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Designing of alternative polymeric nano-chelator for treatment in acute iron poisoning by molecular imprinting approach

Year 2020, Volume: 48 Issue: 4, 319 - 331, 06.07.2020
https://doi.org/10.15671/hjbc.723455

Abstract

The aim of this study is to develop an alternative polymeric chelating agent for rapid and selectively removal with high capacity of Fe3+ ions from the gastrointestinal tract for the oral treatment of acute iron poisoning. For this purpose, Fe3+ imprinted poly(hydroxyethyl methacrylate-N-methacryloyl-(l)- glutamic acid) (HEMA-MAGA) nanoparticles synthesized by surfactant free emülsiyon polymerization. Molecular imprinting (MIP) technique is used to enhance the selectivity of nanoparticles. Due to being carboxyl and amide groups on the MAGA monomer, it was chosen as a chelating agent for Fe3+ ions. Before the synthesizing of Fe3+ imprinted polymer, Fe3+ ions were complexed with MAGA and then Fe3+ imprinted nanoparticles were synthesized in the presence of this Fe3+-MAGA complexes. Poly(HEMA-MAGA) nanoparticles were characterized by infrared spectroscopy (FTIR), atomic force microscopy (AFM). Average particle size and size distribution also determined by Zeta sizer. The specific surface area and mead diameter of the Fe3+ imprinted poly(HEMA-MAGA) nanoparticles was 895 m2.g-1 and 95.3 nm, respectively. The maximum Fe3+ ions binding capacity of the poly(HEMA-MAGA) nanoparticles at pH:4.0 were 206.4 mg.g-1 nanoparticles. Fe3+ removal performance of the Fe3+ imprinted poly(HEMA-MAGA) nanoparticles with presence of other ions, optimum medium pH, temperature and equilibrium binding time were also investigated. Fe3+ removal studies were performed in both aqueous solution and intestinal mimicking solution.The results indicate that Fe3+ imprinted poly(HEMA-MAGA) nanoparticles is an alternative chelating agent for the selective Fe3+ ions removal with a short time and very high capacity.

