Development of resveratrol-conjugated gold nanoparticles: interrelationship of increased resveratrol corona on anti-tumor efficacy against breast, pancreatic and prostate cancers

Figures & data

Figure 1 The amount of major polyphenols in red wine (mg/mL) and their chemical structures.Note: Data from Xiang et al.¹⁸

Figure 2 Isomers of resveratrol: (A) structural and (B) ultraviolet–visible spectrum differences.

Scheme 1 Synthetic route for resveratrol gold nanoparticles (Res-AuNPs) and resveratrol-gum arabic- conjugated gold nanoparticles (Res-GA-AuNPs). The 3x Res to increase the resveratrol corona around the AuNPs.

Figure 3 Ultraviolet–visible spectrum: (A) trans-resveratrol used in the reaction; (B) AuNPs in the absence of GA; and (C) AuNPs in the presence of GA. The threefold increase in resveratrol significantly increased the AuNP-conjugated trans-resveratrol molecules. 

Abbreviations: Res, resveratrol; AuNPs, gold nanoparticles; GA, gum arabic.

Table 1 Physicochemical data parameters of Res-AuNPs and Res-GA-AuNPs

Sample	Res-AuNPs	3× Res-AuNPs	Res-GA-AuNPs	3× Res-GA-AuNPs
Size (nm)
Hydrodynamic size	56.1	107.7	64.1	187.7
Core size	16.1±5.0	16.0±4.0	14.9±4.4	16.7±4.6
Capping	40	91.8	49.2	171
Zeta potential (mV)	−25	−26	−22	−24
Au concentration (µg/mL)^a	142	150	153	162
Resveratrol
Res concentration (µg/mL)^b	187	423	188	408
AuNPs per mL	7.3×10^12	7.6×10^12	9.4×10^12	6.7×10^12

Notes: ^aInductively coupled plasma atomic emission spectroscopy; ^bFolin–Ciocalteu polyphenol concentration.

Abbreviations: Res, resveratrol; AuNP, gold nanoparticle; GA, gum arabic.

Figure 4 Transmission electron microscope images of AuNPs and size distribution: (A) Res-AuNPs; (B) Res-GA-AuNPs.

Abbreviations: AuNPs, gold nanoparticles; Res, resveratrol; GA, gum arabic.

Figure 5 Transmission electron microscope images of AuNPs and size distribution: (A) 3× Res-AuNPs; (B) 3× Res-GA-AuNPs.

Abbreviations: AuNPs, gold nanoparticles; Res, resveratrol; GA, gum arabic.

Figure 6 Liquid chromatography–multiple reaction monitoring of (A) Res standard curve and (B) Res-conjugated AuNPs. The signal (AUC) for resveratrol was normalized to the AUC for tolbutamide internal standard. The average response (AUC-mangiferin/AUC-tolbutamide; AUC-RES/AUC-Tol) from triplicate injections was plotted. Linearity for resveratrol was good (R²>0.99) across the entire calibration range.

Abbreviations: Res, resveratrol; AuNPs, gold nanoparticles; GA, gum arabic; AUC, area under the curve.

Figure 7 High-resolution transmission electron microscopy images of AuNPs demonstrating lattice fringes: (A) Res-AuNPs: d=0.17 nm, (B) 3× Res-AuNPs: d=0.14 nm, (C) Res-GA-AuNPs: d=0.17 nm, and (D) 3× Res-GA-AuNPs: d=0.17 nm.

Abbreviations: AuNPs, gold nanoparticles; Res, resveratrol; GA, gum arabic.

Table 2 Anti-tumor IC₅₀ (µg/mL) cell viability efficacy of AuNPs

Sample	Cancer cells
	MDAMB-231	PANC-1	PC-3
Res-AuNPs	N/A	N/A	N/A
3× Res-AuNPs	40	79	38
Res-GA-AuNPs	N/A	200.4	N/A
3× Res-GA-AuNPs	72	72	59

Abbreviations: AuNP, gold nanoparticle; Res, Resveratrol; GA, gum arabic; MDAMB-231, breast cancer; PANC-1, pancreatic cancer; PC-3, prostate cancer; N/A, not applicable.

Figure 8 In vitro stability study of (A) Res-AuNPs, (B) 3× Res-AuNPs (insert, magnified plasmon peak), (C) Res-GA-AuNPs, and (D) 3×Res-GA-AuNPs (insert, magnified plasmon peak) in different biological media after 24 hours.

Abbreviations: Res, resveratrol; AuNPs, gold nanoparticles; GA, gum arabic.

Figure 9 Infrared spectrum of: (A) Res-AuNPs; 3× Re-AuNPs and (B) Res-GA-AuNPs; 3× Res-GA-AuNPs.

Abbreviations: Res, resveratrol; AuNPs, gold nanoparticles; GA, gum arabic.

Figure 10 (A) Cellular internalization of Res-AuNPs and Res-GA-AuNPs in breast (MDAMB-231), pancreatic (PANC-1) and prostate (PC-3) cancer cell lines incubated for 24 hours at 42 µg/mL. (B) Cellular internalization of 3× Res-AuNPs and 3× Res-GA-AuNPs in MDAMB-231, pancreatic and prostate cancer cell lines incubated for 24 hours at 42 µg/mL.

Abbreviations: Res, resveratrol; AuNPs, gold nanoparticles; GA, gum arabic.

Figure 11 (A) Cellular morphological changes after treatment with Res-AuNPs and Res-GA-AuNPs for 24 hours. (B) Cellular morphological changes after treatment with 3× Res-AuNPs and 3× Res-GA-AuNPs for 24 hours. The red circles show the cell debris, representing cell death.

Abbreviations: Res, resveratrol; AuNPs, gold nanoparticles; GA, gum arabic.

Figure 12 Effectiveness of Res-AuNPs and Res-GA-AuNPs on cell viability of breast (MDAMB-231), pancreatic (PANC-1) and prostate (PC-3) cancer cells. 

Abbreviations: Res, resveratrol; AuNPs, gold nanoparticles; GA, gum arabic.

Xiang L, Xiao L, Wang Y, Li H, Huang Z, He X. Health benefits of wine: don’t expect resveratrol too much. Food Chem. 2014;156:258–263. doi:10.1016/j.foodchem.2014.01.00624629966

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