pH-sensitive docetaxel-loaded chitosan/thiolated hyaluronic acid polymeric nanoparticles for colorectal cancer

Papers of special note have been highlighted as: • of interest; •• of considerable interest

References

• 1. Wathoni N, Nguyen AN, Rusdin A et al. Enteric-coated strategies in colorectal cancer nanoparticle drug delivery system. Drug Des. Devel. Ther. 14, 4387 (2020).
  Medline CASGoogle Scholar
• 2. Chiu HI, Ayub AD, Mat Yusuf SNA, Yahaya N, Abd Kadir E, Lim V. Docetaxel-loaded disulfide cross-linked nanoparticles derived from thiolated sodium alginate for colon cancer drug delivery. Pharmaceutics 12(1), 38 (2020).
  Medline CASGoogle Scholar
• 3. Yu Y, Fan P, Li J, Wang S. Preparation of biocompatible manganese selenium-based nanoparticles with antioxidant and catalytic functions. Molecules 28(11), 4498 (2023).
  Medline CASGoogle Scholar
• 4. Maqbool I, Noreen S. A review of novel techniques for nanoparticles preparation. GDDDR 4(1), 41–50 (2019).
  Google Scholar
• 5. Noreen S, Maqbool A, Maqbool I et al. Multifunctional mesoporous silica-based nanocomposites: synthesis and biomedical applications. Mater. Chem. Phys. 285, 126132 (2022).
  CASGoogle Scholar
• 6. Pervaiz F, Saleem M, Ashames A et al. Development and ex-vivo skin permeation studies of finasteride–poly (lactic acid-co-glycolic acid) and minoxidil–chitosan nanoparticulate systems. J. Bioact. Compat. Polym. 35(2), 77–91 (2020).
  CASGoogle Scholar
• 7. Kurakula M, Gorityala S, Moharir K. Recent trends in design and evaluation of chitosan-based colon targeted drug delivery systems: update 2020. J. Drug Deliv. Sci. Technol. 64, 102579 (2021).
  CASGoogle Scholar
• 8. Noreen S, Ma J-X, Saeed M et al. Natural polysaccharide-based biodegradable polymeric platforms for transdermal drug delivery system: a critical analysis. Drug Deliv. Transl. Res. 1–18 (2022).
  Google Scholar
• 9. Duggan S, Cummins W, O'Donovan O, Hughes H, Owens E. Thiolated polymers as mucoadhesive drug delivery systems. Eur. J. Pharm. Sci. 100, 64–78 (2017).
  Medline CASGoogle Scholar
• 10. Sobia N, Andreas B-S. Thiolated poly- and oligosaccharide-based hydrogels for tissue engineering and wound healing. Adv. Funct. Mater. 2310129 (2023). https://doi.org/10.1002/adfm.202310129 •• Similar mechanisms and drug-release justification for thiolated drug-delivery system as the current study.
  Google Scholar
• 11. Shahzadi I, Fürst A, Akkus-Dagdeviren ZB et al. Less reactive thiol ligands: key towards highly mucoadhesive drug delivery systems. Polymers 12(6), 1259 (2020).
  Medline CASGoogle Scholar
• 12. Alotaibi BS, Buabeid M, Ibrahim NA et al. Potential of nanocarrier-based drug delivery systems for brain targeting: a current review of literature. Int. J. Nanomed. 16, 7517 (2021).
  Medline CASGoogle Scholar
• 13. Cheng Z, Li M, Dey R, Chen Y. Nanomaterials for cancer therapy: current progress and perspectives. J. Hematol. Oncol. 14(1), 1–27 (2021).
  MedlineGoogle Scholar
• 14. Kesharwani P, Chadar R, Sheikh A, Rizg WY, Safhi AY. CD44-targeted nanocarrier for cancer therapy. Front. Pharmacol. 12, 800481 (2022).
  MedlineGoogle Scholar
• 15. Noreen S, Pervaiz F, Ijaz M, Shoukat H. Synthesis and characterization of pH-sensitive chemically crosslinked block copolymer [hyaluronic acid/poloxamer 407-co-poly (methacrylic acid)] hydrogels for colon targeting. POLYM-PLAST TECH MAT 1–17 (2022).
