Advertisement

The incorporation and controlled release of dopamine from a sulfonated β–cyclodextrin–doped conducting polymer

  • Gillian M. Hendy
  • Carmel B. BreslinEmail author
ORIGINAL PAPER

Abstract

Pyrrole was electropolymerised in the presence of sulfonated β–cyclodextrin to give a conducting polypyrrole film doped with the anionic cyclodextrin, PPy–sβ–CD. On reduction of the polymer film at −0.80 V vs SCE, high concentrations of dopamine (DA) were incorporated and the DA was subsequently released at a potential of 0.10 V vs SCE. Much higher levels of DA were incorporated and released at PPy–sβ–CD compared to polypyrrole films doped with smaller anions and doped with the larger para–toluene sulfonic acid. In addition to releasing higher concentrations of DA, the DA was less prone to oxidation and degradation in the presence of the sulfonated β–cyclodextrin. This was attributed to the formation of an inclusion complex between the protonated DA molecule and the anionic CD. The higher release rates were explained in terms of the immobile nature of the large CD and the high charge density with approximately 9 sulfonated groups attached to the rim of the CD cavity, which facilitated the uptake of high levels of DA. Approximately 6.0 μmol cm−2 of DA was released at 0.10 V vs SCE over 60 min on reducing the PPy–sβ–CD film for 30 min at −0.80 V vs SCE. Higher levels of 9.6 μmol cm−2 were obtained on increasing the reduction period to 60 min, while levels of 14.0 μmol cm−2 were achieved with thicker polymer films.

Keywords

Polypyrrole Sulfonated β–cyclodextrin Dopamine Controlled release Inclusion complex 

Notes

Acknowledgments

This work was financially funded by the Irish Research Council for Science, Engineering and Technology (IRCSET) Ireland.

