Targeted pH-responsive delivery of rosmarinic acid via phenylboronic acid functionalized mesoporous silica nanoparticles for liver and lung cancer therapy

References

• Abdelnasir S, Anwar A, Kawish M, Anwar A, Raza M, Siddiqui R, Khan N. 2020. Metronidazole conjugated magnetic nanoparticles loaded with amphotericin B exhibited potent effects against pathogenic Acanthamoeba castellanii belonging to the T4 genotype. AMB Express. 10(1):127. doi:10.1186/s13568-020-01061-z.
   PubMed Web of Science ®Google Scholar
• Akbar N, Kawish M, Jabri T, Khan NA, Shah MR, Siddiqui R. 2021. Enhancing efficacy of existing antibacterials against selected multiple drug resistant bacteria using cinnamic acid-coated magnetic iron oxide and mesoporous silica nanoparticles. Pathog Glob Health. 116(7):438–454. doi:10.1080/20477724.2021.2014235.
   PubMed Web of Science ®Google Scholar
• Akbar N, Kawish M, Khan NA, Shah MR, Alharbi AM, Alfahemi H, Siddiqui R. 2022. Hesperidin-, curcumin-, and amphotericin B-based nano-formulations as potential antibacterials. Antibiotics. 11(5):696. doi:10.3390/antibiotics11050696.
   Google Scholar
• Cao J, Gao X, Cheng M, Niu X, Li X, Zhang Y, Liu Y, Wang W, Yuan Z. 2019. Reversible shielding between dual ligands for enhanced tumor accumulation of ZnPc-loaded micelles. Nano Lett. 19(3):1665–1674. doi:10.1021/acs.nanolett.8b04645.
   PubMed Web of Science ®Google Scholar
• Chan MH, Lin HM. 2015. Preparation and identification of multifunctional mesoporous silica nanoparticles for in vitro and in vivo dual-mode imaging, theranostics, and targeted tracking. Biomaterials. 46:149–158. doi:10.1016/j.biomaterials.2014.12.034.
   PubMed Web of Science ®Google Scholar
• Chen H, Kuang Y, Liu R, Chen Z, Jiang B, Sun Z, Chen X, Li C. 2018. Dual-pH-sensitive mesoporous silica nanoparticle-based drug delivery system for tumor-triggered intracellular drug release. J Mater Sci. 53(15):10653–10665. doi:10.1007/s10853-018-2363-8.
   Web of Science ®Google Scholar
• Chen W, Xie W, Zhao G, Shuai Q. 2023. Efficient pH-responsive nano-drug delivery system based on dynamic boronic acid/ester transformation. Molecules. 28(11):4461. doi:10.3390/molecules28114461.
   PubMed Web of Science ®Google Scholar
• Cheng W, Nie J, Xu L, Liang C, Peng Y, Liu G, Wang T, Mei L, Huang L, Zeng X. 2017. pH-Sensitive delivery vehicle based on folic acid-conjugated polydopamine-modified mesoporous silica nanoparticles for targeted cancer therapy. ACS Appl Mater Interfaces. 9(22):18462–18473. doi:10.1021/acsami.7b02457.
   PubMed Web of Science ®Google Scholar
• Date AA, Nagarsenker MS, Patere S, Dhawan V, Gude R, Hassan P, Aswal V, Steiniger F, Thamm J, Fahr A. 2011. Lecithin-based novel cationic nanocarriers (Leciplex) II: improving therapeutic efficacy of quercetin on oral administration. Mol Pharm. 8(3):716–726. doi:10.1021/mp100305h.
   PubMed Web of Science ®Google Scholar
• Derkacheva O, Sukhov D. 2008. Investigation of lignins by FTIR spectroscopy. Macromolecular Symposia. 265(1):61–68.
   Google Scholar
• Elsabahy M, Heo GS, Lim SM, Sun G, Wooley KL. 2015. Polymeric nanostructures for imaging and therapy. Chem Rev. 115(19):10967–11011. doi:10.1021/acs.chemrev.5b00135.
   PubMed Web of Science ®Google Scholar
• Elsabahy M, Wooley KL. 2015. Data mining as a guide for the construction of cross-linked nanoparticles with low immunotoxicity via control of polymer chemistry and supramolecular assembly. Acc Chem Res. 48(6):1620–1630. doi:10.1021/acs.accounts.5b00066.
