Synthesis and characterization of β-cyclodextrin nanosponges for N,N-diethyl-meta-toluamide complexation and their application on polyester fabrics

Abstract β-Cyclodextrin polymer, namely nanosponges (NSs), were synthesized using two cross-linkers: 1,1′-carbonyldiimidazole (CDI) and pyromellitic dianhydride (PMDA). The synthesized NSs were complexed with N,N-diethyl-meta-toluamide (DEET) and, after complex characterization, the NSs cross-linked with CDI were found more effective than those cross-linked with PMDA in terms of encapsulation efficiency and loading capacity. The CDI-NSs were dispersed in a polyacrylic resin, which was thermally polymerized on a polyester fabric surface. The fabric functionalization was evaluated through quantification of DEET extracted from the polyester fabrics, before and after three washing cycles. The results showed that encapsulation into NSs prolongs the persistence of DEET on polyester fabrics.

[1]  장윤희,et al.  Y. , 2003, Industrial and Labor Relations Terms.

[2]  R. Cavalli,et al.  Cyclodextrin-based nanosponges: a versatile platform for cancer nanotherapeutics development. , 2016, Wiley interdisciplinary reviews. Nanomedicine and nanobiotechnology.

[3]  A. Wilder-Smith,et al.  Insecticide‐treated clothes for the control of vector‐borne diseases: a review on effectiveness and safety , 2014, Medical and veterinary entomology.

[4]  A. Banerjee,et al.  Zika virus: an emerging arboviral disease , 2016 .

[5]  B. Knols,et al.  DEET microencapsulation: a slow-release formulation enhancing the residual efficacy of bed nets against malaria vectors. , 2008, Transactions of the Royal Society of Tropical Medicine and Hygiene.

[6]  이화영 X , 1960, Chinese Plants Names Index 2000-2009.

[7]  M. Cherniack,et al.  Review of the biodistribution and toxicity of the insect repellent N,N-diethyl-m-toluamide (DEET). , 1986, Journal of toxicology and environmental health.

[8]  G. C. Türkoğlu,et al.  In-vivo and in-vitro tick repellent properties of cotton fabric , 2015 .

[9]  C. Mansur,et al.  Polymer-based Drug Delivery Systems Applied to Insects Repellents Devices: A Review. , 2016, Current drug delivery.

[10]  G. G. Stokes "J." , 1890, The New Yale Book of Quotations.

[11]  Nicolly de Lima Petito,et al.  Increasing solubility of red bell pepper carotenoids by complexation with 2-hydroxypropyl-β-cyclodextrin. , 2016, Food chemistry.

[12]  W. Jones,et al.  Olfactory carbon dioxide detection by insects and other animals , 2013, Molecules and cells.

[13]  D. Sudakin,et al.  Chapter 98 – DEET , 2010 .

[14]  Judit Tulla-Puche,et al.  Polymers and drug delivery systems. , 2012, Current drug delivery.

[15]  Mingzhu Liu,et al.  A novel triple-responsive poly(3-acrylamidephenylboronic acid-co-2-(dimethylamino) ethyl methacrylate)/(β-cyclodextrin-epichlorohydrin)hydrogels: Synthesis and controlled drug delivery , 2011 .

[16]  F. Pessine,et al.  Synthesis and characterization of inclusion complex of the vasodilator drug minoxidil with β-cyclodextrin , 2008 .

[17]  H. Kono,et al.  Polymerization of β-cyclodextrin with 1,2,3,4-butanetetracarboxylic dianhydride: Synthesis, structural characterization, and bisphenol A adsorption capacity , 2013 .

[18]  M M Miró Specos,et al.  Microencapsulated citronella oil for mosquito repellent finishing of cotton textiles. , 2010, Transactions of the Royal Society of Tropical Medicine and Hygiene.

[19]  M. Irfan,et al.  Encapsulation Using Hyperbranched Polymers: From Research and Technologies to Emerging Applications , 2010 .

[20]  Gorjan Alagic,et al.  #p , 2019, Quantum information & computation.

[21]  J. Mccall,et al.  Formulation of topical insect repellent N,N-diethyl-m-toluamide (DEET): vehicle effects on DEET in vitro skin permeation , 1997 .

