Benzocaine-Loaded Polymeric Nanocapsules: Study of the Anesthetic Activities

Melo, Nathalie Ferreira Silva de; Araújo, Daniele Ribeiro de; Grillo, Renato; Moraes, Carolina Morales; Matos, Angélica Prado de; Paula, Eneida de; Rosa, André Henrique; Fraceto, Leonardo Fernandes

doi:10.1002/jps.22829

Cited by 42 publications

(24 citation statements)

References 41 publications

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“…Such drawback may be overcome through the development of carrier systems. Improvement in bioavailability and therapeutic efficacy of benzocaine by its encapsulation in b-cyclodextrin and polymeric nanocapsules has been demonstrated (53,54). In the present work, we showed that p-sulfonic acid calix[n]arenes can form stable inclusion complexes with benzocaine.…”

Section: In Vitro Cytotoxic Testssupporting

confidence: 51%

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Benzocaine Complexation with p‐Sulfonic Acid Calix[n]arene: Experimental (¹H‐NMR) and Theoretical Approaches

et al. 2014

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The aim of this work was to study the interaction between the local anesthetic benzocaine and p-sulfonic acid calix[n]arenes using NMR and theoretical calculations and to assess the effects of complexation on cytotoxicity of benzocaine. The architectures of the complexes were proposed according to (1) H NMR data (Job plot, binding constants, and ROESY) indicating details on the insertion of benzocaine in the cavity of the calix[n]arenes. The proposed inclusion compounds were optimized using the PM3 semiempirical method, and the electronic plus nuclear repulsion energy contributions were performed at the DFT level using the PBE exchange/correlation functional and the 6-311G(d) basis set. The remarkable agreement between experimental and theoretical approaches adds support to their use in the structural characterization of the inclusion complexes. In vitro cytotoxic tests showed that complexation intensifies the intrinsic toxicity of benzocaine, possibly by increasing the water solubility of the anesthetic and favoring its partitioning inside of biomembranes.

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Section: In Vitro Cytotoxic Testssupporting

confidence: 51%

“…Benzocaine, which does not possess such ionizable amino group, can exist at physiological conditions only as a neutral, poor water soluble molecule. Thus, the clinical use of benzocaine is limited to topical formulations, because its low solubility in water hinders its use by parenteral route (53).…”

Section: In Vitro Cytotoxic Testsmentioning

confidence: 99%

Benzocaine Complexation with p‐Sulfonic Acid Calix[n]arene: Experimental (¹H‐NMR) and Theoretical Approaches

et al. 2014

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“…[100][101][102] This method consists in creating an organic phase composed of the drug (benzocaine in all reported works), the polymer, acetone, oil, and the emulsifier. The organic phase is mixed under magnetic stirring with an aqueous solution containing an emulsifier in turn, and acetone is evaporated by rotary evaporation.…”

Section: Nanostructured Systemsmentioning

confidence: 99%

From micro- to nanostructured implantable device for local anesthetic delivery

Zorzetto

Brambilla

Marcello

et al. 2016

IJN

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Local anesthetics block the transmission of painful stimuli to the brain by acting on ion channels of nociceptor fibers, and find application in the management of acute and chronic pain. Despite the key role they play in modern medicine, their cardio and neurotoxicity (together with their short half-life) stress the need for developing implantable devices for tailored local drug release, with the aim of counterbalancing their side effects and prolonging their pharmacological activity. This review discusses the evolution of the physical forms of local anesthetic delivery systems during the past decades. Depending on the use of different biocompatible materials (degradable polyesters, thermosensitive hydrogels, and liposomes and hydrogels from natural polymers) and manufacturing processes, these systems can be classified as films or micro- or nanostructured devices. We analyze and summarize the production techniques according to this classification, focusing on their relative advantages and disadvantages. The most relevant trend reported in this work highlights the effort of moving from microstructured to nanostructured systems, with the aim of reaching a scale comparable to the biological environment. Improved intracellular penetration compared to microstructured systems, indeed, provides specific drug absorption into the targeted tissue and can lead to an enhancement of its bioavailability and retention time. Nanostructured systems are realized by the modification of existing manufacturing processes (interfacial deposition and nanoprecipitation for degradable polyester particles and high- or low-temperature homogenization for liposomes) or development of novel strategies (electrospun matrices and nanogels). The high surface-to-volume ratio that characterizes nanostructured devices often leads to a burst drug release. This drawback needs to be addressed to fully exploit the advantage of the interaction between the target tissues and the drug: possible strategies could involve specific binding between the drug and the material chosen for the device, and a multiscale approach to reach a tailored, prolonged drug release

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“…Thus, the studies and, in turn, literature reports on drug delivery systems employing nanoparticle‐techniques are dominated (>60%) by the use of low‐molar‐mass drugs. This can be exemplified with drugs such as the nucleobase and/or nucleoside analogs acyclovir, cytarabine, and 5‐fluorouracil, local anesthetic benzocaine, non‐opioid analgesic diclofenac and diuretic furosemide …”

Section: Introductionmentioning

confidence: 99%

Novel Insights Into Appropriate Encapsulation Methods for Bioactive Compounds Into Polymers: A Study With Peptides and HDAC Inhibitors

et al. 2013

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The use of different nanoparticles (NPs) for successful encapsulation of bioactive substances is discussed. The inclusion efficiency into liposomes, acetalated dextran (Ac-Dex), and variants of poly[(lactic acid)-co-(glycolic acid)] (PLGA) NPs is analyzed after chemical degradation. Efficient inclusion of SIRT1 inhibitor Ex527 in liposomes, Ac-Dex- and PLGA-NPs is observed for all procedures used. Activity of Ex527 is demonstrated by monitoring the acetylation status of SIRT1-target p53. In contrast, small peptides are only incorporated into acid-terminated PLGA-NPs and marginally into Ac-Dex-NPs. The yield depends on peptide sequence and terminal modifications. Activity is exemplified for angiotensin II using the dynamic mass redistribution technology.

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Benzocaine-Loaded Polymeric Nanocapsules: Study of the Anesthetic Activities

Cited by 42 publications

References 41 publications

Benzocaine Complexation with p‐Sulfonic Acid Calix[n]arene: Experimental (¹H‐NMR) and Theoretical Approaches

Benzocaine Complexation with p‐Sulfonic Acid Calix[n]arene: Experimental (¹H‐NMR) and Theoretical Approaches

From micro- to nanostructured implantable device for local anesthetic delivery

Novel Insights Into Appropriate Encapsulation Methods for Bioactive Compounds Into Polymers: A Study With Peptides and HDAC Inhibitors

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Benzocaine-Loaded Polymeric Nanocapsules: Study of the Anesthetic Activities

Cited by 42 publications

References 41 publications

Benzocaine Complexation with p‐Sulfonic Acid Calix[n]arene: Experimental (1H‐NMR) and Theoretical Approaches

Benzocaine Complexation with p‐Sulfonic Acid Calix[n]arene: Experimental (1H‐NMR) and Theoretical Approaches

From micro- to nanostructured implantable device for local anesthetic delivery

Novel Insights Into Appropriate Encapsulation Methods for Bioactive Compounds Into Polymers: A Study With Peptides and HDAC Inhibitors

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Benzocaine Complexation with p‐Sulfonic Acid Calix[n]arene: Experimental (¹H‐NMR) and Theoretical Approaches

Benzocaine Complexation with p‐Sulfonic Acid Calix[n]arene: Experimental (¹H‐NMR) and Theoretical Approaches