   PubMed Web of Science ®Google Scholar
• Elshaarani, Tarig, Yu, Haojie, Wang, Li, Ullah, Raja Summe, Haroon, Muhammad, Khan, Rizwan Ullah, Fahad, Shah, Khan, Amin, Nazir, Ahsan, Usman, Muhammad, Naveed, Kaleem-Ur-Rahman, 2018. Synthesis of hydrogel-bearing phenylboronic acid moieties and their applications in glucose sensing and insulin delivery. J Mater Chem B. 6(23):3831–3854. doi:10.1039/c7tb03332j.
   PubMed Web of Science ®Google Scholar
• Ferreira-Gonçalves T, Gaspar MM, Coelho JMP, Marques V, Viana AS, Ascensão L, Carvalho L, Rodrigues CMP, Ferreira HA, Ferreira D, et al. 2022. The role of rosmarinic acid on the bioproduction of gold nanoparticles as part of a photothermal approach for breast cancer treatment. Biomolecules. 12(1):71. doi:10.3390/biom12010071.
   PubMed Web of Science ®Google Scholar
• Fuster MG, Carissimi G, Montalbán MG, Víllora G. 2021. Antitumor activity of rosmarinic acid-loaded silk fibroin nanoparticles on HeLa and MCF-7 cells. Polymers (Basel). 13(18):3169. doi:10.3390/polym13183169.
   PubMed Web of Science ®Google Scholar
• Hakemi P, Ghadi A, Mahjoub S, Zabihi E, Tashakkorian H. 2021. Fabrication of PCL-PEG-PCL nanocarrier for Co-loading of docetaxel/quercetin and assessment of its effect on growth inhibition of human liver cancer (Hep-G2) cell line. International Journal of Nano Dimension. 12(4):355–368.
   Web of Science ®Google Scholar
• Hei M, Wu H, Fu Y, Xu Y, Zhu W. 2019. Phenylboronic acid functionalized silica nanoparticles with enlarged ordered mesopores for efficient insulin loading and controlled release. J Drug Delivery Sci Technol. 51:320–326. doi:10.1016/j.jddst.2019.03.031.
   Web of Science ®Google Scholar
• Huang Q, Wang L, Yu H, Ur-Rahman K. 2019. Advances in phenylboronic acid-based closed-loop smart drug delivery system for diabetic therapy. J Control Release. 305:50–64. doi:10.1016/j.jconrel.2019.05.029.
   PubMed Web of Science ®Google Scholar
• Jahan-Abad AJ, Morteza-Zadeh P, Negah SS, Gorji A. 2017. Curcumin attenuates harmful effects of arsenic on neural stem/progenitor cells. Avicenna Journal of Phytomedicine. 7(4):376.
   PubMed Web of Science ®Google Scholar
• Jin B, Liu J, Gao D, Xu Y, He L, Zang Y, Li N, Lin D. 2020. Detailed studies on the anticancer action of rosmarinic acid in human Hep-G2 liver carcinoma cells: evaluating its effects on cellular apoptosis, caspase activation and suppression of cell migration and invasion. Journal of BUON: official Journal of the Balkan Union of Oncology. 25(3):1383–1389. eng.
   PubMed Web of Science ®Google Scholar
• Katara R, Sachdeva S. 2019. Design, characterization, and evaluation of aceclofenac-loaded Eudragit RS 100 nanoparticulate system for ocular delivery. Pharmaceutical Development and Technology. 24(3):368–379.
   Google Scholar
• Kawish M, Elhissi A, Jabri T, Muhammad Iqbal K, Zahid H, Shah MR. 2020. Enhancement in oral absorption of ceftriaxone by highly functionalized magnetic iron oxide nanoparticles. Pharmaceutics. 12(6):492. doi:10.3390/pharmaceutics12060492.
   PubMed Web of Science ®Google Scholar
• Kinoh H, Miura Y, Chida T, Liu X, Mizuno K, Fukushima S, Morodomi Y, Nishiyama N, Cabral H, Kataoka K. 2016. Nanomedicines eradicating cancer stem-like cells in vivo by pH-triggered intracellular cooperative action of loaded drugs. ACS Nano. 10(6):5643–5655. doi:10.1021/acsnano.6b00900.
   PubMed Web of Science ®Google Scholar
• Kong Z-L, Kuo H-P, Johnson A, Wu L-C, Chang KLB. 2019. Curcumin-loaded mesoporous silica nanoparticles markedly enhanced cytotoxicity in hepatocellular carcinoma cells. Int J Mol Sci. 20(12):2918. doi:10.3390/ijms20122918.
   PubMed Web of Science ®Google Scholar
• Kundu M, Sadhukhan P, Ghosh N, Chatterjee S, Manna P, Das J, Sil PC. 2019. pH-responsive and targeted delivery of curcumin via phenylboronic acid-functionalized ZnO nanoparticles for breast cancer therapy. J Adv Res. 18:161–172. doi:10.1016/j.jare.2019.02.036.
