Mannose-functionalized porous silica-coated magnetic nanoparticles for two-photon imaging or PDT of cancer cells
Source abstract
Abstract
An original fluorophore engineered for two-photon excitation or a porphyrin derivative were entrapped in the silica shell of magnetic porous silica nanoparticles during the synthesis of the silica moiety without damaging the structure of the organic part. The mild conditions involved allowed obtaining microporous or mesoporous silica magnetic nanoparticles, respectively. Mannose was grafted on the surface of the nanoparticles to target MCF-7 breast cancer cells. The studies of magnetic properties of these hybrid nanoparticles show that they present a blocking temperature at 190 K. The nano-objects designed with the two-photon fluorophore were efficient for two-photon imaging of MCF-7 cancer cells, whereas the nano-objects with the photosensitizer efficiently killed cancer cells. The presence of the mannose moiety was demonstrated to improve both imaging and therapy properties.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Porphyrin and Phthalocyanine Chemistry · Nanoplatforms for cancer theranostics · Nonlinear Optical Materials Studies
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (59)
Show source-provided references
1. Bechet D, Couleaud P, Frochot C, Viriot M-L, Guillemin F, Barberi-Heyob M (2008) Nanoparticles as vehicles for delivery of photodynamic therapy agents. Trends Biotechnol 26(11):612–62110.1016/j.tibtech.2008.07.007 ↗
2. Brevet D, Gary-Bobo M, Raehm L, Richeter S, Hocine O, Amro K, Loock B, Couleaud P, Frochot C, Morere A, Maillard P, Garcia M, Durand JO (2009) Mannose-targeted mesoporous silica nanoparticles for photodynamic therapy. Chem Commun 12:1475–1477. doi: 10.1039/b900427k10.1039/b900427k ↗
3. Brunauer S, Emmet PH, Teller E (1938) Adsorption of gases in multimolecular layers. J Am Chem Soc 60:309–31910.1021/ja01269a023 ↗
4. Castanon SL, Beristain MF, Ortega A, Gomez-Sosa G, Munoz E, Perez-Martinez AL, Ogawa T, Halim MF, Smith F, Walser A, Dorsinville R (2011) The synthesis, characterization and third-order nonlinear optical character of poly(2,5-dipropargyloxybenzoate) containing a polar aromatic diacetylene. Dyes Pigment 88(2):129–134. doi: 10.1016/j.dyepig.2010.05.01210.1016/j.dyepig.2010.05.012 ↗
5. Chang B, Guo J, Liu C, Qian J, Yang W (2010) Surface functionalization of magnetic mesoporous silica nanoparticles for controlled drug release. J Mater Chem 20(44):9941–994710.1039/c0jm01237h ↗
6. Chatterjee DK, Fong LS, Zhang Y (2008) Nanoparticles in photodynamic therapy: an emerging paradigm. Adv Drug Deliv Rev 60(15):1627–163710.1016/j.addr.2008.08.003 ↗
7. Chelebaeva E, Raehm L, Durand JO, Guari Y, Larionova J, Guerin C, Trifonov A, Willinger M, Thangavel K, Lascialfari A, Mongin O, Mir Y, Blanchard-Desce M (2010) Mesoporous silica nanoparticles combining two-photon excited fluorescence and magnetic properties. J Mater Chem 20(10):1877–1884. doi: 10.1039/b922052f10.1039/b922052f ↗
8. Chikazumi S (1997) Physics of ferromagnetism, 2nd edn. Clarendon, Oxford10.1093/oso/9780198517764.001.0001 ↗
