Progress and prospects in chitosan derivatives: Modification strategies and medical applications

doi:10.1016/j.jmst.2020.12.008

Abstract

Abstract:

Chitosan (CS) is the only natural alkaline polysaccharide originated from deacetylation of chitin that is the main component of shell from marine organisms. It has great potential medical application due to its broad-spectrum antimicrobial activity and good water solubility originated from its protonated amino groups under acidic condition and abundant hydroxyl groups. However, unprotonated NH₂ group of CS leads to its poor solubility under physiological condition and limits its diverse applications. Therefore, it is highly necessary to summarize the modification strategies of CS derivatives systematically to help researchers select the most appropriate strategies for their specific applications. Herein, we have summarized the modification strategies of CS derivatives for improving their antimicrobial activity, water solubility, biocompatibility, and mechanical property by chemical reaction and physical integration. And then we have reviewed the CS derivatives in hydrogels, nanoparticles, or coatings for medical application in wound dressing, drug delivery, medical implant. Last but not the least, we have put forward the future perspectives of deep studies about structure-activity relationship and clinical applications of CS derivatives.

Key words: Chitosan, Modification, Structure and property, Antimicrobial, Biomedical applications

Sheng Ding, Yuanfeng Wang, Jianna Li, Shiguo Chen. Progress and prospects in chitosan derivatives: Modification strategies and medical applications[J]. J. Mater. Sci. Technol., 2021, 89: 209-224.

Figures/Tables 13

References 216

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Modification strategies	Systems	Enhanced property				Refs.
Modification strategies	Systems	Antimicrobial activity	Water solubility	Biocompatibility	Mechanical property	Refs.
Positive charges	QAS	+	+	+		[10,37,134]
	N-QPCS	+	+			[18]
	Ammonium	+				[39,55]
Zwitterion	COOH group, QAS	+				[74]
	Betaine	+	+	+		[10,106]
	CS ascorbate			+		[111]
	QAS/Betaine	+	+	+		[10]
Neutral antimicrobial compound	CS derivative bearing with multi-NH₂ groups	+	+	+	+	[24,96,135]
	CS-g-PCL	+		+	+	[25]
	CPC	+				[52]
	Catechol	+		+		[76]
	Brij-S20	+				[82]
	Arg	+				[83,84]
	Reactive Blue 19	+				[86]
	Diethoxyphosphoryl polyaminoethyl CS Schiff bases	+	+	+		[81]
	NO-release CS derivative	+				[57]
	polyNiPAAm	+				[136]
	Glycol CS	+				[137]
	CMCS			+	+	[94]
	HA/mPEG			+		[106]
	Ferulic acid/ethyl ferulate			+		[113]
Metal	Cu (II) CS complex	+	+			[64]
	Ag (I) CS complex	+				[138]
	AgNPs	+		+		[60]
	Cu (II)/Zn (II) CS complex	+		+		[139]
	Gelatin/Ag@ZnO	+			+	[132]
Carbon	MWCNT based CS derivatives	+				[66]
	GO based CS derivatives	+				[72]
	GO based CS derivatives			+	+	[117,119]
	PPS/rGO			+	+	[120]
Hybridization	Capsaicin	+				[67]
	PAA	+				[68]
	Cellulose nanocrystals	+				[69]
	Gelatin			+	+	[116]
	BNNTs			+	+	[121]
	1%Ga₂O₃/MBG			+		[124]
	SA/Ca (II)				+	[130]
	SA				+	[131]
	PVA			+	+	[133]
	DN hydrogel	+		+	+	[9]

