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Molecules
Volume 25
Issue 11
10.3390/molecules25112581
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Article

Comparative Molecular Transporter Properties of Cyclic Peptides Containing Tryptophan and Arginine Residues Formed through Disulfide Cyclization

by
Eman H. M. Mohammed
1,2,†,
Dindyal Mandal
1,†,
Saghar Mozaffari
1,
Magdy Abdel-Hamied Zahran
2,
Amany Mostafa Osman
2,3,
Rakesh Kumar Tiwari
1,* and
Keykavous Parang
1,*
1
Center for Targeted Drug Delivery, Department of Biomedical and Pharmaceutical Sciences, Chapman University School of Pharmacy, Harry and Diane Rinker Health Science Campus, Irvine, CA 92618, USA
2
Chemistry Department, Faculty of Science, Chemistry department, Menoufia University, Shebin El-Koam 51132, Egypt
3
Department of Chemistry, College of Science and Humanities in Al-Kharj, Prince Sattam Bin Abdulaziz University, Al-Kharj 11942, Saudi Arabia
*
Authors to whom correspondence should be addressed.
†
These authors contributed equally to this work.
Academic Editors: Silvia Panzavolta and Luisa Stella Dolci
Molecules 2020, 25(11), 2581; https://doi.org/10.3390/molecules25112581
Received: 14 April 2020 / Revised: 27 May 2020 / Accepted: 27 May 2020 / Published: 2 June 2020
(This article belongs to the Special Issue Applications of Materials in Drug Delivery)
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Abstract

We have previously reported cyclic cell-penetrating peptides [WR]5 and [WR]4 as molecular transporters. To optimize further the utility of our developed peptides for targeted therapy in cancer cells using the redox condition, we designed a new generation of peptides and evaluated their cytotoxicity as well as uptake behavior against different cancer cell lines. Thus, cyclic [C(WR)xC] and linear counterparts (C(WR)xC), where x = 4–5, were synthesized using Fmoc/tBu solid-phase peptide synthesis, purified, and characterized. The compounds did not show any significant cytotoxicity (at 25 µM) against ovarian (SK-OV-3), leukemia (CCRF-CEM), gastric adenocarcinoma (CRL-1739), breast carcinoma (MDA-MB-231), and normal kidney (LLCPK) cells after 24 and 72 h incubation. Both cyclic [C(WR)5C] and linear (C(WR)5C) demonstrated comparable molecular transporter properties versus [WR]5 in the delivery of a phosphopeptide (F′-GpYEEI) in CCRF-CEM cells. The uptake of F′-GpYEEI in the presence of 1,4-dithiothreitol (DTT) as the reducing agent was significantly improved in case of l(C(WR)5C), while it was not changed by [C(WR)5C]. Fluorescence microscopy also demonstrated a significant uptake of F′-GpYEEI in the presence of l(C(WR)5C). Cyclic [C(WR)5C] improved the uptake of the fluorescent-labeled anti-HIV drugs F′-d4T, F′-3TC, and F′-FTC by 3.0–4.9-fold. These data indicate that both [C(WR)5C] and linear (C(WR)5C) peptides can act as molecular transporters. View Full-Text
Keywords: cell-penetrating peptide; cancer; cytotoxicity; cellular uptake; disulfide bridge; drug delivery; phosphopeptide cell-penetrating peptide; cancer; cytotoxicity; cellular uptake; disulfide bridge; drug delivery; phosphopeptide
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Mohammed, E.H.M.; Mandal, D.; Mozaffari, S.; Abdel-Hamied Zahran, M.; Mostafa Osman, A.; Kumar Tiwari, R.; Parang, K. Comparative Molecular Transporter Properties of Cyclic Peptides Containing Tryptophan and Arginine Residues Formed through Disulfide Cyclization. Molecules 2020, 25, 2581. https://doi.org/10.3390/molecules25112581

AMA Style

Mohammed EHM, Mandal D, Mozaffari S, Abdel-Hamied Zahran M, Mostafa Osman A, Kumar Tiwari R, Parang K. Comparative Molecular Transporter Properties of Cyclic Peptides Containing Tryptophan and Arginine Residues Formed through Disulfide Cyclization. Molecules. 2020; 25(11):2581. https://doi.org/10.3390/molecules25112581

Chicago/Turabian Style

Mohammed, Eman H. M., Dindyal Mandal, Saghar Mozaffari, Magdy Abdel-Hamied Zahran, Amany Mostafa Osman, Rakesh Kumar Tiwari, and Keykavous Parang. 2020. "Comparative Molecular Transporter Properties of Cyclic Peptides Containing Tryptophan and Arginine Residues Formed through Disulfide Cyclization" Molecules 25, no. 11: 2581. https://doi.org/10.3390/molecules25112581

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