9. Coti KK, Belowich ME, Liong M, Ambrogio MW, Lau YA, Khatib HA, Zink JI, Khashab NM, Stoddart JF (2009) Mechanised nanoparticles for drug delivery. Nanoscale 1(1):16–3910.1039/b9nr00162j ↗
10. Couleaud P, Morosini V, Frochot C, Richeter S, Raehm L, Durand JO (2010) Silica-based nanoparticles for photodynamic therapy applications. Nanoscale 2(7):1083–1095. doi: 10.1039/c0nr00096e10.1039/c0nr00096e ↗
11. Denk W, Strickler JH, Webb WW (1990) Two-photon laser scanning fluorescence microscopy. Science 248(4951):73–7610.1126/science.2321027 ↗
12. Djurberg C, Svedlindh P, Nordblad P, Hansen MF, Bodker F, Morup S (1997) Dynamics of an interacting particle system: evidence of critical slowing down. Phys Rev Lett 79(25):5154–5157. doi: 10.1103/PhysRevLett.79.515410.1103/PhysRevLett.79.5154 ↗
13. Eaton DF (1988) Reference materials for fluorescence measurement. Pure Appl Chem 60(7):1107–111410.1351/pac198860071107 ↗
14. Feng J, Song SY, Deng RP, Fan WQ, Zhang HJ (2010) Novel multifunctional nanocomposites: magnetic mesoporous silica nanospheres covalently bonded with near-infrared luminescent lanthanide complexes. Langmuir 26(5):3596–3600. doi: 10.1021/la903008z10.1021/la903008z ↗
15. Folch B, Larionova J, Guari Y, Molvinger K, Luna C, Sangregorio C, Innocenti C, Caneschi A, Guerin C (2010) Synthesis and studies of water-soluble prussian blue-type nanoparticles into chitosan beads. Phys Chem Chem Phys 12(39):12760–12770. doi: 10.1039/c002432e10.1039/c002432e ↗
16. Gai SL, Yang PP, Li CX, Wang WX, Dai YL, Niu N, Lin J (2010) Synthesis of magnetic, up-conversion luminescent, and mesoporous core-shell-structured nanocomposites as drug carriers. Adv Funct Mater 20(7):1166–1172. doi: 10.1002/adfm.20090227410.1002/adfm.200902274 ↗
17. Gary-Bobo M, Mir Y, Rouxel C, Brevet D, Basile I, Maynadier M, Vaillant O, Mongin O, Blanchard-Desce M, Morere A, Garcia M, Durand J-O, Raehm L (2011) Mannose-functionalized mesoporous silica nanoparticles for efficient two-photon photodynamic therapy of solid tumors. Angew Chem Int Ed 50(48):11425–1142910.1002/anie.201104765 ↗
18. Gary-Bobo M, Hocine O, Brevet D, Maynadier M, Raehm L, Richeter S, Charasson V, Loock B, Morere A, Maillard P, Garcia M, Durand J-O (2012) Cancer therapy improvement with mesoporous silica nanoparticles combining targeting, drug delivery and PDT. Int J Pharm 423(2):509–51510.1016/j.ijpharm.2011.11.045 ↗
19. Girtu MA (2002) The dynamic susceptibility of a quasi-one-dimensional Mn porphyrin-based hybrid magnet: cole–cole analysis. J Opt Adv Mater 4(1):85–92
20. He Q, Shi J (2011) Mesoporous silica nanoparticle based nano drug delivery systems: synthesis, controlled drug release and delivery, pharmacokinetics and biocompatibility. J Mater Chem 21(16):5845–585510.1039/c0jm03851b ↗
21. Hocine O, Gary-Bobo M, Brevet D, Maynadier M, Fontanel S, Raehm L, Richeter S, Loock B, Couleaud P, Frochot C, Charnay C, Derrien G, Smaihi M, Sahmoune A, Morere A, Maillard P, Garcia M, Durand J-O (2010) Silicalites and mesoporous silica nanoparticles for photodynamic therapy. Int J Pharm 402(1–2):221–23010.1016/j.ijpharm.2010.10.004 ↗
