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Hba, S.; Ghaddar, S.; Pinon, A.; El Kebbaj, R.; Pouget, C.; Sol, V.; Liagre, B.; Oudghiri, M.; Limami, Y. Natural Chalcones and Derivatives in Colon Cancer. Encyclopedia. Available online: https://encyclopedia.pub/entry/52303 (accessed on 14 June 2024).
Hba S, Ghaddar S, Pinon A, El Kebbaj R, Pouget C, Sol V, et al. Natural Chalcones and Derivatives in Colon Cancer. Encyclopedia. Available at: https://encyclopedia.pub/entry/52303. Accessed June 14, 2024.
Hba, Soufyane, Suzan Ghaddar, Aline Pinon, Riad El Kebbaj, Christelle Pouget, Vincent Sol, Bertrand Liagre, Mounia Oudghiri, Youness Limami. "Natural Chalcones and Derivatives in Colon Cancer" Encyclopedia, https://encyclopedia.pub/entry/52303 (accessed June 14, 2024).
Hba, S., Ghaddar, S., Pinon, A., El Kebbaj, R., Pouget, C., Sol, V., Liagre, B., Oudghiri, M., & Limami, Y. (2023, December 04). Natural Chalcones and Derivatives in Colon Cancer. In Encyclopedia. https://encyclopedia.pub/entry/52303
Hba, Soufyane, et al. "Natural Chalcones and Derivatives in Colon Cancer." Encyclopedia. Web. 04 December, 2023.
Natural Chalcones and Derivatives in Colon Cancer
Edit

Colon cancer poses a complex and substantial global health challenge, necessitating innovative therapeutic approaches. Chalcones, a versatile class of compounds with diverse pharmacological properties, have emerged as promising candidates for addressing colon cancer. Their ability to modulate pivotal signaling pathways in the development and progression of colon cancer makes them invaluable as targeted therapeutics. Nevertheless, it is crucial to recognize that although chalcones exhibit promise, further pre-clinical studies are required to validate their efficacy and safety. The journey toward effective colon cancer treatment is multifaceted, involving considerations such as optimizing the sequencing of therapeutic agents, comprehending the resistance mechanisms, and exploring combination therapies incorporating chalcones.

natural chalcones colon cancer chalcones-based nanoparticles drug delivery system

1. Introduction

In 2023, a concerning statistical forecast indicated that approximately 153,020 individuals will receive a diagnosis of colorectal cancer (CRC), while 52,550 lives will tragically be claimed by this disease [1]. Notably, this includes 19,550 cases and 3750 deaths among individuals younger than 50, underscoring this healthcare challenge’s pressing significance [1]. Colon cancer, also known as CRC, affects the colon or rectum, which are both critical digestive system components [2]. CRC arises when abnormal cells in the colon or rectum divide uncontrollably, forming malignant tumors. Colon cancer is one of the most common cancers worldwide, and its incidence continues to rise [2]. It imposes a considerable burden on healthcare systems and patients alike, necessitating the development of innovative and effective therapeutic strategies. Given the diverse mechanisms and pathways involved in its tumorigenesis, colon cancer demands a multifaceted approach to treatment.
In recent years, one promising avenue in colon cancer treatment has emerged in the form of chalcones, a class of compounds with diverse pharmacological activities. Chalcones have garnered attention for their potential to modulate the multiple signaling pathways implicated in CRC development and progression [3]. Chalcones (except for curcumin, which may be considered a bis-chalcone derivative) are characterized by their chemical structure, which consists of two aromatic rings linked by a three-carbon α,β-unsaturated carbonyl system [4] (Figure 1). This unique structure allows them to interact with specific molecular targets within the cancer cells. They have demonstrated significant anticancer properties, making them attractive candidates for targeted therapeutics in the fight against colon cancer [3].
Figure 1. General skeleton of the chemical structure of chalcones.

2. Anticancer Activity of Chalcones against Colon Cancer

2.1. Curcumin

Curcumin (CUR), which may be considered a bis-chalcone derivative [5], is a natural compound found in Curcuma longa, a flowering plant native to South Asia that is known for its rhizomes, which are ground to produce the spice known as turmeric [6]. CUR is a mixture of 3 compounds, the main structure of which is (1E,6E)-1,7-bis (4-hydroxy-3-methoxyphenyl) -1,6- heptadiene-3,5-dione (or curcumin I). CUR, which is responsible for turmeric’s color and health benefits, has potential therapeutic properties [7] (Figure 2).
Figure 2. Anticancer mechanisms of action of curcumin, xanthohumol, sappanchalcone flavokawain B, flavokawain C, and isoliquiritigenin.

2.2. Xanthohumol

Xanthohumol (XH) is a naturally occurring prenylated chalcone that is frequently extracted from the hop plant (Humulus lupulus) and is renowned for its multifaceted array of biological effects [8], encompassing various biological effects such as antiviral, antimicrobial, anti-inflammatory, and immunomodulatory functions [9] (Figure 2).
Previous research has examined the impact of XH on CRC inhibition or eradication. In a study by Liu et al., XH demonstrated a significant anti-tumor effect on CRC by reducing HK2 expression and glycolysis. XH effectively inhibited CRC cell growth in both in vitro and in vivo models [10]. Additionally, XH treatment stimulated cytochrome C release and activated the intrinsic apoptosis pathway [10][11]. Furthermore, the study findings indicated that XH downregulated the EGFR-Akt signaling pathway. When constitutively activated Akt1 was overexpressed exogenously, it notably compromised XH-induced glycolysis suppression and apoptosis induction [10].

