journal article·2022-05

Development of stimulus-sensitive electrospun membranes based on novel biodegradable segmented polyurethane as triggered delivery system for doxorubicin

Salvatore Federico, Annalisa Martorana, Giovanna Pitarresi, Fabio S. Palumbo, Calogero Fiorica, Gaetano Giammona

Publisher page

Abstract

In this work, redox-sensitive polyurethane urea (PUU) based electrospun membranes have been exploited to chemically tether a pH-sensitive doxorubicin derivative achieved by linking a lipoyl hydrazide to the drug via a hydrazone linkage. First, the lipoyl-hydrazone-doxorubicin derivative labelled as LA-Hy-Doxo has been synthesized and characterized. Then, the molecule has been tethered, via a thiol-disulfide exchange reaction, to the redox-sensitive PUU (PolyCEGS) electrospun membrane. The redox-sensitive PolyCEGS PUU has been produced by using PCL-PEG-PCL polyol and glutathione-tetramethyl ester (GSSG-OMe)4 as a chain extender. The LA-Hy-Doxo tethered electrospun membrane has showed a dually controlled release triggered by acidic and reducing conditions, producing a significant cytotoxic effect in human breast cancer cell lines (MCF-7) which has validated the system for the post-surgical treatment of solid tumors to contrast recurrence.
Source: europepmc · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Electrospun Nanofibers in Biomedical Applications · Dendrimers and Hyperbranched Polymers · Nanoplatforms for cancer theranostics

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (98)