  Google Scholar
• 16. Maqbool I, Akhtar M, Ahmad R et al. Novel multiparticulate pH triggered delayed release chronotherapeutic drug delivery of celecoxib-β-cyclodextrin inclusion complexes by using Box–Behnken design. Eur. J. Pharm. Sci. 146, 105254 (2020). •• Similar design for Eudragit S-coated drug-delivery system as the current study.
  Medline CASGoogle Scholar
• 17. Lee SH, Bajracharya R, Min JY, Han J-W, Park BJ, Han H-K. Strategic approaches for colon targeted drug delivery: an overview of recent advancements. Pharmaceutics 12(1), 68 (2020).
  Medline CASGoogle Scholar
• 18. Chiu HI, Lim V. Wheat germ agglutinin-conjugated disulfide cross-linked alginate nanoparticles as a docetaxel carrier for colon cancer therapy. Int. J. Nanomed. 16, 2995 (2021).
  MedlineGoogle Scholar
• 19. Ibrahim MA, Shazly GA, Aleanizy FS, Alqahtani FY, Elosaily GM. Formulation and evaluation of docetaxel nanosuspensions: in-vitro evaluation and cytotoxicity. SPJ 27(1), 49–55 (2019).
  MedlineGoogle Scholar
• 20. Ijaz M, Griessinger JA, Mahmood A, Laffleur F, Bernkop-Schnürch A. Thiolated cyclodextrin: development of a mucoadhesive vaginal delivery system for acyclovir. J. Pharm. Sci. 105(5), 1714–1720 (2016). • Similar design for conjugation as the current study.
  Medline CASGoogle Scholar
• 21. Ijaz M, Matuszczak B, Rahmat D et al. Synthesis and characterization of thiolated β-cyclodextrin as a novel mucoadhesive excipient for intra-oral drug delivery. Carbohydr. Polym. 132, 187–195 (2015).
  Medline CASGoogle Scholar
• 22. Noreen S, Pervaiz F, Ashames A et al. Optimization of novel naproxen-loaded chitosan/carrageenan nanocarrier-based gel for topical delivery: ex vivo, histopathological, and in vivo evaluation. Pharmaceuticals 14(6), 557 (2021).
  Medline CASGoogle Scholar
• 23. Sakulwech S, Lourith N, Ruktanonchai U, Kanlayavattanakul M. Preparation and characterization of nanoparticles from quaternized cyclodextrin-grafted chitosan associated with hyaluronic acid for cosmetics. Asian J. Pharm. Sci. 13(5), 498–504 (2018).
  MedlineGoogle Scholar
• 24. Sladek S, McCartney F, Eskander M et al. An enteric-coated polyelectrolyte nanocomplex delivers insulin in rat intestinal instillations when combined with a permeation enhancer. Pharmaceutics 12(3), 259 (2020).
  Medline CASGoogle Scholar
• 25. Sajjad M, Khan MI, Naveed S et al. Folate-functionalized thiomeric nanoparticles for enhanced docetaxel cytotoxicity and improved oral bioavailability. AAPS PharmSciTech 20(2), 81 (2019).
  Medline CASGoogle Scholar
• 26. Suchaoin W, Bonengel S, Hussain S, Huck CW, Ma BN, Bernkop-Schnürch A. Synthesis and in vitro evaluation of thiolated carrageenan. J. Pharm. Sci. 104(8), 2523–2530 (2015).
  Medline CASGoogle Scholar
• 27. Iqbal J, Sarti F, Perera G, Bernkop-Schnürch A. Development and in vivo evaluation of an oral drug delivery system for paclitaxel. Biomaterials 32(1), 170–175 (2011).
  Medline CASGoogle Scholar
• 28. Suchaoin W, Bonengel S, Grießinger JA et al. Novel bioadhesive polymers as intra-articular agents: chondroitin sulfate-cysteine conjugates. Eur. J. Pharm. Biopharm. 101, 25–32 (2016).
