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Preparation and Characterization of Intrinsically Fluorescent Polyphosphazene Microspheres

Year 2022, Volume: 26 Issue: 4, 789 - 798, 31.08.2022

Abstract

The novel polyphosphazene and cyclomatrix type microspheres were synthesized via a one-pot self-assembly polycondensation method. Octachlorocyclotetraphosphazene and two fluorescent compounds; fluorescein and curcumin were used as a crosslinker and monomers, respectively. The prepared microspheres were characterized by SEM, EDX, FTIR, XRD, UV-vis techniques. Also, the fluorescence properties of the microspheres were investigated. The microspheres exhibited fluorescence emissions both in ethanol and as solid-state when excited at 470 nm. The optimum pH was determined as 9.0 for fluorescence measurements. Owing to fluorescent properties of the microspheres, the delivery of curcumin from the prepared microspheres, and cell imaging can be investigated in the future. It is thought that the obtained intrinsically fluorescent polyphosphazene microspheres have the potential for use as sensors and labels, also.

References

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  • [2] C. Wan, X. Huang, “Cyclomatrix polyphosphazenes frameworks (Cyclo-POPs) and the related nanomaterials: synthesis, assembly and functionalization”, Materials Today Communications, vol. 11 pp. 38–60, 2017.
  • [3] J. Fu, S, Wang, J. Zhu, K. Wang, M. Gao, X. Wang, Q. Xu, “Au-Ag bimetallic nanoparticles decorated multi-amino cyclophosphazene hybrid microspheres as enhanced activity catalysts for the reduction of 4-nitrophenol”, Materials Chemistry and Physics, vol. 207, pp. 315-324, 2018.
  • [4] Y. Sui, H. Sima, W. Shao, C. Zhang, “Novel bioderived cross-linked polyphosphazene microspheres decorated with FeCo-layered double hydroxide as an all-in-one intumescent flame retardant for epoxy resin”, Composites Part B, vol. 229, pp. 109463, 2022.
  • [5] W. Wei, R. Lu, H. Xie, Y. Zhang, X. Bai, L. Gu, R. Da, X. Liu, “Selective adsorption and separation of dyes from an aqueous solution on organic–inorganic hybrid cyclomatrix polyphosphazene submicro-spheres”, Journal of Materials Chemistry A, vol. 3, pp. 4314, 2015.
  • [6] G. Elmas, A. Okumuş, Z. Kılıç, P. Özbeden, L. Açık, B. Ç. Tunalı, M. Türk, N. A. Çerçi, T. Hökelek, “Phosphorus-nitrogen compounds. Part 48. Syntheses of the phosphazenium salts containing 2-pyridyl pendant arm: Structural characterizations, thermal analysis, antimicrobial and cytotoxic activity studies”, Indian Journal of Chemistry -Section A, vol. 59A, pp.533-550, 2020.
  • [7] S. P. Mucur, B. Canımkurbey, P. Kavak, H. Akbaş, A. Karadağ, “Charge carrier performance of phosphazene-based ionic liquids doped hole transport layer in organic light-emitting diodes”, Applied Physics A, vol. 126 (12), pp. 923, 2020.
  • [8] S. O. Tümay, “A novel selective “turn-on” fluorescent chemosensor based on thiophene appended cyclotriphosphazene schiff base for detection of Ag+ ions”, ChemistrySelect, vol. 6(39), pp. 10561-10572, 2021.
  • [9] A. Okumuş, G. Elmas, Z. Kılıç, A. Binici, N. Ramazanoğlu, L. Açık, B. Çoşut, T. Hökelek, R. Güzel, B. Ç. Tunalı, M. Türk, H. Şimşek, “The comparative reactions of 2‐cis‐4‐ansa and spiro cyclotetraphosphazenes with difunctional ligands: Structural and stereogenic properties, electrochemical, antimicrobial and cytotoxic activity studies”, Applied Organometallic Chemistry, vol. 35 (4), pp. e6150, 2021.
