4D printable salicylic acid photopolymers for sustained drug releasing, shape memory, soft tissue scaffolds

3D printing of pharmaceuticals offers a unique opportunity for long-term, sustained drug release profiles for an array of treatment options. Unfortunately, this approach is often limited by physical compounding or processing limitations. Modification of the active drug into a prodrug compound allows...

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Detalhes bibliográficos
Autores: King, Olivia, Pérez Madrigal, Maria del Mar|||0000-0002-2498-8485, Murphy, Erin, Al Rida Hmayed, Ali, Dove, Andrew, Weems, Andrew C.
Formato: artículo
Fecha de publicación:2023
País:España
Recursos:Universitat Politècnica de Catalunya (UPC)
Repositorio:UPCommons. Portal del coneixement obert de la UPC
Idioma:inglés
OAI Identifier:oai:upcommons.upc.edu:2117/407027
Acesso em linha:https://hdl.handle.net/2117/407027
https://dx.doi.org/10.1021/acs.biomac.3c00416
Access Level:acceso abierto
Palavra-chave:Biomedical materials
3D printing
Allyl group
Drug release
Organic compounds
Organic polymers
Materials biomèdics
Àrees temàtiques de la UPC::Enginyeria biomèdica::Biomaterials
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spelling 4D printable salicylic acid photopolymers for sustained drug releasing, shape memory, soft tissue scaffoldsKing, OliviaPérez Madrigal, Maria del Mar|||0000-0002-2498-8485Murphy, ErinAl Rida Hmayed, AliDove, AndrewWeems, Andrew C.Biomedical materials3D printingAllyl groupDrug releaseOrganic compoundsOrganic polymersMaterials biomèdicsÀrees temàtiques de la UPC::Enginyeria biomèdica::Biomaterials3D printing of pharmaceuticals offers a unique opportunity for long-term, sustained drug release profiles for an array of treatment options. Unfortunately, this approach is often limited by physical compounding or processing limitations. Modification of the active drug into a prodrug compound allows for seamless incorporation with advanced manufacturing methods that open the door to production of complex tissue scaffold drug depots. Here we demonstrate this concept using salicylic acids with varied prodrug structures for control of physical and chemical properties. The role of different salicylic acid derivatives (salicylic acid, bromosalicylic allyl ester, iodosalicylic allyl ester) and linker species (allyl salicylate, allyl 2-(allyloxy)benzoate, allyl 2-(((allyloxy)carbonyl)oxy)benzoate) were investigated using thiol–ene cross-linking in digital light processing (DLP) 3D printing to produce porous prodrug tissue scaffolds containing more than 50% salicylic acid by mass. Salicylic acid photopolymer resins were all found to be highly reactive (solidification within 5 s of irradiation at ¿ = 405 nm), while the cross-linked solids display tunable thermomechanical behaviors with low glass transition temperatures (Tgs) and elastomeric behaviors, with the carbonate species displaying an elastic modulus matching that of adipose tissue (approximately 65 kPa). Drug release profiles were found to be zero order, sustained release based upon hydrolytic degradation of multilayered scaffolds incorporating fluorescent modeling compounds, with release rates tuned through selection of the linker species. Cytocompatibility in 2D and 3D was further demonstrated for all species compared to polycarbonate controls, as well as salicylic acid-containing composites (physical incorporation), over a 2-week period using murine fibroblasts. The use of drugs as the matrix material for solid prodrug tissue scaffolds opens the door to novel therapeutic strategies, longer sustained release profiles, and even reduced complications for advanced medicine.American Chemical Society20232023-01-0120242024-04-24journal articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/2117/407027https://dx.doi.org/10.1021/acs.biomac.3c00416reponame:UPCommons. Portal del coneixement obert de la UPCinstname:Universitat Politècnica de Catalunya (UPC)Inglésengopen accesshttp://purl.org/coar/access_right/c_abf2info:eu-repo/semantics/openAccessoai:upcommons.upc.edu:2117/4070272026-05-27T15:37:01Z
dc.title.none.fl_str_mv 4D printable salicylic acid photopolymers for sustained drug releasing, shape memory, soft tissue scaffolds
title 4D printable salicylic acid photopolymers for sustained drug releasing, shape memory, soft tissue scaffolds
spellingShingle 4D printable salicylic acid photopolymers for sustained drug releasing, shape memory, soft tissue scaffolds
King, Olivia
