Anti-inflammatory and antioxidant effects of nanoformulations composed of metal-organic frameworks delivering rutin and/or piperine natural agents

References

• Aarsland D , Brønnick K , Larsen JP , et al. (2009). Cognitive impairment in incident, untreated Parkinson disease: the Norwegian ParkWest study. Neurology 72: 1121–6.
   PubMed Web of Science ®Google Scholar
• Abánades Lázaro I , Wells CJR , Forgan RS. (2020). Multivariate modulation of the Zr MOF UiO-66 for defect-controlled combination anticancer drug delivery. Angew Chem Int Ed Engl 59: 5211–7.
   PubMed Web of Science ®Google Scholar
• Abdelhameed RM , Rehan M , Emam HE. (2018). Figuration of Zr-based MOF@cotton fabric composite for potential kidney application. Carbohydr Polym 195: 460–7.
   PubMed Web of Science ®Google Scholar
• Abdelhameed RM , Simões MMQ , Silva AMS , Rocha J. (2015). Enhanced photocatalytic activity of MIL-125 by post-synthetic modification with Cr(III) and Ag nanoparticles. Chemistry 21: 11072–81.
   PubMed Web of Science ®Google Scholar
• AbouAitah K , Stefanek A , Higazy IM , et al. (2020a). Effective targeting of colon cancer cells with piperine natural anticancer prodrug using functionalized clusters of hydroxyapatite nanoparticles. Pharmaceutics 12: 70.
   PubMed Web of Science ®Google Scholar
• AbouAitah K , Swiderska-Sroda A , Kandeil A , et al. (2020b). Virucidal action against avian influenza H5N1 virus and immunomodulatory effects of nanoformulations consisting of mesoporous silica nanoparticles loaded with natural prodrugs. Int J Nanomedicine 15: 5181–202.
   PubMed Web of Science ®Google Scholar
• Alkholief M. (2019). Optimization of lecithin-chitosan nanoparticles for simultaneous encapsulation of doxorubicin and piperine. J Drug Deliv Sci Technol 52: 204–14.
   Web of Science ®Google Scholar
• Alonso-Castro AJ , Domínguez F , García-Carrancá A. (2013). Rutin exerts antitumor effects on nude mice bearing SW480 tumor. Arch Med Res 44: 346–51.
   PubMed Web of Science ®Google Scholar
• Al-Rejaie SS , Aleisa AM , Sayed-Ahmed MM , et al. (2013). Protective effect of rutin on the antioxidant genes expression in hypercholestrolemic male Westar rat. BMC Complement Altern Med 13: 136.
   PubMed Web of Science ®Google Scholar
• Annapurna A , Reddy CS , Akondi RB , Rao SR. (2009). Cardioprotective actions of two bioflavonoids, quercetin and rutin, in experimental myocardial infarction in both normal and streptozotocin-induced type I diabetic rats. J Pharm Pharmacol 61: 1365–74.
   PubMed Web of Science ®Google Scholar
• Asfour MH , Mohsen AM. (2018). Formulation and evaluation of pH-sensitive rutin nanospheres against colon carcinoma using HCT-116 cell line. J Adv Res 9: 17–26.
   PubMed Web of Science ®Google Scholar
• Atanasov AG , Zotchev SB , Dirsch VM , et al. (2021). Natural products in drug discovery: advances and opportunities. Nat Rev Drug Discov 20: 200–16.
   PubMed Web of Science ®Google Scholar
• Azza Z , Oudghiri M. (2015). In vivo anti-inflammatory and antiarthritic activities of aqueous extracts from Thymelaea hirsuta . Pharmacogn Res 7: 213–6.
   PubMed Web of Science ®Google Scholar
• Bang JS , Oh DH , Choi HM , et al. (2009). Anti-inflammatory and antiarthritic effects of piperine in human interleukin 1beta-stimulated fibroblast-like synoviocytes and in rat arthritis models. Arthritis Res Ther 11: R49.