References

  • 1. G. Papanikolaoua, K. Pantopoulos, Iron metabolism and toxicity, Toxicol. Appl. Pharmacol., 202 (2005) 199- 211. 2. J. Wang, K. Pantopoulos, Regulation of cellular iron metabolism, Biochem. J., 434 (2011) 365-381. 3. Lindsay H. Allen, Iron Supplements: Scientific Issues Concerning Efficacy and Implications for Research and Programs, J. Nutr., 132 (2002) 813-819. 4. Jeffrey S. Fine, Iron Poisoning, Curr. Probl. Pediatr. and Adolescent Health Care 30, 3 (2000) 71-90 . • 5. Britton RS, Leicester KL, Bacon BR. Iron toxicity and chelation therapy. Int J Hematol. 76 (2002) 219-228 . 6. Crisponi G, Remelli M., Iron chelating agents for the treatment of iron overload., Coord Chem Rev., 252 (2008) 1225-1240 . 7. H. Heli, S. Mirtorabi, K. Karimian, Advances in iron chelation: an update, Expert Opin. Ther. Patents ., 21 (2011) 819 -856. 8. D. R. Rıchardson And P. Ponka, Pyridoxal isonicotinoyl hydrazone and its analogs: Potential orally effective iron-chelating agents for the treatment of iron overload disease. J Lab Clin Med., 131 (1998) 306-316 . 9. JB Mowry, DA Spyker, DE Brooks, A Zimmerman, JL Schauben. 2015 Annual Report of the American Association of Poison Control Centers' National Poison Data System (NPDS): 33rd Ann. Rep. Clin Toxicol (Phila). 54 (2016) 924-1109 . 10. J. R. Mahoney, Jr., P. E. Hallaway, B. E. Hedlund, J. W. Eaton, Acute Iron Poisoning Rescue with Macromolecular Chelators, J Clin Invest. 84 (1989)1362 -1366. 11. M. Berkovitch, A. Livne, G. Lushkov, M. Segal, C. Talmor, Y. Bentur, J. Klein, G. Koren, The efficacy of oral deferiprone in acute iron poisoning, Am. J. Emerg Med., 18 (2000) 36-40 . 12. M Yassin, AT Soliman, V De Sanctis, A young adult with unintended acute intravenous iron intoxication treated with oral chelation: The use of liver ferriscan for diagnosing and monitoring tissue iron load. Mediterr J Hematol Infect Dis. 9 (2017) 1-6 . 13. H Halil, N Tuygun, E. Polat, C. Demir Karacan, Minimum ingested iron cut-off triggering serious iron toxicity in children. Pediatrics International 61 (2019) 444- 448. 14. H.F Gomez, H. H Mc Clafferty, D. Flory, J. Brent, R. C Dart, Prevention of Gastrointestinal Iron Absorption by Chelation From an Orally Administered Premixed Deferoxamine/Charcoal Slurry. Ann. Emerg. Med., 30 (1997) 587-592. 15. Zu D. Liu, Robert C. Hider, Design of Clinically Useful Iron(III)-Selective Chelators. Med Res Rev., 22 (2002) 26- 64 16. D. Y Liu, Z. DLiu, R. C Hider, Oral iron chelators - development and application, Best Pract. Res. Clin. Haematol., 15 (2002)369- 384 17. Manoj R. Gumber, Vivek B. Kute, Pankaj R. Shah, Aruna V. Vanikar, Himanshu V. Patel, Manish R. Balwani, Pramod P Ghuge & Hargovind L. Trivedi Successful Treatment of Severe Iron Intoxication with Gastrointestinal Decontamination, Deferoxamine, and Hemodialysis, Renal Failure, 35:5 (2013) 729-731, 18. Zu D. Liu, Robert C. Hider, Design of iron chelators with therapeutic application, Coord. Chem. Rev., 232 (2002) 151- 171 19. Paul R. Dragsten, Phılıp E. Hallaway, Gregory J. Hanson, Arthur E. Berger, Bruce Bernard, And Bo E. Hedlund, First human studies with a high-molecular-weight iron Chelator .J. Lab. Clin. Med. 135 (2000) 57-65 20. Parisa Mirhoseini Moosavi Ali Reza Astaraei Alireza Karimi Mohammad Moshirib Leila Etemad Majid Zeinali Gholamreza Karimi, Efficacy of orally administered montmorillonite for acute iron poisoning detoxification in rat. J. Appl. Clay, 103 (2015)62-66 21. Ergün B, Baydemir G, Andaç M, Yavuz H, Denizli A. Ion imprinted beads embedded cryogels for in vitro removal of iron from b-thalassemic human plasma. J Appl Polym Sci. 125 (2012) 254-262. 22. Zu D. Lıu, Hıcham H. Khodr, Shu L. Lu And Robert C. Hıder. Design, Synthesis and Evaluation of N-Basic Substituted 3-Hydroxypyridin-4-ones: Orally Active Iron Chelators with Lysosomotrophic Potential J. Pharm. Pharmacol. 52 (2000) 263-272 . 