Photochemical mechanisms of light-triggered release from nanocarriers

Advanced Drug Delivery Reviews

Volumn 64, Issue 11, 2012, Pages 1005-1020

  Fomina, Nadezda ^a   Sankaranarayanan, Jagadis ^a   Almutairi, Adah ^a  

^a UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

Author keywords

Light; Nanocarriers; Nanoparticles; Near infrared; Photochemical; Triggered release

Indexed keywords

BIOMEDICAL APPLICATIONS; CLINICAL PRACTICES; NANOCARRIERS; NANOSCALE ASSEMBLIES; NEAR INFRARED; PHOTOCHEMICAL; PHOTOCHEMICAL MECHANISM; PHOTORESPONSIVE; PHOTOTHERMAL EFFECTS; POLYMER BACKBONES; SPATIO-TEMPORAL; SURFACE PLASMON ABSORPTION; TRIGGERED RELEASE;

LIGHT; MEDICAL APPLICATIONS; NANOPARTICLES;

REMOTE CONTROL;

2 DIAZONAPHTHOQUINONE; 4',6 DIAMIDINO 2 PHENYLINDOLE; AZOBENZENE; CAMPTOTHECIN; COPOLYMER; CURCUMIN; DOXORUBICIN; GOLD NANOPARTICLE; LIPOSOME; MACROGOL; NANOCARRIER; NANOCRYSTAL; NANOSHELL; NAPHTHOQUINONE; PACLITAXEL; POLYGLACTIN; SILVER NANOPARTICLE; UNCLASSIFIED DRUG;

ANTISENSE THERAPY; CANCER CELL CULTURE; CRITICAL MICELLE CONCENTRATION; CROSS LINKING; DRUG CYTOTOXICITY; DRUG RELEASE; HYDROPHILICITY; HYDROPHOBICITY; ISOMERIZATION; LIGHT SCATTERING; LIPOSOMAL DELIVERY; MICELLE; NANOENCAPSULATION; NANOFABRICATION; NANOPHARMACEUTICS; NONHUMAN; OXIDATION; PHOTOCHEMISTRY; PHOTODEGRADATION; PHOTOSENSITIZATION; PHOTOSTIMULATION; POLYMERIZATION; PRIORITY JOURNAL; RADIATION ABSORPTION; REVIEW; RISK BENEFIT ANALYSIS; SURFACE PLASMON RESONANCE; ULTRAVIOLET RADIATION;

DRUG CARRIERS; LIGHT; NANOSTRUCTURES; PHARMACEUTICAL PREPARATIONS; PHOTOCHEMICAL PROCESSES;

EID: 84864526832     PISSN: 0169409X     EISSN: 18728294     Source Type: Journal    
DOI: 10.1016/j.addr.2012.02.006     Document Type: Review

References (92)