  • [10] A. Binici, G. Elmas, A. Okumuş, S. Erden Tayhan, T. Hökelek, L. Açık, B. N. Şeker, Z. Kılıç, “Phosphorus-nitrogen compounds. part 58. syntheses, structural characterizations and biological activities of 4-fluorobenzyl-spiro(N/O)cyclotriphosphazene derivatives”, Journal of Biomolecular Structure and Dynamics, 2021.
  • [11] G. Elmas, Z. Kılıç, B. Çoşut, G. Keşan, L. Açık, M. Çam, B. Ç. Tunalı, M. Türk, T. Hökelek, “Synthesis of bis(2,2,3,3-tetrafluoro-1,4-butanedialkoxy)-2-trans-6-bis(4-fluorobenzyl)spiro cyclotetraphosphazene: structural characterization, biological activity and dft studies”, Journal of Chemical Crystallography, vol. 51, pp. 235-250, 2020.
  • [12] L. C. Xu, C. Chen, J. Zhu, M. Tang, A. Chen, H. R. Allcock, C. A. Siedlecki, “New cross-linkable poly[bis(octafluoropentoxy) phosphazene] biomaterials: synthesis, surface characterization, bacterial adhesion, and plasma coagulation responses”, Journal of Biomedical Materials Research Part A, vol.108(8), pp. 3250-3260, 2020.
  • [13] H. R. Allcock, “The background and scope of polyphosphazenes as biomedical materials”, Regenerative Engineering and Translational Medicine, vol. 7, pp. 66–75, 2021.
  • [14] K. S. Ogueri, K. S. Ogueri, H. R. Allcock, C.T. Laurencin,“Polyphosphazene polymers: the next generation of biomaterials for regenerative engineering and therapeutic drug delivery”, Journal of Vacuum Science and Technology B, vol. 38, pp. 030801, 2020.
  • [15] S. Mehmood, L. Wang, H. Yu, F. Haq, S. Fahad, B. Amin, M. A. Uddin, M. Haroon, “Recent progress on the preparation of cyclomatrix-polyphosphazene based micro/nanospheres and their application for drug release”, Chemistry Select, vol. 5, pp. 5939 –5958, 2020.
  • [16] W. Wei, X. Huang, K. Chen, Y. Tao, X. Tang, “Fluorescent organic–inorganic hybrid polyphosphazene microspheres for the trace detection of nitroaromatic explosives”, RSC Advances, vol. 2, pp. 3765–3771, 2012.
  • [17] K. Chen, Y. Liu, Y. Hu, M. Yuan, X. Zheng, X. Huang, “Facile synthesis of amino-functionalized polyphosphazene microspheres and their application for highly sensitive fluorescence detection of Fe3+”, Journal of Applied Polymer Science, vol. 137, no. 32, pp. 48937, 2020.
  • [18] S. Hong, J. Li, X. Huang, H.Liu, “A facile approach to generate cross-linked poly(cyclotriphosphazeneco-oxyresveratrol) nanoparticle with intrinsically fluorescence”, Journal of Inorganic and Organometallic Polymers and Materials, vol. 28, pp. 2258–2263, 2018.
  • [19] T. Pan, X. Huang, H. Wei, W. Wei, X. Tang, “Intrinsically fluorescent microspheres with superior thermal stability and broad ultraviolet-visible absorption based on hybrid polyphosphazene material”, Macromolecular Chemistry and Physics, vol. 213, pp. 1590−1595, 2012.
  • [20] W. Liu, X. Huang, H. Wei, X. Tang, L. Zhua, “Intrinsically fluorescent nanoparticles with excellent stability based on a highly crosslinked organic–inorganic hybrid polyphosphazene material”, Chemical Communications, vol. 47, pp. 11447–11449, 2011.
  • [21] Y. Hu, L. Meng, Q. Lu, “Fastening porphyrin in highly cross-linked polyphosphazene hybrid nanoparticles: powerful red fluorescent probe for detecting mercury ion”, Langmuir, vol. 30, pp. 4458−4464, 2014.