Modification strategies	Systems	Enhanced property				Refs.
Modification strategies	Systems	Antimicrobial activity	Water solubility	Biocompatibility	Mechanical property	Refs.
Positive charges	QAS	+	+	+		[10,37,134]
	N-QPCS	+	+			[18]
	Ammonium	+				[39,55]
Zwitterion	COOH group, QAS	+				[74]
	Betaine	+	+	+		[10,106]
	CS ascorbate			+		[111]
	QAS/Betaine	+	+	+		[10]
Neutral antimicrobial compound	CS derivative bearing with multi-NH₂ groups	+	+	+	+	[24,96,135]
	CS-g-PCL	+		+	+	[25]
	CPC	+				[52]
	Catechol	+		+		[76]
	Brij-S20	+				[82]
	Arg	+				[83,84]
	Reactive Blue 19	+				[86]
	Diethoxyphosphoryl polyaminoethyl CS Schiff bases	+	+	+		[81]
	NO-release CS derivative	+				[57]
	polyNiPAAm	+				[136]
	Glycol CS	+				[137]
	CMCS			+	+	[94]
	HA/mPEG			+		[106]
	Ferulic acid/ethyl ferulate			+		[113]
Metal	Cu (II) CS complex	+	+			[64]
	Ag (I) CS complex	+				[138]
	AgNPs	+		+		[60]
	Cu (II)/Zn (II) CS complex	+		+		[139]
	Gelatin/Ag@ZnO	+			+	[132]
Carbon	MWCNT based CS derivatives	+				[66]
	GO based CS derivatives	+				[72]
	GO based CS derivatives			+	+	[117,119]
	PPS/rGO			+	+	[120]
Hybridization	Capsaicin	+				[67]
	PAA	+				[68]
	Cellulose nanocrystals	+				[69]
	Gelatin			+	+	[116]
	BNNTs			+	+	[121]
	1%Ga₂O₃/MBG			+		[124]
	SA/Ca (II)				+	[130]
	SA				+	[131]
	PVA			+	+	[133]
	DN hydrogel	+		+	+	[9]

Form	System	Preparation	Mechanism & Advantages	Refs.
Textile	CS/(α)-tocopherol nanosphere on CF	Emulsion formation, and pad-dry-cure	In vitro release of α-tocopherol and preserve skin moisture	[140]
	CS hydrogel/CF	in-situ crosslinking	pH-responsive, altered basic mechanical and comfort	[141]
	CMCS/Met/Ag/CF	Pad-dry-cure, in-situ reduction	Outstanding laundering durability (98 % BR after 150 washes) due to the covalent bonds	[142]
	CS/Ag/linen fabric	Padding, in-situ reduction	Green synthesis, 100 % bacterial reduction, UPF 50 +, 97 % antioxidant activity, LOI of 23, and sustained for 50 washes	[143]
Film/coating	CS/P(PA-co-AA) micelles	Layer-by-layer assembly	UV-induced generation of ROS to destroy biofilms, and increased roughness and hydrophilicity for better tissue integration	[144]
	Carrot cellulose nanofibrils/low-viscosity CS	Vacuum filtration	Good optical transparency, good stability at high temperature (degradation occurred above 300 °C)	[145]
	AQCS/EDTA/Cu²⁺	Substrate plasma treatment, AQCS spreading, EDTA grafting, Cu²⁺ loading in CuSO₄·5H₂O solution	Cu²⁺ release for bacterial membrane damage and death, transparent, sustained for 100 wipes	[124]
	CMC/CS/PEG	Layer-by-layer assembly and subsequent crosslinking	Super hydrophilic surface, formed thin water film to prevent biofilm adhesion, improved chemical resistance and mechanical stability	[146]
	Capsaicin@CS/PDPA/sodium alginate	Microemulsion polymerization, alternately deposition	pH-responsive release of capsaicin, self-healing in artificial sea water	[67]
	CS/PAA brushes/TOB	Surface-initiated ATRP	pH-responsive TOB delivery, changeable adhesion, and elastic modulus	[68]
	CNF/ZnO-CS-Cl	Vacuum filtration and heat-press processing	Remarkable UV light stability, quick in vitro contact antimicrobial activity	[147]
Particle/fiber	TSC-PGMA-malic acidic CS	Esterification of MA with CS and surface grafting of GMA and TSC	Hg(II) adsorption (242.7 mg/g), reusable for 5 cycles	[147]
	Ce6	Amide formation between COOH group in Ce6 and free NH₂ group in CS	Light-induced localized singlet oxygen generation, kill drug-resistance bacteria, photodynamic therapy	[148]
	QCS (carbon) nanospheres	One-pot hydrothermal treatment	Homogeneous size distribution (∼110 nm), superior antimicrobial activity with a MIC of 2.0 - 5.0 μg/mL, biocompatibility for liver, lung, and red blood cells	[15]
	CS/PHA-g-AA nanofibers	Grinding black soldier fly pupa shell in water-acid-alkali to obtain CS and electrospinning with PHA-g-AA	Fully degradable, enhanced interface compatibility, and mechanical properties, excellent cytocompatibility	[149]
	PLNP@PANI-GCS	Grafting PANI and glycol GCS onto the surface of persistent luminescence nanoparticles (PLNPs)	Photothermal therapy, combating multidrug-resistant bacteria, developing no drug resistance, little harm to normal cells	[150]
	Mannosylated CS/imatinib-laden NPs	Covalently conjugated of mannose with CS oligosaccharides, then incubated with imatinib-laden NPs	Induce macrophage polarization toward the M1 phenotype, decrease M2 phenotype production, lessen fungus burden	[151]
Others	CS/PVAm/cellulose fiber foam	One-batch foam-forming process with drying under ambient conditions	Low density (33 - 66 kg/m³), water-stability, and microbial growth inhibition,	[152]
	CS-g-PAM	UV-initiation grafting copolymerization	Enhanced sterilization and flocculation	[37]