2.3. Sappanchalcone

Sappanchalcone (SPC) is a natural compound derived from the heartwood of the Sappan tree (Caesalpinia sappan), which is native to Southeast Asia [12]. This phytochemical has emerged as a subject of interest in cancer research due to its cytotoxic effects on various cancer cell lines, including colon cancer (Figure 2).
Studies have explored the cytotoxic effects of SPC on colon cancer cells, particularly HCT116 and SW480 cells with different p53 statuses [13]. The study demonstrates that SPC inhibits the growth of both cell lines, with HCT116 cells being more sensitive [13]. It induces apoptosis in both cell lines via the caspase-dependent and caspase-independent pathways [13]. SPC disrupts the mitochondrial membrane potential, regulates Bcl-2 family proteins, and increases ROS production, leading to apoptosis. In HCT116 cells, SPC activates p53, suggesting a p53-associated apoptotic mechanism, whereas this effect is absent in SW480 cells, due to the lack of significant changes in cleaved caspase expression [13].

2.4. Isoliquiritigenin

Isoliquiritigenin (ISL) is a natural compound with a simple chalcone structure that belongs to the flavonoid group. It is known for its various potential health benefits and is found in a variety of plant sources, primarily in the roots of licorice (Glycyrrhiza glabra) and some other plants [14][15]. Various in vitro studies have explored its anticancer activity, suggesting that ISL may have the potential to inhibit the growth of cancer cells and induce apoptosis, making it a subject of interest in cancer research [16].
In fact, ISL was found to induce G2 cell cycle arrest [17], and to have an effect on death-associated protein kinase 1 (DAPK1) promoter methylation in the colon cancer cell line, indicating its role in influencing the epigenetic regulation of genes associated with cancer [15].

2.5. Flavokawains

2.5.1. Flavokawain B

Flavokawain B (FKB) is a naturally occurring compound derived from the roots of Alpinia pricei, a plant native to specific regions, including Taiwan [18][19]. This chalcone compound is part of the flavonoid family and is known for its bioactive properties and potential as an anticancer agent [19]. It is one of the constituents found in the extracts from the rhizomes of this plant, which has gained attention for its medicinal properties, particularly its ability to inhibit the growth of cancer cells and induce various cellular processes related to cancer treatment [18][19][20] (Figure 2).

2.5.2. Flavokawain C

Flavokawain C (FKC) is a bioactive compound with a fascinating origin that is deeply rooted in nature. This natural compound is primarily found in the kava plant (Piper methysticum), which is native to the South Pacific region. Kava has a long history of traditional use in this region for its calming and stress-reducing effects when consumed as a beverage [21] (Figure 2).
Recent studies have explored its interesting anticancer activity. Researchers investigated the growth-inhibitory and apoptosis-inducing effects of FKC on human cancer cell lines, particularly HCT116 carcinoma cells, while it showed minimal cytotoxicity toward normal colon cells [22]. The study also examined a structurally related compound, gymnogrammene (GMM), for comparison, revealing that FKC exerted pronounced cytotoxicity against HCT116 cells, while GMM had no such effect. This underscored the importance of structural variations in these compounds and their cytotoxicity. The molecular mechanisms of FKC-induced apoptosis were explored, involving the intrinsic and extrinsic pathways. FKC influenced the intrinsic pathway by modifying the expression of Bcl-2 family proteins, Bak and Bax, resulting in mitochondrial membrane permeabilization and the release of apoptogenic proteins such as cytochrome C, Smac/DIABLO, and apoptosis-inducing factor (AIF) [22]. Extrinsic pathway activation was mediated by FKC through increased death receptor levels (DR4 and DR5) and the downregulation of c-FLIPL, along with the activation of caspase-8, caspase-9, and caspase-3 [22]. FKC also disrupted the cell cycle by regulating proteins such as CDK2, CDK4, p21Cip, and p27Kip, causing S-phase arrest. Additionally, FKC-induced ER stress was evident from the elevated CHOP levels [22].

2.6. Derricin and Derricidin

Derricin (DCN) and derricidin (DCD) are flavonoids belonging to the chalcone subclass [23]. These compounds are natural plant-derived chemicals with similar chemical structures. They have been studied for their potential therapeutic properties, particularly in the context of cancer research (Figure 3).
Figure 3. Anticancer mechanisms of action of derricin, derricidin, hydroxysafflor yellow A, 3-deoxysappanchalcone, cardamonin, and licochalcone A.

2.7. Hydroxysafflor Yellow A

Hydroxysafflor Yellow A (HSYA) is a natural compound found in Carthamus tinctorius and has gained attention for its potential therapeutic applications, particularly in cancer treatment (Figure 3).
The anticancer potential of HSYA in CRC was investigated in vitro, focusing on the underlying molecular mechanisms. HSYA demonstrated concentration-dependent inhibitory effects on CRC cell proliferation, migration, and invasion while promoting apoptosis [24]. These actions were associated with regulating the EMT markers, such as the upregulation of E-cadherin and the downregulation of N-cadherin and vimentin. Additionally, HSYA was found to activate the PPARγ/PTEN/Akt signaling pathway, with increased expression of PPARγ and PTEN and decreased phosphorylation of Akt in CRC cells [24]. The role of PPARγ in mediating PTEN expression and subsequently inhibiting the PI3K/Akt pathway was highlighted. The study also revealed that inhibiting PPARγ with GW9662 or the PPARγ knockdown reversed the anticancer effects of HSYA on CRC cells, implicating PPARγ as a key player in HSYA’s therapeutic action [24].