[22]  F. Tsai,et al.  Effect of hydroxypropyl-β-cyclodextrin complexation on the aqueous solubility, structure, thermal stability, antioxidant activity, and tyrosinase inhibition of paeonol , 2012, Journal of Inclusion Phenomena and Macrocyclic Chemistry.

[23]  A. Hebert,et al.  Insect repellents: historical perspectives and new developments. , 2008, Journal of the American Academy of Dermatology.

[24]  V. Brunella,et al.  Molecularly imprinted cyclodextrin nanosponges for the controlled delivery of L-DOPA: perspectives for the treatment of Parkinson’s disease , 2016, Expert opinion on drug delivery.

[25]  C. Peterson,et al.  Insect repellents - past, present and future , 2001 .

[26]  L. Leclercq Smart medical textiles based on cyclodextrins for curative or preventive patient care , 2016 .

[27]  B. Liederer,et al.  Preformulation study of epigallocatechin gallate, a promising antioxidant for topical skin cancer prevention. , 2002, Journal of pharmaceutical sciences.

[28]  M. Rahaie,et al.  Stability and loading properties of curcumin encapsulated in Chlorella vulgaris. , 2016, Food chemistry.

[29]  M. Kallen,et al.  Topical formulation studies with DEET (N,N-diethyl-3-methylbenzamide) and cyclodextrins. , 2002, Journal of pharmaceutical sciences.

[30]  P. Schlagenhauf,et al.  The efficacy of repellents against Aedes, Anopheles, Culex and Ixodes spp. - a literature review. , 2013, Travel medicine and infectious disease.

[31]  M. Brown,et al.  Insect repellents: an overview. , 1997, Journal of the American Academy of Dermatology.

[32]  Petar Skundric,et al.  Microencapsulation in the textile industry , 2006 .

[33]  Robert I. Krieger,et al.  HANDBOOK OF PESTICIDE TOXICOLOGY , 2001 .

[34]  C. Fruchart-Gaillard,et al.  The Repellent DEET Potentiates Carbamate Effects via Insect Muscarinic Receptor Interactions: An Alternative Strategy to Control Insect Vector-Borne Diseases , 2015, PloS one.

[35]  J. Diaz Chemical and Plant-Based Insect Repellents: Efficacy, Safety, and Toxicity. , 2016, Wilderness & environmental medicine.

[36]  C. Carr,et al.  Surface chemical analysis of tencel and cotton treated with a monochlorotriazinyl (MCT) β-cyclodextrin derivative , 2006 .

[37]  G. González‐Gaitano,et al.  Extraction of phenols from aqueous solutions by β-cyclodextrin polymers. Comparison of sorptive capacities with other sorbents , 2008 .

[38]  Thomas de Quincey [C] , 2000, The Works of Thomas De Quincey, Vol. 1: Writings, 1799–1820.

[39]  Tianyuan Liu,et al.  An effective β-cyclodextrin polyurethane spherical adsorbent for the chromatographic enrichment of corilagin from Phyllanthus niruri L. extract , 2016 .

[40]  H. Ichiura,et al.  Low temperature-dependence of N,N-dimethyl-3-methylbenzamide (DEET) release from a functional paper containing paraffin–DEET composites prepared using interfacial polymerization , 2014 .

[41]  R. Cavalli,et al.  Synthesis and characterization of a hyper-branched water-soluble β-cyclodextrin polymer , 2014, Beilstein journal of organic chemistry.

[42]  A. Hebeish,et al.  New textiles of biocidal activity by introduce insecticide in cotton-poly (GMA) copolymer containing β-Cd. , 2014, Carbohydrate polymers.

[43]  P. Westh,et al.  Thermodynamic investigation of the interaction between cyclodextrins and preservatives - Application and verification in a mathematical model to determine the needed preservative surplus in aqueous cyclodextrin formulations. , 2016, European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.

[44]  António Pedro Souto,et al.  Properties and controlled release of chitosan microencapsulated limonene oil , 2014 .

[45]  R. Neubert,et al.  Microencapsulation of citronella oil for mosquito-repellent application: formulation and in vitro permeation studies. , 2012, European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V.