   PubMed Web of Science ®Google Scholar
• Bi J , Lu Y , Dong Y , Gao P. (2018). Synthesis of folic acid-modified DOX@ZIF-8 nanoparticles for targeted therapy of liver cancer. J Nanomater 2018: 1–5.
   Web of Science ®Google Scholar
• Chedid G , Yassin A. (2018). Recent trends in covalent and metal organic frameworks for biomedical applications. Nanomaterials 8: 916.
   Web of Science ®Google Scholar
• Chen G , Luo J , Cai M , et al. (2019). Investigation of metal–organic framework-5 (MOF-5) as an antitumor drug oridonin sustained release carrier. Molecules 24: 3369.
   PubMed Web of Science ®Google Scholar
• Chevreau H , Permyakova A , Nouar F , et al. (2016). Synthesis of the biocompatible and highly stable MIL-127(Fe): from large scale synthesis to particle size control. CrystEngComm 18: 4094–101.
   Web of Science ®Google Scholar
• Costa P , Sousa Lobo JM. (2001). Modeling and comparison of dissolution profiles. Eur J Pharm Sci 13: 123–33.
   PubMed Web of Science ®Google Scholar
• Cunha D , Ben Yahia M , Hall S , et al. (2013a). Rationale of drug encapsulation and release from biocompatible porous metal–organic frameworks. Chem Mater 25: 2767–76.
   Web of Science ®Google Scholar
• Cunha D , Gaudin C , Colinet I , et al. (2013b). Rationalization of the entrapping of bioactive molecules into a series of functionalized porous zirconium terephthalate MOFs. J Mater Chem B 1: 1101–8.
   PubMed Web of Science ®Google Scholar
• Damanhouri Z , Ahmad A. (2014). A review on therapeutic potential of Piper nigrum L. (black pepper): the king of spices. Med Aromat Plants 3: 161.
   Google Scholar
• de Almeida M , da Rocha BA , Francisco CRL , et al. (2018). Evaluation of the in vivo acute antiinflammatory response of curcumin-loaded nanoparticles. Food Funct 9: 440–9.
   PubMed Web of Science ®Google Scholar
• Do MT , Kim HG , Choi JH , et al. (2013). Antitumor efficacy of piperine in the treatment of human HER2-overexpressing breast cancer cells. Food Chem 141: 2591–9.
   PubMed Web of Science ®Google Scholar
• Domingos S , André V , Quaresma S , et al. (2015). New forms of old drugs: improving without changing. J Pharm Pharmacol 67: 830–46.
   PubMed Web of Science ®Google Scholar
• Dong H , Yang G-X , Zhang X , et al. (2018). Folic acid functionalized zirconium-based metal–organic frameworks as drug carriers for active tumor-targeted drug delivery. Chemistry 24: 17148–54.
   PubMed Web of Science ®Google Scholar
• Enogieru AB , Haylett W , Hiss DC , et al. (2018). Rutin as a potent antioxidant: implications for neurodegenerative disorders. Oxid Med Cell Longev 2018: 6241017.
   PubMed Web of Science ®Google Scholar
• Eze FI , Siwe Noundou X , Osadebe PO , Krause RWM. (2019). Phytochemical, anti-inflammatory and anti-trypanosomal properties of Anthocleista vogelii Planch (Loganiaceae) stem bark. J Ethnopharmacol 238: 111851.
   PubMed Web of Science ®Google Scholar
• Feng J-f , Gao S-y , Shi J , et al. (2018). C-QDs@UiO-66-(COOH)2 composite film via electrophoretic deposition for temperature sensing. Inorg Chem 57: 2447–54.
   PubMed Web of Science ®Google Scholar
• Frank LA , Onzi GR , Morawski AS , et al. (2020). Chitosan as a coating material for nanoparticles intended for biomedical applications. React Funct Polym 147: 104459.