2.8. The 3-deoxysappanchalcone Compound

The compound 3-DSC, which is short for 3-deoxysappanchalcone, is a natural compound derived from Caesalpinia sappan L. [25]. This compound has gained attention due to its potential therapeutic properties, particularly in the context of cancer treatment (Figure 3).
An in vitro study conducted by Zhao et al. focused on the compound’s potential anticancer properties against CRC [26]. The abnormal signaling of T-LAK cell-originated protein kinase (TOPK) is associated with various cancers, including CRC, and has been considered as a therapeutic target [27]. Although previous TOPK inhibitors had several limitations, 3-DSC was identified as a promising candidate [26]. The research demonstrated that 3-DSC specifically inhibits TOPK activity, inhibiting CRC cell growth, cell cycle arrest, and apoptosis. Importantly, 3-DSC showed selectivity for cancer cells, sparing the normal colon cells. This specificity is linked to its ability to induce apoptosis in CRC cells with wild-type p53 while sparing those with mutant p53 [26].

2.9. Cardamonin

Cardamonin (CDN), a compound derived from traditional Chinese medicine that is primarily found in the seeds of black cardamom (Amomum subulatum), exhibits promising effects in the treatment of chemotherapy-resistant colon cancer [28] (Figure 3).
Studies have shown that CDN significantly reduces cell viability and induces apoptosis in resistant cancer cells, potentially overcoming chemotherapy resistance [29]. Furthermore, CDN suppresses the expression of the key proteins associated with cancer growth and proliferation, including c-Myc and Oct4. Additionally, it inhibits the NF-κB signaling pathway, which is linked to oncogenesis and chemotherapy resistance [29].

2.10. Licochalcone A

Licochalcone A (LCA) is a bioactive compound that is naturally found in certain plants, particularly in the roots of licorice plants (Glycyrrhiza species). Glycyrrhiza uralensis Fisch. ex DC, commonly known as licorice, is a primary source of LCA. This compound has garnered attention for its potential medicinal properties and has been the subject of research in various fields, including its use in cancer therapy and anti-inflammatory applications [30][31][32] (Figure 3).
Researchers evaluated the effects of LCA on specific proteins and pathways [33]. The results, both in vitro and in vivo in a xenograft mouse model, showed the ability of LCA to significantly suppress PD-L1 expression, a vital immune checkpoint molecule often upregulated in various human tumor cells. Moreover, LCA inhibited the NF-κB signaling pathway, which is crucial in cancer cell survival, inflammation, and immunity, and affected the Ras/Raf/MEK pathway [33], which is known for its role in cell growth and cancer [34].

2.11. Garcinol

Garcinol (GAR), a chalcone derivative, is a natural compound renowned for its anti-inflammatory and anti-carcinogenic properties. It has been the focus of recent studies investigating its effects on cell growth in colon cancer cells and immortalized intestinal cells [35][36] (Figure 4).
Figure 4. Anticancer mechanisms of action of garcinol, isobavachalcone, and lonchocarpin.

2.12. Isobavachalcone

Isobavachalcone (IBC) is a bioactive molecule derived from Psoralea corylifolia, a well-known traditional Chinese medicinal herb. IBC has garnered significant attention for its potential anticancer properties and ability to modulate various cellular pathways involved in cancer progression (Figure 4). In a duration- and dose-dependent manner, IBC demonstrated significant cytotoxicity against CRC cell lines, including SW480 and HCT116 [37]. Morphological changes and decreased cell viability were observed in IBC-treated cells, which was consistent with previous findings showing IBC’s inhibitory effects on tumor cell growth [37].

2.13. Lonchocarpin

Lonchocarpin (LCPN), a chalcone compound, is derived from the Lonchocarpus sericeus plant, often referred to as the “Lancepod” or “Yopo” tree, which is native to various regions in Central and South America [38]. LCPN has displayed significant potential in several research studies, particularly regarding its role as a negative modulator of the Wnt/β-catenin pathway and its prospects as an anticancer agent [39].

3. Challenges Related to Chalcones Administration

3.1. Poor Solubility

The poor solubility of chalcones presents a significant challenge when it comes to their administration as potential therapeutic agents [40][41]. One of the primary obstacles posed by poor chalcone solubility is the limited rate and extent of their dissolution in the gastrointestinal tract [42]. This leads to inadequate absorption in the body, resulting in lower plasma concentrations and reduced bioactivity [41]. As a result, higher doses may be required to achieve the desired therapeutic effect, potentially increasing the risks of toxicity and adverse effects. Overcoming the poor solubility of chalcones is essential for harnessing their therapeutic potential and incorporating them into effective pharmaceutical formulations.

3.2. Therapeutic Window

The efficacy of chalcones in various therapeutic contexts often hinges on the timing and dosing regimens employed. Achieving the optimal sequencing and dosage is a challenging aspect of chalcone research, as it depends on the specific disease target and the pharmacokinetic properties of the chalcone in question [43].
Determining the therapeutic window for chalcone-based therapies is critical to balance efficacy and safety [43][44]. The therapeutic window represents the range of doses at which a chalcone exerts its desired effects without causing unacceptable toxicity [45].

3.3. Resistance Mechanisms

The cancer resistance mechanism involves the overexpression of efflux pumps in cancer cells [46][47]. Efflux pumps can actively remove drugs from the intracellular environment, reducing their intracellular concentrations [48]. Chalcones have garnered significant attention for their ability to sensitize cancer cells to chemotherapy and improve the pharmacokinetics of poorly absorbed cancer drugs. Numerous studies have investigated the potential of chalcones as modulators of resistance to conventional chemotherapy drugs, particularly by targeting multidrug efflux transporters such as P-glycoprotein [49][50][51], multidrug resistance-associated protein 1 [52][53], and breast cancer resistance protein [54][55]. These transporters play a crucial role in drug accumulation within cancer cells and contribute to multidrug resistance (MDR) [47].

