Advertisement

Acid and light stimuli-responsive mesoporous silica nanoparticles for controlled release

  • Mingdong Wang
  • Ting Wang
  • Dong Wang
  • Wei Jiang
  • Jiajun Fu
Chemical routes to materials
  • 12 Downloads

Abstract

We constructed a novel stimuli-responsive system, MSNPs 1, based on mechanized silica nanoparticles, in which mesoporous silica nanoparticles (MSNs) acted as nanocontainers to load cargo, and supramolecular switches consisting of hydrazone bond, azobenzene and α-cyclodextrin (α-CD) realized the controlled release of cargo molecules from MSNPs 1. In neutral solution and without UV light irradiation, the azobenzene component on functional stalks was in trans form, and combined with α-CD to block the mesoporous channels and prevent the cargo from escaping. Upon adjusting the solution pH to acid range, the acid-sensitive hydrazone bonds rapidly hydrolyzed, resulting in the disconnection between pseudorotaxanes and MSNs. The encapsulated cargo molecules were released simultaneously from MSNPs 1 due to the removal of supramolecular switches. On the other hand, when the neutral solution was irradiated with UV light at 365 nm, trans-azobenzene converted to cis, disassociating with α-CD to activate the switches and release the cargo. The unique acid- and light-triggered controlled release properties of MSNPs 1 have potential application in various fields. In this manuscript, doxorubicin (DOX) was selected to be stored in MSNPs 1, due to the anticancer property. MCF-7 human breast cancer cells could phagocytose DOX-loaded MSNPs 1 easily, and the released DOX showed the killing effect.

Notes

Acknowledgements

The authors thank the Fundamental Research Funds for the Central University, Grant Nos. 30915012207 and 30918012201; the National Nature Science Foundation of China, Grant Nos. U1737105 and 51672133; the National Science Foundation of Jiangsu Province, Grant No. BK20161496; the QingLan Project, Jiangsu Province, China; a project funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

10853_2019_3325_MOESM1_ESM.docx (2.2 mb)
Supporting Information associated with this article, including, synthesis procedure details of HMAB and Compound B, UV detection of Compound B and α-CD, SEM, XRD, N2 adsorption–desorption isotherm, and pore size distribution of MSNs, FTIR spectra of MSNs, MSNs 1 and MSNs 2, UV/visible absorption spectra of BTA released from MSNPs 1, and Control experiment (DOCX 2259 kb)