Show source-provided references
1. Electrospinning of polymeric nanofibers for drug delivery applications10.1016/j.jconrel.2014.04.018 ↗
2. Electrospinning: applications in drug delivery and tissue engineering10.1016/j.biomaterials.2008.01.011 ↗
3. Electrospinning for drug delivery applications: a review10.1016/j.jconrel.2021.03.033 ↗
4. Recent advances in electrospun nanofiber- mediated drug delivery strategies for localized cancer chemotherapy10.1002/jbm.a.36912 ↗
5. Controlled release of a hydrophilic drug from coaxially electrospun polycaprolactone nanofibers10.1016/j.ijpharm.2016.03.032 ↗
6. Current strategies for sustaining drug release from electrospun nanofibers10.1016/j.jconrel.2015.09.008 ↗
7. Biphasic drug release from electrospun polyblend nanofibers for optimized local cancer treatment10.1039/C7BM01018D ↗
8. Functional electrospun fibers for local therapy of cancer10.1007/s42765-020-00053-9 ↗
9. Tailored design of electrospun composite nanofibers with staged release of multiple angiogenic growth factors for chronic wound healing10.1016/j.actbio.2014.05.001 ↗
10. Polyaspartamide-polylactide electrospun scaffolds for potential topical release of Ibuprofen10.1002/jbm.a.34095 ↗
11. Electrospun biphasic drug release polyvinylpyrrolidone / ethyl cellulose core / sheath nanofibers10.1016/j.actbio.2012.10.021 ↗
12. A fiber distribution model for predicting drug release rates10.1016/j.jconrel.2017.05.021 ↗
13. Uhrich · 1999 · 3181
14. Zeng · 2003 · 92 · 227
15. An asymmetric electrospun membrane for the controlled release of ciprofloxacin and FGF-2: evaluation of antimicrobial and chemoattractant properties10.1016/j.msec.2021.112001 ↗
16. Asymmetric membranes as ideal wound dressings: an overview on production methods, structure, properties and performance relationship10.1016/j.memsci.2015.04.064 ↗
17. Controlled delivery of stromal derived factor-1α from poly lactic-co-glycolic acid core-shell particles to recruit mesenchymal stem cells for cardiac regeneration10.1016/j.jcis.2015.04.005 ↗
18. European journal of pharmaceutics and biopharmaceutics recent advances in multiaxial electrospinning for drug delivery10.1016/j.ejpb.2016.11.010 ↗
19. Drug delivery applications of Core-sheath nanofibers prepared by coaxial electrospinning : a review10.3390/pharmaceutics11070305 ↗
20. Processing-structure-property correlations of polyethersulfone/ perfluorosulfonic acid nanofibers fabricated via electrospinning from polymer-nanoparticle suspensions10.1021/am201843y ↗
21. Neurite outgrowth on nanofiber scaffolds with different orders, structures, and surface properties10.1021/nn900070z ↗
22. Gelation of gellan - a review10.1016/j.foodhyd.2012.01.004 ↗
23. Hyaluronan alkyl derivatives-based electrospun membranes for potential guided bone regeneration: fabrication, characterization and in vitro osteoinductive properties10.1016/j.colsurfb.2020.111438 ↗
24. Electrospun poly(N-isopropylacrylamide)/poly(caprolactone)-based polyurethane nanofibers as drug carriers and temperature-controlled release10.1039/c3nj00275f ↗
25. A drug-self-gated mesoporous antitumor nanoplatform based on pH-sensitive dynamic covalent bond10.1002/adfm.201605985 ↗
26. Thermally switched release from a nanogel-in-microfiber device10.1002/adhm.201500267 ↗
27. Regulation of cytoplasmic pH in phagocytic cell function and dysfunction10.1016/0009-9120(91)80014-T ↗
28. Implications of acidic tumor microenvironment for neoplastic growth and cancer treatment: a computer analysis10.1159/000217977 ↗
29. Conducting polymer artificial muscles10.1016/0379-6779(96)80158-5 ↗
30. Collapse of gels in an electric field10.1126/science.218.4571.467 ↗
31. The use of chitosan gels as matrices for electrically-modulated drug delivery10.1016/S0168-3659(00)00333-3 ↗
32. Loading into and electro-stimulated release of peptides and proteins from chondroitin 4-sulphate hydrogels10.1016/S0928-0987(01)00193-2 ↗
33. Conducting-polymer nanotubes for controlled drug release10.1002/adma.200501726 ↗
34. Use of conducting electroactive polymers for drug delivery and sensing of bioactive molecules. A redox chemistry approach10.1021/jp994274o ↗
35. Highly elastic and conductive human-based protein hybrid hydrogels10.1002/adma.201503255 ↗