3.4. Combination Therapies

Chalcones are often explored as a possible part of combination therapies with other drugs or treatments [29][36][56][57][58][59]. This strategy aims to enhance their efficacy while minimizing toxicity [56][57][60]. The optimal sequencing and dosage of chalcones in combination therapies depend on multiple factors, including the mechanism of action of the co-administered agents and the potential drug–drug interactions.

4. Nanoparticle-Based Delivery Systems for Chalcones

4.1. Advantages of Nanoparticles for Chalcone Delivery

4.1.1. Enhanced Drug Stability

One of the most significant advantages of NPs is their ability to enhance drug stability [61]. Conventional drugs often degrade rapidly, making it challenging to maintain their efficacy. NPs can encapsulate drugs, protecting them from environmental factors such as oxidation, light, temperature, moisture, and chemical reactions [62][63]. This preservation of drug integrity extends the shelf life and ensures consistent therapeutic effects.

4.1.2. Prolonged Circulation Time

NPs possess the unique ability to extend the circulation time of drugs within the body [62]. Their small size allows them to evade rapid clearance mechanisms, such as renal filtration, enabling drugs to remain in the bloodstream longer [64]. This prolonged circulation time enhances drug bioavailability and reduces the need for frequent dosing, ultimately improving patient compliance.

4.1.3. Enhanced Cellular Uptake

NPs facilitate the delivery of therapeutic agents to target cells and tissues [65]. Their small size and customizable surface properties enable them to interact favorably with cell membranes, promoting cellular uptake [65][66]. This targeted delivery minimizes off-target effects and enhances the therapeutic efficacy of drugs.

4.1.4. Controlled Release of Therapeutic Agents

Controlling the release of therapeutic agents is crucial to achieving optimal drug efficacy while minimizing side effects. NPs can be engineered to release drugs in a controlled and sustained manner [64][67]. This precise control ensures that therapeutic concentrations are maintained over an extended period, reducing the need for frequent dosing and mitigating adverse reactions [67].

4.2. Chalcone-Based NPs for CRC Treatment and Pre-Clinical Studies

One of the primary derivatives of chalcones explored in the context of colon cancer treatment is CUR. Notably, several NP-based formulations, including liposomes, micelles, nanogels, chitosan, and polymeric NPs, have been developed, demonstrating their effectiveness in combatting colon cancer in both in vitro and in vivo studies [68][69][70][71][72][73][74][75][76]. Additionally, innovative delivery systems have emerged. For instance, Ndong Ntoutoume et al. developed CUR-cyclodextrin/cellulose nanocrystal complexes (CUR-CD/CNCx), which have exhibited promising in vitro results, demonstrating lower IC50 values and a more significant anti-proliferative effect against HT-29 colon cancer cell lines [77].

5. Conclusions

Natural chalcones and derivatives are promising candidates for colon cancer treatment. Their potential to modulate crucial signaling pathways in colon cancer development and progression makes them valuable as targeted therapeutics. However, it is essential to acknowledge that while chalcones show promise, more pre-clinical studies are needed to validate their efficacy and safety further. Additionally, the integration of NP-based drug delivery systems presents a novel avenue by which to enhance the effectiveness of chalcones in treating colon cancer. While researchers have made strides in developing encapsulated synthetic chalcones that target various cancer cell lines [78][79][80], their specific applicability in the context of colon cancer and their mechanisms of action remain relatively unexplored.
In essence, the success of colon cancer treatment is multifaceted, and future research endeavors should strive to unravel the complexities of this promising therapeutic approach. By delving deeper into these aspects, we can pave the way for more targeted, effective, and safe treatments for colon cancer in the years to come.

