Synthesis and characterization of polylactide-PAMAM “Janus-type” linear-dendritic hybrids
Abstract
In this report, we introduce a facile and comprehensive synthetic methodology for the preparation of polyester-polyamidoamine (PAMAM) (i.e., polyester: polylactide [PLA] (hydrophobic) and polyamidoamine, PAMAM [hydrophilic]) polymers. A library of PLA-PAMAM linear dendritic block copolymers (LDBCs) in which both l and d, l polylactide were employed in mass ratios of 30:70, 50:50, 70:30, and 90:10 (PLA:PAMAM) were synthesized and analyzed. When placed in aqueous media, the immiscibility of the hydrophilic and hydrophobic segments leads to nanophase-segregation exhibited as the formation of aggregates (e.g., vesicles, worms, and/or micelles). By employing both stereochemical configurations of PLA, the differentiation in mass ratios of PLA-PAMAM aided in elucidating the structure–property relationships of the LDBC system and provided a means toward the control of nanoparticle morphology. Transmission electron microscopy and dynamic light scattering afford the size and shape of the nanoparticles with diameters ranging from 10.6 for low mass ratios to 122.4 nm for high mass ratios of PLA-PAMAM and positive zeta-potential values between +24 mV and +48.2 mV. Moreover, small-angle X-ray scattering (SAXS) studies were employed to obtain more detailed information on the morphological assemblies constructed via direct dissolution. Such insights provide a pathway toward nanomaterials with unique morphologies and tunable properties deemed relevantmore »
- Authors:
-
- Univ. of Mississippi, Oxford, MS (United States)
- Louisiana State Univ., Baton Rouge, LA (United States)
- Tulane Univ., New Orleans, LA (United States)
- Argonne National Lab. (ANL), Lemont, IL (United States)
- Publication Date:
- Research Org.:
- Argonne National Lab. (ANL), Argonne, IL (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES); Experimental Program to Stimulate Competitive Research (EPSCoR); Northwestern Univ.; Materials Research Science and Engineering Center (NU-MRSEC); National Science Foundation (NSF)
- OSTI Identifier:
- 1559534
- Alternate Identifier(s):
- OSTI ID: 1514742
- Grant/Contract Number:
- AC02-06CH11357; SC0012432
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Journal of Polymer Science. Part A, Polymer Chemistry
- Additional Journal Information:
- Journal Volume: 57; Journal Issue: 13; Journal ID: ISSN 0887-624X
- Publisher:
- Wiley
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; amphiphiles; block copolymers; drug delivery systems; nanoparticles; self‐assembly
Citation Formats
Chandrasiri, Indika, Abebe, Daniel G., Gupta, Sudipta, Williams, Jon Steven Dal, Rieger, William D., Simms, Briana L., Yaddehige, Mahesh Loku, Noh, YeRim, Payne, Molly E., Fortenberry, Alexander W., Smith, Adam E., Ilavsky, Jan, Grayson, Scott M., Schneider, Gerald J., and Watkins, Davita L. Synthesis and characterization of polylactide-PAMAM “Janus-type” linear-dendritic hybrids. United States: N. p., 2019.
Web. doi:10.1002/pola.29409.
Chandrasiri, Indika, Abebe, Daniel G., Gupta, Sudipta, Williams, Jon Steven Dal, Rieger, William D., Simms, Briana L., Yaddehige, Mahesh Loku, Noh, YeRim, Payne, Molly E., Fortenberry, Alexander W., Smith, Adam E., Ilavsky, Jan, Grayson, Scott M., Schneider, Gerald J., & Watkins, Davita L. Synthesis and characterization of polylactide-PAMAM “Janus-type” linear-dendritic hybrids. United States. https://doi.org/10.1002/pola.29409
Chandrasiri, Indika, Abebe, Daniel G., Gupta, Sudipta, Williams, Jon Steven Dal, Rieger, William D., Simms, Briana L., Yaddehige, Mahesh Loku, Noh, YeRim, Payne, Molly E., Fortenberry, Alexander W., Smith, Adam E., Ilavsky, Jan, Grayson, Scott M., Schneider, Gerald J., and Watkins, Davita L. Mon .