22. Huang D-M, Hung Y, Ko B-S, Hsu S-C, Chen W-H, Chien C-L, Tsai C-P, Kuo C-T, Kang J-C, Yang C-S, Mou C-Y, Chen Y-C (2005) Highly efficient cellular labeling of mesoporous nanoparticles in human mesenchymal stem cells: implication for stem cell tracking. Faseb J 19(14):2014–201610.1096/fj.05-4288fje ↗
23. Katan C, Tretiak S, Werts MHV, Bain AJ, Marsh RJ, Leonczek N, Nicolaou N, Badaeva E, Mongin O, Blanchard-Desce M (2007) Two-photon transitions in quadrupolar and branched chromophores: experiment and theory. J Phys Chem B 111(32):9468–948310.1021/jp071069x ↗
24. Kim HM, Cho BR (2009) Two-photon probes for intracellular free metal ions, acidic vesicles, and lipid rafts in live tissues. Acc Chem Res 42(7):863–872. doi: 10.1021/ar800185u10.1021/ar800185u ↗
25. Kim J, Kim HS, Lee N, Kim T, Kim H, Yu T, Song IC, Moon WK, Hyeon T (2008) Multifunctional uniform nanoparticles composed of a magnetite nanocrystal core and a mesoporous silica shell for magnetic resonance and fluorescence imaging and for drug delivery. Angew Chem Int Ed 47(44):8438–8441. doi: 10.1002/anie.20080246910.1002/anie.200802469 ↗
26. Lartigue L, Oumzil K, Guari Y, Larionova J, Guerin C, Montero JL, Barragan-Montero V, Sangregorio C, Caneschi A, Innocenti C, Kalaivani T, Arosio P, Lascialfari A (2009) Water-soluble rhamnose-coated Fe3O4 nanoparticles. Org Lett 11(14):2992–2995. doi: 10.1021/ol900949y10.1021/ol900949y ↗
27. Lartigue L, Innocenti C, Kalaivani T, Awwad A, Duque MdMS, Guari Y, Larionova J, Guerin C, Montero J-LG, Barragan-Montero V, Arosio P, Lascialfari A, Gatteschi D, Sangregorio C (2011) Water-dispersible sugar-coated iron oxide nanoparticles: an evaluation of their relaxometric and magnetic hyperthermia properties. J Am Chem Soc 133(27):10459–10472. doi: 10.1021/ja111448t10.1021/ja111448t ↗
28. Lartigue L, Oh S, Prouzet E, Guari Y, Larionova J (2012) Superspin-glass behavior of Co-3[Fe(CN)(6)](2) prussian blue nanoparticles confined in mesoporous silica. Mater Chem Phys 132(2–3):438–445. doi: 10.1016/j.matchemphys.2011.11.05010.1016/j.matchemphys.2011.11.050 ↗
29. Lebret V, Raehm L, Durand JO, Smaihi M, Gerardin C, Nerambourg N, Werts MHV, Blanchard-Desce M (2008a) Synthesis and characterization of fluorescently doped mesoporous nanoparticles for two-photon excitation. Chem Mater 20(6):2174–218310.1021/cm703487b ↗
30. Lebret V, Raehm L, Durand JO, Smaihi M, Werts MHV, Blanchard-Desce M, Methy-Gonnod D, Dubernet C (2008b) Surface functionalization of two-photon dye-doped mesoporous silica nanoparticles with folic acid: cytotoxicity studies with HeLa and MCF-7 cancer cells. J Sol Gel Sci Technol 48(1–2):32–39. doi: 10.1007/s10971-008-1724-110.1007/s10971-008-1724-1 ↗
31. Lebret V, Raehm L, Durand JO, Smaihi M, Gerardin C, Nerambourg N, Werts MHV, Blanchard-Desce M, Methy-Gonnod D, Dubernet C (2009) Mesoporous silica nanoparticles for two-photon fluorescence. Med Sci 25(8–9):744–746
32. Lebret V, Raehm L, Durand JO, Smaihi M, Werts MHV, Blanchard-Desce M, Methy-Gonnod D, Dubernet C (2010) Folic acid-targeted mesoporous silica nanoparticles for two-photon fluorescence. J Biomed Nanotechnol 6(2):176–180. doi: 10.1166/jbn.2010.111210.1166/jbn.2010.1112 ↗