1. Weissleder R. A clearer vision for in vivo imaging. Nat. Biotechnol. 2001, 19:316-317.
2. Shum P., Kim J.-M., Thompson D.H. Phototriggering of liposomal drug delivery systems. Adv. Drug Delivery Rev. 2001, 53:273-284.
3. Yavlovich A., Smith B., Gupta K., Blumenthal R., Puri A. Light-sensitive lipid-based nanoparticles for drug delivery: design principles and future considerations for biological applications. Mol. Membr. Biol. 2010, 27:364-381.
4. Alvarez-Lorenzo C., Bromberg L., Concheiro A. Light-sensitive intelligent drug delivery systems. Photochem. Photobiol. 2009, 85:848-860.
5. Zhao Y. Photocontrollable block copolymer micelles: what can we control?. J. Mater. Chem. 2009, 19:4887-4895.
6. Schumers J.-M., Fustin C.-A., Gohy J.-F. Light-responsive block copolymers. Macromol. Rapid Commun. 2010, 31:1588-1607.
7. Kano K., Tanaka Y., Ogawa T., Shimoura M., Okahata Y., Kunitake T. Photoresponsive membranes. regulation of membrane properties by photoreversible cis-trans isomerization of azobenzenes. Chem. Lett. 1980, 421-424.
8. Bisby R.H., Mead C., Mitchell A.C., Morgan C.G. Fast laser-induced solute release from liposomes sensitized with photochromic lipid: effects of temperature, lipid host, and sensitizer concentration. Biochem. Biophys. Res. Commun. 1999, 262:406-410.
9. Bisby R.H., Mead C., Morgan C.G. Photosensitive liposomes as 'cages' for laser-triggered solute delivery: the effect of bilayer cholesterol on kinetics of solute release. FEBS Lett. 1999, 463:165-168.
10. Bisby R.H., Mead C., Morgan C.G. Wavelength-programmed solute release from photosensitive liposomes. Biochem. Biophys. Res. Commun. 2000, 276:169-173.
11. Bisby R.H., Mead C., Morgan C.G. Active uptake of drugs into photosensitive liposomes and rapid release on UV photolysis. Photochem. Photobiol. 2000, 72:57-61.
12. Morgan C.G., Thomas E.W., Sandhu S.S., Yianni Y.P., Mitchell A.C. Light-induced fusion of liposomes with release of trapped marker dye is sensitised by photochromic phospholipid. Biochim. Biophys. Acta, Biomembr. 1987, 903:504-509.
13. Morgan C.G., Yianni Y.P., Sandhu S.S., Mitchell A.C. Liposome fusion and lipid exchange on ultraviolet irradiation of liposomes containing a photochromic phospholipid. Photochem. Photobiol. 1995, 62:24-29.
14. Smith Alan M., Harris Jonathan J., Shelton Richard M., Perrie Y. 3D culture of bone-derived cells immobilised in alginate following light-triggered gelation. J. Control Release 2007, 119:94-101.
15. Eastoe J., Vesperinas A. Self-assembly of light-sensitive surfactants. Soft Matter 2005, 1:338-347.
16. Orihara Y., Matsumura A., Saito Y., Ogawa N., Saji T., Yamaguchi A., Sakai H., Abe M. Reversible release control of an oily substance using photoresponsive micelles. Langmuir 2001, 17:6072-6076.
17. Wang Y.P., Han P., Xu H.P., Wang Z.Q., Zhang X., Kabanov A.V. Photocontrolled self-assembly and disassembly of block ionomer complex vesicles: a facile approach toward supramolecular polymer nanocontainers. Langmuir 2010, 26:709-715.
18. Wang G., Tong X., Zhao Y. Preparation of azobenzene-containing amphiphilic diblock copolymers for light-responsive micellar aggregates. Macromolecules 2004, 37:8911-8917.
19. Jochum F.D., Theato P. Thermo- and light responsive micellation of azobenzene containing block copolymers. Chem. Commun. (Cambridge, U. K.) 2010, 46:6717-6719.
