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Artificial Cells, Nanomedicine, and Biotechnology
An International Journal
Volume 46, 2018 - Issue sup1: Supplement 1
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Research Article

Effects of N-terminal and C-terminal modification on cytotoxicity and cellular uptake of amphiphilic cell penetrating peptides

Mehdi Soleymani-Goloujeha Department of Medical Nanotechnology, Faculty of Advanced Medical Sciences, Tabriz University of Medical Sciences, Tabriz, Iran;b Department of Stem Cells and Developmental Biology at Cell Science Research Center, Royan Institute for Stem Cell Biology and Technology, ACECR, Tehran, IranView further author information
,
Ali Nokhodchic Pharmaceutics Research Laboratory, School of Life Sciences, University of Sussex, Falmer, Brighton, UKView further author information
,
Mehri Niazid Student Research Committee, Faculty of Advanced Medical Sciences, Tabriz University of Medical Sciences, Tabriz, IranView further author information
,
Saeedeh Najafi-Hajivard Student Research Committee, Faculty of Advanced Medical Sciences, Tabriz University of Medical Sciences, Tabriz, IranView further author information
,
Javid Shahbazi-Mojarrade Biotechnology Research Center and Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz, IranView further author information
,
Nosratollah Zarghamif Department of Medical Biotechnology, Faculty of Advanced Medical Sciences, Tabriz University of Medical Sciences, Tabriz, IranView further author information
,
Parvin Zakeri-Milanig Liver and Gastrointestinal Diseases Research Center and Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz, IranORCID Iconhttps://orcid.org/0000-0003-3243-587XView further author information
ORCID Icon,
Ali Mohammadih Immunology Research Center, Tabriz University of Medical Sciences, Tabriz, IranView further author information
,
Mohammad Karimih Immunology Research Center, Tabriz University of Medical Sciences, Tabriz, IranView further author information
&
Hadi Valizadehi Drug Applied Research Center and Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz, IranCorrespondence[email protected]
ORCID Iconhttps://orcid.org/0000-0003-4157-6279View further author information
ORCID Icon show all
Pages 91-103 | Received 11 Jul 2017, Accepted 05 Dec 2017, Published online: 19 Dec 2017

Figures & data

Figure 1. Scheme of solid phase peptide synthesis and final cleavage.

Figure 1. Scheme of solid phase peptide synthesis and final cleavage.

Table 1. Synthesized peptide sequences.

Figure 2. Toxicity of (a) modified peptides and (b) unmodified peptides to MCF-7 cells and (c) drug concentrations to calculate IC50. The cells were incubated for 24, 48 and 72 h at 37 ºC with concentrations of 25 and 50 µM, respectively for cell viability assessment by MTT. (i) (P1: BA-[WR]4-pGlu, P2: BA-QGR-[WK]3-pGlu, P3: BA-QGR-[WR]3-pGlu, P4: BA-[WR]3-QGR-pGlu, P5: BA-WRWQGRWRW-pGlu, P6: BA-R8-pGlu, P7: BA-R10-pGlu, P8: BA-K10-pGlu) and (ii) (P1: COOH-WRWQGRWRW-NH2, P2: COOH-QGR-[WR]3-NH2, P3: COOH-QGR-[WK]3-NH2, P4: COOH-[WR]3-QGR-NH2, P5: COOH-[WR]4-NH2).

Figure 2. Toxicity of (a) modified peptides and (b) unmodified peptides to MCF-7 cells and (c) drug concentrations to calculate IC50. The cells were incubated for 24, 48 and 72 h at 37 ºC with concentrations of 25 and 50 µM, respectively for cell viability assessment by MTT. (i) (P1: BA-[WR]4-pGlu, P2: BA-QGR-[WK]3-pGlu, P3: BA-QGR-[WR]3-pGlu, P4: BA-[WR]3-QGR-pGlu, P5: BA-WRWQGRWRW-pGlu, P6: BA-R8-pGlu, P7: BA-R10-pGlu, P8: BA-K10-pGlu) and (ii) (P1: COOH-WRWQGRWRW-NH2, P2: COOH-QGR-[WR]3-NH2, P3: COOH-QGR-[WK]3-NH2, P4: COOH-[WR]3-QGR-NH2, P5: COOH-[WR]4-NH2).