References

  1. Siegel, R.L.; Wagle, N.S.; Cercek, A.; Smith, R.A.; Jemal, A. Colorectal cancer statistics, 2023. CA Cancer J. Clin. 2023, 73, 233–254.
  2. Rawla, P.; Sunkara, T.; Barsouk, A. Epidemiology of colorectal cancer: Incidence, mortality, survival, and risk factors. Prz. Gastroenterol. 2019, 14, 89–103.
  3. Michalkova, R.; Kello, M.; Cizmarikova, M.; Bardelcikova, A.; Mirossay, L.; Mojzis, J. Chalcones and Gastrointestinal Cancers: Experimental Evidence. Int. J. Mol. Sci. 2023, 24, 5964.
  4. Zhuang, C.; Zhang, W.; Sheng, C.; Zhang, W.; Xing, C.; Miao, Z. Chalcone: A Privileged Structure in Medicinal Chemistry. Chem. Rev. 2017, 117, 7762–7810.
  5. Pereira, R.; Silva, A.M.S.; Ribeiro, D.; Silva, V.L.M.; Fernandes, E. Bis-chalcones: A review of synthetic methodologies and anti-inflammatory effects. Eur. J. Med. Chem. 2023, 252, 115280.
  6. Almatroodi, S.A.; Alrumaihi, F.; Alsahli, M.A.; Alhommrani, M.F.; Khan, A.; Rahmani, A.H. Curcumin, an Active Constituent of Turmeric Spice: Implication in the Prevention of Lung Injury Induced by Benzo(a) Pyrene (BaP) in Rats. Molecules 2020, 25, 724.
  7. Hewlings, S.J.; Kalman, D.S. Curcumin: A Review of Its Effects on Human Health. Foods 2017, 6, 92.
  8. Bizaj, K.; Škerget, M.; Košir, I.J.; Knez, Ž. Hop (Humulus lupulus L.) Essential Oils and Xanthohumol Derived from Extraction Process Using Solvents of Different Polarity. Horticulturae 2022, 8, 368.
  9. Liu, M.; Hansen, P.E.; Wang, G.; Qiu, L.; Dong, J.; Yin, H.; Qian, Z.; Yang, M.; Miao, J. Pharmacological profile of xanthohumol, a prenylated flavonoid from hops (Humulus lupulus). Molecules 2015, 20, 754–779.
  10. Liu, W.; Li, W.; Liu, H.; Yu, X. Xanthohumol inhibits colorectal cancer cells via downregulation of Hexokinases II-mediated glycolysis. Int. J. Biol. Sci. 2019, 15, 2497–2508.
  11. Choi, D.; Schroer, S.A.; Lu, S.Y.; Cai, E.P.; Hao, Z.; Woo, M. Redundant role of the cytochrome c-mediated intrinsic apoptotic pathway in pancreatic β-cells. J. Endocrinol. 2011, 210, 285–292.
  12. Jung, E.G.; Han, K.I.; Kwon, H.J.; Patnaik, B.B.; Kim, W.J.; Hur, G.M.; Nam, K.W.; Han, M.D. Anti-inflammatory activity of sappanchalcone isolated from Caesalpinia sappan L. in a collagen-induced arthritis mouse model. Arch. Pharm. Res. 2015, 38, 973–983.
  13. Seo, H.W.; No, H.; Cheon, H.J.; Kim, J.-K. Sappanchalcone, a flavonoid isolated from Caesalpinia sappan L., induces caspase-dependent and AIF-dependent apoptosis in human colon cancer cells. Chem. Biol. Interact. 2020, 327, 109185.
  14. Babu, V.; Kapkoti, D.S.; Binwal, M.; Bhakuni, R.S.; Shanker, K.; Singh, M.; Tandon, S.; Mugale, M.N.; Kumar, N.; Bawankule, D.U. Liquiritigenin, isoliquiritigenin rich extract of Glycyrrhiza glabra roots attenuates inflammation in macrophages and collagen-induced arthritis in rats. Inflammopharmacology 2023, 31, 983–996.
  15. Zorko, B.A.; Pérez, L.B.; De Blanco, E.J. Effects of ILTG on DAPK1 promoter methylation in colon and leukemia cancer cell lines. Anticancer Res. 2010, 30, 3945–3950.
  16. Wang, K.-L.; Yu, Y.-C.; Hsia, S.-M. Perspectives on the Role of Isoliquiritigenin in Cancer. Cancers 2021, 13, 115.
  17. Auyeung, K.K.; Ko, J.K. Novel herbal flavonoids promote apoptosis but differentially induce cell cycle arrest in human colon cancer cell. Investig. New Drugs 2010, 28, 1–13.
  18. Kuo, Y.-F.; Su, Y.-Z.; Tseng, Y.-H.; Wang, S.-Y.; Wang, H.-M.; Chueh, P.J. Flavokawain B, a novel chalcone from Alpinia pricei Hayata with potent apoptotic activity: Involvement of ROS and GADD153 upstream of mitochondria-dependent apoptosis in HCT116 cells. Free Radic. Biol. Med. 2010, 49, 214–226.
  19. Ji, T.; Lin, C.; Krill, L.S.; Eskander, R.; Guo, Y.; Zi, X.; Hoang, B.H. Flavokawain B, a kava chalcone, inhibits growth of human osteosarcoma cells through G2/M cell cycle arrest and apoptosis. Mol. Cancer 2013, 12, 55.
  20. Malek, S.N.A.; Phang, C.W.; Ibrahim, H.; Abdul Wahab, N.; Sim, K.S. Phytochemical and Cytotoxic Investigations of Alpinia mutica Rhizomes. Molecules 2011, 16, 583–589.
  21. Bian, T.; Corral, P.; Wang, Y.; Botello, J.; Kingston, R.; Daniels, T.; Salloum, R.G.; Johnston, E.; Huo, Z.; Lu, J.; et al. Kava as a Clinical Nutrient: Promises and Challenges. Nutrients 2020, 12, 3044.
  22. Phang, C.W.; Karsani, S.A.; Sethi, G.; Abd Malek, S.N. Flavokawain C Inhibits Cell Cycle and Promotes Apoptosis, Associated with Endoplasmic Reticulum Stress and Regulation of MAPKs and Akt Signaling Pathways in HCT 116 Human Colon Carcinoma Cells. PLoS ONE 2016, 11, e0148775.