33. Li X, Xie QR, Zhang J, Xia W, Gu H (2011a) The packaging of siRNA within the mesoporous structure of silica nanoparticles. Biomaterials 32(35):9546–9556. doi: 10.1016/j.biomaterials.2011.08.06810.1016/j.biomaterials.2011.08.068 ↗
34. Li X, Zhang JX, Gu HC (2011b) Adsorption and desorption behaviors of DNA with magnetic mesoporous silica nanoparticles. Langmuir 27(10):6099–6106. doi: 10.1021/la104653s10.1021/la104653s ↗
35. Lin CR, Chiang RK, Wang JS, Sung TW (2006a) Magnetic properties of monodisperse iron oxide nanoparticles. J Appl Phys 99(8): 08n710. doi: 10.1063/1.217289110.1063/1.2172891 ↗
36. Lin Y-S, Wu S-H, Hung Y, Chou Y-H, Chang C, Lin M-L, Tsai C-P, Mou C-Y (2006b) Multifunctional composite nanoparticles: magnetic, luminescent, and mesoporous. Chem Mater 18(22):5170–517210.1021/cm061976z ↗
37. Liong M, Lu J, Kovochich M, Xia T, Ruehm SG, Nel AE, Tamanoi F, Zink JI (2008) Multifunctional inorganic nanoparticles for imaging, targeting, and drug delivery. ACS Nano 2(5):889–89610.1021/nn800072t ↗
38. Liu J, Qiao SZ, Hu QH, Lu GQ (2011) Magnetic nanocomposites with mesoporous structures: synthesis and applications. Small 7(4):425–443. doi: 10.1002/smll.20100140210.1002/smll.201001402 ↗
39. Lu J, Liong M, Sherman S, Xia T, Kovochich M, Nel AE, Zink JI, Tamanoi F (2007a) Mesoporous silica nanoparticles for cancer therapy: energy-dependent cellular uptake and delivery of paclitaxel to cancer cells. Nanobiotechnology 3(2):89–9510.1007/s12030-008-9003-3 ↗
40. Lu J, Liong M, Zink JI, Tamanoi F (2007b) Mesoporous silica nanoparticles as a delivery system for hydrophobic anticancer drugs. Small 3(8):1341–1346. doi: 10.1002/smll.20070000510.1002/smll.200700005 ↗
41. Mongin O, Porres L, Charlot M, Katan C, Blanchard-Desce M (2007) Synthesis, fluorescence, and two-photon absorption of a series of elongated rodlike and banana-shaped quadrupolar fluorophores: a comprehensive study of structure–property relationships. Chem Eur J 13(5):1481–1498. doi: 10.1002/chem.20060068910.1002/chem.200600689 ↗
42. Néel L (1949) Theorie du trainage magnetique des ferromagnetiques en grains fins avec applications aux terres cuites. Ann Geophys 5:99–136
43. Pawlicki M, Collins HA, Denning RG, Anderson HL (2009) Two-photon absorption and the design of two-photon dyes. Angew Chem Int Ed 48(18):3244–3266. doi: 10.1002/anie.20080525710.1002/anie.200805257 ↗
44. Robertson CA, Evans DH, Abraharnse H (2009) Photodynamic therapy (PDT): a short review on cellular mechanisms and cancer research applications for PDT. J Photochem Photobiol B 96(1):1–8. doi: 10.1016/j.jphotobiol.2009.04.00110.1016/j.jphotobiol.2009.04.001 ↗
45. Rosenholm JM, Sahlgren C, Linden M (2010) Towards multifunctional, targeted drug delivery systems using mesoporous silica nanoparticles: opportunities and challenges. Nanoscale 2(10):1870–188310.1039/c0nr00156b ↗
46. Slowing I, Trewyn BG, Lin VSY (2006) Effect of surface functionalization of MCM-41-type mesoporous silica nanoparticles on the endocytosis by human cancer cells. J Am Chem Soc 128(46):14792–1479310.1021/ja0645943 ↗