  Medline CASGoogle Scholar
• 29. Asim MH, Silberhumer S, Shahzadi I, Jalil A, Matuszczak B, Bernkop-Schnürch A. S-protected thiolated hyaluronic acid: in-situ crosslinking hydrogels for 3D cell culture scaffold. Carbohydr. Polym. 237, 116092 (2020).
  Medline CASGoogle Scholar
• 30. Maria S, Sarwar HS, Sohail MF et al. Synthesis and characterization of pre-activated thiolated chitosan nanoparticles for oral delivery of octreotide. J. Drug Deliv. Sci. Technol. 101807, 58 (2020).
  Google Scholar
• 31. Sinha P, Udhumansha U, Rathnam G, Ganesh M, Jang HT. Capecitabine encapsulated chitosan succinate-sodium alginate macromolecular complex beads for colon cancer targeted delivery: in vitro evaluation. Int. J. Biol. Macromol. 117, 840–850 (2018).
  Medline CASGoogle Scholar
• 32. Rosengren A, Faxius L, Tanaka N, Watanabe M, Bjursten LM. Comparison of implantation and cytotoxicity testing for initially toxic biomaterials. J. Biomed. Mater. Res. A 75(1), 115–122 (2005).
  MedlineGoogle Scholar
• 33. Valenta C, Auner BG. The use of polymers for dermal and transdermal delivery. Eur. J. Pharm. Biopharm. 58(2), 279–289 (2004).
  Medline CASGoogle Scholar
• 34. Aldawsari HM, Singh S, Alhakamy NA et al. Adenosine conjugated docetaxel nanoparticles – proof of concept studies for non-small cell lung cancer. Pharmaceuticals 15(5), 544 (2022).
  Medline CASGoogle Scholar
• 35. Hua SJFIP. Advances in oral drug delivery for regional targeting in the gastrointestinal tract-influence of physiological, pathophysiological and pharmaceutical factors. Front. Pharmacol. 11, 524 (2020).
  Medline CASGoogle Scholar
• 36. Subudhi MB, Jain A, Jain A et al. Eudragit S100 coated citrus pectin nanoparticles for colon targeting of 5-fluorouracil. Materials 8(3), 832–849 (2015).
  Medline CASGoogle Scholar
• 37. Alsarra IA, Yassin AEB, Alanazi FK, Aljuffali IA, Abdel-Hamid M. Direct UPLC-MS-MS validated method for the quantification of 5-aminolevulinic acid: application to in-vitro assessment of colonic-targeted oral tablets. J. Chromatogr. Sci. 49(6), 428–433 (2011).
  Medline CASGoogle Scholar
• 38. Bugata LSP, Pitta Venkata P, Gundu AR et al. Acute and subacute oral toxicity of copper oxide nanoparticles in female albino Wistar rats. J. Appl. Toxicol. 39(5), 702–716 (2019).
  Medline CASGoogle Scholar
• 39. Mahmood S, Buabeid MA, Ullah K, Murtaza G, Mannan A, Khan SA. Synthesis, characterization and safety profiling of Eudragit-based pH-responsive hydrogels: a promising platform for colonic delivery of losartan potassium. Curr. Drug Deliv. 16(6), 548–564 (2019).
  Medline CASGoogle Scholar
• 40. Kafedjiiski K, Jetti RK, Föger F et al. Synthesis and in vitro evaluation of thiolated hyaluronic acid for mucoadhesive drug delivery. Int. J. Pharm. 343(1–2), 48–58 (2007).
  Medline CASGoogle Scholar
• 41. Kotla NG, Bonam SR, Rasala S et al. Recent advances and prospects of hyaluronan as a multifunctional therapeutic system. JCR 336, 598–620 (2021).
  Medline CASGoogle Scholar
• 42. Xia D, Wang F, Pan S, Yuan S, Liu Y, Xu YJP. Redox/pH-responsive biodegradable thiol-hyaluronic acid/chitosan charge-reversal nanocarriers for triggered drug release. Polymers 13(21), 3785 (2021).