  • [22] W. Wei, R. Lu, S. Tang, X. Liu, “Highly cross-linked fluorescent poly(cyclotriphosphazene-co-curcumin) microspheres for the selective detection of picric acid in solution phase”, Journal of Materials Chemistry A, vol. 3, pp. 4604-4611, 2015.
  • [23] D. Wang, Y. Hu, L. Meng, X. Wang, Q. Lu, “One-pot synthesis of fluorescent and cross-linked polyphosphazene nanoparticles for highly sensitive and selective detection of dopamine in body fluids”, RSC Advances, vol. 5, pp. 92762, 2015.
  • [24] L. Meng, C. Xu, T. Liu, H. Li, Q. Lu, J. Long, “One-pot synthesis of highly cross-linked fluorescent polyphosphazene nanoparticles for cell imaging”, Polymer Chemistry, vol. 6, pp. 3155, 2015.
  • [25] Z. Wang, M. Hu, S. Hu, J. Han, Z. Wang, Y. Chen, C. Huang, L. Fu, Z. Zhang, “Facile one-pot synthesis of multifunctional polyphosphazene nanoparticles as multifunctional platform for tumor imaging”, Analytical and Bioanalytical Chemistry vol. 410, pp. 3723–3730, 2018.
  • [26] L. Sun, T. Liu, H. Li, L. Yang, L. Meng, Q. Lu, J. Long, “Fluorescent and cross-linked organic−inorganic hybrid nanoshells for monitoring drug delivery”, ACS Applied Materials and Interfaces, vol. 7, pp. 4990−4997, 2015.
  • [27] K.S.B Sam, L. George, SYN, A. Varghese. “Fluorescein based fluorescence sensors for the selective sensing of various analytes”, Journal of Fluorescence, vol. 31, pp. 1251 –1276, 2021.
  • [28] T. Preiß, A. Zimpel, S. Wuttke, J.O. Rädler, “Kinetic analysis of the uptake and release of fluorescein by metal-organic framework nanoparticles”, Materials, vol. 10, no. 2, pp. 216, 2017.
  • [29] A. Kumar, L. Li, A. Chaturvedi, J. Brzostowski, J. Chittigori, S. Pierce, L. A. Samuelson, D. Sandman, J. Kumar, “Two-photon fluorescence properties of curcumin as a biocompatible marker for confocal imaging”, Applied Physics Letters, vol. 100, pp. 203701, 2012.
  • [30] B. F. Mogharbel, J. C. Francisco, A. C. Irioda, D. S. M. Dziedzic, P. E. Ferreira, D. Souza, C. M. C. O. Souza, N. B. Neto, L. C. Guarita-Souza, C. R. C. Franco, C. V. Nakamura, V. Kaplum, L. Mazzarino, E. Lemos-Senna, R. Borsali, P. A. Soto, P. Setton-Avruj, E. Abdelwahid, K. A. T. Carvalho, “Fluorescence properties of curcumin-loaded nanoparticles for cell tracking”, International Journal of Nanomedicine, vol. 13, pp. 5823–5836, 2018.
  • [31] M. Y. Khorasania, H. Langaric, S. B. T. Sany, M. Rezayib, A. Sahebkar, “The role of curcumin and its derivatives in sensory applications”, Materials Science & Engineering C, vol. 103, pp. 109792, 2019.
  • [32] F. Chang, X. Huang, H, Wei, K. Chen, C. Shan, X. Tang, “Intrinsically fluorescent hollow spheres based on organic–inorganic hybrid polyphosphazene material: synthesis and application in drug release”, Materials Letters, vol. 125, pp. 128–131, 2014.
  • [33] S. Metinoğlu Örüm, “Novel cyclomatrix polyphosphazene nanospheres: preparation, characterization and dual anticancer drug release application”, Polymer Bulletin.
  • [34] Y. Wang, J. Mu, L. Li, L. Shi, W. Zhang, Z. Jiang, “Preparation and properties of novel fluorinated cross-linked polyphosphazene micro-nano spheres”, High Performance Polymers, vol. 24, pp. 229, 2012.
Year 2022, Volume: 26 Issue: 4, 789 - 798, 31.08.2022

