cisplatin. J. Clin. Gastroenterol. 2019, 12(5), 466–472. DOI: 10.1007/s12328-019-00972-0.
  • Hui, Y. F.; Reitz, J. Gemcitabine: A Cytidine Analogue Active Against Solid Tumors. Am. J. Health-System Pharm. 1997, 54(2), 162–170. DOI: 10.1093/ajhp/54.2.162.
  • Sandler, A. B.; Nemunaitis, J.; Denham, C.; Von Pawel, J.; Cormier, Y.; Gatzemeier, U. Einhorn, L. H.; Manegold, C.; Palmer, M. C.; Gregor, A.; Nguyen, B. et al. Phase III Trial of Gemcitabine Plus Cisplatin versus Cisplatin Alone in Patients with Locally Advanced or Metastatic Non–small-Cell Lung Cancer. J. Clin. Oncol. 2000, 18(1), 122–122. DOI: 10.1200/JCO.2000.18.1.122.
  • Albain, K. S.; Nag, S. M.; Calderillo-Ruiz, G.; Jordaan, J. P.; Llombart, A. C.; Pluzanska, A., O’Shaughnessy, J.; Melemed, A. S.; Reyes-Vidal, J. M.; Sekhon, J. S. et al Gemcitabine Plus Paclitaxel versus Paclitaxel Monotherapy in Patients with Metastatic Breast Cancer and Prior Anthracycline Treatment. J. Clin. Oncol. 2008, 26(24), 3950–3957. DOI: 10.1200/JCO.2007.11.9362.
  • Pfisterer, J.; Plante, M.; Vergote, I.; du Bois, A.; Hirte, H.; Lacave, A. J., Eisenhauer, E.; Stähle, A.; Stuart, G.; Kimmig, R.; Olbricht, S. et al. Gemcitabine Plus Carboplatin Compared with Carboplatin in Patients with Platinum-Sensitive Recurrent Ovarian Cancer: An Intergroup Trial of the AGO-OVAR, the NCIC CTG, and the EORTC GCG. J. Clin. Oncol. 2006, 24(29), 4699–4707. DOI: 10.1200/JCO.2006.06.0913.
  • Burris, H. A.; Moore, M. J.; Andersen, J.; Green, M. R.; Rothenberg, M. L.; Modiano, M. R.; Cripps, M. C. Portenoy, R. K.; AM, S.; Tarassoff, P.; Nelson, R.; FA, D.; CD, S.; Von, H. D. Improvements in Survival and Clinical Benefit with Gemcitabine as First-Line Therapy for Patients with Advanced Pancreas Cancer: A Randomized Trial. J. Clin. Oncol. 1997, 15(6), 2403–2413. DOI: 10.1200/JCO.1997.15.6.2403.
  • Graham, K. A.; Leithoff, J.; Coe, I. R.; Mowles, D.; Mackey, J. R.; Young, J. D.; Cass, C. E. Differential Transport of Cytosine-Containing Nucleosides by Recombinant Human Concentrative Nucleoside Transporter Protein hCnt1. Nucleosides Nucleotides Nucleic. Acids. 2000, 19(1–2), 415–434. DOI: 10.1080/15257770008033018.
  • Heinemann, V.; Hertel, L. W.; Grindey, G. B.; Plunkett, W. Comparison of the Cellular Pharmacokinetics and Toxicity of 2′, 2′-Difluorodeoxycytidine and 1-β-D-Arabinofuranosylcytosine. Cancer. Res. 1988, 48(14), 4024–4031.
  • Plunkett, W.; Huang, P.; Gandhi, V. Preclinical Characteristics of Gemcitabine. Anti-Cancer. Drugs. 1995, 6, 7–13. DOI: 10.1097/00001813-199512006-00002.
  • Gokoglan, T. C.; Soylemez, S.; Kesik, M.; Unay, H.; Sayin, S.; Yildiz, H. B. … Cirpan, A., Toppare, L. A Novel Architecture Based on a Conducting Polymer and Calixarene Derivative: Its Synthesis and Biosensor Construction. Rsc. Adv. 2015, 5(45), 35940–35947. DOI: 10.1039/C5RA03933A.
  • Boyacı, E.; Rodríguez-Lafuente, Á.; Gorynski, K.; Mirnaghi, F.; Souza-Silva, É. A.; Hein, D.; Pawliszyn, J. Sample Preparation with Solid Phase Microextraction and Exhaustive Extraction Approaches: Comparison for Challenging Cases. Anal. Chim. Acta. 2015, 873, 14–30. DOI: 10.1016/j.aca.2014.12.051.