Form	System	Preparation	Mechanism & Advantages	Refs.
Textile	CS/(α)-tocopherol nanosphere on CF	Emulsion formation, and pad-dry-cure	In vitro release of α-tocopherol and preserve skin moisture	[140]
	CS hydrogel/CF	in-situ crosslinking	pH-responsive, altered basic mechanical and comfort	[141]
	CMCS/Met/Ag/CF	Pad-dry-cure, in-situ reduction	Outstanding laundering durability (98 % BR after 150 washes) due to the covalent bonds	[142]
	CS/Ag/linen fabric	Padding, in-situ reduction	Green synthesis, 100 % bacterial reduction, UPF 50 +, 97 % antioxidant activity, LOI of 23, and sustained for 50 washes	[143]
Film/coating	CS/P(PA-co-AA) micelles	Layer-by-layer assembly	UV-induced generation of ROS to destroy biofilms, and increased roughness and hydrophilicity for better tissue integration	[144]
	Carrot cellulose nanofibrils/low-viscosity CS	Vacuum filtration	Good optical transparency, good stability at high temperature (degradation occurred above 300 °C)	[145]
	AQCS/EDTA/Cu²⁺	Substrate plasma treatment, AQCS spreading, EDTA grafting, Cu²⁺ loading in CuSO₄·5H₂O solution	Cu²⁺ release for bacterial membrane damage and death, transparent, sustained for 100 wipes	[124]
	CMC/CS/PEG	Layer-by-layer assembly and subsequent crosslinking	Super hydrophilic surface, formed thin water film to prevent biofilm adhesion, improved chemical resistance and mechanical stability	[146]
	Capsaicin@CS/PDPA/sodium alginate	Microemulsion polymerization, alternately deposition	pH-responsive release of capsaicin, self-healing in artificial sea water	[67]
	CS/PAA brushes/TOB	Surface-initiated ATRP	pH-responsive TOB delivery, changeable adhesion, and elastic modulus	[68]
	CNF/ZnO-CS-Cl	Vacuum filtration and heat-press processing	Remarkable UV light stability, quick in vitro contact antimicrobial activity	[147]
Particle/fiber	TSC-PGMA-malic acidic CS	Esterification of MA with CS and surface grafting of GMA and TSC	Hg(II) adsorption (242.7 mg/g), reusable for 5 cycles	[147]
	Ce6	Amide formation between COOH group in Ce6 and free NH₂ group in CS	Light-induced localized singlet oxygen generation, kill drug-resistance bacteria, photodynamic therapy	[148]
	QCS (carbon) nanospheres	One-pot hydrothermal treatment	Homogeneous size distribution (∼110 nm), superior antimicrobial activity with a MIC of 2.0 - 5.0 μg/mL, biocompatibility for liver, lung, and red blood cells	[15]
	CS/PHA-g-AA nanofibers	Grinding black soldier fly pupa shell in water-acid-alkali to obtain CS and electrospinning with PHA-g-AA	Fully degradable, enhanced interface compatibility, and mechanical properties, excellent cytocompatibility	[149]
	PLNP@PANI-GCS	Grafting PANI and glycol GCS onto the surface of persistent luminescence nanoparticles (PLNPs)	Photothermal therapy, combating multidrug-resistant bacteria, developing no drug resistance, little harm to normal cells	[150]
	Mannosylated CS/imatinib-laden NPs	Covalently conjugated of mannose with CS oligosaccharides, then incubated with imatinib-laden NPs	Induce macrophage polarization toward the M1 phenotype, decrease M2 phenotype production, lessen fungus burden	[151]
Others	CS/PVAm/cellulose fiber foam	One-batch foam-forming process with drying under ambient conditions	Low density (33 - 66 kg/m³), water-stability, and microbial growth inhibition,	[152]
	CS-g-PAM	UV-initiation grafting copolymerization	Enhanced sterilization and flocculation	[37]