  Medline CASGoogle Scholar
• 43. Bencherif SA, Washburn NR, Matyjaszewski KJB. Synthesis by AGET ATRP of degradable nanogel precursors for in situ formation of nanostructured hyaluronic acid hydrogel. Biomacromolecules 10(9), 2499–2507 (2009).
  Medline CASGoogle Scholar
• 44. Nyquist R, Potts W. Characteristic infrared absorption frequencies of thiol esters and related compounds. Spectrochim. Acta 15, 514–538 (1959).
  Google Scholar
• 45. Li R. A Novel Thiolated Hyaluronic acid Hydrogel for Spinal Cord Injury Repair. (Doctoral dissertation, Université d'Ottawa/University of Ottawa). (2014).
  Google Scholar
• 46. Chiesa E, Dorati R, Conti B et al. Hyaluronic acid-decorated chitosan nanoparticles for CD44-targeted delivery of everolimus. Int. J. Mol. Sci. 19(8), 2310 (2018).
  MedlineGoogle Scholar
• 47. Umair M, Javed I, Rehman M et al. Nanotoxicity of inert materials: the case of gold, silver and iron. J. Pharm. Pharm. Sci. 19(2), 161–180 (2016).
  Medline CASGoogle Scholar
• 48. Alvi Z, Akhtar M, Rahman NU et al. Utilization of gelling polymer to formulate nanoparticles loaded with epalrestat-cyclodextrin inclusion complex: formulation, characterization, in-silico modelling and in-vivo toxicity evaluation. Polymers 13(24), 4350 (2021).
  Medline CASGoogle Scholar
• 49. Geethakumari D, Sathyabhama AB, Sathyan KR, Mohandas D, Somasekharan JV, Puthiyedathu ST. Folate functionalized chitosan nanoparticles as targeted delivery systems for improved anticancer efficiency of cytarabine in MCF-7 human breast cancer cell lines. Int. J. Biol. Macromol. 199, 150–161 (2022).
  Medline CASGoogle Scholar
• 50. Gan Q, Wang T, Cochrane C, McCarron P. Modulation of surface charge, particle size and morphological properties of chitosan–TPP nanoparticles intended for gene delivery. Colloids Surf. B 44(2), 65–73 (2005).
  Medline CASGoogle Scholar
• 51. Yang W, Fu J, Wang T, He N. Chitosan/sodium tripolyphosphate nanoparticles: preparation, characterization and application as drug carrier. J. Biomed. Nanotechnol. 5(5), 591–595 (2009).
  Medline CASGoogle Scholar
• 52. Shanmuga S, Singhal M, Sen S. Synthesis and characterization of carrageenan coated magnetic nanoparticles for drug delivery applications. Transl. Biomed. 6(3), 19 (2015).
  Google Scholar
• 53. Kendall RA, Alhnan MA, Nilkumhang S, Murdan S, Basit AW. Fabrication and in vivo evaluation of highly pH-responsive acrylic microparticles for targeted gastrointestinal delivery. Eur. J. Pharm. Sci. 37(3–4), 284–290 (2009).
  Medline CASGoogle Scholar
• 54. Agarwal D, Ranawat MS, Chauhan CS, Kamble R. Formulation and chracterization of colon targeted pH dependent microspheres of capecitabine for colorectal cancer. J. Drug Deliv. Ther. 3(6), 215–222 (2013).
  Google Scholar
• 55. Paharia A, Yadav AK, Rai G, Jain SK, Pancholi SS, Agrawal GP. Eudragit-coated pectin microspheres of 5-fluorouracil for colon targeting. AAPS PharmSciTech 8(1), e87–e93 (2007).
  Google Scholar
• 56. Sareen R, Jain N, Rajkumari A, Dhar KL. pH triggered delivery of curcumin from Eudragit-coated chitosan microspheres for inflammatory bowel disease: characterization and pharmacodynamic evaluation. Drug Deliv. 23(1), 55–62 (2016).