20. Zhao Y., Tremblay L., Zhao Y. Doubly photoresponsive and water-soluble block copolymers: synthesis and thermosensitivity. J. Polym. Sci. A1 2010, 48:4055-4066.
21. Han D., Tong X., Zhao Y., Galstian T., Zhao Y. Cyclic azobenzene-containing side-chain liquid crystalline polymers: synthesis and topological effect on mesophase transition, order, and photoinduced birefringence. Macromolecules (Washington, DC, U. S.) 2010, 43:3664-3671.
22. Patnaik S., Sharma Ashwani K., Garg B.S., Gandhi R.P., Gupta K.C. Photoregulation of drug release in azo-dextran nanogels. Int. J. Pharm. 2007, 342:184-193.
23. Angelos S., Choi E., Voegtle F., De Cola L., Zink J.I. Photo-driven expulsion of molecules from mesostructured silica nanoparticles. J. Phys. Chem. C 2007, 111:6589-6592.
24. Lu J., Choi E., Tamanoi F., Zink J.I. Light-activated nanoimpeller-controlled drug release in cancer cells. Small 2008, 4:421-426.
25. Regen S.L., Singh A., Oehme G., Singh M. Polymerized phosphatidyl choline vesicles. Stabilized and controllable time-release carriers. Biochem. Biophys. Res. Commun. 1981, 101:131-136.
26. Yavlovich A., Singh A., Blumenthal R., Puri A. A novel class of photo-triggerable liposomes containing DPPC:DC8,9PC as vehicles for delivery of doxorubicin to cells. Biochim. Biophys. Acta, Biomembr. 2011, 1808:117-126.
27. Park M.-K., Deng S., Advincula Rigoberto C. pH-sensitive bipolar ion-permselective ultrathin films. J. Am. Chem. Soc. 2004, 126:13723-13731.
28. Park M.-K., Deng S., Advincula Rigoberto C. Sustained release control via photo-cross-linking of polyelectrolyte layer-by-layer hollow capsules. Langmuir 2005, 21:5272-5277.
29. Shi D., Matsusaki M., Kaneko T., Akashi M. Photo-cross-linking and cleavage induced reversible size change of bio-based nanoparticles. Macromolecules (Washington, DC, United States) 2008, 41:8167-8172.
30. Shi D., Matsusaki M., Akashi M. Unique size-change behavior of photo-crosslinked cinnamic acid derivative nanoparticles during hydrolytic degradation. Macromol. Biosci. 2009, 9:248-255.
31. Pooler J.P. Photomodification of human erythrocytes: external heavy atom effect, selective permeability and properties of the anion permeation pathway. Photochem. Photobiol. 1988, 47:369-376.
32. Pooler J.P. Photooxidation of cell membranes using eosin derivatives that locate in lipid or protein to study the role of diffusible intermediates. Photochem. Photobiol. 1989, 50:55-68.
33. Girotti A.W. Photodynamic lipid peroxidation in biological systems. Photochem. Photobiol. 1990, 51:497-509.
34. Snipes W., Keller G., Woog J., Vickroy T., Deering R., Keith A. Inactivation of lipid-containing viruses by hydrophobic photosensitizers and near-ultraviolet radiation. Photochem. Photobiol. 1979, 29:785-790.
35. Torinuki W., Miura T., Seiji M. Lysosome destruction and lipoperoxide formation due to active oxygen generated from haematoporphyrin and UV irradiation. Br. J. Dermatol. 1980, 102:17-27.
36. Dahl T.A., Midden W.R., Hartman P.E. Pure singlet oxygen cytotoxicity for bacteria. Photochem. Photobiol. 1987, 46:345-352.
37. Deziel M.R., Girotti A.W. Photodynamic action of bilirubin on liposomes and erythrocyte membranes. J. Biol. Chem. 1980, 255:8192-8198.