47. Slowing II, Vivero-Escoto JL, Wu C-W, Lin VSY (2008) Mesoporous silica nanoparticles as controlled release drug delivery and gene transfection carriers. Adv Drug Deliv Rev 60(11):1278–128810.1016/j.addr.2008.03.012 ↗
48. Slowing II, Vivero-Escoto JL, Trewyn BG, Lin VSY (2010) Mesoporous silica nanoparticles: structural design and applications. J Mater Chem 20(37):7924–793710.1039/c0jm00554a ↗
49. Suteewong T, Sai H, Lee J, Bradbury M, Hyeon T, Gruner SM, Wiesner U (2010) Ordered mesoporous silica nanoparticles with and without embedded iron oxide nanoparticles: structure evolution during synthesis. J Mater Chem 20(36):7807–7814. doi: 10.1039/c0jm01002b10.1039/c0jm01002b ↗
50. Taylor-Pashow KML, Della JR, Huxford RC, Lin WB (2010) Hybrid nanomaterials for biomedical applications. Chem Commun 46(32):5832–5849. doi: 10.1039/c002073g10.1039/c002073g ↗
51. Terenziani F, Katan C, Badaeva E, Tretiak S, Blanchard-Desce M (2008) Enhanced two-photon absorption of organic chromophores: theoretical and experimental assessments. Adv Mater 20(24):4641–4678. doi: 10.1002/adma.20080040210.1002/adma.200800402 ↗
52. Thomas CR, Ferris DP, Lee JH, Choi E, Cho MH, Kim ES, Stoddart JF, Shin JS, Cheon J, Zink JI (2010) Noninvasive remote-controlled release of drug molecules in vitro using magnetic actuation of mechanized nanoparticles. J Am Chem Soc 132(31):10623–10625. doi: 10.1021/ja102226710.1021/ja1022267 ↗
53. Wandersman E, Dupuis V, Dubois E, Perzynski R, Nakamae S, Vincent E (2008) Growth of a dynamical correlation length in an aging superspin glass. EPL 84(3):37011. doi: 10.1209/0295-5075/84/3701110.1209/0295-5075/84/37011 ↗
54. Wang GN, Su XG (2011) The synthesis and bio-applications of magnetic and fluorescent bifunctional composite nanoparticles. Analyst 136(9):1783–1798. doi: 10.1039/c1an15036g10.1039/c1an15036g ↗
55. Wang F, Chen X, Zhao Z, Tang S, Huang X, Lin C, Cai C, Zheng N (2011) Synthesis of magnetic, fluorescent and mesoporous core-shell-structured nanoparticles for imaging, targeting and photodynamic therapy. J Mater Chem 21(30):11244–11252. doi: 10.1039/c1jm10329f10.1039/c1jm10329f ↗
56. Wang M, Zhang J, Yuan Z, Yang W, Wu Q, Gu H (2012) Targeted thrombolysis by using of magnetic mesoporous silica nanoparticles. J Biomed Nanotechnol 8(4):624–632. doi: 10.1166/jbn.2012.141610.1166/jbn.2012.1416 ↗
57. Wu SH, Lin YS, Hung Y, Chou YH, Hsu YH, Chang C, Mou CY (2008) Multifunctional mesoporous silica nanoparticles for intracellular labeling and animal magnetic resonance imaging studies. ChemBioChem 9(1):53–57. doi: 10.1002/cbic.20070050910.1002/cbic.200700509 ↗
58. Xu C, Webb WW (1996) Measurement of two-photon excitation cross sections of molecular fluorophores with data from 690 to 1050 nm. J Opt Soc Am B 13(3):481–49110.1364/JOSAB.13.000481 ↗
59. Zhang J, Li X, Rosenholm JM, Gu H-c (2011) Synthesis and characterization of pore size-tunable magnetic mesoporous silica nanoparticles. J Coll Int Sci 361(1):16–24. doi: 10.1016/j.jcis.2011.05.03810.1016/j.jcis.2011.05.038 ↗