Natural Product-Based Hybrids as Potential Candidates for the Treatment of Cancer: Focus on Curcumin and Resveratrol
Abstract
:1. Introduction
2. Chemical Features and Anticancer Effect of Curcumin and Resveratrol
3. Hybrid Compounds Containing Curcumin and Resveratrol
4. Gold-Based Hybrid Nanosystems
5. Perspectives and Conclusions
Funding
Conflicts of Interest
Abbreviations
AuNP | gold nanoparticle |
CTS | chitosan |
Cur | curcumin |
Cur@AuNP | Cur-containing AuNP |
DDS | drug delivery system |
DNMT | DNA methyltransferase |
Dox | doxorubicin |
DSS | dextran sodium sulfate |
ECM | extracellular matrix |
EGFR TK | epidermal growth factor receptor tyrosine kinase |
ER | estrogen receptor |
FA | folic acid |
G | graphene |
GO | graphene oxide |
GSH | reduced glutathione |
HSPC | hydrogenated soya phosphatidylcholine |
LA | lipoic acid |
Lip | liposome |
MMP | matrix metalloproteinase |
MRI | magnetic resonance imaging |
MUC-1 | mucin-1 |
NF-κB | nuclear factor-κB |
NIR | near-infrared |
NP | nanoparticle |
PAMAM | poly(amidoamine) |
PDT | photodynamic therapy |
PEG | polyethylene glycol |
PS | polystyrene |
PTT | photothermal therapy |
PVP | polyvinylpyrrolidone |
Res | resveratrol |
rGO | reduced graphene oxide |
ROS | reactive oxygen species |
SAR | structure-activity relationship |
SDT | sonodynamic treatment |
STAT3 protein | signal transducer and activator of transcription 3 protein |
TDD | targeted drug delivery |
TPA | 12-O-tetradecanoylphorbol-13-acetate |
TrxR | thioredoxin reductase |
VEGF | vascular endothelial growth factor |
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Pharmacophore 1 | Pharmacophore 2 | Hybrids | Pathology | In Vitro Cell-Free or In Silico Model | In Vitro Cell-Based Model | In Vivo Model | Ref. |
---|---|---|---|---|---|---|---|
Res | ebselen | Benzoselenazole–stilbene hybrids | cancer | inhibition of TrxR | human liver carcinoma Bel-7402 | [48] | |
Res | cinnamic acid | Res linked to cinnamic acid through an acyl ester group | cancer | tubulin polymerization assay; molecular docking with tubulin | lung cancer A549, MCF-7, hepatoma HepG2, cervical cancer HeLa, and breast cancer MDA-231 cells | [49] | |
Res | salicylate | addition of a carboxylic acid or its methyl ester attached ortho to one of the phenol groups present in hydroxystilbene | cancer | molecular docking with human DNMT | human colorectal adenocarcinoma HT-29, hepatoma HepG2 cells, and mammary gland/breast SK-BR-3 cells | [50] | |
Res | caffeic acid | Res-caffeic acid hybrids possessing an amide linker or an ester linkage | breast cancer | molecular docking with STAT3 protein | human breast cancer MDA-MB-231 cells and colonic carcinoma HT29 cells | female Kunming mice bearing breast cancer 4T1 cells | [51] |
Res | obhs | conjugation of Res with OBHS | breast cancer | estrogen receptor ERα antagonistic activity | human breast cancer MCF-7 cells | female Balb/c nude mice inoculated with MCF-7 breast cancer cells | [52] |
Res | Cur | an o-substituted conjugated-phenyl system from Res linked to a 3-methoxy-4-hydroxycynamoil subunit, with a hydrazone functionality as a spacer | breast cancer | estrogen-positive human breast cancer MCF-7 cells | [53] | ||
Res | Cur | Res linked to a 3-methoxy-4-hydroxycynamoil subunit from Cur | colonic cancer | human colon adenocarcinoma SW480 and SW620 cells | [54] | ||
Res | Aspirin | addition of a carboxylic acid group adjacently to one of the phenols in the Res structure | colonic cancer and intestinal inflammation | normal mouse intestinal ModeK cells and human colon cancer HCT116 cells | C57BL/6 mice bearing HCT116 colon cancer cells; DSS-induced colitis in male C57BL/6 mice | [55] | |