38. Bally M.B., Nayar R., Masin D., Hope M.J., Cullis P.R., Mayer L.D. Liposomes with entrapped doxorubicin exhibit extended blood residence times. Biochim. Biophys. Acta, Biomembr. 1990, 1023:133-139.
39. Foote C.S., Dobrowolski D.C. Singlet oxygen production from photodynamic sensitizers. Oxygen Radicals Chem. Biol., Proc., Int. Conf., 3rd 1984, 465-472.
40. Thompson D.H., Gerasimov O.V., Wheeler J.J., Rui Y.J., Anderson V.C. Triggerable plasmalogen liposomes: improvement of system efficiency. Biomembranes 1996, 1279:25-34.
41. Anderson V.C., Thompson D.H. Triggered release of hydrophilic agents from plasmalogen liposomes using visible light or acid. Biochim. Biophys. Acta, Biomembr. 1992, 1109:33-42.
42. Hogset A., Prasmickaite L., Selbo P.K., Hellum M., Engesaeter B.O., Bonsted A., Berg K. Photochemical internalisation in drug and gene delivery. Adv. Drug Delivery Rev. 2004, 56:95-115.
43. Nishiyama N., Iriyama A., Jang W.D., Miyata K., Itaka K., Inoue Y., Takahashi H., Yanagi Y., Tamaki Y., Koyama H., Kataoka K. Light-induced gene transfer from packaged DNA enveloped in a dendrimeric photosensitizer. Nat. Mater. 2005, 4:934-941.
44. Febvay S., Marini D.M., Belcher A.M., Clapham D.E. Targeted cytosolic delivery of cell-impermeable compounds by nanoparticle-mediated, light-triggered endosome disruption. Nano Lett. 2010, 10:2211-2219.
45. Oldenburg S.J., Jackson J.B., Westcott S.L., Halas N.J. Infrared extinction properties of gold nanoshells. Appl. Phys. Lett. 1999, 75:2897-2899.
46. Hirsch L.R., Stafford R.J., Bankson J.A., Sershen S.R., Rivera B., Price R.E., Hazle J.D., Halas N.J., West J.L. Nanoshell-mediated near-infrared thermal therapy of tumors under magnetic resonance guidance. Proc. Natl. Acad. Sci. U. S. A. 2003, 100:13549-13554.
47. Xia Y.N., Yang P.D., Sun Y.G., Wu Y.Y., Mayers B., Gates B., Yin Y.D., Kim F., Yan Y.Q. One-dimensional nanostructures: synthesis, characterization, and applications. Adv. Mater. 2003, 15:353-389.
48. Zharov V.P., Galitovsky V., Viegas M. Photothermal detection of local thermal effects during selective nanophotothermolysis. Appl. Phys. Lett. 2003, 83:4897-4899.
49. Lee J., Govorov A.O., Kotov N.A. Nanoparticle assemblies with molecular springs: a nanoscale thermometer. Angew. Chem. Int. Ed. 2005, 44:7439-7442.
50. Huang W., Qian W., El-Sayed M.A. Gold nanoparticles propulsion from surface fueled by absorption of femtosecond laser pulse at their surface plasmon resonance. J. Am. Chem. Soc. 2006, 128:13330-13331.
51. Takahashi H., Niidome T., Nariai A., Niidome Y., Yamada S. Gold nanorod-sensitized cell death: microscopic observation of single living cells irradiated by pulsed near-infrared laser light in the presence of gold nanorods. Chem. Lett. 2006, 35:500-501.
52. Chen J.Y., Wang D.L., Xi J.F., Au L., Siekkinen A., Warsen A., Li Z.Y., Zhang H., Xia Y.N., Li X.D. Immuno gold nanocages with tailored optical properties for targeted photothermal destruction of cancer cells. Nano Lett. 2007, 7:1318-1322.
53. Chen J., Saeki F., Wiley B.J., Cang H., Cobb M.J., Li Z.Y., Au L., Zhang H., Kimmey M.B., Li X.D., Xia Y. Gold nanocages: bioconjugation and their potential use as optical imaging contrast agents. Nano Lett. 2005, 5:473-477.
54. Jain P.K., Lee K.S., El-Sayed I.H., El-Sayed M.A. Calculated absorption and scattering properties of gold nanoparticles of different size, shape, and composition: applications in biological imaging and biomedicine. J. Phys. Chem. B 2006, 110:7238-7248.