23. Steven C. Polomoscanik, C. Pat Cannon, Thomas X. Neenan, S. Randall Holmes-Farley, W. Harry Mandeville, and Pradeep K. Dhal Hydroxamic Acid-Containing Hydrogels for Nonabsorbed Iron Chelation Therapy: Synthesis, Characterization, and Biological Evaluation. Biomacromolecules 6 (2005) 2946-2953. 24. Tao Zhou, Xiao Le Kong, Zu Dong Liu, Ding Yong Liu, and Robert C. Hider, Synthesis and Iron(III)-Chelating Properties of Novel 3-Hydroxypyridin-4-one Hexadentate Ligand-Containing Copolymers. Biomacromolecules 9 (2008) 1372-1380. 25. Muhammad Imran ul-haq, Jasmine L. Hamilton, Benjamin F. L. Lai, Rajesh A. Shenoi, Sonja Horte, Iren Constantinescu, Heather A. Leitch, Jayachandran N. Kizhakkedathu. Design of Long Circulating Nontoxic Dendritic Polymers for the Removal of Iron in Vivo. ACS Nano 7 (2013) 10704 -10716. 26. Jasmine L Hamilton, Jayachandran N Kizhakkedathu. Polymeric nanocarriers for the treatment of systemic iron overload. Mol. Cell. Therap.,3 (2015) 1-15. 27. Tao Zhoua, Günther Winkelmannb, Zhi-Yuan Daia Robert C. Hider. Design of clinically useful macromolecular iron chelators. J. Pharm and Pharmacol. 63 (2011) 893-903 . 28. N. A.A. Rossi, I. Mustafa, J. K. Jackson, H. M. Burt, S. A. Horte, M. D. Scott, J. N. Kizhakkedathu, In vitro chelating, cytotoxicity, and blood compatibility of degradable poly(ethylene glycol)-based macromolecular iron chelators. Biomaterials 30 (2009) 638-648 29. Tao Zhou, Hendrik Neubert, Ding Yong Liu, Zu Dong Liu, Yong Min Ma, Xiao Le Kong, Wei Luo, Sykes Mark, Robert C. Hider, Iron Binding Dendrimers: A Novel Approach for the Treatment of Haemochromatosis, J. Med. Chem., 49 (2006)4171- 4182 30. Özkara S, Andaç M, Karakoç V, Say R, Denizli A. 2011. Ion-imprinted PHEMA based monolith for the removal of Fe3 ions from aqueoussolutions. J Appl Polym Sci. (120) 1829-1836. 31. H. Yavuz, R. Say, A. Denizli. Iron removal from human plasma based on molecular recognition using imprinted beads. Materials Science and Engineering C 25 (2005) 521 - 528 32. H. Yavuz, M. Andaç, L. Uzun, R. Say, A. Denizli, Molecular recognition based iron removal from human plasma with imprinted membranes, Int. J. Art. Org., 29 (2006) 900 -911 33. Sarkaya, K. Bakhshpour, M. Denizli, A., Ag+ ions imprinted cryogels for selective removal of silver ions from aqueous solutions Sep. Scı. Tech., 54 (2019) 2993-3004 34. E. A. Turkoglu, M. Bakhshpour, A. Denizli, Molecularly imprinted biomimetic surface plasmon resonance sensor for hormone detection Bıoınterface Research In Applıed Chem., 9 (2019) 4090- 4095 35. A. Derazshamshir, I.Gokturk, E. Tamahkâr, F Yilmaz, N Saglam, A. Denizli, Phenol removal from wastewater by surface imprinted bacterial cellulose nanofibres. Env. Techn., 40 (2019)1-13 36. C. Esen, R. H. Senay, E. Feyzioglu, S. Akgol, Poly(hydroxyethyl methacrylate-co-methacryloylglutamic acid) nanospheres for adsorption of Cd2+ ions from aqueous solutions. J Nanopart Res., 16 (2014) 2255- 2261 37. V. Karakoc, E. Yılmaz, D. Türkmen, N. Öztürk, S. Akgöl, A. Denizli. Selective separation of human serum albumin with copper(II) chelated poly(hydroxyethyl methacrylate) based nanoparticles Int. J. Bıo. Macromolecules, 45 (2009) 188-193. 38. Y. Saylan, F. Yilmaz, A. Derazshamshir, E. Yilmaz, A. Denizli, Synthesis of hydrophobic nanoparticles for real-time lysozyme detection using surface plasmon resonance sensor, J. Mol. Recog., 30 (2017) 1-7 39. E.B. Altintas, H Yavuz,. R. Say, A Denizli,Methacryloylamidoglutamic acid having porous magnetic beads as a stationary phase in metal chelate affinity chromatography, J. Bıomaterıals Scıence-Polym Edt., 17, (2006) 213-226 40. B. Sellergren, J. Wieschemeyer, K.-S.Boos, D. Seidel, Imprinted Polymers for Selective Adsorption of Cholesterol from Gastrointestinal Fluids Chem. Mater., 10, (1998)4037-4046
Year 2020, Volume: 48 Issue: 4, 319 - 331, 06.07.2020
https://doi.org/10.15671/hjbc.723455