  Medline CASGoogle Scholar
• 57. Obeidat WM, Obeidat SM, Alzoubi NM. Investigations on the physical structure and the mechanism of drug release from an enteric matrix microspheres with a near-zero-order release kinetics using SEM and quantitative FTIR. AAPS PharmSciTech 10(2), 615–623 (2009).
  Medline CASGoogle Scholar
• 58. Rawat M, Saraf S, Saraf S. Influence of selected formulation variables on the preparation of enzyme-entrapped Eudragit S100 microspheres. AAPS PharmSciTech 8(4), 289–297 (2007).
  Google Scholar
• 59. Zhang S, Guo N, Wan G et al. pH and redox dual-responsive nanoparticles based on disulfide-containing poly (β-amino ester) for combining chemotherapy and COX-2 inhibitor to overcome drug resistance in breast cancer. J. Nanobiotechnol. 17(1), 1–17 (2019).
  MedlineGoogle Scholar
• 60. Nowak J, Laffleur F, Bernkop-Schnürch A. Preactivated hyaluronic acid: a potential mucoadhesive polymer for vaginal delivery. Int. J. Pharm. 478(1), 383–389 (2015).
  Medline CASGoogle Scholar
• 61. Tsakalozou E, Eckman AM, Bae Y. Combination effects of docetaxel and doxorubicin in hormone-refractory prostate cancer cells. Biochem. Res. Int. 2012, 832059 (2012).
  MedlineGoogle Scholar
• 62. Lee E, Kim H, Lee I-H, Jon S. In vivo antitumor effects of chitosan-conjugated docetaxel after oral administration. JCR 140(2), 79–85 (2009).
  Medline CASGoogle Scholar
• 63. Asnani GP, Kokare CR. In vitro and in vivo evaluation of colon cancer targeted epichlorohydrin crosslinked Portulaca-alginate beads. Biomol. Concepts 9(1), 190–199 (2018).
  Medline CASGoogle Scholar
• 64. Singh I, Swami R, Jeengar MK, Khan W, Sistla RJC, Lipids PO. p-Aminophenyl-α-D-mannopyranoside engineered lipidic nanoparticles for effective delivery of docetaxel to brain. Chem. Phys. Lipids 188, 1–9 (2015).
  Medline CASGoogle Scholar
• 65. Wei H, Qing D, De-Ying C, Bai X, Fanli-Fang. Pectin/Ethylcellulose as film coatings for colon-specific drug delivery: preparation and in vitro evaluation using 5-fluorouracil pellets. PDA J. Pharm. Sci. Technol. 61(2), 121–130 (2007).
  Medline CASGoogle Scholar
• 66. Bohaumilitzky L, Huber A-K, Stork EM, Wengert S, Woelfl F, Boehm H. A trickster in disguise: hyaluronan's ambivalent roles in the matrix. Front. Oncol. 7, 242 (2017).
  MedlineGoogle Scholar
• 67. Leichner C, Jelkmann M, Bernkop-Schnürch A. Thiolated polymers: bioinspired polymers utilizing one of the most important bridging structures in nature. Adv. Drug Deliv. Rev. 151, 191–221 (2019).
  MedlineGoogle Scholar
• 68. Muhammad M, Willems C, Rodríguez-Fernández J, Gallego-Ferrer G, Groth T. Synthesis and characterization of oxidized polysaccharides for in situ forming hydrogels. Biomolecules 10(8), 1185 (2020).
  Medline CASGoogle Scholar
• 69. Pérez LA, Hernández R, Alonso JM, Pérez-González R, Sáez-Martínez V. Granular disulfide-crosslinked hyaluronic hydrogels: a systematic study of reaction conditions on thiol substitution and injectability parameters. Polymers 15(4), 966 (2023).
  Medline CASGoogle Scholar
• 70. Griesser J, Hetényi G, Bernkop-Schnürch A. Thiolated hyaluronic acid as versatile mucoadhesive polymer: from the chemistry behind to product developments – what are the capabilities? Polymers 10(3), 243 (2018).
  MedlineGoogle Scholar