References

  1. 1.
    Hernandez R, Tseng HR, Wong JW, Stoddart JF, Zink JI (2004) An operational supramolecular nanovalve. J Am Chem Soc 126:3370–3371CrossRefGoogle Scholar
  2. 2.
    Badjic JD, Balzani V, Credi A, Silvi S, Stoddart JF (2004) A molecular elevator. Science 303:1845–1849CrossRefGoogle Scholar
  3. 3.
    Lin YH, Wu L, Huang YY, Ren JS, Qu XG (2015) Positional assembly of hemin and gold nanoparticles in graphene–mesoporous silica nanohybrids for tandem catalysis. Chem Sci 6:1272–1276CrossRefGoogle Scholar
  4. 4.
    Lin YH, Li ZH, Chen ZW, Ren JS, Qu XG (2013) Mesoporous silica-encapsulated gold nanoparticles as artificial enzymes for self-activated cascade catalysis. Biomaterials 34:2600–2610CrossRefGoogle Scholar
  5. 5.
    Peng WH, Lee YY, Wu C, Wu KCW (2012) Acid–base bi-functionalized, large-pored mesoporous silica nanoparticles for cooperative catalysis of one-pot cellulose-to-HMF conversion. J Mater Chem 22:23181–23185CrossRefGoogle Scholar
  6. 6.
    Yang X, Chen D, Liao SJ, Song HY, Li YW, Fu ZY, Su YL (2012) High-performance Pd–Au bimetallic catalyst with mesoporous silica nanoparticles as support and its catalysis of cinnamaldehyde hydrogenation. J Catal 291:36–43CrossRefGoogle Scholar
  7. 7.
    Liu JW, Chen LF, Cui H, Zhang JY, Zhang L, Song CY (2014) Applications of metal–organic frameworks in heterogeneous supramolecular catalysis. Chem Soc Rev 43:6011–6061CrossRefGoogle Scholar
  8. 8.
    Wu JW, Su P, Huang J, Wang SM, Yang Y (2013) Synthesis of teicoplanin-modified hybrid magnetic mesoporous silica nanoparticles and their application in chiral separation of racemic compounds. J Colloid Interface Sci 399:107–144CrossRefGoogle Scholar
  9. 9.
    Kim J, Lee JE, Lee J, Yu JH, Kim BC, An K, Hwang Y, Shin CH, Park JG, Kim J, Hyeon T (2006) Magnetic fluorescent delivery vehicle using uniform mesoporous silica spheres embedded with monodisperse magnetic and semiconductor nanocrystals. J Am Chem Soc 128:688–689CrossRefGoogle Scholar
  10. 10.
    Giri S, Trewyn BG, Stellmarker MP, Lin VSY (2005) Stimuli-responsive controlled-release delivery system based on mesoporous silica nanorods capped with magnetic nanoparticles. Angew Chem Int Ed 44:5038–5044CrossRefGoogle Scholar
  11. 11.
    Li ZX, Barnes JC, Bosoy A, Stoddart JF, Zink JI (2012) Mesoporous silica nanoparticles in biomedical applications. Chem Soc Rev 41:2590–2605CrossRefGoogle Scholar
  12. 12.
    Lai CY, Trewyn BG, Jeftinija DM, Jeftinjia K, Xu S, Jeftinija S, Lin VSY (2003) A mesoporous silica nanosphere-based carrier system with chemically removable CdS nanoparticle caps for stimuli-responsive controlled release of neurotransmitters and drug molecules. J Am Chem Soc 125:4451–4459CrossRefGoogle Scholar
  13. 13.
    Mura S, Nicolas J, Couvreur P (2013) Stimuli-responsive nanocarriers for drug delivery. Nat Mater 12:991–1003CrossRefGoogle Scholar
  14. 14.
    Fu JJ, Chen T, Wang MD, Yang NW, Li SN, Wang Y, Liu XD (2013) Acid and alkaline dual stimuli-responsive mechanized hollow mesoporous silica nanoparticles as smart nanocontainers for intelligent anticorrosion coatings. ACS Nano 7:11397–11408CrossRefGoogle Scholar
  15. 15.
    Liang Y, Wang MD, Wang C, Feng J, Li JS, Wang LJ, Fu JJ (2016) Facile synthesis of smart nanocontainers as key components for construction of self-healing coating with superhydrophobic surfaces. Nanoscale Res Lett 11:231–242CrossRefGoogle Scholar
