Figures & data
Figure 1 Synthesis scheme for SV119-PEG3500-DOA.
Abbreviations: DOA, dioleyl amido aspartic acid; PEG, polyethylene glycol.
![Figure 1 Synthesis scheme for SV119-PEG3500-DOA.Abbreviations: DOA, dioleyl amido aspartic acid; PEG, polyethylene glycol.](/cms/asset/f8776c28-c1a3-4a7a-9036-c07881801849/dijn_a_31981_f0001_b.jpg)
Figure 2 NMR spectrum (A) and MALDI-TOF mass spectrum (B) of SV119-PEG3500-DOA. The peaks in (A) are attributed to the benzene groups on SV119 (a), the double bonds of DOA (b), and the carbon chains of DOA (c).
Abbreviations: DOA, dioleyl amido aspartic acid; MALDI-TOF, matrix-assisted laser desorption/ionisation-time of flight; NMR, nuclear magnetic resonance; PEG, polyethylene glycol.
![Figure 2 NMR spectrum (A) and MALDI-TOF mass spectrum (B) of SV119-PEG3500-DOA. The peaks in (A) are attributed to the benzene groups on SV119 (a), the double bonds of DOA (b), and the carbon chains of DOA (c).Abbreviations: DOA, dioleyl amido aspartic acid; MALDI-TOF, matrix-assisted laser desorption/ionisation-time of flight; NMR, nuclear magnetic resonance; PEG, polyethylene glycol.](/cms/asset/efff25ac-a2e3-48da-ba21-0b299240a26a/dijn_a_31981_f0002_c.jpg)
Table 1 Size and zeta potential of SV119 liposomes
Figure 3 Enhanced intracellular uptake of SV119 liposomes by DU-145 cells, examined by microscopic study (A) and quantitative analysis (B) (n = 4, mean ± SD). In (A), the percentage of SV119-PEG-DOA in the total lipid was 0% (a), 1% (b), 3% (c), and 5% (d), respectively.
Abbreviations: DOA, dioleyl amido aspartic acid; PEG, polyethylene glycol.
![Figure 3 Enhanced intracellular uptake of SV119 liposomes by DU-145 cells, examined by microscopic study (A) and quantitative analysis (B) (n = 4, mean ± SD). In (A), the percentage of SV119-PEG-DOA in the total lipid was 0% (a), 1% (b), 3% (c), and 5% (d), respectively.Abbreviations: DOA, dioleyl amido aspartic acid; PEG, polyethylene glycol.](/cms/asset/4fdc34f8-daa1-4fa5-a410-a24354a2165b/dijn_a_31981_f0003_c.jpg)
Figure 4 Cellular uptake of liposomes by BEAS-2B cells. Microscopic images (A), and quantitative analysis (B) (n = 4, mean ± SD). The percentage of SV119-PEG-DOA in the total lipid was 0% (a), or 3% (b).
Abbreviations: DOA, dioleyl amido aspartic acid; PEG, polyethylene glycol.
![Figure 4 Cellular uptake of liposomes by BEAS-2B cells. Microscopic images (A), and quantitative analysis (B) (n = 4, mean ± SD). The percentage of SV119-PEG-DOA in the total lipid was 0% (a), or 3% (b).Abbreviations: DOA, dioleyl amido aspartic acid; PEG, polyethylene glycol.](/cms/asset/a352fa94-9298-4855-a1fe-e63f514bf0bf/dijn_a_31981_f0004_c.jpg)
Figure 5 Uptake of SV119 liposomes by MCF-7 (A), PC-3 (B), 201T (C), and A549 cells (D) (n = 4, mean ± SD).
Abbreviations: DOA, dioleyl amido aspartic acid; PEG, polyethylene glycol.
![Figure 5 Uptake of SV119 liposomes by MCF-7 (A), PC-3 (B), 201T (C), and A549 cells (D) (n = 4, mean ± SD).Abbreviations: DOA, dioleyl amido aspartic acid; PEG, polyethylene glycol.](/cms/asset/8646518c-ddca-4322-a87c-4df4bf6b92be/dijn_a_31981_f0005_b.jpg)
Figure 6 Time-course of cellular uptake for SV119 liposomes.
Notes: Rhodamine-PE labeled liposomes with 0% or 3% SV119-PEG-DOA were incubated with DU-145 cells for an indicated period at 37°C. (n = 4, mean ± SD).
Abbreviations: DOA, dioleyl amido aspartic acid; PEG, polyethylene glycol.