References

  1. 1.
    Svirskis D, Travas–Sejdic J, Rodgers A, Garg S (2010) Electrochemically–controlled drug delivery based on intrinsically conducting polymers. J Control Release 146:6–15CrossRefGoogle Scholar
  2. 2.
    Alshammary B, Walsh FC, Herrasti P, Ponce de Leon C (2016) Electrodeposited conductive polymers for controlled drug release: polypyrrole. J Solid State Electrochem 4:839–859CrossRefGoogle Scholar
  3. 3.
    Geetha S, Rao CRK, Vijayan M, Trivedi DC (2006) Biosensing and drug delivery by polypyrrole. Anal Chim Acta 568:119–125CrossRefGoogle Scholar
  4. 4.
    Ryan E, Breslin CB (2019) The incorporation of drug molecules with poor water solubility into polypyrrole as dopants: indomethacin and sulindac. Electrochim Acta 296:848–855CrossRefGoogle Scholar
  5. 5.
    Pillay V, Tsai T–S, Choonara YE, du Toit LC, Kumar P, Modi G, Naidoo D, Tomar LK, Tyagi C, Ndesendo VMK (2014) A review of integrating electroactive polymers as responsive systems for specialized drug delivery applications. J Biomed Mater Res 102:2039–2054CrossRefGoogle Scholar
  6. 6.
    Miller LL, Zhou XQ (1987) Poly (N–methylpyrrolylium) poly (styrenesulfonate)–a conductive, electrically switchable cation exchanger that cathodically binds and anodically releases dopamine. Macromolecules 20:1594–1597CrossRefGoogle Scholar
  7. 7.
    Hepel M, Mahdavi F (1997) Application of the electrochemical quartz crystal microbalance for electrochemically controlled binding and release of chlorpromazine from conductive polymer matrix. Microchem J 56:54–64CrossRefGoogle Scholar
  8. 8.
    Sharma M, Waterhouse GIN, Loader SWC, Garg S, Svirskis D (2003) High surface area polypyrrole scaffolds for tunable drug delivery. Int J Pharm 443:163–168CrossRefGoogle Scholar
  9. 9.
    Leprince L, Dogimont A, Magnin D, Demoustier–Champagne S (2010) Dexamethasone electrically controlled release from polypyrrole–coated nanostructured electrodes. J Mater Sci Mater Med 21:925–930CrossRefGoogle Scholar
  10. 10.
    Uppalapati D, Boyd BJ, Garg S, Travas–Sejdic J, Svirskis D (2016) Conducting polymers with defined micro– or nanostructures for drug delivery. Biomaterials 111:149–162CrossRefGoogle Scholar
  11. 11.
    Samanta D, Meiser JL, Zare RN (2015) Polypyrrole nanoparticles for tunable, pH–sensitive and sustained drug release. Nanoscale 7:9497–9504CrossRefGoogle Scholar
  12. 12.
    Samanta D, Hosseini–Nassab N, McCarty AD, Zare RN (2018) Ultra–low voltage triggered release of an anti-cancer drug from polypyrrole nanoparticles. Nanoscale 10:9773–9779CrossRefGoogle Scholar
  13. 13.
    Uppalapati D, Sharma M, Aqrawe Z, Coutinho F, Rupenthal ID, Boyd BJ, Travas-Sejdic J, Svirskis D (2018) Micelle directed chemical polymerization of polypyrrole particles for the electrically triggered release of dexamethasone base and dexamethasone phosphate. Int J Pharm 543:38–45CrossRefGoogle Scholar
  14. 14.
    Lee H, Hong W, Jeon S, Choi Y, Cho Y (2015) Electroactive polypyrrole nanowire arrays: synergistic effect of cancer treatment by on–demand drug release and photothermal therapy. Langmuir 31:4264–4269CrossRefGoogle Scholar
  15. 15.
    Esrafilzadeh D, Razal JM, Moulton SE, Stewart EM, Wallace GG (2013) Multifunctional conducting fibres with electrically controlled release of ciprofloxacin. J Control Release 169:313–320CrossRefGoogle Scholar
  16. 16.
    Tiwari AP, Hwang TI, Oh J–M, Maharjan B, Chun S, Kim BS, Joshi MK, Park CH, Kim CS (2018) pH/NIR–responsive polypyrrole–functionalized fibrous localized drug–delivery platform for synergistic cancer therapy. ACS Appl Mater Interfaces 10:20256–20270CrossRefGoogle Scholar
  17. 17.
    Chen J, Li X, Li J, Li J, Huang L, Ren T, Yang X, Zhong S (2018) Assembling of stimuli-responsive tumor targeting polypyrrole nanotubes drug carrier system for controlled release. Mater Sci Eng C 89:316–327CrossRefGoogle Scholar
  18. 18.
    Paun IA, Zamfirescu M, Luculescu CR, Acasandrei AM, Mustaciosu CC, Mihailescu M, Dinescu M (2017) Electrically responsive microreservoirs for controllable delivery of dexamethasone in bone tissue engineering. Appl Surf Sci 392:321–331CrossRefGoogle Scholar
  19. 19.
    Zhang J, Ma PX (2013) Cyclodextrin–based supramolecular systems for drug delivery: recent progress and future perspective. Adv Drug Deliv Rev 65:1215–1233CrossRefGoogle Scholar
  20. 20.
    Concheiro A, Alvarez–Lorenzo C (2013) Chemically cross–linked and grafted cyclodextrin hydrogels: From nanostructures to drug–eluting medical devices. Adv Drug Deliv Rev 65:1188–1203CrossRefGoogle Scholar
  21. 21.
    Bidan G, Lopez C, Mendes-Viegas F, Vieil E, Gadelle A (1995) Incorporation of sulphonated cyclodextrins into polypyrrole: an approach for the electro–controlled delivering of neutral drugs. Biosens Bioelectron 10:219–229CrossRefGoogle Scholar
  22. 22.
    Reece DA, Ralph SF, Wallace GG (2005) Metal transport studies on inherently conducting polymer membranes containing cyclodextrin dopants. J Membr Sci 249:9–20CrossRefGoogle Scholar
  23. 23.
