Caging metal ions with visible light-responsive nanopolymersomes

Langmuir

Volumn 31, Issue 2, 2015, Pages 799-807

  Griepenburg, Julianne C ^a   Sood, Nimil ^b   Vargo, Kevin B ^b   Williams, Dewight ^c   Rawson, Jeff ^d   Therien, Michael J ^d   Hammer, Daniel A ^b   Dmochowski, Ivan J ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

^c UNIVERSITY OF PENNSYLVANIA   (United States)

^d DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EMISSION SPECTROSCOPY; FLUOROPHORES; HYDROPHOBICITY; MECHANICAL STABILITY; POLYMERS; ZINC;

AMPHIPHILIC DIBLOCK COPOLYMERS; ATTRACTIVE SYSTEMS; BILAYER VESICLES; EMISSION SPECTRUMS; ENVIRONMENTAL COMPATIBILITY; HYDROPHOBIC MEMBRANE; VISIBLE LIGHT RESPONSIVE; ZEBRAFISH EMBRYOS;

METAL IONS;

CALCIUM; POLYMER; ZINC;

CHEMICAL PHENOMENA; CHEMISTRY; CRYOELECTRON MICROSCOPY; LIGHT;

CALCIUM; CRYOELECTRON MICROSCOPY; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; LIGHT; POLYMERS; ZINC;

EID: 84922329910     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la5036689     Document Type: Article

References (54)