  23. Fonseca, B.F.; Predes, D.; Cerqueira, D.M.; Reis, A.H.; Amado, N.G.; Cayres, M.C.; Kuster, R.M.; Oliveira, F.L.; Mendes, F.A.; Abreu, J.G. Derricin and derricidin inhibit Wnt/β-catenin signaling and suppress colon cancer cell growth in vitro. PLoS ONE 2015, 10, e0120919.
  24. Su, D.; Lv, C. Hydroxysafflor yellow A inhibits the proliferation, migration, and invasion of colorectal cancer cells through the PPARγ/PTEN/Akt signaling pathway. Bioengineered 2021, 12, 11533–11543.
  25. Yodsaoue, O.; Cheenpracha, S.; Karalai, C.; Ponglimanont, C.; Tewtrakul, S. Anti-allergic activity of principles from the roots and heartwood of Caesalpinia sappan on antigen-induced β-hexosaminidase release. Phytother. Res. Int. J. Devoted Pharmacol. Toxicol. Eval. Nat. Prod. Deriv. 2009, 23, 1028–1031.
  26. Zhao, R.; Huang, H.; Choi, B.Y.; Liu, X.; Zhang, M.; Zhou, S.; Song, M.; Yin, F.; Chen, H.; Shim, J.-H.; et al. Cell growth inhibition by 3-deoxysappanchalcone is mediated by directly targeting the TOPK signaling pathway in colon cancer. Phytomedicine 2019, 61, 152813.
  27. Zhang, L.; Wang, F.; Yi, H.; Ermakova, S.P.; Malyarenko, O.S.; Mo, J.; Huang, Y.; Duan, Q.; Xiao, J.; Zhu, F. The role of T-LAK cell-originated protein kinase in targeted cancer therapy. Mol. Cell Biochem. 2022, 477, 759–769.
  28. Nawaz, J.; Rasul, A.; Shah, M.A.; Hussain, G.; Riaz, A.; Sarfraz, I.; Zafar, S.; Adnan, M.; Khan, A.H.; Selamoglu, Z. Cardamonin: A new player to fight cancer via multiple cancer signaling pathways. Life Sci. 2020, 250, 117591.
  29. Lu, S.; Lin, C.; Cheng, X.; Hua, H.; Xiang, T.; Huang, Y.; Huang, X. Cardamonin reduces chemotherapy resistance of colon cancer cells via the TSP50/NF-κB pathway in vitro. Oncol. Lett. 2018, 15, 9641–9646.
  30. Li, M.T.; Xie, L.; Jiang, H.M.; Huang, Q.; Tong, R.S.; Li, X.; Xie, X.; Liu, H.M. Role of Licochalcone A in Potential Pharmacological Therapy: A Review. Front. Pharmacol. 2022, 13, 878776.
  31. Park, M.K.; Ji, J.; Haam, K.; Han, T.-H.; Lim, S.; Kang, M.-J.; Lim, S.S.; Ban, H.S. Licochalcone A inhibits hypoxia-inducible factor-1α accumulation by suppressing mitochondrial respiration in hypoxic cancer cells. Biomed. Pharmacother. 2021, 133, 111082.
  32. Fu, Y.; Hsieh, T.-c.; Guo, J.; Kunicki, J.; Lee, M.Y.W.T.; Darzynkiewicz, Z.; Wu, J.M. Licochalcone-A, a novel flavonoid isolated from licorice root (Glycyrrhiza glabra), causes G2 and late-G1 arrests in androgen-independent PC-3 prostate cancer cells. Biochem. Biophys. Res. Commun. 2004, 322, 263–270.
  33. Liu, X.; Xing, Y.; Li, M.; Zhang, Z.; Wang, J.; Ri, M.; Jin, C.; Xu, G.; Piao, L.; Jin, H.; et al. Licochalcone A inhibits proliferation and promotes apoptosis of colon cancer cell by targeting programmed cell death-ligand 1 via the NF-κB and Ras/Raf/MEK pathways. J. Ethnopharmacol. 2021, 273, 113989.
  34. Song, Y.; Bi, Z.; Liu, Y.; Qin, F.; Wei, Y.; Wei, X. Targeting RAS-RAF-MEK-ERK signaling pathway in human cancer: Current status in clinical trials. Genes. Dis. 2023, 10, 76–88.
  35. Hong, J.; Kwon, S.J.; Sang, S.; Ju, J.; Zhou, J.N.; Ho, C.T.; Huang, M.T.; Yang, C.S. Effects of garcinol and its derivatives on intestinal cell growth: Inhibitory effects and autoxidation-dependent growth-stimulatory effects. Free Radic. Biol. Med. 2007, 42, 1211–1221.
  36. Ranjbarnejad, T.; Saidijam, M.; Tafakh, M.S.; Pourjafar, M.; Talebzadeh, F.; Najafi, R. Garcinol exhibits anti-proliferative activities by targeting microsomal prostaglandin E synthase-1 in human colon cancer cells. Hum. Exp. Toxicol. 2017, 36, 692–700.
  37. Li, Y.; Qin, X.; Li, P.; Zhang, H.; Lin, T.; Miao, Z.; Ma, S. Isobavachalcone isolated from Psoralea corylifolia inhibits cell proliferation and induces apoptosis via inhibiting the AKT/GSK-3β/β-catenin pathway in colorectal cancer cells. Drug Des. Dev. Ther. 2019, 13, 1449–1460.
  38. Baudrenghien, J.; Jadot, J.; Huls, R. La structure de la lonchocarpine. Bull. De. L’Académie R. De Belg. 1953, 39, 105–120.
  39. Predes, D.; Oliveira, L.F.S.; Ferreira, L.S.S.; Maia, L.A.; Delou, J.M.A.; Faletti, A.; Oliveira, I.; Amado, N.G.; Reis, A.H.; Fraga, C.A.M.; et al. The Chalcone Lonchocarpin Inhibits Wnt/β-Catenin Signaling and Suppresses Colorectal Cancer Proliferation. Cancers 2019, 11, 1968.