   PubMed Web of Science ®Google Scholar
• Lavan DA, McGuire T, Langer R. 2003. Small-scale systems for in vivo drug delivery. Nat Biotechnol. 21(10):1184–1191. doi:10.1038/nbt876.
   PubMed Web of Science ®Google Scholar
• Li L, Zeng Z, Chen Z, Gao R, Pan L, Deng J, Ye X, Zhang J, Zhang S, Mei C, et al. 2020. Microenvironment-triggered degradable hydrogel for imaging diagnosis and combined treatment of intraocular choroidal melanoma. ACS Nano. 14(11):15403–15416. doi:10.1021/acsnano.0c06000.
   PubMed Web of Science ®Google Scholar
• Li S, Hu K, Cao W, Sun Y, Sheng W, Li F, Wu Y, Liang X-J. 2014. pH-responsive biocompatible fluorescent polymer nanoparticles based on phenylboronic acid for intracellular imaging and drug delivery. Nanoscale. 6(22):13701–13709. doi:10.1039/c4nr04054f.
   PubMed Web of Science ®Google Scholar
• Liao XZ, Gao Y, Sun LL, Liu JH, Chen HR, Yu L, Chen ZZ, Chen WH, Lin LZ. 2020. Rosmarinic acid reverses non-small cell lung cancer cisplatin resistance by activating the MAPK signaling pathway. Phytother Res. 34(5):1142–1153. eng. doi:10.1002/ptr.6584.
   PubMed Web of Science ®Google Scholar
• Liu J, Liu Q, Yang C, Sun Y, Zhang Y, Huang P, Zhou J, Liu Q, Chu L, Huang F, et al. 2016. cRGD-modified benzimidazole-based pH-responsive nanoparticles for enhanced tumor targeted doxorubicin delivery. ACS Appl Mater Interfaces. 8(17):10726–10736. doi:10.1021/acsami.6b01501.
   PubMed Web of Science ®Google Scholar
• Liu J, Luo Z, Zhang J, Luo T, Zhou J, Zhao X, Cai K. 2016. Hollow mesoporous silica nanoparticles facilitated drug delivery via cascade pH stimuli in tumor microenvironment for tumor therapy. Biomaterials. 83:51–65. doi:10.1016/j.biomaterials.2016.01.008.
   PubMed Web of Science ®Google Scholar
• Ma Q, Zhao X, Shi A, Wu J. 2021. Bioresponsive functional phenylboronic acid-based delivery system as an emerging platform for diabetic therapy. Int J Nanomedicine. 16(null):297–314. doi:10.2147/IJN.S284357.
   PubMedGoogle Scholar
• Meng H, Xue M, Xia T, Zhao Y-L, Tamanoi F, Stoddart JF, Zink JI, Nel AE. 2010. Autonomous in vitro anticancer drug release from mesoporous silica nanoparticles by pH-sensitive nanovalves. J Am Chem Soc. 132(36):12690–12697. doi:10.1021/ja104501a.
   PubMed Web of Science ®Google Scholar
• Mohseni M, Gilani K, Mortazavi SA. 2015. Preparation and characterization of rifampin loaded mesoporous silica nanoparticles as a potential system for pulmonary drug delivery. Iranian Journal of Pharmaceutical Research: IJPR. 14(1):27–34. eng.
   PubMed Web of Science ®Google Scholar
• Nakahata M, Mori S, Takashima Y, Hashidzume A, Yamaguchi H, Harada A. 2014. pH-and sugar-responsive gel assemblies based on boronate–catechol interactions. ACS Macro Lett. 3(4):337–340. doi:10.1021/mz500035w.
   PubMed Web of Science ®Google Scholar
• Oliveira L, Bouchmella K, Picco AS, Capeletti LB, Gonçalves KA, Santos J, Kobarg J, Cardoso MB. 2017. Tailored silica nanoparticles surface to increase drug load and enhance bactericidal response. J Braz Chem Soc. 28:1715–1724.
   Web of Science ®Google Scholar
• Palanikumar L, Al-Hosani S, Kalmouni M, Nguyen VP, Ali L, Pasricha R, Barrera FN, Magzoub M. 2020. pH-responsive high stability polymeric nanoparticles for targeted delivery of anticancer therapeutics. Commun Biol. 3(1):95. doi:10.1038/s42003-020-0817-4.
   PubMed Web of Science ®Google Scholar
• Pan F, Giovannini G, Zhang S, Altenried S, Zuber F, Chen Q, Boesel LF, Ren Q. 2022. pH-responsive silica nanoparticles for the treatment of skin wound infections. Acta Biomater. 145:172–184. doi:10.1016/j.actbio.2022.04.009.
