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New Berberine Conjugates With Self-Assembly and Improved Antioxidant/Neuroprotection Properties: Effect of the Anchored Part on Cmc, Shape and Size of the Nanomicelles Publisher



Afroozandeh Z1 ; Rashidi Ranjbar P2 ; Khoobi M3, 4 ; Forootanfar H5, 6 ; Ameri A5 ; Foroumadi A3, 7
Authors
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Authors Affiliations
  1. 1. Kish International Campus, University of Tehran, Kish Island, Iran
  2. 2. School of Chemistry, University of Tehran, Tehran, Iran
  3. 3. Drug Design and Development Research Center, The Institute of Pharmaceutical Sciences (TIPS), Tehran University of Medical Sciences, Tehran, 1417614411, Iran
  4. 4. Department of Radiopharmacy, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  5. 5. Pharmaceutical Sciences and Cosmetic Products Research Center, Kerman University of Medical Sciences, Kerman, Iran
  6. 6. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Kerman University of Medical Sciences, Kerman, Iran
  7. 7. Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran

Source: Journal of Cluster Science Published:2024


Abstract

Berberine (Ber) as a natural isoquinoline alkaloid, with a wide range of biological activities, mainly suffers from low bioavailability, decreasing its therapeutic efficacy. In this study, two novel conjugates of Ber with self-assembly property, Ber–polyethylene glycol (B–PEG) and Ber–diethylene glycol monomethyl ether (B–DG), were synthesized to investigate the effect of the anchoring part on the CMC, morphology as well as antioxidant and neuroprotective properties of the nanomicelles. The CMC increased from 1.2 μmol in B–DG to 3.0 μmol in B–PEG, measured by pendant drop. The anchored part affected greatly the shape and CMC of the self-assembled nanomicelles. A mixture of semi-spherical and cubic nanomicelles in the average hydrodynamic size of 93 nm was achieved for B–PEG, while B–DG nanomicelles were just in semispherical morphology with the hydrodynamic size of 64 nm. The antioxidant property of the nanomicelles was studied by DPPH scavenging and ferric reducing antioxidant power assays, exhibiting improved antioxidant activity of B–PEG and B–DG conjugates compared to free Ber. The neuroprotection potency of Ber was improved significantly after conjugation compared to free Ber against H2O2-induced cell death and B–PEG showed activity as level as that of the standard drug, Quercetin. Owing to the self-assembly property and interesting biological activities of the introduced amphiphilic Ber–PEG conjugate, we propose application of this nanomicelle alone, or as a promising bioactive carrier of the poorly water-soluble drugs, against neurodegenerative diseases. © The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2024.