Abstract

References

  • [1] S. Rothemund, I. Teasdale, “Preparation of polyphosphazenes: a tutorial review”, Chemical Society Reviews, vol. 45, pp. 5200-5215, 2016.
  • [2] C. Wan, X. Huang, “Cyclomatrix polyphosphazenes frameworks (Cyclo-POPs) and the related nanomaterials: synthesis, assembly and functionalization”, Materials Today Communications, vol. 11 pp. 38–60, 2017.
  • [3] J. Fu, S, Wang, J. Zhu, K. Wang, M. Gao, X. Wang, Q. Xu, “Au-Ag bimetallic nanoparticles decorated multi-amino cyclophosphazene hybrid microspheres as enhanced activity catalysts for the reduction of 4-nitrophenol”, Materials Chemistry and Physics, vol. 207, pp. 315-324, 2018.
  • [4] Y. Sui, H. Sima, W. Shao, C. Zhang, “Novel bioderived cross-linked polyphosphazene microspheres decorated with FeCo-layered double hydroxide as an all-in-one intumescent flame retardant for epoxy resin”, Composites Part B, vol. 229, pp. 109463, 2022.
  • [5] W. Wei, R. Lu, H. Xie, Y. Zhang, X. Bai, L. Gu, R. Da, X. Liu, “Selective adsorption and separation of dyes from an aqueous solution on organic–inorganic hybrid cyclomatrix polyphosphazene submicro-spheres”, Journal of Materials Chemistry A, vol. 3, pp. 4314, 2015.
  • [6] G. Elmas, A. Okumuş, Z. Kılıç, P. Özbeden, L. Açık, B. Ç. Tunalı, M. Türk, N. A. Çerçi, T. Hökelek, “Phosphorus-nitrogen compounds. Part 48. Syntheses of the phosphazenium salts containing 2-pyridyl pendant arm: Structural characterizations, thermal analysis, antimicrobial and cytotoxic activity studies”, Indian Journal of Chemistry -Section A, vol. 59A, pp.533-550, 2020.
  • [7] S. P. Mucur, B. Canımkurbey, P. Kavak, H. Akbaş, A. Karadağ, “Charge carrier performance of phosphazene-based ionic liquids doped hole transport layer in organic light-emitting diodes”, Applied Physics A, vol. 126 (12), pp. 923, 2020.
  • [8] S. O. Tümay, “A novel selective “turn-on” fluorescent chemosensor based on thiophene appended cyclotriphosphazene schiff base for detection of Ag+ ions”, ChemistrySelect, vol. 6(39), pp. 10561-10572, 2021.
  • [9] A. Okumuş, G. Elmas, Z. Kılıç, A. Binici, N. Ramazanoğlu, L. Açık, B. Çoşut, T. Hökelek, R. Güzel, B. Ç. Tunalı, M. Türk, H. Şimşek, “The comparative reactions of 2‐cis‐4‐ansa and spiro cyclotetraphosphazenes with difunctional ligands: Structural and stereogenic properties, electrochemical, antimicrobial and cytotoxic activity studies”, Applied Organometallic Chemistry, vol. 35 (4), pp. e6150, 2021.
  • [10] A. Binici, G. Elmas, A. Okumuş, S. Erden Tayhan, T. Hökelek, L. Açık, B. N. Şeker, Z. Kılıç, “Phosphorus-nitrogen compounds. part 58. syntheses, structural characterizations and biological activities of 4-fluorobenzyl-spiro(N/O)cyclotriphosphazene derivatives”, Journal of Biomolecular Structure and Dynamics, 2021.
  • [11] G. Elmas, Z. Kılıç, B. Çoşut, G. Keşan, L. Açık, M. Çam, B. Ç. Tunalı, M. Türk, T. Hökelek, “Synthesis of bis(2,2,3,3-tetrafluoro-1,4-butanedialkoxy)-2-trans-6-bis(4-fluorobenzyl)spiro cyclotetraphosphazene: structural characterization, biological activity and dft studies”, Journal of Chemical Crystallography, vol. 51, pp. 235-250, 2020.
  • [12] L. C. Xu, C. Chen, J. Zhu, M. Tang, A. Chen, H. R. Allcock, C. A. Siedlecki, “New cross-linkable poly[bis(octafluoropentoxy) phosphazene] biomaterials: synthesis, surface characterization, bacterial adhesion, and plasma coagulation responses”, Journal of Biomedical Materials Research Part A, vol.108(8), pp. 3250-3260, 2020.
  • [13] H. R. Allcock, “The background and scope of polyphosphazenes as biomedical materials”, Regenerative Engineering and Translational Medicine, vol. 7, pp. 66–75, 2021.
  • [14] K. S. Ogueri, K. S. Ogueri, H. R. Allcock, C.T. Laurencin,“Polyphosphazene polymers: the next generation of biomaterials for regenerative engineering and therapeutic drug delivery”, Journal of Vacuum Science and Technology B, vol. 38, pp. 030801, 2020.
  • [15] S. Mehmood, L. Wang, H. Yu, F. Haq, S. Fahad, B. Amin, M. A. Uddin, M. Haroon, “Recent progress on the preparation of cyclomatrix-polyphosphazene based micro/nanospheres and their application for drug release”, Chemistry Select, vol. 5, pp. 5939 –5958, 2020.
  • [16] W. Wei, X. Huang, K. Chen, Y. Tao, X. Tang, “Fluorescent organic–inorganic hybrid polyphosphazene microspheres for the trace detection of nitroaromatic explosives”, RSC Advances, vol. 2, pp. 3765–3771, 2012.