Biomedical materials
3D printing
Allyl group
Drug release
Organic compounds
Organic polymers
Materials biomèdics
Àrees temàtiques de la UPC::Enginyeria biomèdica::Biomaterials
title_short 4D printable salicylic acid photopolymers for sustained drug releasing, shape memory, soft tissue scaffolds
title_full 4D printable salicylic acid photopolymers for sustained drug releasing, shape memory, soft tissue scaffolds
title_fullStr 4D printable salicylic acid photopolymers for sustained drug releasing, shape memory, soft tissue scaffolds
title_full_unstemmed 4D printable salicylic acid photopolymers for sustained drug releasing, shape memory, soft tissue scaffolds
title_sort 4D printable salicylic acid photopolymers for sustained drug releasing, shape memory, soft tissue scaffolds
dc.creator.none.fl_str_mv King, Olivia
Pérez Madrigal, Maria del Mar|||0000-0002-2498-8485
Murphy, Erin
Al Rida Hmayed, Ali
Dove, Andrew
Weems, Andrew C.
author King, Olivia
author_facet King, Olivia
Pérez Madrigal, Maria del Mar|||0000-0002-2498-8485
Murphy, Erin
Al Rida Hmayed, Ali
Dove, Andrew
Weems, Andrew C.
author_role author
author2 Pérez Madrigal, Maria del Mar|||0000-0002-2498-8485
Murphy, Erin
Al Rida Hmayed, Ali
Dove, Andrew
Weems, Andrew C.
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Biomedical materials
3D printing
Allyl group
Drug release
Organic compounds
Organic polymers
Materials biomèdics
Àrees temàtiques de la UPC::Enginyeria biomèdica::Biomaterials
topic Biomedical materials
3D printing
Allyl group
Drug release
Organic compounds
Organic polymers
Materials biomèdics
Àrees temàtiques de la UPC::Enginyeria biomèdica::Biomaterials
description 3D printing of pharmaceuticals offers a unique opportunity for long-term, sustained drug release profiles for an array of treatment options. Unfortunately, this approach is often limited by physical compounding or processing limitations. Modification of the active drug into a prodrug compound allows for seamless incorporation with advanced manufacturing methods that open the door to production of complex tissue scaffold drug depots. Here we demonstrate this concept using salicylic acids with varied prodrug structures for control of physical and chemical properties. The role of different salicylic acid derivatives (salicylic acid, bromosalicylic allyl ester, iodosalicylic allyl ester) and linker species (allyl salicylate, allyl 2-(allyloxy)benzoate, allyl 2-(((allyloxy)carbonyl)oxy)benzoate) were investigated using thiol–ene cross-linking in digital light processing (DLP) 3D printing to produce porous prodrug tissue scaffolds containing more than 50% salicylic acid by mass. Salicylic acid photopolymer resins were all found to be highly reactive (solidification within 5 s of irradiation at ¿ = 405 nm), while the cross-linked solids display tunable thermomechanical behaviors with low glass transition temperatures (Tgs) and elastomeric behaviors, with the carbonate species displaying an elastic modulus matching that of adipose tissue (approximately 65 kPa). Drug release profiles were found to be zero order, sustained release based upon hydrolytic degradation of multilayered scaffolds incorporating fluorescent modeling compounds, with release rates tuned through selection of the linker species. Cytocompatibility in 2D and 3D was further demonstrated for all species compared to polycarbonate controls, as well as salicylic acid-containing composites (physical incorporation), over a 2-week period using murine fibroblasts. The use of drugs as the matrix material for solid prodrug tissue scaffolds opens the door to novel therapeutic strategies, longer sustained release profiles, and even reduced complications for advanced medicine.
publishDate 2023
dc.date.none.fl_str_mv 2023
2023-01-01
2024
2024-04-24
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
VoR
http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/2117/407027
https://dx.doi.org/10.1021/acs.biomac.3c00416
url https://hdl.handle.net/2117/407027
https://dx.doi.org/10.1021/acs.biomac.3c00416
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:UPCommons. Portal del coneixement obert de la UPC
instname:Universitat Politècnica de Catalunya (UPC)
instname_str Universitat Politècnica de Catalunya (UPC)
reponame_str UPCommons. Portal del coneixement obert de la UPC
collection UPCommons. Portal del coneixement obert de la UPC
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869423876780326912
score 15,300719

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