   Web of Science ®Google Scholar
• Ganesh M , Hemalatha P , Peng MM , et al. (2012). Drug release evaluation of mesoporous TiO2: a nano carrier for duloxetine. In: Tai-hoon K, Carlos R, Jemal A, Byeong-Ho K, Dominik Ś, Hojjat A, editors. Computer applications for modeling, simulation, and automobile. Berlin, Heidelberg: Springer.
   Google Scholar
• Ganeshpurkar A , Saluja AK. (2017). The pharmacological potential of rutin. Saudi Pharm J 25: 149–64.
   PubMed Web of Science ®Google Scholar
• Gangu KK , Maddila S , Mukkamala SB , Jonnalagadda SB. (2016). A review on contemporary metal–organic framework materials. Inorg Chim Acta 446: 61–74.
   Web of Science ®Google Scholar
• Gorgani L , Mohammadi M , Najafpour GD , Nikzad M. (2017). Piperine – the bioactive compound of black pepper: from isolation to medicinal formulations. Compr Rev Food Sci Food Saf 16: 124–40.
   PubMed Web of Science ®Google Scholar
• Guardia T , Rotelli AE , Juarez AO , Pelzer LE. (2001). Anti-inflammatory properties of plant flavonoids. Effects of rutin, quercetin and hesperidin on adjuvant arthritis in rat. Farmaco 56: 683–7.
   PubMedGoogle Scholar
• Gunasekaran V , Elangovan K , Niranjali Devaraj S. (2017). Targeting hepatocellular carcinoma with piperine by radical-mediated mitochondrial pathway of apoptosis: an in vitro and in vivo study. Food Chem Toxicol 105: 106–18.
   PubMed Web of Science ®Google Scholar
• Han Y , Liu W , Huang J , et al. (2018). Cyclodextrin-based metal–organic frameworks (CD-MOFs) in pharmaceutics and biomedicine. Pharmaceutics 10: 271.
   PubMed Web of Science ®Google Scholar
• Haqqi TM , Anthony DD , Gupta S , et al. (1999). Prevention of collagen-induced arthritis in mice by a polyphenolic fraction from green tea. Proc Natl Acad Sci USA 96: 4524–9.
   PubMed Web of Science ®Google Scholar
• Harborne JB. (1986). Nature, distribution and function of plant flavonoids. Prog Clin Biol Res 213: 15–24.
   PubMedGoogle Scholar
• Harvey AL. (2008). Natural products in drug discovery. Drug Discov Today 13: 894–901.
   PubMed Web of Science ®Google Scholar
• Hasani P , Yasa N , Vosough-Ghanbari S , et al. (2007). In vivo antioxidant potential of Teucrium polium, as compared to alpha-tocopherol.Acta Pharm 57:123–9.
   PubMedGoogle Scholar
• Hassabo AA , Mousa AM , Abdel-Gawad H , et al. (2019). Immobilization of l-methioninase on a zirconium-based metal–organic framework as an anticancer agent.J Mater Chem B 7:3268–78.
   Web of Science ®Google Scholar
• Hidalgo T , Giménez-Marqués M , Bellido E ,et al. (2017). Chitosan-coated mesoporous MIL-100(Fe) nanoparticles as improved bio-compatible oral nanocarriers.Sci Rep 7:43099.
   PubMed Web of Science ®Google Scholar
• Horcajada P , Gref R , Baati T ,et al. (2012). Metal–organic frameworks in biomedicine.Chem Rev 112:1232–68.
   PubMed Web of Science ®Google Scholar
• Horcajada P , Serre C , Maurin G ,et al. (2008). Flexible porous metal–organic frameworks for a controlled drug delivery.J Am Chem Soc 130:6774–80.
   PubMed Web of Science ®Google Scholar
• Horcajada P , Serre C , Vallet-Regí M ,et al. (2006). Metal–organic frameworks as efficient materials for drug delivery.Angew Chem Int Ed Engl 45:5974–8.
   PubMed Web of Science ®Google Scholar
• Horcajada P , Surblé S , Serre C ,et al. (2007). Synthesis and catalytic properties of MIL-100(Fe), an iron(III) carboxylate with large pores.Chem Commun 27:2820–2.