  • [17] K. Chen, Y. Liu, Y. Hu, M. Yuan, X. Zheng, X. Huang, “Facile synthesis of amino-functionalized polyphosphazene microspheres and their application for highly sensitive fluorescence detection of Fe3+”, Journal of Applied Polymer Science, vol. 137, no. 32, pp. 48937, 2020.
  • [18] S. Hong, J. Li, X. Huang, H.Liu, “A facile approach to generate cross-linked poly(cyclotriphosphazeneco-oxyresveratrol) nanoparticle with intrinsically fluorescence”, Journal of Inorganic and Organometallic Polymers and Materials, vol. 28, pp. 2258–2263, 2018.
  • [19] T. Pan, X. Huang, H. Wei, W. Wei, X. Tang, “Intrinsically fluorescent microspheres with superior thermal stability and broad ultraviolet-visible absorption based on hybrid polyphosphazene material”, Macromolecular Chemistry and Physics, vol. 213, pp. 1590−1595, 2012.
  • [20] W. Liu, X. Huang, H. Wei, X. Tang, L. Zhua, “Intrinsically fluorescent nanoparticles with excellent stability based on a highly crosslinked organic–inorganic hybrid polyphosphazene material”, Chemical Communications, vol. 47, pp. 11447–11449, 2011.
  • [21] Y. Hu, L. Meng, Q. Lu, “Fastening porphyrin in highly cross-linked polyphosphazene hybrid nanoparticles: powerful red fluorescent probe for detecting mercury ion”, Langmuir, vol. 30, pp. 4458−4464, 2014.
  • [22] W. Wei, R. Lu, S. Tang, X. Liu, “Highly cross-linked fluorescent poly(cyclotriphosphazene-co-curcumin) microspheres for the selective detection of picric acid in solution phase”, Journal of Materials Chemistry A, vol. 3, pp. 4604-4611, 2015.
  • [23] D. Wang, Y. Hu, L. Meng, X. Wang, Q. Lu, “One-pot synthesis of fluorescent and cross-linked polyphosphazene nanoparticles for highly sensitive and selective detection of dopamine in body fluids”, RSC Advances, vol. 5, pp. 92762, 2015.
  • [24] L. Meng, C. Xu, T. Liu, H. Li, Q. Lu, J. Long, “One-pot synthesis of highly cross-linked fluorescent polyphosphazene nanoparticles for cell imaging”, Polymer Chemistry, vol. 6, pp. 3155, 2015.
  • [25] Z. Wang, M. Hu, S. Hu, J. Han, Z. Wang, Y. Chen, C. Huang, L. Fu, Z. Zhang, “Facile one-pot synthesis of multifunctional polyphosphazene nanoparticles as multifunctional platform for tumor imaging”, Analytical and Bioanalytical Chemistry vol. 410, pp. 3723–3730, 2018.
  • [26] L. Sun, T. Liu, H. Li, L. Yang, L. Meng, Q. Lu, J. Long, “Fluorescent and cross-linked organic−inorganic hybrid nanoshells for monitoring drug delivery”, ACS Applied Materials and Interfaces, vol. 7, pp. 4990−4997, 2015.
  • [27] K.S.B Sam, L. George, SYN, A. Varghese. “Fluorescein based fluorescence sensors for the selective sensing of various analytes”, Journal of Fluorescence, vol. 31, pp. 1251 –1276, 2021.
  • [28] T. Preiß, A. Zimpel, S. Wuttke, J.O. Rädler, “Kinetic analysis of the uptake and release of fluorescein by metal-organic framework nanoparticles”, Materials, vol. 10, no. 2, pp. 216, 2017.
  • [29] A. Kumar, L. Li, A. Chaturvedi, J. Brzostowski, J. Chittigori, S. Pierce, L. A. Samuelson, D. Sandman, J. Kumar, “Two-photon fluorescence properties of curcumin as a biocompatible marker for confocal imaging”, Applied Physics Letters, vol. 100, pp. 203701, 2012.
  • [30] B. F. Mogharbel, J. C. Francisco, A. C. Irioda, D. S. M. Dziedzic, P. E. Ferreira, D. Souza, C. M. C. O. Souza, N. B. Neto, L. C. Guarita-Souza, C. R. C. Franco, C. V. Nakamura, V. Kaplum, L. Mazzarino, E. Lemos-Senna, R. Borsali, P. A. Soto, P. Setton-Avruj, E. Abdelwahid, K. A. T. Carvalho, “Fluorescence properties of curcumin-loaded nanoparticles for cell tracking”, International Journal of Nanomedicine, vol. 13, pp. 5823–5836, 2018.
  • [31] M. Y. Khorasania, H. Langaric, S. B. T. Sany, M. Rezayib, A. Sahebkar, “The role of curcumin and its derivatives in sensory applications”, Materials Science & Engineering C, vol. 103, pp. 109792, 2019.
  • [32] F. Chang, X. Huang, H, Wei, K. Chen, C. Shan, X. Tang, “Intrinsically fluorescent hollow spheres based on organic–inorganic hybrid polyphosphazene material: synthesis and application in drug release”, Materials Letters, vol. 125, pp. 128–131, 2014.
  • [33] S. Metinoğlu Örüm, “Novel cyclomatrix polyphosphazene nanospheres: preparation, characterization and dual anticancer drug release application”, Polymer Bulletin.
  • [34] Y. Wang, J. Mu, L. Li, L. Shi, W. Zhang, Z. Jiang, “Preparation and properties of novel fluorinated cross-linked polyphosphazene micro-nano spheres”, High Performance Polymers, vol. 24, pp. 229, 2012.
There are 34 citations in total.