Res | coumarin | a substituted trans-vinylbenzene moiety on a coumarin backbone | cancer | human lung carcinoma H460, squamous carcinoma A431, and melanoma JR8 cells | [56] |
Pharmacophore 1 | Pharmacophore 2 | Hybrids | Pathology | In Vitro Cell-Free or In Silico Model | In Vitro Cell-Based Model | In Vivo Model | Ref. |
---|---|---|---|---|---|---|---|
Cur | ligustrazine | substituting one of the two aromatic rings of Cur analogs with ligustrazine | lung cancer | inhibition of TrxR | human lung cancer A549, drug-resistant human lung cancer A549/DDP cells | athymic BALB/c nude mice inoculated with A549/DDP cells | [57] |
Cur | coumarin | monocarbonyl Cur linked to coumarin with a trizole as spacer | cancer | molecular docking with tubulin | human leukemia THP-1, colon adenocarcinoma COLO-205, colorectal cancer HCT-116 cells | [58] | |
Cur | Isatin | monocarbonyl Cur linked to isatin with a trizole as a spacer | cancer | tubulin polymerization assay; molecular docking with tubulin | human leukemia THP-1, colon adenocarcinoma COLO-205, colorectal cancer HCT-116, prostate cancer PC-3 cells | [59] | |
Cur | sulfonamide | introduction of sulfanilamide unit into the methylene part of Cur | cancer | molecular docking with EGFR TK | human gastric adenocarcinoma AGS and lung cancer A549 cells | [60] | |
Cur | steroids | pyrazolocurcumin-pyrimidinyl androstane derivative | breast cancer | human breast cancer MCF-7 cells | [61] | ||
Cur | quercetin or genistein | ester of (1E,4E)-1,4-penta-dien-3-one (from Cur) and chromone (from quercetin or genistein) | prostate cancer | human prostate cancer androgen-independent PC-3b and DU-145 cells, and androgen-dependent LNCaP cells | [62] | ||
Cur | myricetin | monocarbonyl analogs of curcumin linked to myricetin | gastric cancer | human gastric cancer SGC-7901 cells | [63] | ||
Cur | artesunate | linkage of Cur with two artesunate molecules | melanoma | melanoma SK-MEL3, SK-MEL24, and RPMI-7951 cells | [64] | ||
Cur | thalidomide | thalidomide linked at the methylene position between the two carbonyls of Cur; monoketone Cur linked to thalidomide | multiple myeloma | human multiple myeloma MM1S, RPMI8226, U266 cells | [65] |
Cytotoxic Drug | Hybrid Materials | Aim | Functionalization | Pathology | In Vitro Model | In Vivo Model | Ref. |
---|---|---|---|---|---|---|---|
Res | Res-loaded Au nanospheres | DD | liver cancer | Human liver HepG2 cells | [91] | ||
Res | Res-loaded AuNPs | DD | liver cancer | Human liver HepG2 cells | 15 BALC/c nude mice bearing HepG2 cells | [92] | |
Res | Res-conjugated AuNPs | DD | breast cancer | TPA-induced migration and invasion in breast cancer MCF-7 cells | [93] | ||
Res | Res-conjugated AuNPs stabilized by gum arabic | DD | cancer | breast cancer MDAMB-231, pancreatic cancer PANC-1, and prostate cancer PC-3 cells | [94] | ||
Res Dox | Res-stabilized AuNPs | DD | brain cancer | human glioma LN 229 cells | [95] | ||
Res Dox | AuNPs capped with Res | DD | cervical cancer | human cervical cancer (HeLa, HPV-18 positive, and CaSki, HPV-16 positive) cells | [96] | ||
Res | Res-loaded in chitosan modified liposomes coated by gold nanoshells | NIR- and pH-responsive system | AuNPs Chitosan | cervical cancer | human epithelioid cervix carcinoma HeLa cells | [97] | |
Res | Hollow NPs based on Au-Res complexes | NIR responsive system | AuNPs | melanoma | malignant melanoma A375 cells | [98] |
Cytotoxic Drug | Hybrid Materials | Aim | Functionalization | Pathology | In Vitro Model | In Vivo Model | References |
---|---|---|---|---|---|---|---|
Cur | Cur-conjugated AuNPs | DD | cervical cancer | cervical cancer HeLa cells | [99] | ||