   PubMed Web of Science ®Google Scholar
• Hoskins BF , Robson R. (1989). Infinite polymeric frameworks consisting of three dimensionally linked rod-like segments.J Am Chem Soc 111:5962–4.
   Web of Science ®Google Scholar
• Hu Z , Qiao C , Xia Z ,et al. (2020). A luminescent Mg–metal–organic framework for sustained release of 5-fluorouracil: appropriate host – guest interaction and satisfied acid–base resistance.ACS Appl Mater Interfaces 12:14914–23.
   PubMed Web of Science ®Google Scholar
• Janiak C , Vieth JK. (2010). MOFs, MILs and more: concepts, properties and applications for porous coordination networks (PCNs).New J Chem 34:2366–88.
   Web of Science ®Google Scholar
• Joseph E , Singhvi G. (2019). Chapter 4 – multifunctional nanocrystals for cancer therapy: a potential nanocarrier. In: Grumezescu AM , editor. Nanomaterials for drug delivery and therapy. NY, USA: William Andrew Publishing; p. 91–116.
   Google Scholar
• Kamel KM , Abd El-Raouf OM , Metwally SA ,et al. (2014). Hesperidin and rutin, antioxidant citrus flavonoids, attenuate cisplatin-induced nephrotoxicity in rats.J Biochem Mol Toxicol 28:312–9.
   PubMed Web of Science ®Google Scholar
• Karnopp JCF , Cardoso TFM , Gonçalves DA ,et al. (2020). Preparation of the rutin-SBA-16 drug delivery system.J Biomater Nanobiotechnol 11:1–13.
   Google Scholar
• Kasibhatta R , Naidu MU. (2007). Influence of piperine on the pharmacokinetics of nevirapine under fasting conditions: a randomised, crossover, placebo-controlled study.Drugs R D 8:383–91.
   PubMedGoogle Scholar
• Khan MM , Ahmad A , Ishrat T ,et al. (2009). Rutin protects the neural damage induced by transient focal ischemia in rats.Brain Res 1292:123–35.
   PubMed Web of Science ®Google Scholar
• Khan A , Ikram M , Hahm JR , Kim MO. (2020). Antioxidant and anti-inflammatory effects of citrus flavonoid hesperetin: special focus on neurological disorders.Antioxidants 9:609.
   Web of Science ®Google Scholar
• Kim J , Seidler P , Wan LS , Fill C. (2009). Formation, structure, and reactivity of amino-terminated organic films on silicon substrates.J Colloid Interface Sci 329:114–9.
   PubMed Web of Science ®Google Scholar
• Lee W , Ku SK , Bae JS. (2012). Barrier protective effects of rutin in LPS-induced inflammation in vitro and in vivo.Food Chem Toxicol 50:3048–55.
   PubMed Web of Science ®Google Scholar
• Liang Z , Yang Z , Yuan H ,et al. (2018). A protein@metal–organic framework nanocomposite for pH-triggered anticancer drug delivery.Dalton Trans 47:10223–8.
   PubMed Web of Science ®Google Scholar
• Li L , Han S , Zhao S ,et al. (2020). Chitosan modified metal–organic frameworks as a promising carrier for oral drug delivery.RSC Adv 10:45130–8.
   PubMed Web of Science ®Google Scholar
• Li Z , Peng Y , Xia X ,et al. (2019a). Sr/PTA metal organic framework as a drug delivery system for osteoarthritis treatment.Sci Rep 9:17570.
   PubMed Web of Science ®Google Scholar
• Liu C , Guo T , Li W ,et al. (2019). The study of release mechanisms for drug in cyclodextrin metal–organic frameworks.ACS Omega 4:14490–6.
   PubMed Web of Science ®Google Scholar
• Liu C , Xu X , Zhou J ,et al. (2020). Redox-responsive tumor targeted dual-drug loaded biocompatible metal–organic frameworks nanoparticles for enhancing anticancer effects.BMC Mater 2:7.