  • Ramos, L. Critical Overview of Selected Contemporary Sample Preparation Techniques. J. Chromatography. A. 2012, 1221, 84–98. DOI: 10.1016/j.chroma.2011.11.011.
  • Shah, J.; Rasul Jan, M.; Zeeshan, M.; Iqbal, M. Solid Phase Extraction and Removal of 2, 4-Dichlorophenol from Aqueous Samples Using Magnetic Graphene Nanocomposite. Sep. Sci. Technol. 2016, 51(9), 1480–1489. DOI: 10.1080/01496395.2016.1165700.
  • Hamid, Y.; Fat’hi, M. R. A Simple Vortex-Assisted Graphene Oxide Nanosheets Dispersive Micro-Solid Phase Extraction Combined with High-Performance Liquid Chromatography for UV-Vis Detection of Tramadol in Biological Samples. Sep. Sci. Technol. 2018, 53(11), 1689–1697. DOI: 10.1080/01496395.2018.1439960.
  • Demirkol, D. O.; Yildiz, H. B.; Sayın, S.; Yilmaz, M. Enzyme Immobilization in Biosensor Constructions: Self-Assembled Monolayers of Calixarenes Containing Thiols. R.S.C. Adv. 2014, 4(38), 19900–19907. DOI: 10.1039/C3RA47642A.
  • Yaacob, S. F. F. S.; Jamil, A. K. M.; Kamboh, M. A.; Ibrahim, W. A. W.; Mohamad, S. Fabrication of Calixarene-Grafted Bio-Polymeric Magnetic Composites for Magnetic Solid Phase Extraction of Non-Steroidal Anti-Inflammatory Drugs in Water Samples. PeerJ. 2018, 6, e5108. DOI: 10.7717/peerj.5108.
  • Joseph, R.; Chinta, J. P.; Rao, C. P. Lower Rim 1, 3-Diderivative of Calix [4] Arene-Appended Salicylidene Imine (H2L): Experimental and Computational Studies of the Selective Recognition of H2L Toward Zn2+ and Sensing Phosphate and Amino Acid by [ZnL]. J. Org. Chem. 2010, 75(10), 3387–3395. DOI: 10.1021/jo1004247.
  • Acharya, A.; Ramanujam, B.; Chinta, J. P.; Rao, C. P. 1, 3-Diamido-Calix [4] Arene Conjugates of Amino Acids: Recognition of− COOH Side Chain Present in Amino Acids, Peptides, and Proteins by Experimental and Computational Studies. J. Org. Chem. 2011, 76(1), 127–137. DOI: 10.1021/jo101759f.
  • Joseph, R.; Chinta, J. P.; Rao, C. P. Calix [4] Arene-Based 1, 3-Diconjugate of Salicylyl Imine Having Dibenzyl Amine Moiety (L): Synthesis, Characterization, Receptor Properties Toward Fe2+, Cu2+, and Zn2+, Crystal Structures of Its Zn2+ and Cu2+ Complexes, and Selective Phosphate Sensing by the [ZnL]. Inorg. Chem. 2011, 50(15), 7050–7058. DOI: 10.1021/ic200544a.
  • Li, J. W.; Wang, Y. L.; Yan, S.; Li, X. J.; Pan, S. Y. Molecularly Imprinted Calixarene Fiber for Solid-Phase Microextraction of Four Organophosphorous Pesticides in Fruits. Food. Chem. 2016, 192, 260–267. DOI: 10.1016/j.foodchem.2015.07.018.
  • Hu, K.; Zhang, W.; Yang, H.; Cui, Y.; Zhang, J.; Zhao, W., Yu, A., Zhang, S., et al. Calixarene Ionic Liquid Modified Silica Gel: A Novel Stationary Phase for Mixed-Mode Chromatography. Talanta. 2016, 152, 392–400. DOI: 10.1016/j.talanta.2016.02.038.
  • Prata, J. V.; Barata, P. D. Fostering Protein–Calixarene Interactions: From Molecular Recognition to Sensing. Rsc. Adv. 2016, 6(2), 1659–1669. DOI: 10.1039/C5RA19887A.
  • A Hussain, M.; U Ashraf, M.; Muhammad, G.; N Tahir, M.; NA Bukhari, S. Calixarene: A Versatile Material for Drug Design and Applications. Curr. Pharm. Des. 2017, 23(16), 2377–2388. DOI: 10.2174/1381612822666160928143328.
  • Wang, S.; Bi, Y.; Hang, X.; Zhu, X.; Liao, W. A Calixarene‐based {co9} Coordination Triangle as an Efficient Heterogenous Catalyst. Z. Anorg Allg. Chem. 2017, 643(2), 160–165. DOI: 10.1002/zaac.201600409.