Form	System	Preparation	Mechanism & Advantages	Refs.
Hydrogel	Fe₃O₄@PDA@Ru-NO@FA imbedded CS-PVA hydrogel	Imbedding during crosslinking	Mild NIR light-controlled NO delivery, selectively accumulate in magnetic field-guided target area	[163]
	CS/gelatin/sodium hyaluronate/AgNPs	Mixed solution crosslinking	Blood absorption and promoting platelet aggregation, antimicrobial, liquid absorption, and wound healing of full thickness	[164]
	CS/PSBMA DN	UV initiated polymerization and crosslinking	High tensile strength (2.0 MPa), strong elastic modulus (0.5 MPa), fast self-recovery ability, toughness retention, anti-fouling	[126]
	Au nanorod@graphitic doped PVA/CS	Aldol condensation reaction	Stable photothermal antibacterial properties under near-infrared laser irradiation, swell to absorb the bacterial solution and kill	[165]
	QCS/ AA-co-MADA-co-DMAEMA	UV-polymerization	Inherent contact-active antibacterial activities, high toughness of 9168 J/m, high cell and tissue affinity	[23]
	GCS/EPL/polysaccharide-peptide cryogels	Radical polymerization	Against MDR bacterial infection, excellent biocompatibility, low cost, lower blood loss	[166]
	CS/AM NSs	Ultrasonic liquid phase exfoliation, bidirectional freeze-casting approach	Gather bacteria on the surface, full-thickness defect wound healing, capture and elimination of bacteria	[167]
	Catechol-methacryloyl CS/ methacryloyl CS	Simultaneous crosslinking	Double-network, injectable, strong adhesion to biological tissues (lap shear strength of 18.1 kPa)	[168]
	CMCS/NB/O-nitrobenzene	UV irradiation	Crosslinking between functional groups and tissue surface upon UV irradiation, strong adhesive performance (97.65 kPa)	[169]
Film	HKUST-1/CS film	Mixing, freeze drying	Local infection therapy, slow release of copper ions and reduced cytotoxicity, promote vessel regeneration	[170]
	Cu-BTTri MOF/CS	Blend	Water stable, impediment of biofilm formation, 85 % bacterial attachment reduction	[171]
	PCL/QCS-PANi	Electrospinning	Young’s modulus ranged from 2.4 - 4.9 MPa, 81.7%-48.1% stretchable, hemocompatibility and cytocompatibility	[172]
Nanocomposite	Cellulose/CS/CuO NPs	Film casting, gelation	Reproducible antibacterial and antiviral activity, green and facile synthesis, against highly resistant bacteria and fungi	[173]
	CS inverse opal particles	Employing CS as scaffold	Inflammation reaction-induced intelligent drug release, real time monitoring of drug release,	[174]
	CS/antibacterial peptide	Self-assembly	On-site transformation, site-specific targeting, accumulation, and retention	[52]
	CS-g-oligolysine	Self-assembly	Selectively kills MDR bacteria, ultralow molecular weight (1450 Da), small zeta potential (+15 mV) and lack of hydrophobicity	[175]
	O-bacterial cellulose/CS/ collagen	Electrostatic attraction self-assembly	Rapid internal hemostasis, a faster biodegradability in vivo, procoagulant property, adhesion of erythrocytes and platelets	[176]