   Google Scholar
• Li Y , Wee LH , Martens JA , Vankelecom IFJ. (2014). ZIF-71 as a potential filler to prepare pervaporation membranes for bio-alcohol recovery.J Mater Chem A 2:10034–40.
   Web of Science ®Google Scholar
• Li Z , Zhao S , Wang H ,et al. (2019b). Functional groups influence and mechanism research of UiO-66-type metal–organic frameworks for ketoprofen delivery.Colloids Surf B Biointerfaces 178:1–7.
   PubMed Web of Science ®Google Scholar
• Losso JN , Khachatryan A , Ogawa M ,et al. (2005). Random centroid optimization of phosphatidylglycerol stabilized lutein-enriched oil-in-water emulsions at acidic pH.Food Chem 92:737–44.
   Web of Science ®Google Scholar
• Lu L , Ma M , Gao C ,et al. (2020). Metal organic framework@polysilsesequioxane core/shell-structured nanoplatform for drug delivery.Pharmaceutics 12:98.
   PubMed Web of Science ®Google Scholar
• Magalingam KB , Radhakrishnan A , Ping NS , Haleagrahara N. (2018). Current concepts of neurodegenerative mechanisms in Alzheimer's disease.Biomed Res Int 2018:3740461.
   PubMed Web of Science ®Google Scholar
• Mahdavi H , Ahmadian-Alam L , Molavi H. (2015). Grafting of sulfonated monomer onto an amino-silane functionalized 2-aminoterephthalate metal–organic framework via surface-initiated redox polymerization: proton-conducting solid electrolytes.Polym Int 64:1578–84.
   Web of Science ®Google Scholar
• Mahmoud AM. (2012). Influence of rutin on biochemical alterations in hyperammonemia in rats.Exp Toxicol Pathol 64:783–9.
   PubMedGoogle Scholar
• Merghem M , Dahamna S , Khennouf S. (2019). In vivo antioxidant activity of Ruta montana L. extracts.Mater Environ Sci 10:470–7.
   Google Scholar
• Mondal A , Maity TK , Bishayee A. (2019). Analgesic and anti-inflammatory activities of quercetin-3-methoxy-4′-glucosyl-7-glucoside isolated from Indian medicinal plant Melothria heterophylla .Medicines 6:59.
   Google Scholar
• Narayanaswamy N , Balakrishnan KP. (2011). Evaluation of some medicinal plants for their antioxidant properties.Int J PharmTech Res 3:381–5.
   Google Scholar
• Nasrabadi M , Ghasemzadeh MA , Zand Monfared MR. (2019). The preparation and characterization of UiO-66 metal–organic frameworks for the delivery of the drug ciprofloxacin and an evaluation of their antibacterial activities.New J Chem 43:16033–40.
   Web of Science ®Google Scholar
• Ojewole JAO. (2006). Analgesic, antiinflammatory and hypoglycaemic effects of ethanol extract of Zingiber officinale (roscoe) rhizomes (Zingiberaceae) in mice and rats.Phytother Res 20:764–72.
   PubMed Web of Science ®Google Scholar
• Pandian SRK , Pavadai P , Vellaisamy S ,et al. (2020). Formulation and evaluation of rutin-loaded solid lipid nanoparticles for the treatment of brain tumor.Naunyn Schmiedebergs Arch Pharmacol 394:735–49.
   PubMed Web of Science ®Google Scholar
• Pashmforosh M , Rajabi Vardanjani H , Rajabi Vardanjani H ,et al. (2018). Topical anti-inflammatory and analgesic activities of Citrullus colocynthis extract cream in rats.Medicina 54:51.
   PubMedGoogle Scholar
• Peppas NA , Narasimhan B. (2014). Mathematical models in drug delivery: how modeling has shaped the way we design new drug delivery systems.J Control Release 190:75–81.
