Structure-function relationship of PAMAM dendrimers as robust oil dispersants

Environmental Science and Technology

Volumn 48, Issue 21, 2014, Pages 12868-12875

  Geitner, Nicholas K ^a   Wang, Bo ^a   Andorfer, Rachel E ^a   Ladner, David A ^b   Ke, Pu Chun ^a   Ding, Feng ^a  

^a CLEMSON UNIVERSITY   (United States)

^b Clemson University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; AROMATIC HYDROCARBONS; BIOCOMPATIBILITY; DENDRIMERS; HYDROGEN BONDS; MEDICAL APPLICATIONS; OIL SHALE; PROTONATION; SURFACE CHEMISTRY;

BIOMEDICAL APPLICATIONS; COMPUTATIONAL APPROACH; ENCAPSULATION CAPACITY; INTRA-MOLECULAR HYDROGEN BONDS; NEGATIVELY CHARGED; POLYCYCLIC AROMATICS; PROTONATION STATE; STRUCTURE-FUNCTION RELATIONSHIP;

FUNCTIONAL POLYMERS;

ANION; DENDRIMER; HYDROCARBON; HYDROGEN; OIL DISPERSANT; POLYAMIDOAMINE; POLYCYCLIC AROMATIC COMPOUND; TERTIARY AMINE; OIL; PAMAM STARBURST; PHENANTHRENE; PHENANTHRENE DERIVATIVE; SURFACTANT;

COMPUTER SIMULATION; ENCAPSULATION; EXPERIMENTAL STUDY; HYDROCARBON; TOXICITY;

ARTICLE; CHEMICAL STRUCTURE; COMPUTATIONAL FLUID DYNAMICS; CONTROLLED STUDY; DISPERSION; ENCAPSULATION; ENVIRONMENT; HYBRID; HYDROGEN BOND; HYDROPHOBICITY; IONIC STRENGTH; MOLECULAR DYNAMICS; PHYSICAL CHEMISTRY; PROTON TRANSPORT; STATIC ELECTRICITY; SURFACE CHARGE; ZETA POTENTIAL; CHEMISTRY; HYDRODYNAMICS; KINETICS; SPECTROFLUOROMETRY; STRUCTURE ACTIVITY RELATION; TEMPERATURE;

DENDRIMERS; HYDROCARBONS; HYDRODYNAMICS; KINETICS; OILS; PHENANTHRENES; SPECTROMETRY, FLUORESCENCE; STATIC ELECTRICITY; STRUCTURE-ACTIVITY RELATIONSHIP; SURFACE-ACTIVE AGENTS; TEMPERATURE;

EID: 84908582605     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es5038194     Document Type: Article

References (44)