  16. 16.
    Jeon WS, Ziiganshina AY, Lee JW, Ko YH, Kang JK, Lee C, Kim K (2003) A [2]pseudorotaxane-based molecular machine: reversible formation of a molecular loop driven by electrochemical and photochemical stimuli. Angew Chem Int Ed 42:4097–4100CrossRefGoogle Scholar
  17. 17.
    Murakami H, Kawabuchi A, Kotoo K, Kunitake M, Nakashima N (1997) A light-driven molecular shuttle based on a rotaxane. J Am Chem Soc 119:7605–7606CrossRefGoogle Scholar
  18. 18.
    Park IH, Medishetty R, Kim JY, Lee SS, Vittal JJ (2014) Distortional supramolecular isomers of polyrotaxane coordination polymers: photoreactivity and sensing of nitro compounds. Angew Chem Int Ed 53:5591–5595CrossRefGoogle Scholar
  19. 19.
    Wang MD, Chen T, Ding CD, Fu JJ (2014) Mechanized silica nanoparticles based on reversible bistable [2]pseudorotaxanes as supramolecular nanovalves for multistage pH-controlled release. Chem Commun 50:5068–5071CrossRefGoogle Scholar
  20. 20.
    Ding CD, Liu Y, Wang T, Fu JJ (2016) Triple-stimuli-responsive nanocontainers assembled by water-soluble pillar[5]arene-based pseudorotaxanes for controlled release. J Mater Chem B 4:2819–2827CrossRefGoogle Scholar
  21. 21.
    Li QL, Sun YF, Su YL, Wen JJ, Zhou Y, Bing QM, Isaacs LD, Jin YH, Gao H, Yang YW (2014) Mesoporous silica nanoparticles coated by layer-by-layer self-assembly using cucurbit[7]uril for in vitro and in vivo anticancer drug release. Chem Mater 26:6418–6431CrossRefGoogle Scholar
  22. 22.
    Patel K, Angelos S, Dichtel WR, Coskun A, Yang YW, Zink JI, Stoddart JF (2008) Enzyme-responsive snap-top covered silica nanocontainers. J Am Chem Soc 130:2382–2383CrossRefGoogle Scholar
  23. 23.
    Ulijn RV (2006) Enzyme-responsive materials: a new class of smart biomaterials. J Mater Chem 16:2217–2225CrossRefGoogle Scholar
  24. 24.
    Thornton PD, Mart RJ, Ulijn RV (2007) Enzyme-responsive polymer hydrogel particles for controlled release. Adv Mater 19:1252–1256CrossRefGoogle Scholar
  25. 25.
    Sun YL, Zhou Y, Li QL, Yang YW (2013) Enzyme-responsive supramolecular nanovalves crafted by mesoporous silica nanoparticles and choline-sulfonatocalix[4]arene [2]pseudorotaxanes for controlled cargo release. Chem Commun 49:9033–9035CrossRefGoogle Scholar
  26. 26.
    Zhou H, Wang X, Tang J, Yang YW (2016) Tuning the growth, crosslinking, and gating effect of disulfide-containing PGMAs on the surfaces of mesoporous silica nanoparticles for redox/pH dual-controlled cargo release. Polym Chem 7:2171–2179CrossRefGoogle Scholar
  27. 27.
    Sun JT, Piao JG, Wang LH, Javed M, Hong CY, Pan CY (2013) One-pot synthesis of redox-responsive polymers-coated mesoporous silica nanoparticles and their controlled drug release. Macromol Rapid Commun 34:1387–1394CrossRefGoogle Scholar
  28. 28.
    Zhou SW, Sha HZ, Liu BR, Du XZ (2014) Integration of simultaneous and cascade release of two drugs into smart single nanovehicles based on DNA-gated mesoporous silica nanoparticles. Chem Sci 5:4424–4433CrossRefGoogle Scholar
  29. 29.
    Li H, Tan LL, Jia P, Li QL, Sun YL, Zhang J, Ning YQ, Yu JH, Yang YW (2014) Near-infrared light-responsive supramolecular nanovalve based on mesoporous silica-coated gold nanorods. Chem Sci 5:2804–2808CrossRefGoogle Scholar
  30. 30.
