Real-Time Drug Release Analysis of Enzyme and pH Responsive Polysaccharide Nanovesicles

Journal of Physical Chemistry B

Volumn 119, Issue 33, 2015, Pages 10511-10523

  Pramod, Poothayil Subash ^a,b   Deshpande, Nilesh Umakant ^a   Jayakannan, Manickam ^a  

^a INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH   (India)

^b GOVERNMENT MEDICAL COLLEGE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHIBIOUS VEHICLES; BINDING ENERGY; BIOCOMPATIBILITY; DIALYSIS; DIALYSIS MEMBRANES; DISEASES; ENZYMES; EXCITED STATES; FLUORESCENCE; KINETICS; PARTICLE BEAMS; POLYMERS; RHODIUM;

DRUG RELEASE KINETICS; DRUG RELEASE PATTERNS; FLUORESCENT LIFETIME; INTRACELLULAR COMPARTMENTS; SEMI-PERMEABLE MEMBRANES; SPECTROSCOPIC TECHNIQUE; TIME-CORRELATED SINGLE PHOTON COUNTING TECHNIQUES; TIME-RESOLVED FLUORESCENCE;

FLUOROPHORES;

CARBOXYLESTERASE; CES1 PROTEIN, HUMAN; DEXTRAN; DOXORUBICIN; DRUG CARRIER; NANOMATERIAL; POLYSACCHARIDE; RHODAMINE; RHODAMINE B; WATER;

ANIMAL; CHEMISTRY; DRUG RELEASE; ENZYME ACTIVE SITE; HUMAN; METABOLISM; MOLECULAR DOCKING; MOUSE; PH; SOLUBILITY; TUMOR CELL LINE;

ANIMALS; CARBOXYLIC ESTER HYDROLASES; CATALYTIC DOMAIN; CELL LINE, TUMOR; DEXTRANS; DOXORUBICIN; DRUG CARRIERS; DRUG LIBERATION; HUMANS; HYDROGEN-ION CONCENTRATION; MICE; MOLECULAR DOCKING SIMULATION; NANOSTRUCTURES; POLYSACCHARIDES; RHODAMINES; SOLUBILITY; WATER;

EID: 84939857184     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/acs.jpcb.5b05795     Document Type: Article

References (42)