Details

Primary Language English
Subjects Chemical Engineering
Journal Section Research Articles
Authors

Simge Metinoğlu Örüm 0000-0003-4166-4973

Publication Date August 31, 2022
Submission Date January 28, 2022
Acceptance Date June 21, 2022
Published in Issue Year 2022 Volume: 26 Issue: 4

Cite

APA Metinoğlu Örüm, S. (2022). Preparation and Characterization of Intrinsically Fluorescent Polyphosphazene Microspheres. Sakarya University Journal of Science, 26(4), 789-798.
AMA Metinoğlu Örüm S. Preparation and Characterization of Intrinsically Fluorescent Polyphosphazene Microspheres. SAUJS. August 2022;26(4):789-798.
Chicago Metinoğlu Örüm, Simge. “Preparation and Characterization of Intrinsically Fluorescent Polyphosphazene Microspheres”. Sakarya University Journal of Science 26, no. 4 (August 2022): 789-98.
EndNote Metinoğlu Örüm S (August 1, 2022) Preparation and Characterization of Intrinsically Fluorescent Polyphosphazene Microspheres. Sakarya University Journal of Science 26 4 789–798.
IEEE S. Metinoğlu Örüm, “Preparation and Characterization of Intrinsically Fluorescent Polyphosphazene Microspheres”, SAUJS, vol. 26, no. 4, pp. 789–798, 2022.
ISNAD Metinoğlu Örüm, Simge. “Preparation and Characterization of Intrinsically Fluorescent Polyphosphazene Microspheres”. Sakarya University Journal of Science 26/4 (August 2022), 789-798.
JAMA Metinoğlu Örüm S. Preparation and Characterization of Intrinsically Fluorescent Polyphosphazene Microspheres. SAUJS. 2022;26:789–798.
MLA Metinoğlu Örüm, Simge. “Preparation and Characterization of Intrinsically Fluorescent Polyphosphazene Microspheres”. Sakarya University Journal of Science, vol. 26, no. 4, 2022, pp. 789-98.
Vancouver Metinoğlu Örüm S. Preparation and Characterization of Intrinsically Fluorescent Polyphosphazene Microspheres. SAUJS. 2022;26(4):789-98.