36. Electro-responsive transdermal drug delivery behavior of PVA/PAA/MWCNT nanofibers10.1016/j.eurpolymj.2011.07.024 ↗
37. Presynaptic modulation of efferent sympathetic and vagal neurotransmission in the canine heart by hypoxia, high K+, low pH, and adenosine. Possible relevance to ischemia-induced denervation10.1161/01.RES.66.2.289 ↗
38. Head group modulated pH-responsive hydrogel of amino acid-based amphiphiles: entrapment and release of cytochrome c and vitamin B1210.1021/la704024p ↗
39. Electrospun fibers of acid-labile biodegradable polymers containing ortho ester groups for controlled release of paracetamol10.1016/j.ejpb.2008.05.003 ↗
40. Light-driven wettability changes on a photoresponsive electrospun mat10.1021/nn103577g ↗
41. Ultra-fine polyelectrolyte fibers from electrospinning of poly(acrylic acid)10.1016/j.polymer.2005.04.039 ↗
42. Smart electrospun nanofibers for controlled drug release: recent advances and new perspectives10.2174/1381612821666150302151959 ↗
43. Smart electrospun nanofibers containing PCL/gelatin/graphene oxide for application in nerve tissue engineering10.1016/j.msec.2019.109768 ↗
44. Hollow MnO2 as a tumor-microenvironment-responsive biodegradable nano-platform for combination therapy favoring antitumor immune responses10.1038/s41467-017-01050-0 ↗
45. Phosphorylcholine-based stealthy nanocapsules enabling tumor microenvironment-responsive doxorubicin release for tumor suppression10.7150/thno.17881 ↗
46. Amphiphilic block copolymers bearing ortho ester side-chains: pH-dependent hydrolysis and self-assembly in water10.1002/mabi.200900229 ↗
47. Evaluation of multivalent dendrimers based on melamine: kinetics of Thiol−Disulfide exchange depends on the structure of the dendrimer10.1021/ja0210906 ↗
48. Design of controlled drug delivery system based on disulfide cleavage trigger10.1021/jp507763a ↗
49. Electrospun nanofibers for cancer diagnosis and therapy10.1039/C6BM00070C ↗
50. Electrospinning: an enabling nanotechnology platform for drug delivery and regenerative medicine10.1016/j.addr.2018.05.001 ↗
51. Doxorubicin-conjugated pH-responsive gold nanorods for combined photothermal therapy and chemotherapy of cancer
52. Disulfide-cleavage-triggered chemosensors and their biological applications10.1021/cr300358b ↗
53. Effect of actively targeted copolymer coating on solid tumors eradication by gold nanorods-induced hyperthermia10.1016/j.ijpharm.2020.119641 ↗
54. Enhanced adhesion and in situ photothermal ablation of cancer cells in surface-functionalized electrospun microfiber scaffold with graphene oxide10.1016/j.ijpharm.2017.04.045 ↗
55. Current applications of electrospun polymeric nanofibers in cancer therapy10.1016/j.msec.2018.12.105 ↗
56. One-pot fabrication of dual-redox sensitive, stabilized supramolecular nanocontainers for potential programmable drug release using a multifunctional cyclodextrin unit10.1016/j.jconrel.2021.04.027 ↗
57. Facile preparation of pH/redox dual-responsive biodegradable polyphosphazene prodrugs for effective cancer chemotherapy10.1016/j.colsurfb.2021.111573 ↗
58. Dual and multi-stimuli responsive polymeric nanoparticles for programmed site-specific drug delivery10.1016/j.biomaterials.2013.01.084 ↗
59. pH/Redox dual-responsive polyplex with effective endosomal escape for codelivery of siRNA and doxorubicin against drug-resistant cancer cells10.1021/acsami.9b02016 ↗
60. Liu · 2018
61. Glutathione responsive polymers and their application in drug delivery systems10.1039/C6PY01365A ↗
62. Dual-responsive multicompartment nanofibers for controlled release of payloads10.1039/C6RA05687C ↗
63. Synthesis and characterization of redox-sensitive polyurethanes based on L-glutathione oxidized and poly(ether ester) triblock copolymers10.1016/j.reactfunctpolym.2021.104986 ↗
64. Development of biodegradable crosslinked urethane-doped polyester elastomers10.1016/j.biomaterials.2008.08.020 ↗
65. Biodegradable poly(ether ester urethane)urea elastomers based on poly(ether ester) triblock copolymers and putrescine: synthesis, characterization and cytocompatibility10.1016/S0142-9612(03)00476-9 ↗