![Figure 6 Time-course of cellular uptake for SV119 liposomes.Notes: Rhodamine-PE labeled liposomes with 0% or 3% SV119-PEG-DOA were incubated with DU-145 cells for an indicated period at 37°C. (n = 4, mean ± SD).Abbreviations: DOA, dioleyl amido aspartic acid; PEG, polyethylene glycol.](/cms/asset/10263a85-9681-48da-979f-4fbd897e4389/dijn_a_31981_f0006_b.jpg)
Figure 7 Uptake of liposomes decorated with modified SV119 (mSV119) by DU-145 cells. Scheme of synthesis (A) and microscopic images (B) (n = 4, mean ± SD). In (B), the percentage of mSV119-PEG-DOA in the total lipid was 0% (a), 1% (b), 3% (c), and 5% (d), respectively.
Abbreviations: DOA, dioleyl amido aspartic acid; PEG, polyethylene glycol.
![Figure 7 Uptake of liposomes decorated with modified SV119 (mSV119) by DU-145 cells. Scheme of synthesis (A) and microscopic images (B) (n = 4, mean ± SD). In (B), the percentage of mSV119-PEG-DOA in the total lipid was 0% (a), 1% (b), 3% (c), and 5% (d), respectively.Abbreviations: DOA, dioleyl amido aspartic acid; PEG, polyethylene glycol.](/cms/asset/fd9e272c-4ecf-4053-a487-16441aea60cc/dijn_a_31981_f0007_c.jpg)
Figure 8 Cytotoxic effect of free and liposomal DOX on DU-145 prostate cancer cells. Cells were treated with free DOX, DOX-loaded SV119 liposomes or DOX-loaded unmodified liposomes with DOX concentrations of 0.2, 1, or 10 μg/mL. Cytotoxicity was assessed by MTT assay. Cells receiving no treatment were defined as the maximal cell viability. Values presented are the mean ± SD of six replicates.
Note: *P < 0.05 compared to the control treatments with unmodified liposomes.
Abbreviations: DOX, doxorubicin; L[D], DOX-loaded unmodified liposomes.
![Figure 8 Cytotoxic effect of free and liposomal DOX on DU-145 prostate cancer cells. Cells were treated with free DOX, DOX-loaded SV119 liposomes or DOX-loaded unmodified liposomes with DOX concentrations of 0.2, 1, or 10 μg/mL. Cytotoxicity was assessed by MTT assay. Cells receiving no treatment were defined as the maximal cell viability. Values presented are the mean ± SD of six replicates.Note: *P < 0.05 compared to the control treatments with unmodified liposomes.Abbreviations: DOX, doxorubicin; L[D], DOX-loaded unmodified liposomes.](/cms/asset/2b001240-59fa-40ab-a57b-e3cf49d4724c/dijn_a_31981_f0008_b.jpg)
Figure 9 Localization of SV119 liposomes in DU-145 cells. Cells were incubated with rhodamine-PE labeled SV119 liposomes for 3 hours (A–C) or 16 hours (D–F) in a serum-free medium, stained with markers of early endosomes (anti-EEA1; A–C) or lysosomes (LysoTracker®; Life Technologies, Carlsbad, CA) (D–F), and imaged using confocal microscopy. Red fluorescence represents rhodamine-PE labeled liposomes (A and D), green fluorescence represents early endosomes B) or lysosomes (E). Yellow color observed in the red + green overlay (C and F) indicates colocalization of red liposomes with the green endosomes (C) or lysosomes (F).
Note: Scale bar = 10 μm.
![Figure 9 Localization of SV119 liposomes in DU-145 cells. Cells were incubated with rhodamine-PE labeled SV119 liposomes for 3 hours (A–C) or 16 hours (D–F) in a serum-free medium, stained with markers of early endosomes (anti-EEA1; A–C) or lysosomes (LysoTracker®; Life Technologies, Carlsbad, CA) (D–F), and imaged using confocal microscopy. Red fluorescence represents rhodamine-PE labeled liposomes (A and D), green fluorescence represents early endosomes B) or lysosomes (E). Yellow color observed in the red + green overlay (C and F) indicates colocalization of red liposomes with the green endosomes (C) or lysosomes (F).Note: Scale bar = 10 μm.](/cms/asset/84580586-ad49-4bd4-8768-2efce088ac8b/dijn_a_31981_f0009_c.jpg)
Figure S1 Scheme of synthesis for SV119-PEG550 (A) and effect of SV119 on the uptake of SV119-liposomes by DU-145 cells (B).
Abbreviation: PEG, polyethylene glycol.
![Figure S1 Scheme of synthesis for SV119-PEG550 (A) and effect of SV119 on the uptake of SV119-liposomes by DU-145 cells (B).Abbreviation: PEG, polyethylene glycol.](/cms/asset/324a08f9-7cfe-4464-b878-76c0e3250d52/dijn_a_31981_sf0001_c.jpg)