    Fang WJ, Yang J, Gong JW, Zheng NF (2012) Photo- and pH-triggered release of anticancer drugs from mesoporous silica-coated Pd@Ag nanoparticles. Adv Funct Mater 22:842–848CrossRefGoogle Scholar
  31. 31.
    Miyata K, Oba M, Nakanishi M, Fukushima S, Yamasaki Y, Koyama H, Nishiyama N, Kataoka K (2008) Polyplexes from poly(aspartamide) bearing 1,2-diaminoethane side chains induce pH-selective, endosomal membrane destabilization with amplified transfection and negligible cytotoxicity. J Am Chem Soc 130:16287–16294CrossRefGoogle Scholar
  32. 32.
    Pang X, Jiang Y, Xiao QC, Leung AW, Hua HY, Xu GS (2016) pH-responsive polymer–drug conjugates: design and progress. J Control Release 222:116–129CrossRefGoogle Scholar
  33. 33.
    Wang MD, Gong GC, Feng J, Wang T, Ding CD, Zhou BJ, Jiang W, Fu JJ (2016) Dual pH-mediated mechanized hollow zirconia nanospheres. ACS Appl Mater Interfaces 8:23289–23301CrossRefGoogle Scholar
  34. 34.
    Gu JX, Cheng WP, Liu JG, Lo SY, Smith D, Qu XZ, Yang ZZ (2008) pH-triggered reversible “Stealth” polycationic micelles. Biomacromolecules 9:255–262CrossRefGoogle Scholar
  35. 35.
    Lai JP, Xu ZY, Tang RP, Ji WH, Wang R, Wang J, Wang C (2014) PEGylated block copolymers containing tertiary amine side-chains cleavable via acid-labile ortho ester linkages for pH-triggered release of DNA. Polymer 55:2761–2771CrossRefGoogle Scholar
  36. 36.
    Su X, Lokov M, Kutt A, Leito I, Aprahamian I (2012) Unusual para-substituent effects on the intramolecular hydrogen-bond in hydrazone-based switches. Chem Commun 48:10490–10492CrossRefGoogle Scholar
  37. 37.
    Long YB, Gu WX, Pang CC, Ma JB, Gao H (2016) Construction of coumarin-based cross-linked micelles with pH responsive hydrazone bond and tumor targeting moiety. J Mater Chem B 4:1480–1488CrossRefGoogle Scholar
  38. 38.
    Prabaharan M, Grailer JJ, Pilla S, Steeber DA, Gong SQ (2009) Amphiphilic multi-arm-block copolymer conjugated with doxorubicin via pH-sensitive hydrazone bond for tumor-targeted drug delivery. Biomaterials 30:5757–5766CrossRefGoogle Scholar
  39. 39.
    Sun TM, Wang YC, Wang F, Du JZ, Mao CQ, Sun CY, Tang RZ, Liu Y, Zhu J, Zhu YH, Yang XZ, Wang J (2014) Cancer stem cell therapy using doxorubicin conjugated to gold nanoparticles via hydrazone bonds. Biomaterials 35:836–845CrossRefGoogle Scholar
  40. 40.
    Sadhukhan D, Maiti M, Pilet G, Bauza A, Frontera A, Mitra S (2015) Hydrogen bond, π–π, and CH–π interactions governing the supramolecular assembly of some hydrazone ligands and their MnII complexes-structural and theoretical interpretation. Eur J Inorg Chem 11:1958–1972CrossRefGoogle Scholar
  41. 41.
    Dai LL, Zhang QF, Shen XK, Sun Q, Mu CY, Gu H, Cai KY (2016) A pH-responsive nanocontainer based on hydrazone-bearing hollow silica nanoparticles for targeted tumor therapy. J Mater Chem B 4:4594–4604CrossRefGoogle Scholar
  42. 42.
    Wu SS, Huang X, Du XZ (2015) pH- and redox-triggered synergistic controlled release of a ZnO-gated hollow mesoporous silica drug delivery system. J Mater Chem B 3:1426–1432CrossRefGoogle Scholar
  43. 43.
    Zhang YY, Ang CY, Li MH, Tan SY, Qu QY, Luo Z, Zhao YL (2015) Polymer-coated hollow mesoporous silica nanoparticles for triple-responsive drug delivery. ACS Appl Mater Interfaces 7:18179–18187CrossRefGoogle Scholar
  44. 44.
