Clickable polysaccharides for biomedical applications: A comprehensive review. (October 2022)

• Record Type: Journal Article
• Authors: Khodadadi Yazdi, Mohsen; Sajadi, S. Mohammad; Seidi, Farzad; Rabiee, Navid; Fatahi, Yousef; Rabiee, Mohammad; Dominic, C.D. Midhun; Zarrintaj, Payam; Formela, Krzysztof; Saeb, Mohammad Reza; Bencherif, Sidi A.
• Is Part Of: Progress in polymer science. Volume 133(2022)
• Publication Date: 2022-10
• Subjects: Polysaccharides -- Click chemistry -- Bioorthogonal reactions -- Biomaterials -- Drug delivery -- Tissue engineering -- Wound healing; 2-APBA 2-acetylphenyl boronic acid -- 2-FPBA 2-formylphenyl boronic acid -- 3D three dimensional -- 4-arm PEG-N3 azide-functionalized four-armed polyethylene glycol -- 4-arm PEG-TCO trans-cyclooctene-functionalized four-armed polyethylene glycol -- β-HHz β-hydroxy hydrazides -- β-CD β-cyclodextrin -- AAC azide-alkyne cycloaddition -- Ac4ManNAz tetraacetylated N-azidoacetyl-D-mannosamine -- Ac-β-CD acetalated β-cyclodextrin -- ADIBO azadibenzocyclooctyne -- ADIBO-Chol ADIBO modified cholesterol -- ADIBO-DSPE ADIBO modified distearyl phosphatidyl ethanolamine -- ADIBO-PEG4-NOTA-64Cu azadibenzocyclooctyne (ADIBO) and 1, 4, 7-triazacyclononane-N, N', N''-triacetic acid (NOTA) dually functionalized 4-unit polyethylene glycol labeled with 64Cu radioisotope -- ADSC adipose-derived mesenchymal stem cells -- Ag silver -- AGA automated glycan assembly -- AHA oxidized hyaluronic acid -- AI artificial intelligence -- AIBN azobisisobutyronitrile -- Alg alginate -- Alg-Nor norbornene-functionalized alginate -- Alg-Tz tetrazine-functionalized alginate -- Alkylated-PEG alkylated polyethylene glycol -- Alkyne-β-CD alkyne-functionalized β-cyclodextrin -- Aminooxy-PEG-aminooxy aminooxy-terminated polyethylene glycol (i.e., aminooxy group at two ends) -- AMP antimicrobial peptides -- AMR antimicrobial resistance -- ANR double-layer-coated gold nanorods -- AO-4-arm PEG four-armed aminooxy-polyethylene glycol -- Au gold -- Azide-Dex-PA azidedextran polyampholyte -- Azide-DOX 5-azidopentanehydrazide-functionalized doxorubicine -- BCN bicyclo[6.1.0]non-4-yne -- BDNF brain derived neurotrophic factor -- BMP2 bone morphogenetic protein-2 -- BMP4 bone morphogenetic protein-4 -- BMSC bone marrow mesenchymal stem cells -- BP bisphosphonate -- BSA bovine serum albumin -- CAPAC click activated protodrugs against cancer -- CBT cyanobenzothiazole -- Ce6 chlorin e6 -- c-FLIP cellular FLICE-like inhibitory protein -- CHO Chinese hamster ovary -- Chol cholesterol -- CMC carboxymethyl chitosan -- CMT controlled morphology transformation -- CNS central nervous system -- CnS chondroitin sulfate -- CnS-furan furan grafted chondroitin sulfate -- CnS-HS thiolated chondroitin sulfate -- Col 1 collagen type I -- COS chitooligosaccharides -- CRP controlled radical polymerization -- CS chitosan -- CS-HS thiolated chitosan -- CS-N3 azide-functionalized chitosan -- Cu(II) sulfate copper(II) sulfate -- CuBr copper(I) bromide -- CuAAC copper(I)-catalyzed azide-alkyne cycloaddition -- Cx43 connexin 43 -- Cy3-PNA cyanine3 fluorescent dye-labeled antiPNA21 -- Cy5 cyanine5 dye -- Cys cysteine -- D-Cy5 cyanine5-labeled dendrimers -- DA Diels–Alder -- DBCO dibenzylcyclooctyne -- DCC dynamic click chemistry -- D-Cys dendrimer-cysteine conjugate -- D-Dexa dendrimer-dexamethasone conjugate -- DDS drug delivery systems -- D-Ene dendrimer-pentenoic acid -- Dex dextran -- Dex-ADIBO azadibenzocyclooctyne-modified dextran -- Dex-DBCO dibenzylcyclooctyne-modified dextran -- Dex-N3 azide-functionalized dextran -- DHHC dihydroxyphenyl/hydrazide bifunctionalized hydroxyethyl chitosan -- Dhvar-5 a synthetic antimicrobial peptide -- DIFO difluorinated cyclooctyne -- DLQ DBCO-modified low molecular weight heparin-quercetin conjugates -- DMTMM 4-(4, 6-dimethoxy triazine)-4-methyl morpholine hydrochloride -- DNA deoxyribonucleic acid -- DOX doxorubicin -- DR4/5 death receptors DR4 and DR5 -- DS degree of substitution of ADIBO -- DSPE distearyl phosphatidyl ethanolamine -- ECM extracellular matrix -- EDC 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide -- EDG electron-donating groups -- EDTA ethylenediaminetetraacetic acid -- EGF epidermal growth factor -- EPC endothelial progenitor cell -- EPR enhanced permeability and retention -- ES electrophilic substitution -- EWG electron-withdrawing groups -- F127-maleimide maleimide-functionalized Pluronic F127 -- FAK focal adhesion kinase -- FBS fetal bovine serum -- FDA food and drug administration -- G' storage modulus -- GALA a 30-residue fusogenic peptide (WEAALAEALAEALAEHLAEALAEALEALAA) -- GCS-NP glycol chitosan nanoparticles -- Gel-furan furan-functionalized gelatin -- GF growth factors -- Glycolipids lipid-glycan conjugates -- Glycoproteins protein-glycan conjugates -- GlycoRNA ribonucleic acid-glycan conjugates -- GNR gold nanorod -- GO graphene oxide -- GSH glutathione -- HAase hyaluronidase -- HA hyaluronic acid -- HA-acrylate acrylated hyaluronic acid -- HA-benzaldehyde benzaldehyde-functionalized hyaluronic acid -- HA-CBT cyanobenzothiazole-modified hyaluronic acid -- HA-CHO aldehyde-functionalized hyaluronic acid -- HA-Cys-MA cystamine-methacrylate modified hyaluronic acid -- HA-D-Cys D-cysteine-functionalized hyaluronic acid -- HA-furan furan-functionalized hyaluronic acid -- HA-furan-ADH dually functionalized hyaluronic acid with furan and hydrazide -- HA-furan-CHO dually functionalized hyaluronic acid with furan and aldehyde -- HA-g-AMA 2-aminoethyl methacrylate grafted hyaluronic acid -- HA-BP bisphosphonate modified hyaluronic acid -- HA-g-Cys-MA cystamine-methacrylate grafted hyaluronic acid -- HA-g-Lys-MTet lysine-4-(4(dimethylamino)phenyl-tetrazole)-benzoic acid grafted hyaluronic acid -- HA-g-Lys-Tz lysine-tetrazole grafted hyaluronic acid -- HA-GO HA-conjugated graphene oxide -- HA-g-OEG-DBCO diarylcyclooctyne-modified oligo(ethylene glycol) grafted hyaluronic acid -- HA-HS thiolated hyaluronic acid -- HA-HS-ADH thiol and hydrazide-functionalized hyaluronic acid -- HA-hydrazine hydrazine-functionalized hyaluronic acid -- HA-Lys-Tet lysine-tetrazole modified hyaluronic acid -- HA-MA methacrylated hyaluronic acid -- HA-maleimide maleimide-functionalized hyaluronic acid -- HA-Tz tetrazine-functionalized hyaluronic acid -- HECS hydroxyethyl chitosan -- HIF-1α hypoxia-inducible factor-1α -- HOMO highest occupied molecular orbital -- HP-PEG hyperbranched polyethylene glycol -- HTL-HCl DL-Homocysteine thiolactone hydrochloride -- iEDDA inverse electron demand Diels–Alder -- IEG iterative exponential growth -- IL-2 interleukin-2 -- IPN interpenetrating polymer network -- JR2EK-Az azide-functionalized JR2EK peptide -- L929 mouse fibroblast cells -- LMWH low molecular weight heparin -- LUMO lowest unoccupied molecular orbital -- Lys lysine -- MAA methacrylic acid -- MAA-g-CS methacrylic acid grafted chitosan -- mAb monoclonal antibody -- MAL-PEG-MAL dimaleimide poly(ethylene glycol) -- MAL-PPO-PEG-PPO-Mal poly(propylene oxide)-b-poly(ethylene oxide)-b-poly(propylene oxide) bismaleimide -- MDa megadalton -- MeOH methanol -- MES 2-morpholinoethane sulfonic acid -- MGE metabolic glycoengineering -- MITCH mixing-induced two-component injectable hydrogels -- MMP2 matrix metalloproteinase 2 -- mPEG methoxy polyethylene glycol -- mPEG-b-PPLG methoxy polyethylene glycol-b-poly(γ-propargyl-ʟ-glutamate) -- MSC mesenchymal stem cell -- MTD maximum tolerated dose -- Mw molecular weight -- N2 nitrogen -- N2H4.H2O hydrazine hydrate -- N3-HA azide-modified hyaluronic acid -- N3-s-TRAIL azide-modified TRAIL-bound MMP 2 sensitive peptide -- N3-HGP21 Cy3-labeled antisense miR-21 PNA probes loaded onto HA-GO -- NAC N-acetyl-L-cysteine -- NaN3 sodium azide -- Nb norbornene -- Nb-Tz norbornene-tetrazine -- NEDDA normal electron demand Diels–Alder -- NHS N-hydroxysuccinimide -- NIR near-infrared -- NK natural killer -- NP nanoparticles -- O2 oxygen -- 1O2 singlet oxygen -- O-CnS oxidized chondroitin sulfate -- o-NB ortho-nitrobenzyl -- OSA oligosaccharide -- PBAE poly(β-amino ester) -- PDT photodynamic therapy -- PEG polyethylene glycol -- PEGDA poly(ethylene glycol) diacrylate -- Photo-DIBO cyclopropenone-masked dibenzocyclooctyne -- PhTAD N-phenyltriazolinedione -- PLGA poly(lactic-co-glycolic acid) -- PLL poly-L-lysine -- PLL-SH