Cur | Cur-capped AuNP-reduced graphene oxide nanocomposite | DD | colon and liver cancer | human colon cancer HT-29 and SW-948 cells | [100] | ||
Cur | MUC-1 aptamer conjugated and Cur-loaded PEGylated amine-terminated generation 5 poly(amidoamine) dendrimers/gold hybrid structures | active TDD | MUC-1 aptamer | colon adenocarcinoma | colon cancer HT29 and C26 cells | C26 tumor-bearing BALB/c female mice | [101] |
Cur Lipoic acid | Lipoic acid-Cur and GSH attached to gold-iron oxide nanocomposites | active targeted and pH-responsive DD MRI | GSH Lipoic acid Iron NPs | Brain cancer | fetal human astrocyte and U87MG cell lines | [102] | |
Cur | Cur-loaded gliadin-stabilized folic acid-functionalized Au quantum clusters | active targeted and pH-responsive DD | Folic acid Gliadin | Cancer | brain cancer C6 glioma cells and breast cancer MDA-MB231 cells | [103] | |
Cur | Cur-loaded in protein polymer-Au NPs (protein polymer based on elastin-like peptide and the coiled-coil region of Cartilage Oligomeric Matrix protein, both bearing an N-terminal hexahistidine group) | Breast cancer | human breast cancer MCF7 cells | [104] | |||
Cur | Folate-Cur-loaded Au-polyvinylpyrrolidone NPs | active targeted DD | Folic acid | breast cancer | human breast adenocarcinoma MDA-MB-231 and MCF-7, epithelial MCF 10A cells; mouse mammary carcinoma 4T1 cells | female Balb/c mice bearing 4T1 cancer | [105] |
Cur | AuNPs immobilized on folate-conjugated dendritic mesoporous silica-coated reduced graphene oxide nanosheets loaded with Cur | active targeted DD NIR- and pH-responsive system | AuNPs Folic acid | breast cancer | human breast adenocarcinoma MCF-7 cells | [106] | |
Cur | chitosan-coated halloysite nanotubes loaded with Cur-Au NPs | NIR- and pH-responsive systems | AuNPs Chitosan | breast cancer | human breast adenocarcinoma MCF-7 cells | [107] | |
Cur | Cur-loaded in gold-coated liposome NPs | NIR-responsive system | AuNPs | melanoma | mouse melanoma B16 cells | C57BL/6 female mice bearing B16 cells | [108] |
Cur | Cur-loaded HSPC liposomes coated with gold | NIR-responsive system | AuNPs | melanoma | mouse melanoma B16 F10 cells | [109] | |
Cur | Cur-Au-PEG-NPs | NIR-responsive and sonosensitive system | AuNPs Ultrasounds | melanoma | mouse melanoma C540 (B16/F10) cells | inbred male BALB/c mice bearing B16/F10 cells | [110] |
Cur | PEG-Cur-AuNPs | NIR-responsive system | AuNPs | melanoma | mouse melanoma C540 (B16/F10) cells | [111] | |
Cur | PEG-Cur-AuNPs | NIR-responsive system | AuNPs | melanoma | mouse melanoma C540 (B16/F10) cells | male C57/inbred mice implanted with B16/F10 cells | [112] |
Cur | Cur-loaded Ag/Au bimetallic NPs coated with polystyrene- and PEG-based gel layers | NI- responsive system | AuNPs | melanoma | mouse melanoma B16F10 cells | [113] |
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Micale, N.; Molonia, M.S.; Citarella, A.; Cimino, F.; Saija, A.; Cristani, M.; Speciale, A. Natural Product-Based Hybrids as Potential Candidates for the Treatment of Cancer: Focus on Curcumin and Resveratrol. Molecules 2021, 26, 4665. https://doi.org/10.3390/molecules26154665
Micale N, Molonia MS, Citarella A, Cimino F, Saija A, Cristani M, Speciale A. Natural Product-Based Hybrids as Potential Candidates for the Treatment of Cancer: Focus on Curcumin and Resveratrol. Molecules. 2021; 26(15):4665. https://doi.org/10.3390/molecules26154665
Chicago/Turabian StyleMicale, Nicola, Maria Sofia Molonia, Andrea Citarella, Francesco Cimino, Antonina Saija, Mariateresa Cristani, and Antonio Speciale. 2021. "Natural Product-Based Hybrids as Potential Candidates for the Treatment of Cancer: Focus on Curcumin and Resveratrol" Molecules 26, no. 15: 4665. https://doi.org/10.3390/molecules26154665