   PubMed Web of Science ®Google Scholar
• Pettinari C , Marchetti F , Mosca N ,et al. (2017). Application of metal–organic frameworks.Polym Int 66:731–44.
   Web of Science ®Google Scholar
• Pham H , Ramos K , Sua A ,et al. (2020). Tuning crystal structures of iron-based metal–organic frameworks for drug delivery applications.ACS Omega 5:3418–27.
   PubMed Web of Science ®Google Scholar
• Rachmawati H , Safitri D , Pradana AT , Adnyana IK. (2016). TPGS-stabilized curcumin nanoparticles exhibit superior effect on carrageenan-induced inflammation in wistar rat.Pharmaceutics 8:24.
   PubMed Web of Science ®Google Scholar
• Ramaswamy S , Dwarampudi LP , Kadiyala M ,et al. (2017). Formulation and characterization of chitosan encapsulated phytoconstituents of curcumin and rutin nanoparticles.Int J Biol Macromol 104:1807–12.
   PubMed Web of Science ®Google Scholar
• Rezaei M , Abbasi A , Varshochian R ,et al. (2018). NanoMIL-100(Fe) containing docetaxel for breast cancer therapy.Artif Cells Nanomed Biotechnol 46:1390–401.
   PubMed Web of Science ®Google Scholar
• Rojas S , Colinet I , Cunha D ,et al. (2018). Toward understanding drug incorporation and delivery from biocompatible metal–organic frameworks in view of cutaneous administration.ACS Omega 3:2994–3003.
   PubMed Web of Science ®Google Scholar
• Rothstein SN , Federspiel WJ , Little SR. (2009). A unified mathematical model for the prediction of controlled release from surface and bulk eroding polymer matrices.Biomaterials 30:1657–64.
   PubMed Web of Science ®Google Scholar
• Samykutty A , Shetty AV , Dakshinamoorthy G ,et al. (2013). Piperine, a bioactive component of pepper spice exerts therapeutic effects on androgen dependent and androgen independent prostate cancer cells.PLOS One 8:e65889.
   PubMed Web of Science ®Google Scholar
• Santos JH , Quimque MTJ , Macabeo APG ,et al. (2020). Enhanced oral bioavailability of the pharmacologically active lignin magnolol via Zr-based metal organic framework impregnation.Pharmaceutics 12:437.
   PubMed Web of Science ®Google Scholar
• Sarker M , Jhung SH. (2019). Zr-MOF with free carboxylic acid for storage and controlled release of caffeine.J Mol Liq 296:112060.
   Web of Science ®Google Scholar
• Sarker M , Shin S , Jhung SH. (2019). Synthesis and functionalization of porous Zr-diaminostilbenedicarboxylate metal–organic framework for storage and stable delivery of ibuprofen.ACS Omega 4:9860–7.
   PubMed Web of Science ®Google Scholar
• Selvendiran K , Banu SM , Sakthisekaran D. (2004). Protective effect of piperine on benzo(a)pyrene-induced lung carcinogenesis in Swiss albino mice.Clin Chim Acta 350:73–8.
   PubMed Web of Science ®Google Scholar
• Selvendiran K , Singh JP , Krishnan KB , Sakthisekaran D. (2003). Cytoprotective effect of piperine against benzo[a]pyrene induced lung cancer with reference to lipid peroxidation and antioxidant system in Swiss albino mice.Fitoterapia 74:109–15.
   PubMed Web of Science ®Google Scholar
• Shearer GC , Chavan S , Bordiga S ,et al. (2016). Defect engineering: tuning the porosity and composition of the metal–organic framework UiO-66 via modulated synthesis.Chem Mater 28:3749–61.
   Web of Science ®Google Scholar
• Shoba G , Joy D , Joseph T ,et al. (1998). Influence of piperine on the pharmacokinetics of curcumin in animals and human volunteers.Planta Med 64:353–6.