55. Link S., El-Sayed M.A. Shape and size dependence of radiative, non-radiative and photothermal properties of gold nanocrystals. Int. Rev. Phys. Chem. 2000, 19:409-453.
56. Prevo B.G., Esakoff S.A., Mikhailovsky A., Zasadzinski J.A. Scalable routes to gold nanoshells with tunable sizes and response to near-infrared pulsed-laser irradiation. Small 2008, 4:1183-1195.
57. Wu G., Mikhailovsky A., Khant H.A., Fu C., Chiu W., Zasadzinski J.A. Remotely triggered liposome release by near-infrared light absorption via hollow gold nanoshells. J. Am. Chem. Soc. 2008, 130:8175-8177.
58. Volodkin D.V., Skirtach A.G., Moehwald H. Near-IR remote drug release from assemblies of liposomes and nanoparticles. Angew. Chem. Int. Ed. 2009, 48:1807-1809.
59. Huang X.H., Jain P.K., El-Sayed I.H., El-Sayed M.A. Plasmonic photothermal therapy (PPTT) using gold nanoparticles. Laser Med. Sci. 2008, 23:217-228.
60. Radt B., Smith T.A., Caruso F. Optically addressable nanostructured capsules. Adv. Mater. (Weinheim, Ger.) 2004, 16:2184-2189.
61. Oishi M., Nakamura T., Jinji Y., Matsuishi K., Nagasaki Y. Multi-stimuli-triggered release of charged dye from smart PEGylated nanogels containing gold nanoparticles to regulate fluorescence signals. J. Mater. Chem. 2009, 19:5909-5912.
62. Wu W., Shen J., Banerjee P., Zhou S. Water-dispersible multifunctional hybrid nanogels for combined curcumin and photothermal therapy. Biomaterials 2011, 32:598-609.
63. Huschka R., Neumann O., Barhoumi A., Halas N.J. Visualizing Light-Triggered Release of Molecules Inside Living Cells. Nano Lett. 2009, 10:4117-4122.
64. Barhoumi A., Huschka R., Bardhan R., Knight M.W., Halas N.J. Light-induced release of DNA from plasmon-resonant nanoparticles: towards light-controlled gene therapy. Chem. Phys. Lett. 2009, 482:171-179.
65. Park H., Yang J., Lee J., Haam S., Choi I.H., Yoo K.H. Multifunctional nanoparticles for combined doxorubicin and photothermal treatments. ACS Nano 2009, 3:2919-2926.
66. You J., Zhang G., Li C. Exceptionally High Payload of Doxorubicin in Hollow Gold Nanospheres for Near-Infrared Light-Triggered Drug Release. ACS Nano 2010, 4:1033-1041.
67. Göppert-Mayer M. Über Elementarakte mit zwei Quantensprüngen. Ann. Phys. 1931, 401:273-294.
68. Marder S.R., Lee Kwang-Sup Photoresponsive polymers I. Adv. Pol. Sci. 2008, Springer.
69. 2+. Phys. Rev. Lett. 1961, 7:229-231.
70. Mark J.E. Physical properties of polymers handbook 2007, Springer.
71. Goodwin A.P., Mynar J.L., Ma Y., Fleming G.R., Frechet J.M.J. Synthetic micelle sensitive to ir light via a two-photon process. J. Am. Chem. Soc. 2005, 127:9952-9953.
72. Mynar J.L., Goodwin A.P., Cohen J.A., Ma Y., Fleming G.R., Frachet J.M.J. Two-photon degradable supramolecular assemblies of linear-dendritic copolymers. Chem. Commun. 2007, 2081-2082.
73. Jiang J.Q., Tong X., Morris D., Zhao Y. Toward photocontrolled release using light-dissociable block copolymer micelles. Macromolecules 2006, 39:4633-4640.
74. Furuta T., Wang S.S.-H., Dantzker J.L., Dore T.M., Bybee W.J., Callaway E.M., Denk W., Tsien R.Y. Brominated 7-hydroxycoumarin-4-ylmethyls: photolabile protecting groups with biologically useful cross-sections for two photon photolysis. Proc. Natl. Acad. Sci. U. S. A. 1999, 96:1193-1200.
