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Synthesis, characterization and applications of copolymer of β – cyclodextrin: a review

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Abstract

Herein, this review the synthesis of different types of copolymer of β-cyclodextrin (β-CD) by different functional monomers and cross-linkers is discussed. β-CD shows good inclusion property, surface area, porous structure and unique host-guest properties. CDs, the macrocyclic compounds are renowned for their inclusion ability. Several chemical and polymerized derivatives of parent CDs are synthesized to improve the physicochemical/biopharmaceutical properties of drug and inclusion capacity of CD. The future panorama of polymerized CDs is quite bright as they can serve as useful multifunctional tools for pharmaceutical scientists to develop and optimize drug delivery through various routes and in fabrication of biosensors. For drug delivery, the efficacy of monomer is made suitable and the well-known inclusion ability of β-CD is retrospected. The synthesized copolymer of β-CD is characterized via several microscopic and spectroscopic techniques such as synchrotron radiation based PXRD, TGA (thermogravimetric analysis), DSC and FTIR. The aim of this review paper is to study different methods of synthesis of copolymers of β-CD by different functional monomers and cross-linkers. The review suggests methods and conditions used for the optimized synthesis of copolymers of β-CD. Further, the application of β-CD in the field of tissue engineering, packing material, drug delivery, cosmetics, personal care and toiletry, waste management, catalysis adhesive and coating industry have also been discussed here.

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Abbreviations

ATR-IR:

Attenuated total reflection infrared

AzoMA:

6-(4-Phenylazo phenoxy) hexylmethacrylate

ATRP:

Atom transfer radical polymerization

AM:

Acrylamide

AA:

Acrylic acid

AgNPs:

Silver nanoparticles

AIBN:

Azo iso butyro nitrile

A-β-CD:

Allyl-β-CD

APS:

Ammonium persulfate

ARGET:

Atom transfer radical polymerization

β-CD:

β-cyclodextrin

β-CD-PLGA:

β-CD –Poly (Lactide-co-Glycolide)

β-CD–g-PAN:

β-CD -grafted- Polyacrylonitrile

β-CD-MAH:

β-CD -Maleic anhydride

β-CD-PEI:

Polyethyleneimine-modified β-CD

β-CD:

AA Acrylic acid (AA) esterified β-CD

β-CD-SA:

β-CD– Sialic acid

β-CD – HEMA:

β-CD- hydroxyethyl methacrylate

β-PEI:

Polyethyleneimine-modified β-CD

CGTase:

Cyclodextrin glucotransferase

CS-g-HP-β-CD:

Chitosan grafted hydroxy propyl-β-CD

CD-NIPAAM β-CD:

N-isopropylacrylamide

CD-NMA:

Acrylamidomethylated β-CD

CDI1:

1-Carbonyldiimidzole

CDM-AM:

cyclodextrinmaleate -acrylamide

CTA:

Chain transfer agents

DLLAD:

L-lactide.

DPPE:

Dipalmytoylphosphatidylethanolamine.

DNFB:

2, 4 dinitro fluorobenzene

DMAEMA:

2- (Dimethyl amino) ethyl methacrylate

DSC:

Differential scanning Calorimetry

DOC:

Dissolved organic corbon

DPC:

Diphenyl carbonate

DEA:

2-(diethylamino)

DMC:

Dimethyl carbonate

DMF:

Dimethyl formamide

DCC N,N′:

Dicyclohexylcarbodiimide

Ep-β-CD:

Epichlorohydrin -β- CD

EGDMA:

Ethylene glycol dimethacrylate

ε-CL:

ε-caprolactone

EDA:

Ethylene diamine

EDC 3:

ethylcarbodiimide hydrochloride

FT-IR:

Fourier transform infrared spectroscopy

GA:

Glycolic acid

GLU:

Glutamic acid

GC:

Gas Chromatography

GlcN:

N-glycolyl

GPC:

Gel permeation chromatography

GECD:

Mono-methacrylate substituted cyclodextrin

GMA:

Glycidyl methacrylate

HP-β-CD:

Hydroxypropyl-β-CD

HEMA:

2-hydroxylethyl methacrylate

HDI:

Hexamethylene diisocyanate

HMDI:

Hexamethylene diisocyanates

HMTETA1:

1,4,7,10,10-hexamethyltriethylenetetramine

HPCS:

Hydroxypropyl chitosan

HPL CHigh:

performance liquid chromatography

HAD:

Hexamethylenediamine

IEC:

Ion exchange chromatography

LA:

Lactic acid

MIT:

Molecular imprinting technique

MEO2MA:

2(2-methoxyethoxy)ethyl methacrylate

MAA:

Methyl methacrylate

NMR:

Nuclear magnetic resonance

NIPAAM:

N-isopropylacrylamide

NMAN:

Methylolacrylamide

NHS:

N-hydroxysuccinimide

NVP:

N-vinyl-2- pyrrolidone

Ppm:

Parts per million

PXRD:

Powder X-ray diffraction

PAN:

Polyacrylonitrile

PAA:

Poly (acrylic acid)

PNIPA:

Poly (N-isopropylacrylamide)

PEG-HDI:

Polyethylene glycol- hexamethylene diisocyanate

PAA-b-CD:

Poly (acrylic acid)-β-CD

PEG-b-PCD:

Polyethylene glycol –β-CD

PVP-β-CD:

Polyvinyl pyrrolidine–β–CD

PMDA:

Pyromellitic anhydride

PMDETA:

Pentamethyldiethylenetriamine

PEG-β-CD:

Poly(ethylene glycol)- β-CD

PDMAEMA:

[2-(dimethylamino)ethyl methacrylate]

PS:

Polystyrene

PU:

Poly urethane

PVA:

Poly(vinyl alcohol)

PMPI:

p-maleimidophenyl isocyanate

RCD–g-PAN:

Reactive – CCD - grafted- Polyacrylonitrile

RP–HPLC:

Reversed phase-HPLC

ROP:

Ring opening polymerization

RAFT:

Reversible addition fragmentation chain transfer

SB:

Sodium sulphide

SDS PAGE:

Sodium dodecylsulphate polyacrylamide gel electrophoresis

TMAEMC N:

trimethyl methacrylate chloride

Ts- HP β-CD:

Tosylated - hydroxy propyl-β-cyclodextrin

Ts-Cl:

P-toluene sulphonyl chloride

TMAEMC N:

trimethyl methacrylate chloride

Ts- HP β-CD:

Tosylated - hydroxy propyl-β-cyclodextrin

Ts-Cl P:

toluene sulphonyl chloride

TEMED N, N, N, N:

tetramethylenediamine

TDI:

Toluene diisocyanate

TNBSA 2, 4, 6:

trinitrobenzene sulfonic acid

THF:

Tetrahydrofuran

2D NMR:

Two-dimensional nuclear magnetic resonance

TROSY NMR:

Transverse relaxation optimized

TEM:

Transmission electron microscopy.

TEA:

Triethylamine

VBDMH:

Vinylbenzyl-5, 5-dimethylhydantoin

UV:

Ultraviolet Spectroscopy

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Acknowledgements

The authors would like to acknowledge University Grant Commission (Sanction Letter No. 30-303/2016/BSR dated 28/09/2016) for the financial assistance.

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  1. Department of Chemistry, Chaudhary Charan Singh University, Meerut, 250004, India

    Nazia Tarannum,  Suhani & Deepak Kumar

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  1. Nazia Tarannum
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Tarannum, N., Suhani & Kumar, D. Synthesis, characterization and applications of copolymer of β – cyclodextrin: a review. J Polym Res 27, 89 (2020). https://doi.org/10.1007/s10965-020-02058-9

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