thiol-functionalized poly-L-lysine -- PLL-g-CS poly-L-lysine grafted chitosan -- PNBA poly(o-nitrobenzyl acrylate) -- PNA peptide nucleic acid -- PNS peripheral nervous system -- PPLG poly(γ-propargyl-ʟ-glutamate) -- Proteoglycans heavily glycosylated proteins -- PSA polysaccharides -- PTK2 protein tyrosine kinase 2 -- QSI quorum sensing inhibitor -- Qu quercetin -- RAFT reversible addition fragmentation chain-transfer polymerization -- rDA reverse Diels–Alder -- RFP riboflavin phosphate -- Rfv riboflavin -- RGD arginyl-glycyl-aspartic acid -- RNA ribonucleic acid -- RNAi ribonucleic acid interference -- ROS reactive oxygen species -- Se selenium -- Semi-IPN semi-interpenetrating polymer network -- SHA salicylhydroxamic acid -- siHSP70 heat shock protein 70-targeting siRNA -- SPAAC strain-promoted azide-alkyne cycloaddition -- SQ3370 TCO-modified DOX -- SQL70 tetrazine-modified HA -- SSD silver sulfadiazine -- SuFEx sulfur(VI) fluoride exchange -- TA tetra-aniline -- TAD 1, 2, 4-triazoline-3, 5-dione -- TCO trans-cyclooctene -- TE tissue engineering -- TFA trifluoroacetic acid -- tgel gelation time -- TRAIL tumor necrosis factor-related apoptosis-inducing ligand -- Tri-Adam adamantyl trimers -- Tri-β-CD β-cyclodextrin trimers -- TsCl 4-toluene sulfonyl chloride -- TsC-No thiosemicarbazide-functionalized nopoldiol -- Tz tetrazine -- UV ultraviolet -- Van vanillin -- VEGF vascular endothelial growth factor -- ZnPc zinc phthalocyanine; Polymers -- Periodicals; Polymerization -- Periodicals; Polymers -- Industrial applications -- Periodicals; Polymères -- Périodiques; Polymérisation -- Périodiques; 547.7
• DOI: 10.1016/j.progpolymsci.2022.101590
• Languages: English
• ISSNs: 0079-6700

Abstract

Abstract: Recent advances in materials science and engineering highlight the importance of designing sophisticated biomaterials with well-defined architectures and tunable properties for emerging biomedical applications. Click chemistry, a powerful method allowing specific and controllable bioorthogonal reactions, has revolutionized our ability to make complex molecular structures with a high level of specificity, selectivity, and yield under mild conditions. These features combined with minimal byproduct formation have enabled the design of a wide range of macromolecular architectures from quick and versatile click reactions. Furthermore, copper-free click chemistry has resulted in a change of paradigm, allowing researchers to perform highly selective chemical reactions in biological environments to further understand the structure and function of cells. In living systems, introducing clickable groups into biomolecules such as polysaccharides (PSA) has been explored as a general approach to conduct medicinal chemistry and potentially help solve healthcare needs. De novo biosynthetic pathways for chemical synthesis have also been exploited and optimized to perform PSA-based bioconjugation inside living cells without interfering with their native processes or functions. This strategy obviates the need for laborious and costly chemical reactions which normally require extensive and time-consuming purification steps. Using these approaches, various PSA-based macromolecules have been manufactured as building blocks for the design of novel biomaterials. Clickable PSA provide a powerful and versatile toolbox for biomaterials scientists and will increasingly play a crucial role in the biomedical field. Specifically, bioclick reactions with PSA have been leveraged for the design of advanced drug delivery systems and minimally invasive injectable hydrogels. In this review article, we have outlined the key aspects and breadth of PSA-derived bioclick reactions as a powerful and versatile toolbox to design advanced polymeric biomaterials for biomedical applications such as molecular imaging, drug delivery, and tissue engineering. Additionally, we have also discussed the past achievements, present developments, and recent trends of clickable PSA-based biomaterials such as three dimensional printing, as well as their challenges, clinical translatability, and future perspectives. Graphical abstract: Image, graphical abstract