Abstract

References

  • 1. G. Papanikolaoua, K. Pantopoulos, Iron metabolism and toxicity, Toxicol. Appl. Pharmacol., 202 (2005) 199- 211. 2. J. Wang, K. Pantopoulos, Regulation of cellular iron metabolism, Biochem. J., 434 (2011) 365-381. 3. Lindsay H. Allen, Iron Supplements: Scientific Issues Concerning Efficacy and Implications for Research and Programs, J. Nutr., 132 (2002) 813-819. 4. Jeffrey S. Fine, Iron Poisoning, Curr. Probl. Pediatr. and Adolescent Health Care 30, 3 (2000) 71-90 . • 5. Britton RS, Leicester KL, Bacon BR. Iron toxicity and chelation therapy. Int J Hematol. 76 (2002) 219-228 . 6. Crisponi G, Remelli M., Iron chelating agents for the treatment of iron overload., Coord Chem Rev., 252 (2008) 1225-1240 . 7. H. Heli, S. Mirtorabi, K. Karimian, Advances in iron chelation: an update, Expert Opin. Ther. Patents ., 21 (2011) 819 -856. 8. D. R. Rıchardson And P. Ponka, Pyridoxal isonicotinoyl hydrazone and its analogs: Potential orally effective iron-chelating agents for the treatment of iron overload disease. J Lab Clin Med., 131 (1998) 306-316 . 9. JB Mowry, DA Spyker, DE Brooks, A Zimmerman, JL Schauben. 2015 Annual Report of the American Association of Poison Control Centers' National Poison Data System (NPDS): 33rd Ann. Rep. Clin Toxicol (Phila). 54 (2016) 924-1109 . 10. J. R. Mahoney, Jr., P. E. Hallaway, B. E. Hedlund, J. W. Eaton, Acute Iron Poisoning Rescue with Macromolecular Chelators, J Clin Invest. 84 (1989)1362 -1366. 11. M. Berkovitch, A. Livne, G. Lushkov, M. Segal, C. Talmor, Y. Bentur, J. Klein, G. Koren, The efficacy of oral deferiprone in acute iron poisoning, Am. J. Emerg Med., 18 (2000) 36-40 . 12. M Yassin, AT Soliman, V De Sanctis, A young adult with unintended acute intravenous iron intoxication treated with oral chelation: The use of liver ferriscan for diagnosing and monitoring tissue iron load. Mediterr J Hematol Infect Dis. 9 (2017) 1-6 . 13. H Halil, N Tuygun, E. Polat, C. Demir Karacan, Minimum ingested iron cut-off triggering serious iron toxicity in children. Pediatrics International 61 (2019) 444- 448. 14. H.F Gomez, H. H Mc Clafferty, D. Flory, J. Brent, R. C Dart, Prevention of Gastrointestinal Iron Absorption by Chelation From an Orally Administered Premixed Deferoxamine/Charcoal Slurry. Ann. Emerg. Med., 30 (1997) 587-592. 15. Zu D. Liu, Robert C. Hider, Design of Clinically Useful Iron(III)-Selective Chelators. Med Res Rev., 22 (2002) 26- 64 16. D. Y Liu, Z. DLiu, R. C Hider, Oral iron chelators - development and application, Best Pract. Res. Clin. Haematol., 15 (2002)369- 384 17. Manoj R. Gumber, Vivek B. Kute, Pankaj R. Shah, Aruna V. Vanikar, Himanshu V. Patel, Manish R. Balwani, Pramod P Ghuge & Hargovind L. Trivedi Successful Treatment of Severe Iron Intoxication with Gastrointestinal Decontamination, Deferoxamine, and Hemodialysis, Renal Failure, 35:5 (2013) 729-731, 18. Zu D. Liu, Robert C. Hider, Design of iron chelators with therapeutic application, Coord. Chem. Rev., 232 (2002) 151- 171 19. Paul R. Dragsten, Phılıp E. Hallaway, Gregory J. Hanson, Arthur E. Berger, Bruce Bernard, And Bo E. Hedlund, First human studies with a high-molecular-weight iron Chelator .J. Lab. Clin. Med. 135 (2000) 57-65 20. Parisa Mirhoseini Moosavi Ali Reza Astaraei Alireza Karimi Mohammad Moshirib Leila Etemad Majid Zeinali Gholamreza Karimi, Efficacy of orally administered montmorillonite for acute iron poisoning detoxification in rat. J. Appl. Clay, 103 (2015)62-66 21. Ergün B, Baydemir G, Andaç M, Yavuz H, Denizli A. Ion imprinted beads embedded cryogels for in vitro removal of iron from b-thalassemic human plasma. J Appl Polym Sci. 125 (2012) 254-262. 22. Zu D. Lıu, Hıcham H. Khodr, Shu L. Lu And Robert C. Hıder. Design, Synthesis and Evaluation of N-Basic Substituted 3-Hydroxypyridin-4-ones: Orally Active Iron Chelators with Lysosomotrophic Potential J. Pharm. Pharmacol. 