  40. Sweeting, S.G.; Hall, C.L.; Potticary, J.; Pridmore, N.E.; Warren, S.D.; Cremeens, M.E.; D’Ambruoso, G.D.; Matsumoto, M.; Hall, S.R. The solubility and stability of heterocyclic chalcones compared with trans-chalcone. Acta Crystallogr. Sect. B Struct. Sci. Cryst. Eng. Mater. 2020, 76, 13–17.
  41. Gao, S.; Hu, M. Bioavailability challenges associated with development of anti-cancer phenolics. Mini Rev. Med. Chem. 2010, 10, 550–567.
  42. Mendanha, D.; Vieira de Castro, J.; Moreira, J.; Costa, B.M.; Cidade, H.; Pinto, M.; Ferreira, H.; Neves, N.M. A New Chalcone Derivative with Promising Antiproliferative and Anti-Invasion Activities in Glioblastoma Cells. Molecules 2021, 26, 3383.
  43. Papachristos, A.; Patel, J.; Vasileiou, M.; Patrinos, G.P. Dose Optimization in Oncology Drug Development: The Emerging Role of Pharmacogenomics, Pharmacokinetics, and Pharmacodynamics. Cancers 2023, 15, 3233.
  44. Tamargo, J.; Le Heuzey, J.Y.; Mabo, P. Narrow therapeutic index drugs: A clinical pharmacological consideration to flecainide. Eur. J. Clin. Pharmacol. 2015, 71, 549–567.
  45. Muller, P.Y.; Milton, M.N. The determination and interpretation of the therapeutic index in drug development. Nat. Rev. Drug Discov. 2012, 11, 751–761.
  46. Benayad, S.; Wahnou, H.; El Kebbaj, R.; Liagre, B.; Sol, V.; Oudghiri, M.; Saad, E.M.; Duval, R.E.; Limami, Y. The Promise of Piperine in Cancer Chemoprevention. Cancers 2023, 15, 5488.
  47. Xiao, J.; Gao, M.; Diao, Q.; Gao, F. Chalcone Derivatives and their Activities against Drug-resistant Cancers: An Overview. Curr. Top. Med. Chem. 2021, 21, 348–362.
  48. Robey, R.W.; Pluchino, K.M.; Hall, M.D.; Fojo, A.T.; Bates, S.E.; Gottesman, M.M. Revisiting the role of ABC transporters in multidrug-resistant cancer. Nat. Rev. Cancer 2018, 18, 452–464.
  49. Parveen, Z.; Brunhofer, G.; Jabeen, I.; Erker, T.; Chiba, P.; Ecker, G.F. Synthesis, biological evaluation and 3D-QSAR studies of new chalcone derivatives as inhibitors of human P-glycoprotein. Bioorg. Med. Chem. 2014, 22, 2311–2319.
  50. Ngo, T.D.; Tran, T.D.; Le, M.T.; Thai, K.M. Computational predictive models for P-glycoprotein inhibition of in-house chalcone derivatives and drug-bank compounds. Mol. Divers 2016, 20, 945–961.
  51. Bois, F.; Beney, C.; Boumendjel, A.; Mariotte, A.M.; Conseil, G.; Di Pietro, A. Halogenated chalcones with high-affinity binding to P-glycoprotein: Potential modulators of multidrug resistance. J. Med. Chem. 1998, 41, 4161–4164.
  52. Lindamulage, I.K.; Vu, H.Y.; Karthikeyan, C.; Knockleby, J.; Lee, Y.F.; Trivedi, P.; Lee, H. Novel quinolone chalcones targeting colchicine-binding pocket kill multidrug-resistant cancer cells by inhibiting tubulin activity and MRP1 function. Sci. Rep. 2017, 7, 10298.
  53. Nguyen, H.; Zhang, S.; Morris, M.E. Effect of flavonoids on MRP1-mediated transport in Panc-1 cells. J. Pharm. Sci. 2003, 92, 250–257.
  54. Coman, F.-M.; Mbaveng, A.T.; Leonte, D.; Bencze, L.C.; Vlase, L.; Imre, S.; Kuete, V.; Efferth, T.; Zaharia, V. Heterocycles 44. Synthesis, characterization and anticancer activity of new thiazole ortho-hydroxychalcones. Med. Chem. Res. 2018, 27, 1396–1407.
  55. Kraege, S.; Stefan, K.; Juvale, K.; Ross, T.; Willmes, T.; Wiese, M. The combination of quinazoline and chalcone moieties leads to novel potent heterodimeric modulators of breast cancer resistance protein (BCRP/ABCG2). Eur. J. Med. Chem. 2016, 117, 212–229.
  56. Hanahan, D.; Weinberg, R.A. Hallmarks of cancer: The next generation. Cell 2011, 144, 646–674.
  57. Maréchal, A.; Zou, L. DNA damage sensing by the ATM and ATR kinases. Cold Spring Harb. Perspect. Biol. 2013, 5, a012716.
  58. Abouzeid, A.H.; Patel, N.R.; Rachman, I.M.; Senn, S.; Torchilin, V.P. Anti-cancer activity of anti-GLUT1 antibody-targeted polymeric micelles co-loaded with curcumin and doxorubicin. J. Drug Target. 2013, 21, 994–1000.
  59. Wahnou, H.; Youlyouz-Marfak, I.; Liagre, B.; Sol, V.; Oudghiri, M.; Duval, R.E.; Limami, Y. Shining a Light on Prostate Cancer: Photodynamic Therapy and Combination Approaches. Pharmaceutics 2023, 15, 1767.
  60. Ahmed, S.S.T.; Fahim, J.; Abdelmohsen, U.R. Chemical and biological potential of Ammi visnaga (L.) Lam. and Apium graveolens L.: A review (1963–2020). J. Adv. Biomed. Pharm. Sci. 2021, 4, 160–176.
  61. Kadam, R.S.; Bourne, D.W.; Kompella, U.B. Nano-advantage in enhanced drug delivery with biodegradable nanoparticles: Contribution of reduced clearance. Drug Metab. Dispos. 2012, 40, 1380–1388.