1. Bush, A. I. Metals and neuroscience Curr. Opin. Chem. Biol. 2000, 4, 184-191
2. King, J. C.; Shames, D. M.; Woodhouse, L. R. Zinc homeostasis in humans J. Nutr. 2000, 130, 1360S-1366S
3. Takeda, A. Zinc homeostasis and functions of zinc in the brain Biometals 2001, 14, 343-351
4. Kaur, K.; Gupta, R.; Saraf, S. A.; Saraf, S. K. Zinc: The metal of life Compr. Rev. Food. Sci. Food Saf. 2014, 13, 358-376
5. Carafoli, E. Intracellular calcium homeostasis Annu. Rev. Biochem. 1987, 56, 395-433
6. Minta, A.; Kao, J. P.; Tsien, R. Y. Fluorescent indicators for cytosolic calcium based on rhodamine and fluorescein chromophores J. Biol. Chem. 1989, 264, 8171-8178
7. 2+ in hippocampal slices J. Am. Chem. Soc. 2005, 127, 10197-10204
8. Domaille, D. W.; Que, E. L.; Chang, C. J. Synthetic fluorescent sensors for studying the cell biology of metals Nat. Chem. Biol. 2008, 4, 168-175
9. Haas, K. L.; Franz, K. J. Application of metal coordination chemistry to explore and manipulate cell biology Chem. Rev. 2009, 109, 4921-4960
10. Tomat, E.; Lippard, S. J. Imaging mobile zinc in biology Curr. Opin. Chem. Biol. 2010, 14, 225-230
11. Mbatia, H. W.; Burdette, S. C. Photochemical tools for studying metal ion signaling and homeostasis Biochemistry 2012, 51, 7212-7224
12. Tsien, R. Y.; Zucker, R. S. Control of cytoplasmic calcium with photolabile tetracarboxylate 2-nitrobenzhydrol chelators Biophys. J. 1986, 50, 843-853
13. Marcotte, N.; Plaza, P.; Lavabre, D.; Fery-Forgues, S.; Martin, M. M. Calcium photorelease from a symmetrical donor-acceptor-donor bis-crown-fluoroionophore evidenced by ultrafast absorption spectroscopy J. Phys. Chem. A 2003, 107, 2394-2402
14. Momotake, A.; Lindegger, N.; Niggli, E.; Barsotti, R. J.; Ellis-Davies, G. C. R. The nitrodibenzofuran chromophore: a new caging group for ultra-efficient photolysis in living cells Nat. Methods 2006, 3, 35-40
15. Ellis-Davies, G. C. Caged compounds: photorelease technology for control of cellular chemistry and physiology Nat. Methods 2007, 4, 619-628
16. Ellis-Davies, G. C. R. Neurobiology with caged calcium Chem. Rev. 2008, 108, 1603-1613
17. 2+ with ZinCleav-1: A nitrobenzyl-based caged complex Inorg. Chem. 2009, 48, 8445-8455
18. 2+ release system with dual binding-sites and turn-on fluorescence Phys. Chem. Chem. Phys. 2010, 12, 1177-1181
19. Ciesienski, K. L.; Franz, K. J. Keys for unlocking photolabile metal-containing cages Angew. Chem., Int. Ed. 2011, 50, 814-824
20. 2+ photocages using multiple nitrobenzyl groups Inorg. Chem. 2013, 52, 8483-8494
21. Brown, E. B.; Shear, J. B.; Adams, S. R.; Tsien, R. Y.; Webb, W. W. Photolysis of caged calcium in femtoliter volumes using two-photon excitation Biophys. J. 1999, 76, 489-499
22. Canto, E. D.; Natali, M.; Movia, D.; Giordani, S. Photo-controlled release of zinc metal ions by spiropyran receptors anchored to single-walled carbon nanotubes Phys. Chem. Chem. Phys. 2012, 14, 6034-6043
23. Fomina, N.; Sankaranarayanan, J.; Almutairi, A. Photochemical mechanisms of light-triggered release from nanocarriers Adv. Drug Delivery Rev. 2012, 64, 1005-1020
24. Discher, B. M.; Won, Y. Y.; Ege, D. S.; Lee, J. C. M.; Bates, F. S.; Discher, D. E.; Hammer, D. A. Polymersomes: Tough vesicles made from diblock copolymers Science 1999, 284, 1143-1146
25. Lee, J. S.; Feijen, J. Polymersomes for drug delivery: design, formation and characterization J. Controlled Release 2012, 161, 473-483
26. Ghoroghchian, P. P.; Frail, P. R.; Susumu, K.; Blessington, D.; Brannan, A. K.; Bates, F. S.; Chance, B.; Hammer, D. A.; Therien, M. J. Near-infrared-emissive polymersomes: Self-assembled soft matter for in vivo optical imaging Proc. Natl. Acad. Sci. U. S. A. 2005, 102, 2922-2927
27. Katz, J. S.; Zhong, S.; Ricart, B. G.; Pochan, D. J.; Hammer, D. A.; Burdick, J. A. Modular synthesis of biodegradable diblock copolymers for designing functional polymersomes J. Am. Chem. Soc. 2010, 132, 3654-3655
28. Christian, N. A.; Milone, M. C.; Ranka, S. S.; Li, G.; Frail, P. R.; Davis, K. P.; Bates, F. S.; Therien, M. J.; Ghoroghchian, P. P.; June, C. H.; Hammer, D. A. Tat-functionalized near-infrared emissive polymersomes for dendritic cell labeling Bioconjugate Chem. 2007, 18, 31-40
29. Demirgöz, D.; Pangburn, T. O.; Davis, K. P.; Lee, S.; Bates, F. S.; Kokkoli, E. PR-b-targeted delivery of tumor necrosis factor-α by polymersomes for the treatment of prostate cancer Soft Matter 2009, 5, 2011-2019
30. Zupancich, J. A.; Bates, F. S.; Hillmyer, M. A. Synthesis and self-assembly of RGD-functionalized PEO-PB amphiphiles Biomacromolecules 2009, 10, 1554-1563
