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Article

Halloysite Nanotube-Based Delivery of Pyrazolo[3,4-d]pyrimidine Derivatives for Prostate and Bladder Cancer Treatment

by
Marina Massaro
1,
Rebecca Ciani
1,
Giancarlo Grossi
2,
Gianfranco Cavallaro
3,
Raquel de Melo Barbosa
4,
Marta Falesiedi
2,
Cosimo G. Fortuna
3,*,
Anna Carbone
2,
Silvia Schenone
2,
Rita Sánchez-Espejo
5,
César Viseras
5,6,
Riccardo Vago
7 and
Serena Riela
3,*
1
Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche (STEBICEF), Università di Palermo, Viale delle Scienze, Parco d’Orleans II, Ed. 17, 90128 Palermo, Italy
2
Department of Pharmacy, University of Genoa, Viale Benedetto XV, 16132 Genoa, Italy
3
Dipartimento di Scienze Chimiche (DSC), Università di Catania, Viale Andrea Doria 6, 95125 Catania, Italy
4
Department of Pharmacy and Pharmaceutical Technology, School of Pharmacy, University of Seville, C/Professor García González 2, 41012 Sevilla, Spain
5
Department of Pharmacy and Pharmaceutical Technology, Faculty of Pharmacy, University of Granada, Campus Universitario de Cartuja, 18071 Granada, Spain
6
Andalusian Institute of Earth Sciences, CSIC-UGR, 18100 Armilla, Spain
7
Istituto San Raffaele (IRCCS), Istituto di Ricerca Urologica, Divisione di Oncologia Sperimentale, 20132 Milano, Italy
*
Authors to whom correspondence should be addressed.
Pharmaceutics 2024, 16(11), 1428; https://doi.org/10.3390/pharmaceutics16111428
Submission received: 30 August 2024 / Revised: 4 November 2024 / Accepted: 6 November 2024 / Published: 9 November 2024
(This article belongs to the Special Issue Applications of Nanomaterials in Drug Delivery and Drug Release)
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Abstract

Background/Objectives: The development of therapies targeting unregulated Src signaling through selective kinase inhibition using small-molecule inhibitors presents a significant challenge for the scientific community. Among these inhibitors, pyrazolo[3,4-d]pyrimidine heterocycles have emerged as potent agents; however, their clinical application is hindered by low solubility in water. To overcome this limitation, some carrier systems, such as halloysite nanotubes (HNTs), can be used. Methods: Herein, we report the development of HNT-based nanomaterials as carriers for pyrazolo[3,4-d]pyrimidine molecules. To achieve this objective, the clay was modified by two different approaches: supramolecular loading into the HNT lumen and covalent grafting onto the HNT external surface. The resulting nanomaterials were extensively characterized, and their morphology was imaged by high-angle annular dark-field scanning transmission electron microscopy (HAADF-STEM). In addition, the kinetic release of the molecules supramolecularly loaded into the HNTs was also evaluated. QSAR studies were conducted to elucidate the physicochemical and pharmacokinetic properties of these inhibitors, and structure-based virtual screening (SBVS) was performed to analyze their binding poses in protein kinases implicated in cancer. Results: The characterization methods demonstrate successful encapsulation of the drugs and the release properties under physiological conditions. Furthermore, QSAR studies and SBVS provide valuable insights into the physicochemical, pharmacokinetic, and binding properties of these inhibitors, reinforcing their potential efficacy. Conclusions: The cytotoxicity of these halloysite-based nanomaterials, and of pure molecules for comparison, was tested on RT112, UMUC3, and PC3 cancer cell lines, demonstrating their potential as effective agents for prostate and bladder cancer treatment.
Keywords: pyrazolo[3,4-d]pyrimidine derivatives; halloysite; carrier; prostate cancer; bladder cancer; structure-based virtual screening pyrazolo[3,4-d]pyrimidine derivatives; halloysite; carrier; prostate cancer; bladder cancer; structure-based virtual screening

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MDPI and ACS Style

Massaro, M.; Ciani, R.; Grossi, G.; Cavallaro, G.; de Melo Barbosa, R.; Falesiedi, M.; Fortuna, C.G.; Carbone, A.; Schenone, S.; Sánchez-Espejo, R.; et al. Halloysite Nanotube-Based Delivery of Pyrazolo[3,4-d]pyrimidine Derivatives for Prostate and Bladder Cancer Treatment. Pharmaceutics 2024, 16, 1428. https://doi.org/10.3390/pharmaceutics16111428

AMA Style

Massaro M, Ciani R, Grossi G, Cavallaro G, de Melo Barbosa R, Falesiedi M, Fortuna CG, Carbone A, Schenone S, Sánchez-Espejo R, et al. Halloysite Nanotube-Based Delivery of Pyrazolo[3,4-d]pyrimidine Derivatives for Prostate and Bladder Cancer Treatment. Pharmaceutics. 2024; 16(11):1428. https://doi.org/10.3390/pharmaceutics16111428

Chicago/Turabian Style

Massaro, Marina, Rebecca Ciani, Giancarlo Grossi, Gianfranco Cavallaro, Raquel de Melo Barbosa, Marta Falesiedi, Cosimo G. Fortuna, Anna Carbone, Silvia Schenone, Rita Sánchez-Espejo, and et al. 2024. "Halloysite Nanotube-Based Delivery of Pyrazolo[3,4-d]pyrimidine Derivatives for Prostate and Bladder Cancer Treatment" Pharmaceutics 16, no. 11: 1428. https://doi.org/10.3390/pharmaceutics16111428

APA Style

Massaro, M., Ciani, R., Grossi, G., Cavallaro, G., de Melo Barbosa, R., Falesiedi, M., Fortuna, C. G., Carbone, A., Schenone, S., Sánchez-Espejo, R., Viseras, C., Vago, R., & Riela, S. (2024). Halloysite Nanotube-Based Delivery of Pyrazolo[3,4-d]pyrimidine Derivatives for Prostate and Bladder Cancer Treatment. Pharmaceutics, 16(11), 1428. https://doi.org/10.3390/pharmaceutics16111428

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