52 (2000) 263-272 . 23. Steven C. Polomoscanik, C. Pat Cannon, Thomas X. Neenan, S. Randall Holmes-Farley, W. Harry Mandeville, and Pradeep K. Dhal Hydroxamic Acid-Containing Hydrogels for Nonabsorbed Iron Chelation Therapy: Synthesis, Characterization, and Biological Evaluation. Biomacromolecules 6 (2005) 2946-2953. 24. Tao Zhou, Xiao Le Kong, Zu Dong Liu, Ding Yong Liu, and Robert C. Hider, Synthesis and Iron(III)-Chelating Properties of Novel 3-Hydroxypyridin-4-one Hexadentate Ligand-Containing Copolymers. Biomacromolecules 9 (2008) 1372-1380. 25. Muhammad Imran ul-haq, Jasmine L. Hamilton, Benjamin F. L. Lai, Rajesh A. Shenoi, Sonja Horte, Iren Constantinescu, Heather A. Leitch, Jayachandran N. Kizhakkedathu. Design of Long Circulating Nontoxic Dendritic Polymers for the Removal of Iron in Vivo. ACS Nano 7 (2013) 10704 -10716. 26. Jasmine L Hamilton, Jayachandran N Kizhakkedathu. Polymeric nanocarriers for the treatment of systemic iron overload. Mol. Cell. Therap.,3 (2015) 1-15. 27. Tao Zhoua, Günther Winkelmannb, Zhi-Yuan Daia Robert C. Hider. Design of clinically useful macromolecular iron chelators. J. Pharm and Pharmacol. 63 (2011) 893-903 . 28. N. A.A. Rossi, I. Mustafa, J. K. Jackson, H. M. Burt, S. A. Horte, M. D. Scott, J. N. Kizhakkedathu, In vitro chelating, cytotoxicity, and blood compatibility of degradable poly(ethylene glycol)-based macromolecular iron chelators. Biomaterials 30 (2009) 638-648 29. Tao Zhou, Hendrik Neubert, Ding Yong Liu, Zu Dong Liu, Yong Min Ma, Xiao Le Kong, Wei Luo, Sykes Mark, Robert C. Hider, Iron Binding Dendrimers: A Novel Approach for the Treatment of Haemochromatosis, J. Med. Chem., 49 (2006)4171- 4182 30. Özkara S, Andaç M, Karakoç V, Say R, Denizli A. 2011. Ion-imprinted PHEMA based monolith for the removal of Fe3 ions from aqueoussolutions. J Appl Polym Sci. (120) 1829-1836. 31. H. Yavuz, R. Say, A. Denizli. Iron removal from human plasma based on molecular recognition using imprinted beads. Materials Science and Engineering C 25 (2005) 521 - 528 32. H. Yavuz, M. Andaç, L. Uzun, R. Say, A. Denizli, Molecular recognition based iron removal from human plasma with imprinted membranes, Int. J. Art. Org., 29 (2006) 900 -911 33. Sarkaya, K. Bakhshpour, M. Denizli, A., Ag+ ions imprinted cryogels for selective removal of silver ions from aqueous solutions Sep. Scı. Tech., 54 (2019) 2993-3004 34. E. A. Turkoglu, M. Bakhshpour, A. Denizli, Molecularly imprinted biomimetic surface plasmon resonance sensor for hormone detection Bıoınterface Research In Applıed Chem., 9 (2019) 4090- 4095 35. A. Derazshamshir, I.Gokturk, E. Tamahkâr, F Yilmaz, N Saglam, A. Denizli, Phenol removal from wastewater by surface imprinted bacterial cellulose nanofibres. Env. Techn., 40 (2019)1-13 36. C. Esen, R. H. Senay, E. Feyzioglu, S. Akgol, Poly(hydroxyethyl methacrylate-co-methacryloylglutamic acid) nanospheres for adsorption of Cd2+ ions from aqueous solutions. J Nanopart Res., 16 (2014) 2255- 2261 37. V. Karakoc, E. Yılmaz, D. Türkmen, N. Öztürk, S. Akgöl, A. Denizli. Selective separation of human serum albumin with copper(II) chelated poly(hydroxyethyl methacrylate) based nanoparticles Int. J. Bıo. Macromolecules, 45 (2009) 188-193. 38. Y. Saylan, F. Yilmaz, A. Derazshamshir, E. Yilmaz, A. Denizli, Synthesis of hydrophobic nanoparticles for real-time lysozyme detection using surface plasmon resonance sensor, J. Mol. Recog., 30 (2017) 1-7 39. E.B. Altintas, H Yavuz,. R. Say, A Denizli,Methacryloylamidoglutamic acid having porous magnetic beads as a stationary phase in metal chelate affinity chromatography, J. Bıomaterıals Scıence-Polym Edt., 17, (2006) 213-226 40. B. Sellergren, J. Wieschemeyer, K.-S.Boos, D. Seidel, Imprinted Polymers for Selective Adsorption of Cholesterol from Gastrointestinal Fluids Chem. Mater., 10, (1998)4037-4046
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Details