1. Tomalia, D. A.; Fréchet, J. M. J. Discovery of Dendrimers and Dendritic Polymers: A Brief Historical Perspective J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 2719-2728
2. Bhattacharya, P.; Conroy, N.; Rao, A. M.; Powell, B. A.; Ladner, D. A.; Ke, P. C. PAMAM Dendrimer for Mitigating Humic Foulant RSC Adv. 2012, 2, 7997
3. Diallo, M. S.; Balogh, L.; Shafagati, A.; Johnson, J. H.; Goddard, W. A., III; Tomalia, D. A. Poly (amidoamine) Dendrimers: A New Class of High Capacity Chelating Agents for Cu (II) Ions Environ. Sci. Technol. 1999, 33, 820-824
4. Xu, Y.; Zhao, D. Removal of Copper from Contaminated Soil by Use of Poly(amidoamine) Dendrimers Environ. Sci. Technol. 2005, 39, 2369-2375
5. Bradshaw, D. S.; Andrews, D. L. Mechanisms of Light Energy Harvesting in Dendrimers and Hyperbranched Polymers Polymers (Basel) 2011, 3, 2053-2077
6. Nantalaksakul, A.; Reddy, D. R.; Bardeen, C. J.; Thayumanavan, S. Light Harvesting Dendrimers Photosynth. Res. 2006, 87, 133-150
7. Kurtoglu, Y. E.; Mishra, M. K.; Kannan, S.; Kannan, R. M. Drug Release Characteristics of PAMAM Dendrimer-Drug Conjugates with Different Linkers Int. J. Pharm. 2010, 384, 189-194
8. Chandrasekar, D.; Sistla, R.; Ahmad, F. J.; Khar, R. K.; Diwan, P. V. The Development of Folate-PAMAM Dendrimer Conjugates for Targeted Delivery of Anti-Arthritic Drugs and Their Pharmacokinetics and Biodistribution in Arthritic Rats Biomaterials 2007, 28, 504-512
9. Watkins, D. M.; Sayed-sweet, Y.; Klimash, J. W.; Turro, N. J.; Tomalia, D. A. Dendrimers with Hydrophobic Cores and the Formation of Supramolecular Dendrimer-Surfactant Assemblies Langmuir 1997, 13, 3136-3141
10. Jansen, J. F. G. A.; Meijer, E. W.; de Brabander-van den Berg, E. M. M. The Dendritic Box: Shape-Selective Liberation of Encapsulated Guests J. Am. Chem. Soc. 1995, 117, 4417-4418
11. Geitner, N. K.; Bhattacharya, P.; Steele, M.; Chen, R.; Ladner, D. A.; Ke, P. C. Understanding Dendritic Polymer-hydrocarbon Interactions for Oil Dispersion RSC Adv. 2012, 2, 9371
12. Board, C. on E. of O. D. M. Using Oil Spill Dispersants on the Sea; National Academy Press: Washington, DC, 1989; p 352.
13. Anderson, S. E.; Franko, J.; Lukomska, E.; Meade, B. J. Potential Immunotoxicological Health Effects Following Exposure to COREXIT 9500A during Cleanup of the Deepwater Horizon Oil Spill Science (80-.) 2011, 74, 1419-1430
14. Goodbody-Gringley, G.; Wetzel, D. L.; Gillon, D.; Pulster, E.; Miller, A.; Ritchie, K. B. Toxicity of Deepwater Horizon Source Oil and the Chemical Dispersant, Corexit® 9500, to Coral Larvae PLoS One 2013, 8, e45574
15. Hemmer, M. J.; Barron, M. G.; Greene, R. M. Comparative Toxicity of Eight Oil Dispersants, Louisiana Sweet Crude Oil (LSC), and Chemically Dispersed LSC to Two Aquatic Test Species Environ. Toxicol. Chem. 2011, 30, 2244-2252
16. Geitner, N. K.; Powell, R. R.; Bruce, T.; Ladner, D. A.; Ke, P. C. Effects of Dendrimer Oil Dispersants on Dictyostelium Discoideum RSC Adv. 2013, 3, 25930
17. Petit, A.-N.; Debenest, T.; Eullaffroy, P.; Gagné, F. Effects of a Cationic PAMAM Dendrimer on Photosynthesis and ROS Production of Chlamydomonas Reinhardtii Nanotoxicology 2012, 6, 315-326
18. Cancino, J.; Paino, I. M. M.; Micocci, K. C.; Selistre-de-Araujo, H. S.; Zucolotto, V. In Vitro Nanotoxicity of Single-Walled Carbon Nanotube-Dendrimer Nanocomplexes against Murine Myoblast Cells Toxicol. Lett. 2013, 219, 18-25
19. Lewis, T.; Ganesan, V. Interactions between Grafted Cationic Dendrimers and Anionic Bilayer Membranes J. Phys. Chem. B 2013, 117, 9806-9820
20. Thomas, T. P.; Majoros, I.; Kotlyar, A.; Mullen, D.; Holl, M. M. B.; Baker, J. R. Cationic Poly(amidoamine) Dendrimer Induces Lysosomal Apoptotic Pathway at Therapeutically Relevant Concentrations Biomacromolecules 2009, 10, 3207-3214
21. Jones, C. F.; Campbell, R. A.; Brooks, A. E.; Assemi, S.; Tadjiki, S.; Thiagarajan, G.; Mulcock, C.; Weyrich, A. S.; Brooks, B. D.; Ghandehari, H. Cationic PAMAM Dendrimers Aggressively Initiate Blood Clot Formation ACS Nano 2012, 6, 9900-9910
22. Bhattacharya, P.; Geitner, N. K.; Sarupria, S.; Ke, P. C. Exploiting the Physicochemical Properties of Dendritic Polymers for Environmental and Biological Applications Phys. Chem. Chem. Phys. 2013, 15, 4477-4490
