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Synthesis, Characterization, and Drug Delivery Application of Self-assembling Amphiphilic Cyclodextrin

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Abstract

The main aim of the research was to synthesize amphiphilic cyclodextrin (AMCD) by substituting C12 alkyl chain to a β-cyclodextrin (βCD) in a single step and to study its self-assembly in an aqueous medium. The drug delivery application of the AMCD was also evaluated by encapsulating tamoxifen citrate as a model hydrophobic drug. AMCD was able to self-assemble in aqueous media, forming nanovesicles of size < 200 nm, capable of encapsulating tamoxifen citrate (TMX). Molecular docking and MD simulation studies revealed the interaction between TMX and AMCD which formed a stable complex. TEM and AFM studies showed that nanovesicles were perfectly spherical having a smooth surface and a theoretical AMCD bilayer thickness of ~ 7.2 nm as observed from SANS studies. XRD and DSC studies revealed that TMX was amorphized and molecularly dispersed in AMCD bilayer which was released slowly following Fickian diffusion. AMCD has excellent hemocompatibility as opposed to βCD and no genotoxicity. IC50 of TMX against MCF-7 cell lines was significantly reduced from 11.43 to 7.96 μg/ml after encapsulation in nanovesicle because of nanovesicles being endocytosed by the MCF-7 cells. AMCD was well tolerated by IV route at a dose of > 2000 mg/kg in rats. Pharmacokinetic profile of TMX after encapsulation was improved giving 3-fold higher AUC; extended mean residence time is improving chances of nanovesicle to extravasate in tumor via EPR effect.

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Abbreviations

13C NMR:

carbon-13 nuclear magnetic resonance

1H NMR:

proton nuclear magnetic resonance

AFM :

atomic force microscopy

AMCD:

amphiphilic cyclodextrin

ATCC:

American type culture collection

CD:

Cyclodextrin

CO2 :

carbon dioxide

DCM:

dichloromethane

DLS:

dynamic light scattering

DMEM:

Dulbecco’s modified Eagle medium

DMF:

N,N-dimethylformamide

DMSO:

dimethyl sulfoxide

DMSO-D6 :

deuterated dimethyl sulfoxide

Ds:

degree of substitution

DSC:

differential scanning calorimetry

FBS:

fetal bovine serum

FNV:

fluorescein-loaded AMCD nanovesicles

FTIR:

Fourier-transform infrared spectroscopy

HPLC:

high-performance liquid chromatography

HSQC:

heteronuclear single quantum correlation

IC50 :

half maximal inhibitory concentration

IV:

intravenous

KBr:

potassium bromide

LD50 :

median lethal dose

MALDI-TOF:

matrix-assisted laser desorption/ionization-time-of-flight

MTT:

[3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide]

MβCD:

methyl beta cyclodextrin

PBS:

phosphate buffer saline

PES:

polyether sulfone

PLGA:

poly(lactic-co-glycolic acid)

PM:

physical mixture

R.T.:

room temperature

RBC:

red blood cells

SANS:

small-angle neutron scattering

SMEDDS:

self-micro emulsifying drug delivery system

TEA:

triethylamine

TEM:

transmission electron microscopy

TLC:

thin-layer chromatography

TMX:

tamoxifen citrate

UV:

ultraviolet

βCD:

beta cyclodextrin

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Acknowledgments

The authors are thankful to DST-INSPIRE for fellowship (DST/INSPIRE/120736) and travel assistant. They are also grateful to the British council and DST for Newton-Bhabha Ph.D. Placement program (DST/INSPIRE/NBHF/2015/24). The authors would like to thank F. Philipp Seib (University of Strathclyde) and John D. Totten (University of Strathclyde) for providing tissue culture training and assistance with the experimental design of cytotoxicity, flow cytometry, and endocytosis studies. The authors want to acknowledge Dr. V. K. Aswal for helping with SANS study. They would also like to acknowledge TIFR (Mumbai, India) for proving the XRD facility for characterization, the Institute of Chemical Technology, AICTE/NAFETIC for providing laboratory facilities, and the Strathclyde Institute of Pharmacy & Biomedical Sciences (SIPBS) for necessary infrastructure and facilities.

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Authors and Affiliations

  1. Center for Novel Drug Delivery Systems, Department of Pharmaceutical Sciences and Technology, Institute of Chemical Technology, University Under Section 3 of UGC Act – 1956, Elite Status and Centre of Excellence – Govt. of Maharashtra, TEQIP Phase III Funded, Matunga (E), Mumbai, 400019, India

    Mayank R. Patel & Pradeep R. Vavia

  2. Strathclyde Institute of Pharmacy and Biomedical Sciences (SIPBS), University of Strathclyde, 161 Cathedral Street, Glasgow, G4 0RE, UK

    Dimitrios A. Lamprou

  3. School of Pharmacy, Queen’s University Belfast, 97 Lisburn Road, Belfast, BT9 7BL, UK

    Dimitrios A. Lamprou

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Contributions

M.R.P. and P.R.V. conceived the study. M.R.P. manufactured and characterized AMCD nanovesicles as well as performed transmission microscopy and AFM studies. D.A.L. provided training for AFM and host for the majority of experiments at the University of Strathclyde. M.R.P. performed all molecular docking and MD simulation studies. M.R.P and P.R.V. interpreted all the results of in silico studies. In vitro and in vivo experiments were conducted by M.R.P. M.R.P. performed all animal studies. All authors (M.P., D.A.L, and P.R.V.) designed research, discussed the results, and/or advised on the analysis. M.R.P. and P.R.V wrote the manuscript with support from all the authors.

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Correspondence to Pradeep R. Vavia.

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Patel, M.R., Lamprou, D.A. & Vavia, P.R. Synthesis, Characterization, and Drug Delivery Application of Self-assembling Amphiphilic Cyclodextrin. AAPS PharmSciTech 21, 11 (2020). https://doi.org/10.1208/s12249-019-1572-z

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