Figure 3. Cytotoxicity of (a) unmodified and (b) modified peptides interaction with MTX (physical linkage) and MCF-7 cells; (c) Cytotoxicity of unmodified peptides conjugated with MTX. The cells were incubated for 24, 48 and 72 h at 37 °C with concentrations of 25 and 50 nM, respectively for cell viability assessment by MTT. (i) (BA-WRWQGRWRW-pGlu, BA-QGR-[WK]3-pGlu), (ii) (COOH-QGR-[WK]3-NH2, COOH-[WR]3-QGR-NH2, COOH-WRWQGRWRW-NH2) and (iii) (COOH-QGR-[WK]3-MTX, COOH-WRWQGRWRW-MTX, COOH-[WR]4-MTX, COOH-[WR]3-QGR-MTX, COOH-QGR-[WR]3-MTX).

Figure 3. Cytotoxicity of (a) unmodified and (b) modified peptides interaction with MTX (physical linkage) and MCF-7 cells; (c) Cytotoxicity of unmodified peptides conjugated with MTX. The cells were incubated for 24, 48 and 72 h at 37 °C with concentrations of 25 and 50 nM, respectively for cell viability assessment by MTT. (i) (BA-WRWQGRWRW-pGlu, BA-QGR-[WK]3-pGlu), (ii) (COOH-QGR-[WK]3-NH2, COOH-[WR]3-QGR-NH2, COOH-WRWQGRWRW-NH2) and (iii) (COOH-QGR-[WK]3-MTX, COOH-WRWQGRWRW-MTX, COOH-[WR]4-MTX, COOH-[WR]3-QGR-MTX, COOH-QGR-[WR]3-MTX).

Figure 4. Live cell images. Row (a) Bright field (40×): A (R8-FAM, 25 µM), D (R8-FAM/E8, 25 µM), G (Mem-R8-FAM, 50 µM) and J (Mem-R8-FAM/E8, 50 µM). Row (b) Fluorescent (40×): B (R8-FAM, 25 µM), E (R8-FAM/E8, 25 µM), H (Mem-R8-FAM, 50 µM) and K (Mem-R8-FAM/E8, 50 µM). Row (c) Merged: C (R8-FAM, 25 µM), F (R8-FAM/E8, 25 µM), I (Mem-R8-FAM, 50 µM) and L (Mem-R8-FAM/E8, 50 µM).

Figure 4. Live cell images. Row (a) Bright field (40×): A (R8-FAM, 25 µM), D (R8-FAM/E8, 25 µM), G (Mem-R8-FAM, 50 µM) and J (Mem-R8-FAM/E8, 50 µM). Row (b) Fluorescent (40×): B (R8-FAM, 25 µM), E (R8-FAM/E8, 25 µM), H (Mem-R8-FAM, 50 µM) and K (Mem-R8-FAM/E8, 50 µM). Row (c) Merged: C (R8-FAM, 25 µM), F (R8-FAM/E8, 25 µM), I (Mem-R8-FAM, 50 µM) and L (Mem-R8-FAM/E8, 50 µM).

Figure 5. CLSM images. Row (a) Propidium iodide (63×): A (R8-FAM, 50 µM), D (R8-FAM, 25 µM) and G (Mem-R8-FAM/E8, 50 µM). Row (b) Fluorescent (63×): B (R8-FAM, 50 µM), E (R8-FAM, 25 µM) and H (Mem-R8-FAM/E8, 50 µM). Row (c) Merged: C (R8-FAM, 50 µM), F (R8-FAM, 25 µM) and I (Mem-R8-FAM/E8, 50 µM).

Figure 5. CLSM images. Row (a) Propidium iodide (63×): A (R8-FAM, 50 µM), D (R8-FAM, 25 µM) and G (Mem-R8-FAM/E8, 50 µM). Row (b) Fluorescent (63×): B (R8-FAM, 50 µM), E (R8-FAM, 25 µM) and H (Mem-R8-FAM/E8, 50 µM). Row (c) Merged: C (R8-FAM, 50 µM), F (R8-FAM, 25 µM) and I (Mem-R8-FAM/E8, 50 µM).

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