23. Ciolkowski, M.; Petersen, J. F.; Ficker, M.; Janaszewska, A.; Christensen, J. B.; Klajnert, B.; Bryszewska, M. Surface Modification of PAMAM Dendrimer Improves Its Biocompatibility Nanomedicine 2012, 8, 815-817
24. Maiti, P. K.; Li, Y.; Cagin, T.; Goddard, W. A. Structure of Polyamidoamide Dendrimers up to Limiting Generations: A Mesoscale Description J. Chem. Phys. 2009, 130, 144902
25. Wu, B.; Kerkeni, B.; Egami, T.; Do, C.; Liu, Y.; Wang, Y.; Porcar, L.; Hong, K.; Smith, S. C.; Liu, E. L. Structured Water in Polyelectrolyte Dendrimers: Understanding Small Angle Neutron Scattering Results through Atomistic Simulation J. Chem. Phys. 2012, 136, 144901
26. Wu, B.; Liu, Y.; Li, X.; Mamontov, E.; Kolesnikov, A. I.; Diallo, S. O.; Do, C.; Porcar, L.; Hong, K.; Smith, S. C. Charge-Dependent Dynamics of a Polyelectrolyte Dendrimer and Its Correlation with Invasive Water J. Am. Chem. Soc. 2013, 135, 5111-5117
27. Liu, Y.; Porcar, L.; Hong, K.; Shew, C.-Y.; Li, X.; Liu, E.; Butler, P. D.; Herwig, K. W.; Smith, G. S.; Chen, W.-R. Effect of Counterion Valence on the pH Responsiveness of Polyamidoamine Dendrimer Structure J. Chem. Phys. 2010, 132, 124901
28. Maingi, V.; Kumar, M. V. S.; Maiti, P. K. PAMAM Dendrimer-Drug Interactions: Effect of pH on the Binding and Release Pattern J. Phys. Chem. B 2012, 116, 4370-4376
29. Lin, S.-T.; Maiti, P. K.; Goddard, W. A. Dynamics and Thermodynamics of Water in PAMAM Dendrimers at Subnanosecond Time Scales J. Phys. Chem. B 2005, 109, 8663-8672
30. Maiti, P. K.; Bagchi, B. Diffusion of Flexible, Charged, Nanoscopic Molecules in Solution: Size and pH Dependence for PAMAM Dendrimer J. Chem. Phys. 2009, 131, 214901
31. Ding, F.; Tsao, D.; Nie, H.; Dokholyan, N. V. Ab Initio Folding of Proteins with All-Atom Discrete Molecular Dynamics Structure 2008, 16, 1010-1018
32. Ding, F.; Dokholyan, N. V. Emergence of Protein Fold Families through Rational Design PLoS Comput. Biol. 2006, 2, e85
33. Yin, S.; Biedermannova, L.; Vondrasek, J.; Dokholyan, N. V. MedusaScore: An Accurate Force Field-Based Scoring Function for Virtual Drug Screening J. Chem. Inf. Model. 2008, 48, 1656-1662
34. Neria, E.; Fischer, S.; Karplus, M. Simulation of Activation Free Energies in Molecular Systems J. Chem. Phys. 1996, 105, 1902
35. Lazaridis, T.; Karplus, M. Effective Energy Functions for Protein Structure Prediction Curr. Opin. Struct. Biol. 2000, 10, 139-145
36. Andersen, H. C. Molecular Dynamics Simulations at Constant Pressure And/or Temperature J. Chem. Phys. 1980, 72, 2384
37. Antosiewicz, J. M.; Shugar, D. Poisson-Boltzmann Continuum-Solvation Models: Applications to pH-Dependent Properties of Biomolecules Mol. Biosyst. 2011, 7, 2923-2949
38. Porcar, L.; Liu, Y.; Verduzco, R.; Hong, K.; Paul, D.; Magid, L. J.; Smith, G. S.; Chen, W.; Butler, P. D. Structural Investigation of PAMAM Dendrimers in Aqueous Solutions Using Small-Angle Neutron Scattering: Effect of Generation J. Phys. Chem. B 2008, 112, 14772-14778
39. Porcar, L.; Hong, K.; Butler, P. D.; Herwig, K. W.; Smith, G. S.; Liu, Y.; Chen, W. Intramolecular Structural Change of PAMAM Dendrimers in Aqueous Solutions Revealed by Small-Angle Neutron Scattering J. Phys. Chem. B 2010, 114, 1751-1756
40. Liu, Y.; Chen, C.-Y.; Chen, H.-L.; Hong, K.; Shew, C.-Y.; Li, X.; Liu, L.; Melnichenko, Y. B.; Smith, G. S.; Herwig, K. W. Electrostatic Swelling and Conformational Variation Observed in High-Generation Polyelectrolyte Dendrimers J. Phys. Chem. Lett. 2010, 1, 2020-2024
41. Liu, Y.; Bryantsev, V. S.; Diallo, M. S.; Goddard, W. A. PAMAM Dendrimers Undergo pH Responsive Conformational Changes without Swelling J. Am. Chem. Soc. 2009, 131, 2798-2799
42. Lee, H.; Larson, R. G. Molecular Dynamics Simulations of PAMAM Dendrimer-Induced Pore Formation in DPPC Bilayers with a Coarse-Grained Model J. Phys. Chem. B 2006, 110, 18204-18211
43. Yang, L.; da Rocha, S. R. P. PEGylated, NH2-Terminated PAMAM Dendrimers: A Microscopic View from Atomistic Computer Simulations Mol. Pharmaceutics 2014, 11, 1459-1470
44. Niu, S.; Turro, C.; Bossmann, S. H.; Tomalia, D. A.; Turro, N. J. Binding of Ru(phen)32+ to Starburst Dendrimers and Its Quenching by Co(phen)33+: Generation Dependence of the Quenching Rate Constant J. Phys. Chem. 1995, 99, 5512-5517