π-Donor/π-Acceptor Interactions for the Encapsulation of Neurotransmitters on Functionalized Polysilicon-Based Microparticles

Giraldo, Sandra; Alea-Reyes, María E.; Limón, David; González, Asensio; Duch, Marta; Plaza, José A.; Ramos-López, David; de Lapuente, Joaquín; González-Campo, Arántzazu; Pérez-García, Lluïsa

doi:10.3390/pharmaceutics12080724

Open AccessArticle

π-Donor/π-Acceptor Interactions for the Encapsulation of Neurotransmitters on Functionalized Polysilicon-Based Microparticles

by

Sandra Giraldo

^1,2,3

,

María E. Alea-Reyes

^1,3,

David Limón

^1,3

,

Asensio González

¹,

Marta Duch

⁴,

José A. Plaza

⁴

,

David Ramos-López

⁵,

Joaquín de Lapuente

⁵,

Arántzazu González-Campo

^2,*

and

Lluïsa Pérez-García

^1,3,†

¹

Departament de Farmacologia, Toxicologia i Química Terapèutica, Universitat de Barcelona, Avda. Joan XXIII 27-31, 08028 Barcelona, Spain

²

Institut de Ciència de Materials de Barcelona (ICMAB-CSIC), Campus UAB, 08193 Bellaterra, Barcelona, Spain

³

Institut de Nanociència i Nanotecnologia UB (IN2UB), Universitat de Barcelona, Avda. Joan XXIII 27-31, 08028 Barcelona, Spain

⁴

Institut de Microelectrónica de Barcelona (IMB-CNM-CSIC), Campus UAB, 08193 Bellaterra, Barcelona, Spain

⁵

Parc Científic de Barcelona, Unitat de Toxicologia Experimental i Ecotoxicologia (UTOX-PCB), Baldiri i Reixac 10-12, 08028 Barcelona, Spain

^*

Author to whom correspondence should be addressed.

^†

Current address: Advanced Materials and Healthcare Technologies, School of Pharmacy, University of Nottingham, University Park, Nottingham NG7 2RD, UK.

Pharmaceutics 2020, 12(8), 724; https://doi.org/10.3390/pharmaceutics12080724

Submission received: 3 July 2020 / Revised: 28 July 2020 / Accepted: 29 July 2020 / Published: 1 August 2020

(This article belongs to the Special Issue Nano-Micro Encapsulation of Drugs)

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Abstract

Bipyridinium salts, commonly known as viologens, are π-acceptor molecules that strongly interact with π-donor compounds, such as porphyrins or amino acids, leading their self-assembling. These properties have promoted us to functionalize polysilicon microparticles with bipyridinium salts for the encapsulation and release of π-donor compounds such as catecholamines and indolamines. In this work, the synthesis and characterization of four gemini-type amphiphilic bipyridinium salts (1·4PF₆–4·4PF₆), and their immobilization either non-covalently or covalently on polysilicon surfaces and microparticles have been achieved. More importantly, they act as hosts for the subsequent incorporation of π-donor neurotransmitters such as dopamine, serotonin, adrenaline or noradrenaline. Ultraviolet-visible absorption and fluorescence spectroscopies and high-performance liquid chromatography were used to detect the formation of the complex in solution. The immobilization of bipyridinium salts and neurotransmitter incorporation on polysilicon surfaces was corroborated by contact angle measurements. The reduction in the bipyridinium moiety and the subsequent release of the neurotransmitter was achieved using ascorbic acid, or Vitamin C, as a triggering agent. Quantification of neurotransmitter encapsulated and released from the microparticles was performed using high-performance liquid chromatography. The cytotoxicity and genotoxicity studies of the bipyridinium salt 1·4PF₆, which was selected for the non-covalent functionalization of the microparticles, demonstrated its low toxicity in the mouse fibroblast cell line (3T3/NIH), the human liver carcinoma cell line (HepG2) and the human epithelial colorectal adenocarcinoma cell line (Caco-2).

Keywords: π-donor/π-acceptor complexes; viologens; polysilicon microparticles; drug encapsulation; drug delivery; neurotransmitters

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MDPI and ACS Style

Giraldo, S.; Alea-Reyes, M.E.; Limón, D.; González, A.; Duch, M.; Plaza, J.A.; Ramos-López, D.; de Lapuente, J.; González-Campo, A.; Pérez-García, L. π-Donor/π-Acceptor Interactions for the Encapsulation of Neurotransmitters on Functionalized Polysilicon-Based Microparticles. Pharmaceutics 2020, 12, 724. https://doi.org/10.3390/pharmaceutics12080724

AMA Style

Giraldo S, Alea-Reyes ME, Limón D, González A, Duch M, Plaza JA, Ramos-López D, de Lapuente J, González-Campo A, Pérez-García L. π-Donor/π-Acceptor Interactions for the Encapsulation of Neurotransmitters on Functionalized Polysilicon-Based Microparticles. Pharmaceutics. 2020; 12(8):724. https://doi.org/10.3390/pharmaceutics12080724

Chicago/Turabian Style

Giraldo, Sandra, María E. Alea-Reyes, David Limón, Asensio González, Marta Duch, José A. Plaza, David Ramos-López, Joaquín de Lapuente, Arántzazu González-Campo, and Lluïsa Pérez-García. 2020. "π-Donor/π-Acceptor Interactions for the Encapsulation of Neurotransmitters on Functionalized Polysilicon-Based Microparticles" Pharmaceutics 12, no. 8: 724. https://doi.org/10.3390/pharmaceutics12080724

APA Style

Giraldo, S., Alea-Reyes, M. E., Limón, D., González, A., Duch, M., Plaza, J. A., Ramos-López, D., de Lapuente, J., González-Campo, A., & Pérez-García, L. (2020). π-Donor/π-Acceptor Interactions for the Encapsulation of Neurotransmitters on Functionalized Polysilicon-Based Microparticles. Pharmaceutics, 12(8), 724. https://doi.org/10.3390/pharmaceutics12080724

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π-Donor/π-Acceptor Interactions for the Encapsulation of Neurotransmitters on Functionalized Polysilicon-Based Microparticles

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