    Ling XX, Samuel EL, Patchell DL, Masson E (2010) Cucurbituril slippage: translation is a complex. Motion Org Lett 12:2730–2733CrossRefGoogle Scholar
  45. 45.
    Wang YP, Ma N, Wang ZQ, Zhang X (2007) Photo controlled reversible supramolecular assemblies of an azobenzene-containing surfactant with a-cyclodextrin. Angew Chem Int Ed 46:2823–2826CrossRefGoogle Scholar
  46. 46.
    Yan H, Zhu LL, Li X, Kwork A, Li X, Agren H, Zhao YL (2013) Photothermal-responsive [2]rotaxanes. RSC Adv 3:2341–2350CrossRefGoogle Scholar
  47. 47.
    Yu GC, Han CY, Zhang ZB, Chen JZ, Yan XZ, Zheng B, Liu SY, Huang FH (2012) Pillar[6]arene-based photo responsive host-guest complexation. J Am Chem Soc 134:8711–8717CrossRefGoogle Scholar
  48. 48.
    Ogoshi T, Kida K, Yamagishi T (2012) Photoreversible switching of the lower critical solution temperature in a photo responsive host-guest system of pillar[6]arene with triethylene oxide substituents and an azobenzene derivative. J Am Chem Soc 134:20146–20150CrossRefGoogle Scholar
  49. 49.
    Zhang HC, Strutt NL, Stoll RS, Li H, Zhu ZX, Stoddart JF (2011) Dynamic clicked surfaces based on functionalised pillar[5]arene. Chem Commun 47:11420–11422CrossRefGoogle Scholar
  50. 50.
    May BL, Gerber J, Clements P, Buntine MA, Brittain DRB, Lincoln SF, Easton CJ (2005) Cyclodextrin and modified cyclodextrin complexes of E-4-tert-butylphenyl-4-oxyazobenzene: UV–visible, 1H NMR and ab initio studies. Org Biomol Chem 3:1481–1488CrossRefGoogle Scholar
  51. 51.
    Wang T, Wang MD, Ding CD, Fu JJ (2014) Mono-benzimidazole functionalized b-cyclodextrins as supramolecular nanovalves for pH-triggered release of p-coumaric acid. Chem Commun 50:12469–12472CrossRefGoogle Scholar
  52. 52.
    Chen X, Soeriyadi AH, Lu X, Sagnella SM, Kavallaris M, Gooding JJ (2014) Dual bioresponsive mesoporous silica nanocarrier as an “AND” logic gate for targeted drug delivery cancer cells. Adv Funct Mater 24:6999–7006CrossRefGoogle Scholar
  53. 53.
    Johnson JA, Lu YY, Burts AO, Lim YH, Finn MG, Koberstein JT, Turro NJ, Tirrell DA, Grubbs RH (2011) Core-clickable PEG-branch-azide bivalent-bottle-brush polymers by ROMP: grafting-through and clicking-to. J Am Chem Soc 133:559–566CrossRefGoogle Scholar
  54. 54.
    Meng H, Liong M, Xia T, Li ZX, Ji ZX, Zink JI, Nel AE (2010) Engineered design of mesoporous silica nanoparticles to deliver doxorubicin and P-glycoprotein siRNA to overcome drug resistance in a cancer cell line. ACS Nano 4:4539–4550CrossRefGoogle Scholar
  55. 55.
    Yao C, Wang PY, Li XM, Hu XY, Hou JL, Wang LY, Zhang F (2016) Near-infrared-triggered azobenzene-liposome/upconversion nanoparticle hybrid vesicles for remotely controlled drug delivery to overcome cancer multidrug resistance. Adv Mater 28:9341–9348CrossRefGoogle Scholar
  56. 56.
    Zhou XJ, Chen L, Nie W, Wang WZ, Qin M, Mo XM, Wang HS, He CL (2016) Dual-responsive mesoporous silica nanoparticles mediated vodelivery of foxorubicin and Bcl–2 SiRNA for targeted treatment of breast cancer. J Phys Chem C 120:22375–22387CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.School of Chemical EngineeringNanjing University of Science and TechnologyNanjingPeople’s Republic of China
  2. 2.National Special Superfine Powder Engineering Research Centre, Nanjing University of Science and TechnologyNanjingPeople’s Republic of China

Personalised recommendations