31. Cabane, E.; Malinova, V.; Menon, S.; Palivan, C. G.; Meier, W. Photoresponsive polymersomes as smart, triggerable nanocarriers Soft Matter 2011, 7, 9167-9176
32. Zhang, Q.; Ko, N. R.; Oh, J. K. Modulated morphologies and tunable thiol-responsive shedding of aqueous block copolymer aggregates RSC Adv. 2012, 2, 8079-8086
33. 2+) release in aqueous Tween-20 micelle solution Phys. Chem. Chem. Phys. 2012, 14, 2312-2316
34. Chen, C.-J.; Liu, G.-Y.; Liu, X.-S.; Li, D.-D.; Ji, J. Construction of photo-responsive micelles from azobenzene-modified hyperbranched polyphosphates and study of their reversible self-assembly and disassembly behaviours New J. Chem. 2012, 36, 694-701
35. Olejniczak, J.; Sankaranarayanan, J.; Viger, M. L.; Almutairi, A. Highest efficiency two-photon degradable copolymer for remote controlled release ACS Macro Lett. 2013, 2, 683-687
36. Jiang, J.; Tong, X.; Morris, D.; Zhao, Y. Toward photocontrolled release using light-dissociable block copolymer micelles Macromolecules 2006, 39, 4633-4640
37. Fomina, N.; McFearin, C.; Sermsakdi, M.; Edigin, O.; Almutairi, A. UV and near-IR triggered release from polymeric nanoparticles J. Am. Chem. Soc. 2010, 132, 9540-9542
38. Cong, L. V.; Wang, Z.; Wang, P.; Tang, X. J. Photodegradable polyurethane self-assembled nanoparticles for photocontrollable release Langmuir 2012, 28, 9387-9394
39. Liu, X.; Tian, Z.; Chen, C.; Allcock, H. R. UV-cleavable unimolecular micelles: synthesis and characterization toward photocontrolled drug release carriers Polym. Chem. 2013, 4, 1115-1125
40. Bansal, A.; Zhang, Y. Photocontrolled nanoparticle delivery systems for biomedical applications Acc. Chem. Res. 2014, 47, 3052-3060
41. Barman, S.; Mukhopadhyay, S. K.; Behara, K. K.; Dey, S.; Singh, N. D. P. 1-acetylpyrene-salicylic acid: photoresponsive fluorescent organic nanoparticles for the regulated release of a natural antimicrobial compound, salicylic acid ACS Appl. Mater. Interfaces 2014, 6, 7045-7054
42. Xing, Q.; Li, N.; Chen, D.; Sha, W.; Jiao, Y.; Qi, X.; Xu, Q.; Lu, J. Light-responsive amphiphilic copolymer coated nanoparticles as nanocarriers and real-time monitors for controlled drug release J. Mater. Chem. B 2014, 2, 1182-1189
43. Ghoroghchian, P. P.; Frail, P. R.; Susumu, K.; Park, T.-H.; Wu, S. P.; Uyeda, H. T.; Hammer, D. A.; Therien, M. J. Broad spectral domain fluorescence wavelength modulation of visible and near-infrared emissive polymersomes J. Am. Chem. Soc. 2005, 127, 15388-15390
44. Robbins, G. P.; Jimbo, M.; Swift, J.; Therien, M. J.; Hammer, D. A.; Dmochowski, I. J. Photoinitiated destruction of composite porphyrin-protein polymersomes J. Am. Chem. Soc. 2009, 131, 3872-3874
45. Kamat, N. P.; Robbins, G. P.; Rawson, J.; Therien, M. J.; Dmochowski, I. J.; Hammer, D. A. A generalized system for photoresponsive membrane rupture in polymersomes Adv. Funct. Mater. 2010, 20, 2588-2596
46. Duncan, T. V.; Susumu, K.; Sinks, L. E.; Therien, M. J. Exceptional near-infrared fluorescence quantum yields and excited-state absorptivity of highly conjugated porphyrin arrays J. Am. Chem. Soc. 2006, 128, 9000-9001
47. Lin, V. S.-Y.; DiMagno, S. G.; Therien, M. J. Highly conjugated, acetylenyl bridged porphyrins: new models for light-harvesting antenna systems Science 1994, 264, 1105-1111
48. Jain, S.; Bates, F. S. On the origins of morphological complexity in block copolymer surfactants Science 2003, 300, 460-464
49. Onaca, O.; Enea, R.; Hughes, D. W.; Meier, W. Stimuli-responsive polymersomes as nanocarriers for drug and gene delivery Macromol. Biosci. 2009, 9, 129-139
50. Kamat, N. P.; Liao, Z.; Moses, L. E.; Rawson, J.; Therien, M. J.; Dmochowski, I. J.; Hammer, D. A. Sensing membrane stress with near IR-emissive porphyrins Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 13984-13989
51. Bermudez, H.; Brannan, A. K.; Hammer, D. A.; Bates, F. S.; Discher, D. E. Molecular weight dependence of polymersome membrane structure, elasticity, and stability Macromolecules 2002, 4, 8203-8208
52. Stork, C. J.; Li, Y. V. Zinc release from thapsigargin/IP3-sensitive stores in cultured cortical neurons J. Mol. Signal 2010, 5, 1-6
53. Anraku, Y.; Kishimura, A.; Kobayashi, A.; Oba, M.; Kataoka, K. Size-controlled long-circulating PICsome as a ruler to measure critical cut-off disposition size into normal and tumor tissues Chem. Commun. 2011, 47, 6054-6056
54. Lee, J. S.; Ankone, M.; Pieters, E.; Schiffelers, R. M.; Hennink, W. E.; Feijen, J. Circulation kinetics and biodistribution of dual-labeled polymersomes with modulated surface charge in tumor-bearing mice: comparison with stealth liposomes J. Controlled Release 2011, 155, 282-288