  62. Mitchell, M.J.; Billingsley, M.M.; Haley, R.M.; Wechsler, M.E.; Peppas, N.A.; Langer, R. Engineering precision nanoparticles for drug delivery. Nat. Rev. Drug Discov. 2021, 20, 101–124.
  63. Ansari, S.A.; Satar, R.; Jafri, M.A.; Rasool, M.; Ahmad, W.; Kashif Zaidi, S. Role of Nanodiamonds in Drug Delivery and Stem Cell Therapy. Iran. J. Biotechnol. 2016, 14, 130–141.
  64. Alyautdin, R.; Khalin, I.; Nafeeza, M.I.; Haron, M.H.; Kuznetsov, D. Nanoscale drug delivery systems and the blood–brain barrier. Int. J. Nanomed. 2014, 9, 795–811.
  65. Yue, J.; Feliciano, T.J.; Li, W.; Lee, A.; Odom, T.W. Gold Nanoparticle Size and Shape Effects on Cellular Uptake and Intracellular Distribution of siRNA Nanoconstructs. Bioconjugate Chem. 2017, 28, 1791–1800.
  66. Hoshyar, N.; Gray, S.; Han, H.; Bao, G. The effect of nanoparticle size on in vivo pharmacokinetics and cellular interaction. Nanomedicine 2016, 11, 673–692.
  67. Cai, X.J.; Xu, Y.Y. Nanomaterials in controlled drug release. Cytotechnology 2011, 63, 319–323.
  68. Wong, K.E.; Ngai, S.C.; Chan, K.G.; Lee, L.H.; Goh, B.H.; Chuah, L.H. Curcumin Nanoformulations for Colorectal Cancer: A Review. Front. Pharmacol. 2019, 10, 152.
  69. Pandelidou, M.; Dimas, K.; Georgopoulos, A.; Hatziantoniou, S.; Demetzos, C. Preparation and characterization of lyophilised egg PC liposomes incorporating curcumin and evaluation of its activity against colorectal cancer cell lines. J. Nanosci. Nanotechnol. 2011, 11, 1259–1266.
  70. Chen, Y.; Du, Q.; Guo, Q.; Huang, J.; Liu, L.; Shen, X.; Peng, J. A W/O emulsion mediated film dispersion method for curcumin encapsulated pH-sensitive liposomes in the colon tumor treatment. Drug Dev. Ind. Pharm. 2019, 45, 282–291.
  71. Raveendran, R.; Bhuvaneshwar, G.; Sharma, C.P. In vitro cytotoxicity and cellular uptake of curcumin-loaded Pluronic/Polycaprolactone micelles in colorectal adenocarcinoma cells. J. Biomater. Appl. 2013, 27, 811–827.
  72. Xiao, B.; Han, M.K.; Viennois, E.; Wang, L.; Zhang, M.; Si, X.; Merlin, D. Hyaluronic acid-functionalized polymeric nanoparticles for colon cancer-targeted combination chemotherapy. Nanoscale 2015, 7, 17745–17755.
  73. Sanoj Rejinold, N.; Thomas, R.G.; Muthiah, M.; Chennazhi, K.P.; Manzoor, K.; Park, I.K.; Jeong, Y.Y.; Jayakumar, R. Anti-cancer, pharmacokinetics and tumor localization studies of pH-, RF- and thermo-responsive nanoparticles. Int. J. Biol. Macromol. 2015, 74, 249–262.
  74. Wahnou, H.; Liagre, B.; Sol, V.; El Attar, H.; Attar, R.; Oudghiri, M.; Duval, R.E.; Limami, Y. Polyphenol-Based Nanoparticles: A Promising Frontier for Enhanced Colorectal Cancer Treatment. Cancers 2023, 15, 3826.
  75. Hu, S.; Xia, K.; Huang, X.; Zhao, Y.; Zhang, Q.; Huang, D.; Xu, W.; Chen, Z.; Wang, C.; Zhang, Z. Multifunctional CaCO3@Cur@QTX125@HA nanoparticles for effectively inhibiting growth of colorectal cancer cells. J. Nanobiotechnol. 2023, 21, 353.
  76. Jain, S.; Lenaghan, S.; Dia, V.; Zhong, Q. Co-delivery of curcumin and quercetin in shellac nanocapsules for the synergistic antioxidant properties and cytotoxicity against colon cancer cells. Food Chem. 2023, 428, 136744.
  77. Ndong Ntoutoume, G.M.A.; Granet, R.; Mbakidi, J.P.; Brégier, F.; Léger, D.Y.; Fidanzi-Dugas, C.; Lequart, V.; Joly, N.; Liagre, B.; Chaleix, V.; et al. Development of curcumin-cyclodextrin/cellulose nanocrystals complexes: New anticancer drug delivery systems. Bioorg. Med. Chem. Lett. 2016, 26, 941–945.
  78. Rioux, B.; Pinon, A.; Gamond, A.; Martin, F.; Laurent, A.; Champavier, Y.; Barette, C.; Liagre, B.; Fagnère, C.; Sol, V.; et al. Synthesis and biological evaluation of chalcone-polyamine conjugates as novel vectorized agents in colorectal and prostate cancer chemotherapy. Eur. J. Med. Chem. 2021, 222, 113586.
  79. Rioux, B.; Pouget, C.; Fidanzi-Dugas, C.; Gamond, A.; Laurent, A.; Semaan, J.; Pinon, A.; Champavier, Y.; Léger, D.Y.; Liagre, B.; et al. Design and multi-step synthesis of chalcone-polyamine conjugates as potent antiproliferative agents. Bioorg. Med. Chem. Lett. 2017, 27, 4354–4357.
  80. Ismail, B.; Ghezali, L.; Gueye, R.; Limami, Y.; Pouget, C.; Leger, D.Y.; Martin, F.; Beneytout, J.-L.; Duroux, J.-L.; Diab-Assaf, M.; et al. Novel methylsulfonyl chalcones as potential antiproliferative drugs for human prostate cancer: Involvement of the intrinsic pathway of apoptosis. Int. J. Oncol. 2013, 43, 1160–1168.
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