1. Larson, N.; Ghandehari, H. Polymeric Conjugates for Drug Delivery Chem. Mater. 2012, 24, 840-853 10.1021/cm2031569
2. Nicolas, J.; Mura, S.; Brambilla, D.; Mackiewicz, N.; Couvreur, P. Design, Functionalization Strategies and Biomedical Applications of Targeted Biodegradable/Biocompatible Polymer-Based Nanocarriers for Drug Delivery Chem. Soc. Rev. 2013, 42, 1147-1235 10.1039/C2CS35265F
3. Ahmad, Z.; Shah, A.; Siddiq, M.; Kraatz, H.-B. Polymeric Micelles as Drug Delivery Vehicles RSC Adv. 2014, 4, 17028-17038 10.1039/c3ra47370h
4. Brinkhuis, R. P.; Rutjes, F. P. J. T.; van Hest, J. C. M. Polymeric Vesicles in Biomedical Applications Polym. Chem. 2011, 2, 1449-1462 10.1039/c1py00061f
5. Maity, A. R.; Chakraborty, A.; Mondal, A.; Jana, N. R. Carbohydrate Coated, Folate Functionalized Colloidal Graphene as a Nanocarrier for Both Hydrophobic and Hydrophilic Drugs Nanoscale 2014, 6, 2752-2758 10.1039/c3nr05431d
6. Torchilin, V. P. Multifunctional, Stimuli-Sensitive Nanoparticulate Systems for Drug Delivery Nat. Rev. Drug Discovery 2014, 13, 813-827 10.1038/nrd4333
7. Maeda, H. Tumor-Selective Delivery of Macromolecular Drugs Via the EPR Effect: Background and Future Prospects Bioconjugate Chem. 2010, 21, 797-802 10.1021/bc100070g
8. Fang, J.; Nakamura, H.; Maeda, H. The Epr Effect: Unique Features of Tumor Blood Vessels for Drug Delivery, Factors Involved, and Limitations and Augmentation of the Effect Adv. Drug Delivery Rev. 2011, 63, 136-151 10.1016/j.addr.2010.04.009
9. Du, J.; O'Reilly, R. K. Advances and Challenges in Smart and Functional Polymer Vesicles Soft Matter 2009, 5, 3544-3561 10.1039/b905635a
10. Meng, F.; Zhong, Z.; Feijen, J. Stimuli-Responsive Polymersomes for Programmed Drug Delivery Biomacromolecules 2009, 10, 197-209 10.1021/bm801127d
11. Saito, G.; Swanson, J. A.; Lee, K.-D. Drug Delivery Strategy Utilizing Conjugation Via Reversible Disulfide Linkages: Role and Site of Cellular Reducing Activities Adv. Drug Delivery Rev. 2003, 55, 199-215 10.1016/S0169-409X(02)00179-5
12. Guo, D.-S.; Wang, K.; Wang, Y.-X.; Liu, Y. Cholinesterase-Responsive Supramolecular Vesicle J. Am. Chem. Soc. 2012, 134, 10244-10250 10.1021/ja303280r
13. Feng, A.; Yuan, J. Smart Nanocontainers: Progress on Novel Stimuli-Responsive Polymer Vesicles Macromol. Rapid Commun. 2014, 35, 767-779 10.1002/marc.201300866
14. Rodriguez, A. R.; Kramer, J. R.; Deming, T. J. Enzyme-Triggered Cargo Release from Methionine Sulfoxide Containing Copolypeptide Vesicles Biomacromolecules 2013, 14, 3610-3614 10.1021/bm400971p
15. Habraken, G. J. M.; Peeters, M.; Thornton, P. D.; Koning, C. E.; Heise, A. Selective Enzymatic Degradation of Self-Assembled Particles from Amphiphilic Block Copolymers Obtained by the Combination of N-Carboxyanhydride and Nitroxide-Mediated Polymerization Biomacromolecules 2011, 12, 3761-3769 10.1021/bm2010033
16. Moreno-Bautista, G.; Tam, K. C. Evaluation of Dialysis Membrane Process for Quantifying the in Vitro Drug-Release from Colloidal Drug Carriers Colloids Surf., A 2011, 389, 299-303 10.1016/j.colsurfa.2011.07.032
17. Modi, S.; Anderson, B. D. Determination of Drug Release Kinetics from Nanoparticles: Overcoming Pitfalls of the Dynamic Dialysis Method Mol. Pharmaceutics 2013, 10, 3076-3089 10.1021/mp400154a
18. Weinstain, R.; Segal, E.; Satchi-Fainaro, R.; Shabat, D. Real-Time Monitoring of Drug Release Chem. Commun. 2010, 46, 553-555 10.1039/B919329D
19. Cui, W.; Lu, X.; Cui, K.; Wu, J.; Wei, Y.; Lu, Q. Fluorescent Nanoparticles of Chitosan Complex for Real-Time Monitoring Drug Release Langmuir 2011, 27, 8384-8390 10.1021/la200552k
20. Viger, M. L.; Sheng, W.; McFearin, C. L.; Berezin, M. Y.; Almutairi, A. Application of Time-Resolved Fluorescence for Direct and Continuous Probing of Release from Polymeric Delivery Vehicles J. Controlled Release 2013, 171, 308-314 10.1016/j.jconrel.2013.06.018
21. Berezin, M. Y.; Achilefu, S. Fluorescence Lifetime Measurements and Biological Imaging Chem. Rev. 2010, 110, 2641-2684 10.1021/cr900343z
22. Aigner, D.; Dmitriev, R. I.; Borisov, S. M.; Papkovsky, D. B.; Klimant, I. pH-Sensitive Perylenebisimide Probes for Live Cell fluorescence Lifetime Imaging J. Mater. Chem. B 2014, 2, 6792-6801 10.1039/C4TB01006J
23. Becker, W. Fluorescence Life Time Imaging- Techniques and Applications J. Microsc. 2012, 247, 119-136 10.1111/j.1365-2818.2012.03618.x
24. Bunge, A.; Fischlechner, M.; Loew, M.; Arbuzova, A.; Herrmann, A.; Huster, D. Characterization of Lipid Bilayers Adsorbed on Spherical LbL-Support Soft Matter 2009, 5, 3331-3339 10.1039/b902264c