66. Synthesis, characterization and cytocompatibility of polyurethaneurea elastomers with designed elastase sensitivity10.1021/bm0503322 ↗
67. Analysis for disulfide bonds in peptides and proteins10.1016/0076-6879(87)43020-6 ↗
68. Evaluation in vitro of adriamycin immunoconjugates synthesized using an acid-sensitive hydrazone linker
69. Synthesis and thermal properties of poly(ethylene glycol)-poly(e-caprolactone) copolymers10.1016/S0032-3861(97)00444-8 ↗
70. Kinetics of Sn(Oct)2-catalyzed ring opening polymerization of ε-caprolactone10.1007/s13233-017-5148-z ↗
71. A convenient synthesis of amino acid methyl esters10.3390/molecules13051111 ↗
72. Combining inulin multifunctional polycation and magnetic nanoparticles: redox-responsive siRNA-loaded systems for magnetofection10.3390/polym11050889 ↗
73. Characterisation of the conjugate of the (6-maleimidocaproyl)hydrazone derivative of doxorubicin with lactosaminated human albumin by 13C NMR spectroscopy10.1016/j.ejps.2009.08.001 ↗
74. Selective reduction of disulfides by Tris(2-carboxyethyl)phosphine10.1021/jo00008a014 ↗
75. Novel doxorubicin derivatives: synthesis and cytotoxicity study in 2D and 3D in vitro models10.15171/apb.2017.071 ↗
76. Synthesis of doxorubicin α-linolenic acid conjugate and evaluation of its antitumor activity10.1021/mp4004139 ↗
77. Photochemical transformation of lipoic acid-based ligands: probing the effects of solvent, ligand structure, oxygen and pH10.1039/C7CP06350D ↗
78. Biodegradable poly(ester urethane)urea elastomers with variable amino content for subsequent functionalization with phosphorylcholine10.1016/j.actbio.2014.08.008 ↗
79. Efficient esterification of oxidized l-glutathione and other small peptides10.3390/molecules200610487 ↗
80. Synthesis and characterization of a novel biodegradable thermoplastic shape memory polymer10.1016/j.matlet.2008.10.014 ↗
81. Preparation of poly(ethylene glycol)-block-poly(caprolactone) copolymers and their applications as thermo-sensitive materials10.1002/jbm.a.30049 ↗
82. Role of chain entanglements on fiber formation during electrospinning of polymer solutions: good solvent, non-specific polymer-polymer interaction limit10.1016/j.polymer.2005.03.011 ↗
83. Effect of alkyl derivatization of gellan gum during the fabrication of electrospun membranes
84. Properties-morphology relationships in electrospun mats based on polylactic acid and graphene nanoplatelets10.1016/j.compositesa.2018.02.026 ↗
85. Preparation, optimisation and characterisation of novel wound healing film dressings loaded with streptomycin and diclofenac10.1016/j.colsurfb.2012.08.014 ↗
86. Surface modification of au nanoparticles with heteroleptic Cu(I) diimine complexes10.1021/acs.jpcc.0c01881 ↗
87. The ultra-sensitive electrochemical detection of As(III) in ground water using disposable L-cysteine/Lipoic acid functionalised gold nanoparticle modified screen-printed electrodes10.1007/s12678-021-00658-7 ↗
88. Simultaneous determination of α-lipoic acid and its reduced form by high-performance liquid chromatography with fluorescence detection10.1016/j.jchromb.2007.04.003 ↗
89. NIR initiated and pH sensitive single-wall carbon nanotubes for doxorubicin intracellular delivery10.1039/c3tb21362e ↗
90. Electrospun matrices for localized drug delivery: current technologies and selected biomedical applications10.1016/j.ejpb.2012.01.016 ↗
91. Reduction-sensitive polymers and bioconjugates for biomedical applications10.1016/j.biomaterials.2009.01.026 ↗
92. Synthesis and antiproliferative activities of doxorubicin thiol conjugates and doxorubicin-SS-cyclic peptide10.1016/j.ejmech.2018.10.042 ↗
93. Disulfide-crosslinked reduction-responsive prodrug micelles for on-demand paclitaxel release
94. Conjugation of doxorubicin to siRNA through disulfide-based self-immolative linkers10.3390/molecules25112714 ↗
95. Synthesis of doxorubicin conjugates through hydrazone bonds to melanotransferrin p9710.1081/SCC-120021827 ↗
96. Preparation and characterization of lipophilic doxorubicin pro-drug micelles
97. NADH-linked metabolic plasticity of MCF-7 breast cancer cells surviving in a nutrient-deprived microenvironment10.1002/jcb.25038 ↗
98. Acidification prevents endothelial cell apoptosis by axl activation10.1161/01.RES.0000036753.50601.E9 ↗