Primary Language English
Subjects Engineering
Journal Section Articles
Authors

Veyis Karakoç 0000-0002-2511-6478

Publication Date July 6, 2020
Acceptance Date May 20, 2020
Published in Issue Year 2020 Volume: 48 Issue: 4

Cite

APA Karakoç, V. (2020). Designing of alternative polymeric nano-chelator for treatment in acute iron poisoning by molecular imprinting approach. Hacettepe Journal of Biology and Chemistry, 48(4), 319-331. https://doi.org/10.15671/hjbc.723455
AMA Karakoç V. Designing of alternative polymeric nano-chelator for treatment in acute iron poisoning by molecular imprinting approach. HJBC. July 2020;48(4):319-331. doi:10.15671/hjbc.723455
Chicago Karakoç, Veyis. “Designing of Alternative Polymeric Nano-Chelator for Treatment in Acute Iron Poisoning by Molecular Imprinting Approach”. Hacettepe Journal of Biology and Chemistry 48, no. 4 (July 2020): 319-31. https://doi.org/10.15671/hjbc.723455.
EndNote Karakoç V (July 1, 2020) Designing of alternative polymeric nano-chelator for treatment in acute iron poisoning by molecular imprinting approach. Hacettepe Journal of Biology and Chemistry 48 4 319–331.
IEEE V. Karakoç, “Designing of alternative polymeric nano-chelator for treatment in acute iron poisoning by molecular imprinting approach”, HJBC, vol. 48, no. 4, pp. 319–331, 2020, doi: 10.15671/hjbc.723455.
ISNAD Karakoç, Veyis. “Designing of Alternative Polymeric Nano-Chelator for Treatment in Acute Iron Poisoning by Molecular Imprinting Approach”. Hacettepe Journal of Biology and Chemistry 48/4 (July 2020), 319-331. https://doi.org/10.15671/hjbc.723455.
JAMA Karakoç V. Designing of alternative polymeric nano-chelator for treatment in acute iron poisoning by molecular imprinting approach. HJBC. 2020;48:319–331.
MLA Karakoç, Veyis. “Designing of Alternative Polymeric Nano-Chelator for Treatment in Acute Iron Poisoning by Molecular Imprinting Approach”. Hacettepe Journal of Biology and Chemistry, vol. 48, no. 4, 2020, pp. 319-31, doi:10.15671/hjbc.723455.
Vancouver Karakoç V. Designing of alternative polymeric nano-chelator for treatment in acute iron poisoning by molecular imprinting approach. HJBC. 2020;48(4):319-31.

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