"Synthesis and characterization of polylactide-PAMAM “Janus-type” linear-dendritic hybrids". United States. https://doi.org/10.1002/pola.29409. https://www.osti.gov/servlets/purl/1559534.
@article{osti_1559534,
title = {Synthesis and characterization of polylactide-PAMAM “Janus-type” linear-dendritic hybrids},
author = {Chandrasiri, Indika and Abebe, Daniel G. and Gupta, Sudipta and Williams, Jon Steven Dal and Rieger, William D. and Simms, Briana L. and Yaddehige, Mahesh Loku and Noh, YeRim and Payne, Molly E. and Fortenberry, Alexander W. and Smith, Adam E. and Ilavsky, Jan and Grayson, Scott M. and Schneider, Gerald J. and Watkins, Davita L.},
abstractNote = {In this report, we introduce a facile and comprehensive synthetic methodology for the preparation of polyester-polyamidoamine (PAMAM) (i.e., polyester: polylactide [PLA] (hydrophobic) and polyamidoamine, PAMAM [hydrophilic]) polymers. A library of PLA-PAMAM linear dendritic block copolymers (LDBCs) in which both l and d, l polylactide were employed in mass ratios of 30:70, 50:50, 70:30, and 90:10 (PLA:PAMAM) were synthesized and analyzed. When placed in aqueous media, the immiscibility of the hydrophilic and hydrophobic segments leads to nanophase-segregation exhibited as the formation of aggregates (e.g., vesicles, worms, and/or micelles). By employing both stereochemical configurations of PLA, the differentiation in mass ratios of PLA-PAMAM aided in elucidating the structure–property relationships of the LDBC system and provided a means toward the control of nanoparticle morphology. Transmission electron microscopy and dynamic light scattering afford the size and shape of the nanoparticles with diameters ranging from 10.6 for low mass ratios to 122.4 nm for high mass ratios of PLA-PAMAM and positive zeta-potential values between +24 mV and +48.2 mV. Moreover, small-angle X-ray scattering (SAXS) studies were employed to obtain more detailed information on the morphological assemblies constructed via direct dissolution. Such insights provide a pathway toward nanomaterials with unique morphologies and tunable properties deemed relevant in the development of next generation biomaterials.},
doi = {10.1002/pola.29409},
journal = {Journal of Polymer Science. Part A, Polymer Chemistry},
number = 13,
volume = 57,
place = {United States},
year = {2019},
month = {5}
}
Web of Science
Works referenced in this record:
Colloidal particles for cellular uptake and delivery
journal, January 2009
- Hu, Ling; Mao, Zhengwei; Gao, Changyou
- Journal of Materials Chemistry, Vol. 19, Issue 20
Effects of lithium bromide on the gel-permeation chromatography of polyester-based polyurethanes in dimethylformamide
journal, June 1977
- Hann, Nancy D.
- Journal of Polymer Science: Polymer Chemistry Edition, Vol. 15, Issue 6
DLS and zeta potential – What they are and what they are not?
journal, August 2016
- Bhattacharjee, Sourav
- Journal of Controlled Release, Vol. 235
Block Copolymer Assembly via Kinetic Control
journal, August 2007
- Cui, H.; Chen, Z.; Zhong, S.
- Science, Vol. 317, Issue 5838
Dendrimers and dendritic polymers in drug delivery
journal, January 2005
- Gillies, E.; Frechet, J.
- Drug Discovery Today, Vol. 10, Issue 1
Characterization of Polystyrenes of Extremely High Molecular Weights
journal, May 1980
- Appelt, Bernd; Meyerhoff, Günther
- Macromolecules, Vol. 13, Issue 3
Dendrimers as macroinitiators for anionic ring-opening polymerization. Polymerization of ɛ-caprolactone
journal, May 1994
- Gitsov, Ivan; Ivanova, Pavlina T.; Fréchet, Jean M. J.