   PubMed Web of Science ®Google Scholar
• Si L , Yang R , Lin R , Yang S. (2018). Piperine functions as a tumor suppressor for human ovarian tumor growth via activation of JNK/p38 MAPK-mediated intrinsic apoptotic pathway.Biosci Rep 38:BSR20180503.
   PubMed Web of Science ®Google Scholar
• Silva IMP , Carvalho MA , Oliveira CS ,et al. (2016). Enhanced performance of a metal–organic framework analogue to MIL-101(Cr) containing amine groups for ibuprofen and nimesulide controlled release.Inorg Chem Commun 70:47–50.
   Web of Science ®Google Scholar
• Soltani B , Nabipour H , Nasab NA. (2018). Efficient storage of gentamicin in nanoscale zeolitic imidazolate framework-8 nanocarrier for pH-responsive drug release.J Inorg Organomet Polym 28:1090–7.
   Web of Science ®Google Scholar
• Su F , Jia Q , Li Z ,et al. (2019). Aptamer-templated silver nanoclusters embedded in zirconium metal–organic framework for targeted antitumor drug delivery.Microporous Mesoporous Mater 275:152–62.
   Web of Science ®Google Scholar
• Sur B , Kang S , Kim M , Oh S. (2019). Inhibition of carrageenan/kaolin-induced arthritis in rats and of inflammatory cytokine expressions in human IL-1β-stimulated fibroblast-like synoviocytes by a benzylideneacetophenone derivative.Inflammation 42:928–36.
   PubMed Web of Science ®Google Scholar
• Vilela SMF , Salcedo-Abraira P , Colinet I ,et al. (2017). Nanometric MIL-125-NH2 metal–organic framework as a potential nerve agent antidote carrier.Nanomaterials 7:321.
   Web of Science ®Google Scholar
• Wu Y , Luo Y , Zhou B ,et al. (2019). Porous metal–organic framework (MOF) Carrier for incorporation of volatile antimicrobial essential oil.Food Control 98:174–8.
   Web of Science ®Google Scholar
• Xu X , Zhao C , Yang H ,et al. (2011). Anti-inflammatory activity of injectable dexamethasone acetate-loaded nanostructured lipid carriers.Drug Deliv 18:485–92.
   PubMed Web of Science ®Google Scholar
• Yaffe PB , Power Coombs MR , Doucette CD ,et al. (2015). Piperine, an alkaloid from black pepper, inhibits growth of human colon cancer cells via G1 arrest and apoptosis triggered by endoplasmic reticulum stress.Mol Carcinog 54:1070–85.
   PubMed Web of Science ®Google Scholar
• Yang W , Chen YH , Liu H , Qu HD. (2015). Neuroprotective effects of piperine on the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced Parkinson's disease mouse model.Int J Mol Med 36:1369–76.
   PubMed Web of Science ®Google Scholar
• Yang Q , Vaesen S , Ragon F ,et al. (2013). A water stable metal–organic framework with optimal features for CO2 capture.Angew Chem Int Ed Engl 52:10316–20.
   PubMed Web of Science ®Google Scholar
• Yavarpour-Bali H , Ghasemi-Kasman M , Pirzadeh M. (2019). Curcumin-loaded nanoparticles: a novel therapeutic strategy in treatment of central nervous system disorders.Int J Nanomedicine 14:4449–60.
   PubMed Web of Science ®Google Scholar
• Yoo ES , Choo GS , Kim SH ,et al. (2019). Antitumor and apoptosis-inducing effects of piperine on human melanoma cells.Anticancer Res 39:1883–92.
   PubMed Web of Science ®Google Scholar
• Zhao Y. (2016). Emerging applications of metal–organic frameworks and covalent organic frameworks.Chem Mater 28:8079–81.
   Web of Science ®Google Scholar
• Zhu L , Chen J , Tan J ,et al. (2017). Flavonoids from Agrimonia pilosa Ledeb: free radical scavenging and DNA oxidative damage protection activities and analysis of bioactivity-structure relationship based on molecular and electronic structures.Molecules 22:195.
   PubMed Web of Science ®Google Scholar