  • Hu, Y.; Wang, Y.; Hu, Y.; Li, G. Liquid–Liquid–Solid Microextraction Based on Membrane-Protected Molecularly Imprinted Polymer Fiber for Trace Analysis of Triazines in Complex Aqueous Samples. J. Chromatography. A. 2009 47, 1216(47), 8304–8311. DOI:10.1016/j.chroma.2009.09.063.
  • Cao, L. L.; Yin, S. M.; Liang, Y. B.; Zhu, J. M.; Fang, C.; Chen, Z. C. Preparation and Characterisation of Magnetic Fe3O4/Graphene Oxide Nanocomposites. Mater. Res. Innovations. 2015, 19(sup1), S1–364. DOI: 10.1179/1432891715Z.0000000001571.
  • Qi, T.; Huang, C.; Yan, S.; Li, X. J.; Pan, S. Y. Synthesis, Characterization and Adsorption Properties of Magnetite/Reduced Graphene Oxide Nanocomposites. Talanta. 2015, 144, 1116–1124. DOI: 10.1016/j.talanta.2015.07.089.
  • Farooq, M. U.; Jalees, M. I.; Jalees, M. I. Application of Magnetic Graphene Oxide for Water Purification: Heavy Metals Removal and Disinfection. J. Water Process Eng. 2020, 33, 101044. DOI: 10.1016/j.jwpe.2019.101044.
  • Malatesta, L.; Cosco, D.; Paolino, D.; Cilurzo, F.; Costa, N.; Di Tullio, A, Fresta, M, Celia, C, Di Marzio, L, Locatelli, M. et al Simultaneous Quantification of Gemcitabine and Irinotecan Hydrochloride in Rat Plasma by Using High Performance Liquid Chromatography-Diode Array Detector. J. Pharm. Biomed. Anal. 2018, 159, 192–199. DOI: 10.1016/j.jpba.2018.06.060.
  • Bjånes, T.; Kamčeva, T.; Eide, T.; Riedel, B.; Schjøtt, J.; Svardal, A. Preanalytical Stability of Gemcitabine and Its Metabolite 2′, 2′-Difluoro-2′-Deoxyuridine in Whole Blood—Assessed by Liquid Chromatography Tandem Mass Spectrometry. J. Pharm. Sci. 2015, 104(12), 4427–4432. DOI: 10.1002/jps.24638.
  • Mangamma, K.; VenkataRao, D.; Mohan, V. S.; Prasanna, A. Method Development and Validation of Gemcitabine and Irinotecan by RP-HPLC in Pharmaceutical Formulation. Int. J. Chem. Anal. Sci. 2012, 3(8), 1500–1502.
  • VIDAL, H.; Gonçalinho, H.; MONTEIRO, J.; NEVES, J. D.; SARMENTO, B.; DINIZ, C.; FRESCO, P. Development and Validation of a Rapid and Simple Reversed-Phase HPLC Method for the Determination of Gemcitabine in Human Plasma. Int. J. Pharm. Pharm. Sci. 2014, 6, 59–65.
  • Singh, R.; Shakya, A. K.; Naik, R.; Shalan, N. Stability-Indicating HPLC Determination of Gemcitabine in Pharmaceutical Formulations. Int. J. Anal. Chem. 2015, 2015, 1–12. DOI: 10.1155/2015/862592.
  • Khatri, A.; Fisher, J. E.; Kirstein, M. N. Enhanced Sensitivity Method for Measuring Gemcitabine in Human Plasma. Chromatographia. 2010, 72(9–10), 1005–1008. DOI: 10.1365/s10337-010-1751-2.
  • Wang, G.; Zhao, D.; Chen, H.; Ding, D.; Kou, L.; Sun, L., Sun, J.; Li, X.; Jia, K.; Kan, Q. et al Development and Validation of a UPLC–MS/MS Assay for the Determination of Gemcitabine and Its L-Carnitine Ester Derivative in Rat Plasma and Its Application in Oral Pharmacokinetics. Asian J. Pharm. Sci. 2017, 12(5), 478–485. DOI: 10.1016/j.ajps.2017.01.001.
  • Xu, Y.; Keith, B.; Grem, J. L. Measurement of the Anticancer Agent Gemcitabine and Its Deaminated Metabolite at Low Concentrations in Human Plasma by Liquid Chromatography-Mass Spectrometry. J. Chromatogr. B. 2004, 802(2), 263–270. DOI: 10.1016/j.jchromb.2003.11.038.

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