   PubMed Web of Science ®Google Scholar
• Petros RA, DeSimone JM. 2010. Strategies in the design of nanoparticles for therapeutic applications. Nat Rev Drug Discov. 9(8):615–627. doi:10.1038/nrd2591.
   PubMed Web of Science ®Google Scholar
• Ralph J, Lapierre C, Boerjan W. 2019. Lignin structure and its engineering. Curr Opin Biotechnol. 56:240–249. doi:10.1016/j.copbio.2019.02.019.
   PubMed Web of Science ®Google Scholar
• Ren J, Zhang Y, Zhang J, Gao H, Liu G, Ma R, An Y, Kong D, Shi L. 2013. pH/sugar dual responsive core-cross-linked PIC micelles for enhanced intracellular protein delivery. Biomacromolecules. 14(10):3434–3443. doi:10.1021/bm4007387.
   PubMed Web of Science ®Google Scholar
• Shi Z, Pu L, Guo Y, Fu Z, Zhao W, Zhu Y, Wu J, Wang F. 2017. Boronic acid-modified magnetic Fe3O4@mTiO2 microspheres for highly sensitive and selective enrichment of n-glycopeptides in amniotic fluid. Sci Rep. 7(1):4603. doi:10.1038/s41598-017-04517-8.
   PubMedGoogle Scholar
• Song Y, Zhu P, Xu Z, Chen J. 2020. Dual-responsive dual-drug-loaded bioinspired polydopamine nanospheres as an efficient therapeutic nanoplatform against drug-resistant cancer cells. ACS Appl Bio Mater. 3(9):5730–5740. doi:10.1021/acsabm.0c00512.
   PubMedGoogle Scholar
• Su J, Chen F, Cryns VL, Messersmith PB. 2011. Catechol polymers for ph-responsive, targeted drug delivery to cancer cells. J Am Chem Soc. 133(31):11850–11853. doi:10.1021/ja203077x.
   PubMed Web of Science ®Google Scholar
• Torchilin VP. 2014. Multifunctional, stimuli-sensitive nanoparticulate systems for drug delivery. Nat Rev Drug Discov. 13(11):813–827. doi:10.1038/nrd4333.
   PubMed Web of Science ®Google Scholar
• Volk T, Jähde E, Fortmeyer H, Glüsenkamp K, Rajewsky M. 1993. pH in human tumour xenografts: effect of intravenous administration of glucose. Br J Cancer. 68(3):492–500. doi:10.1038/bjc.1993.375.
   PubMed Web of Science ®Google Scholar
• Wang B, Yuan T, Zha L, Liu Y, Chen W, Zhang C, Bao Y, Dong Q. 2021. Oral delivery of gambogenic acid by functional polydopamine nanoparticles for targeted tumor therapy. Mol Pharm. 18(3):1470–1479. doi:10.1021/acs.molpharmaceut.1c00030.
   PubMedGoogle Scholar
• Wang J, Lee JS, Kim D, Zhu L. 2017. Exploration of zinc oxide nanoparticles as a multitarget and multifunctional anticancer nanomedicine. ACS Appl Mater Interfaces. 9(46):39971–39984. doi:10.1021/acsami.7b11219.
   PubMed Web of Science ®Google Scholar
• Wang X, Xia N, Liu L. 2013. Boronic acid-based approach for separation and immobilization of glycoproteins and its application in sensing. Int J Mol Sci. 14(10):20890–20912. doi:10.3390/ijms141020890.
   PubMed Web of Science ®Google Scholar
• Wang Y, Zhang X, Han Y, Cheng C, Li C. 2012. pH-and glucose-sensitive glycopolymer nanoparticles based on phenylboronic acid for triggered release of insulin. Carbohydr Polym. 89(1):124–131. doi:10.1016/j.carbpol.2012.02.060.
   PubMed Web of Science ®Google Scholar
• Wu S-H, Mou C-Y, Lin H-P. 2013. Synthesis of mesoporous silica nanoparticles. Chem Soc Rev. 42(9):3862–3875. doi:10.1039/c3cs35405a.
   PubMed Web of Science ®Google Scholar
• Zhang Y, Cai K, Li C, Guo Q, Chen Q, He X, Liu L, Zhang Y, Lu Y, Chen X, et al. 2018. Macrophage-membrane-coated nanoparticles for tumor-targeted chemotherapy. Nano Lett. 18(3):1908–1915. doi:10.1021/acs.nanolett.7b05263.
   PubMed Web of Science ®Google Scholar