    Harley CC, Rooney AD, Breslin CB (2010) The selective detection of dopamine at a polypyrrole film doped with sulfonated β–cyclodextrins. Sensors Actuators B Chem 150:498–504CrossRefGoogle Scholar
  24. 24.
    Hamilton A, Breslin CB (2014) The development of a highly sensitive urea sensor due to the formation of an inclusion complex between urea and sulfonated–β–cyclodextrins. Electrochim Acta 125:250–257CrossRefGoogle Scholar
  25. 25.
    Hamilton A, Breslin CB (2014) The development of a novel urea sensor using polypyrrole. Electrochim Acta 145:19–26CrossRefGoogle Scholar
  26. 26.
    Li Y, Maciel D, Rodrigues J, Shi X, Tomas H (2015) Biodegradable polymer nanogels for drug/nucleic acid delivery. Chem Rev 115:8564–8608CrossRefGoogle Scholar
  27. 27.
    Yi P, Wang Y, Zhang S, Zhan Y, Zhang Y, Sun Z, Li Y, He P (2017) Stimulative nanogels with enhanced thermosensitivity for therapeutic delivery via β–cyclodextrin–induced formation of inclusion complexes. Carbohydr Polym 166:219–227CrossRefGoogle Scholar
  28. 28.
    Hu Y, Peng J, Ke L, Zhao D, Zhao H, Xiao X (2016) Alginate/carboxymethyl chitosan composite gel beads for oral drug delivery. J Polym Res 23:129CrossRefGoogle Scholar
  29. 29.
    Zhou B, Wu B, Wang J, Qian Q, Wang J, Xu H, Yang S, Feng P, Chen W, Li Y, Jiang J, Han B (2018) Drug-mediation formation of nanohybrids for sequential therapeutic delivery in cancer cells. Colloids Surf B: Biointerfaces 163:284–290CrossRefGoogle Scholar
  30. 30.
    Maciel D, Figueira P, Xiao S, Hu D, Shi X, Rodrigues J, Tomas H, Li Y (2013) Redox–responsive alginate nanogels with enhanced anticancer cytotoxicity. Biomacromolecules 14:3140–3146CrossRefGoogle Scholar
  31. 31.
    Che Y, Li D, Liu Y, Yue Z, Zhao J, Ma Q, Zhang Q, Tan Y, Yue Q, Meng F (2018) Design and fabrication of a triple–responsive chitosan–based hydrogel with excellent mechanical properties for controlled drug delivery. J Polym Res 25:169CrossRefGoogle Scholar
  32. 32.
    Thompson BC, Richardson RT, Moulton SE, Evans JA, O'Leary S, Clark GM, Wallace GG (2010) Conducting polymers, dual neurotrophins and pulsed electrical stimulation — dramatic effects on neurite outgrowth. J Control Release 141:161–167CrossRefGoogle Scholar
  33. 33.
    Forciniti L, Ybarra J, Zaman MH, Schmidt CE (2014) Schwann cell response on polypyrrole substrates upon electrical stimulation. Acta Biomater 10:2423–2433CrossRefGoogle Scholar
  34. 34.
    Xu Q, Jin L, Li C, Kuddannayai S, Zhang Y (2018) The effect of electrical stimulation on cortical cells in 3D nanofibrous scaffolds. RSC Adv 8:11027–11035CrossRefGoogle Scholar
  35. 35.
    Backman L, Lindenberger U, Li C–S, Nyberg L (2010) Linking cognitive aging to alterations in dopamine neurotransmitter functioning: recent data and future avenues. Neurosci Biobehav Rev 34:670–677CrossRefGoogle Scholar
  36. 36.
    Fabregat G, Gimenex A, Diaz A, Puiggali J, Aleman C (2018) Dual-functionalization device for therapy through dopamine release and monitoring. Macromol Biosci 18:1800014CrossRefGoogle Scholar
  37. 37.
    Asavapiriyanont S, Chandler GK, Gunawardena GA, Pletcher D (1984) The electrodeposition of polypyrrole films from aqueous solutions. J Electroanal Chem 177:229–244CrossRefGoogle Scholar
  38. 38.
    Lee C–Y, Hsu D–Y, Prasannan A, Kalaivani R, Hong P–D (2016) Facile synthesis of hexagonal–​shaped polypyrrole self–​assembled particles for the electrochemical detection of dopamine. Appl Surf Sci 363:451–458CrossRefGoogle Scholar
  39. 39.
    Arjomandi J, Holze R (2006) Spectroelectrochemistry of conducting polypyrrole and poly(pyrrole–​cyclodextrin) prepared in aqueous and nonaqueous solvents. J Solid State Electrochem 11:1093–1100CrossRefGoogle Scholar
  40. 40.
    Hendy GM, Breslin CB (2011) A spectrophotometric and NMR study on the formation of an inclusion complex between dopamine and a sulfonated Cyclodextrin host. J Electroanal Chem 661:179–185CrossRefGoogle Scholar
  41. 41.
    Hendy GM, Breslin CB (2012) An electrochemical study in aqueous solutions on the binding of dopamine to a sulfonated Cyclodextrin host. Electrochim Acta 59:290–295CrossRefGoogle Scholar
  42. 42.
    Kontturi K, Pentti P, Sundholm G (1998) Polypyrrole as a model membrane for drug delivery. J Electroanal Chem 453:231–238CrossRefGoogle Scholar
  43. 43.
    Zinger B, Miller LL (1984) Timed release of chemicals from polypyrrole films. J Am Chem Soc 106:6861–6863CrossRefGoogle Scholar
  44. 44.
    Pyo M, Reynolds JR (1995) Poly(pyrrole adenosine 5′–triphosphate) (PP–ATP) and conducting polymer bilayers for transport of biologically active ions. Synth Met 71:2233–2236CrossRefGoogle Scholar
  45. 45.
    Suematsu S, Oura Y, Tsujimoto H, Kanno H, Naoi K (2000) Conducting polymer films of cross–linked structure and their QCM analysis. Electrochim Acta 45:3813–3821CrossRefGoogle Scholar

Copyright information

© The Polymer Society, Taipei 2019

Authors and Affiliations

  1. 1.Department of ChemistryMaynooth UniversityMaynoothIreland

Personalised recommendations