25. Pramod, P. S.; Takamura, K.; Chaphekar, S.; Balasubramanian, N.; Jayakannan, M. Dextran Vesicular Carriers for Dual Encapsulation of Hydrophilic and Hydrophobic Molecules and Delivery into Cells Biomacromolecules 2012, 13, 3627-3640 10.1021/bm301583s
26. Sridhar, U.; Pramod, P. S.; Jayakannan, M. Creation of Dextrin Vesicles and Their Loading-Delivering Capabilities RSC Adv. 2013, 3, 21237-21241 10.1039/c3ra43652g
27. Pramod, P. S.; Shah, R.; Chaphekar, S.; Balasubramanian, N.; Jayakannan, M. Polysaccharide Nano-Vesicular Multidrug Carriers for Synergistic Killing of Cancer Cells Nanoscale 2014, 6, 11841-11855 10.1039/C4NR03514C
28. Pramod, P. S.; Shah, R.; Jayakannan, M. Dual Stimuli Polysaccharide Nanovesicles for Conjugated and Physically Loaded Doxorubicin Delivery in Breast Cancer Cells Nanoscale 2015, 7, 6636-6652 10.1039/C5NR00799B
29. Lakowicz, J. R. Principles of Fluorescence Spectroscopy; Springer: New York, 2010; Vol. 3, pp 102-106.
30. Hemmert, A. C.; Otto, T. C.; Wierdl, M.; Edwards, C. C.; Fleming, C. D.; MacDonald, M.; Cashman, J. R.; Potter, P. M.; Cerasoli, D. M.; Redinbo, M. R. Human Carboxylesterase 1 Stereoselectively Binds the Nerve Agent Cyclosarin and Spontaneously Hydrolyzes the Nerve Agent Sarin Mol. Pharmacol. 2010, 77, 508-516 10.1124/mol.109.062356
31. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision C.02, Gaussian Inc.: Wallingford, CT, 2003.
32. Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Kollmann, P. A. Application of Resp Charges to Calculate Conformational Energies, Hydrogen Bond Energies, and Free Energies of Solvation J. Am. Chem. Soc. 1993, 115, 9620-9631 10.1021/ja00074a030
33. Case, D. A.; Cheatham, T. E., 3rd; Darden, T.; Gohlke, H.; Luo, R.; Merz, K. M., Jr.; Onufriev, A.; Simmerling, C.; Wang, B.; Woods, R. J. The Amber Biomolecular Simulation Programs J. Comput. Chem. 2005, 26, 1668-88 10.1002/jcc.20290
34. Hornak, V.; Abel, R.; Okur, A.; Strockbine, B.; Roitberg, A.; Simmerling, C. Comparison of Multiple Amber Force Fields and Development of Improved Protein Backbone Parameters Proteins: Struct., Funct., Genet. 2006, 65, 712-725 10.1002/prot.21123
35. Case, D. A.; Darden, T. A.; T.E. Cheatham, I.; Simmerling, C. L.; Wang, J.; Duke, R. E.; Luo, R.; Walker, R. C.; Zhang, W.; Merz, K. M.; Roberts, B. P.; Wang, B.; Hayik, S.; Roitberg, A.; Seabra, G.; Kolossváry, I.; Wong, K. F.; Paesani, F.; Vanicek, J.; Wu, X.; Brozell, S. R.; Steinbrecher, T.; Gohlke, H.; Cai, Q.; Ye, X.; Wang, J.; Hsieh, M.-J.; Cui, G.; Roe, D. R.; Mathews, D. H.; Seetin, M. G.; Sagui, C.; Babin, V.; Luchko, T.; Gusarov, S.; Kovalenko, A.; Kollman, P. A. Amber 11, University of California: San Francisco, 2010.
36. Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. Automated Docking Using a Lamarckian Genetic Algorithm and An Empirical Binding Free Energy Function J. Comput. Chem. 1998, 19, 1639-1662 10.1002/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B
37. Morris, G. M.; Huey, R.; Lindstrom, W.; Sanner, M. F.; Belew, R. K.; Goodsell, D. S.; Olson, A. J. Autodock4 and Autodocktools4: Automated Docking with Selective Receptor Flexibility J. Comput. Chem. 2009, 30, 2785-2791 10.1002/jcc.21256
38. Zhang, X.; Shastry, S.; Bradforth, S. E.; Nadeau, J. L. Nuclear Uptake of Ultrasmall Gold-Doxorubicin Conjugates Imaged by Fluorescence Lifetime Imaging Microscopy (Flim) and Electron Microscopy Nanoscale 2015, 7, 240-251 10.1039/C4NR04707A
39. Sharma, V.; Shivalingaiah, S.; Peng, Y.; Euhus, D.; Gryczynski, Z.; Liu, H. Auto-Fluorescence Lifetime and Light Reflectance Spectroscopy for Breast Cancer Diagnosis: Potential Tools for Intraoperative Margin Detection Biomed. Opt. Express 2012, 3, 1825-1840 10.1364/BOE.3.001825
40. Duncan, R.; Richardson, S. C. W. Endocytosis and Intracellular Trafficking as Gateways for Nanomedicine Delivery: Opportunities and Challenges Mol. Pharmaceutics 2012, 9, 2380-2402 10.1021/mp300293n
41. Xu, G.; Zhang, W.; Ma, M. K. Human Carboxylesterase 2 Is Commonly Expressed in Tumor Tissue and Is Correlated with Activation of Irinotecan Clin. Cancer Res. 2002, 8, 2605-2611
42. Richter, F.; Blomberg, R.; Khare, S. D.; Kiss, G.; Kuzin, A. P.; Smith, A. J. T.; Gallaher, J.; Pianowski, Z.; Helgeson, R. C.; Grjasnow, A.; Xiao, R.; Seetharaman, J.; Su, M.; Vorobiev, S.; Lew, S.; Forouhar, F.; Kornhaber, G. J.; Hunt, J. F.; Montelione, G. T.; Tong, L.; Houk, K. N.; Hilvert, D.; Baker, D. Computational Design of Catalytic Dyads and Oxyanion Holes for Ester Hydrolysis J. Am. Chem. Soc. 2012, 134, 16197-16206 10.1021/ja3037367