75. Babin J., Pelletier M., Lepage M., Allard J.-F., Morris D., Zhao Y. A new two-photon-sensitive block copolymer nanocarrier. Angew. Chem. Int. Ed. 2009, 121:3379-3382.
76. Lee H.-i., Wu W., Oh J.K., Mueller L., Sherwood G., Peteanu L., Kowalewski T., Matyjaszewski K. Light-induced reversible formation of polymeric micelles. Angew. Chem. Int. Ed. 2007, 119:2505-2509.
77. Jiang X., Lavender C.A., Woodcock J.W., Zhao B. Multiple micellization and dissociation transitions of thermo- and light-sensitive poly(ethylene oxide)-b-poly(ethoxytri(ethylene glycol) acrylate-co-o-nitrobenzyl acrylate) in water. Macromolecules 2008, 41:2632-2643.
78. Uda R.M., Hiraishi E., Ohnishi R., Nakahara Y., Kimura K. Morphological changes in vesicles and release of an encapsulated compound triggered by a photoresponsive malachite green leuconitrile derivative. Langmuir 2010, 26:5444-5450.
79. Cui W., Lu X., Cui K., Wu J., Wei Y., Lu Q. Photosensitive nanoparticles of chitosan complex for controlled release of dye molecules. Nanotechnology 2011, 22:065702.
80. Gorostiza P., Isacoff E.Y. Nanoengineering ion channels for optical control. Physiology 2008, 23:238-247.
81. Kocer A., Walko M., Meijberg W., Feringa B.L. A light-actuated nanovalve derived from a channel protein. Science 2005, 309:755-758.
82. Carling C.J., Boyer J.C., Branda N.R. Remote-control photoswitching using NIR light. J. Am. Chem. Soc. 2009, 131:10838-10839.
83. Carling C.J., Nourmohammadian F., Boyer J.C., Branda N.R. Remote-control photorelease of caged compounds using near-infrared light and upconverting nanoparticles. Angew. Chem. Int. Ed. 2010, 49:3782-3785.
84. Yan B., Boyer J.-C., Branda N.R., Zhao Y. Near-infrared light-triggered dissociation of block copolymer micelles using upconverting nanoparticles. J. Am. Chem. Soc. 2011, 133:19714-19717.
85. Heer S., Kompe K., Gudel H.U., Haase M. Highly efficient multicolour upconversion emission in transparent colloids of lanthanide-doped NaYF4 nanocrystals. Adv. Mater. 2004, 16:2102-2105.
86. N. Fomina, C. McFearin, M. Sermsakdi, O. Edigin, A. Almutairi, UV and Near-IR Triggered Release from Polymeric Nanoparticles, J. Am. Chem. Soc., 132 9540-9542.
87. Fomina N., McFearin C.L., Sermsakdi M., Morachis J.M., Almutairi A. Low power, biologically benign NIR light triggers polymer disassembly. Macromolecules 2011, 44:8590-8597.
88. Johnson J.A., Lu Y.Y., Burts A.O., Lim Y.H., Finn M.G., Koberstein J.T., Turro N.J., Tirrell D.A., Grubbs R.H. Core-clickable PEG-branch-azide bivalent-bottle-brush polymers by ROMP: grafting-through and clicking-to. J. Am. Chem. Soc. 2011, 133:559-566.
89. He J., Tong X., Zhao Y. Photoresponsive nanogels based on photocontrollable cross-links. Macromolecules 2009, 42:4845-4852.
90. Härtner S., Kim H.-C., Hampp N. Photodimerized 7-hydroxycoumarin with improved solubility in PMMA: single-photon and two-photon-induced photocleavage in solution and PMMA films. J. Photochem. Photobiol. B 2007, 187:242-246.
91. Yu L. Photosensitive cross-linked block copolymers with controllable release. Photochem. Photobiol. 2011, 87:646-652.
92. Tomatsu I., Peng K., Kros A. Photoresponsive hydrogels for biomedical applications. Adv. Drug Delivery Rev. 2011, 63:1257-1266.