- Macromolecular Rapid Communications, Vol. 15, Issue 5
Emerging concepts in dendrimer-based nanomedicine: from design principles to clinical applications
journal, July 2014
- Kannan, R. M.; Nance, E.; Kannan, S.
- Journal of Internal Medicine, Vol. 276, Issue 6
Effects of particle size and surface charge on cellular uptake and biodistribution of polymeric nanoparticles
journal, May 2010
- He, Chunbai; Hu, Yiping; Yin, Lichen
- Biomaterials, Vol. 31, Issue 13
An overview of the recent developments in polylactide (PLA) research
journal, November 2010
- Madhavan Nampoothiri, K.; Nair, Nimisha Rajendran; John, Rojan Pappy
- Bioresource Technology, Vol. 101, Issue 22
A Simple and Universal Gel Permeation Chromatography Technique for Precise Molecular Weight Characterization of Well-Defined Poly(ionic liquid)s
journal, March 2013
- He, Hongkun; Zhong, Mingjiang; Adzima, Brian
- Journal of the American Chemical Society, Vol. 135, Issue 11
Principles of nanoparticle design for overcoming biological barriers to drug delivery
journal, September 2015
- Blanco, Elvin; Shen, Haifa; Ferrari, Mauro
- Nature Biotechnology, Vol. 33, Issue 9
Self-Assembly of Janus Dendrimers into Uniform Dendrimersomes and Other Complex Architectures
journal, May 2010
- Percec, V.; Wilson, D. A.; Leowanawat, P.
- Science, Vol. 328, Issue 5981
Guanidine and Amidine Organocatalysts for Ring-Opening Polymerization of Cyclic Esters
journal, December 2006
- Lohmeijer, Bas G. G.; Pratt, Russell C.; Leibfarth, Frank
- Macromolecules, Vol. 39, Issue 25
Independent effect of polymeric nanoparticle zeta potential/surface charge, on their cytotoxicity and affinity to cells
journal, May 2015
- Shao, Xiao-Ru; Wei, Xue-Qin; Song, Xu
- Cell Proliferation, Vol. 48, Issue 4
Three-Layered Biodegradable Micelles Prepared by Two-Step Self-Assembly of PLA-PEI-PLA and PLA-PEG-PLA Triblock Copolymers as Efficient Gene Delivery System: Three-Layered Biodegradable Micelles …
journal, February 2015
- Abebe, Daniel G.; Kandil, Rima; Kraus, Teresa
- Macromolecular Bioscience, Vol. 15, Issue 5
Amphiphilic block copolymers for drug delivery
journal, July 2003
- Adams, Monica L.; Lavasanifar, Afsaneh; Kwon, Glen S.
- Journal of Pharmaceutical Sciences, Vol. 92, Issue 7
Synthesis and Properties of Star-Shaped Polylactide Attached to Poly(Amidoamine) Dendrimer
journal, May 2003
- Cai, Qing; Zhao, Youliang; Bei, Jianzhong
- Biomacromolecules, Vol. 4, Issue 3
Effect of Chain Length and Unsaturation on Elasticity of Lipid Bilayers
journal, July 2000
- Rawicz, W.; Olbrich, K. C.; McIntosh, T.
- Biophysical Journal, Vol. 79, Issue 1
Polymeric micelle stability
journal, February 2012
- Owen, Shawn C.; Chan, Dianna P. Y.; Shoichet, Molly S.
- Nano Today, Vol. 7, Issue 1
Self-Sorting and Coassembly of Fluorinated, Hydrogenated, and Hybrid Janus Dendrimers into Dendrimersomes
journal, September 2016
- Xiao, Qi; Rubien, Jack D.; Wang, Zhichun
- Journal of the American Chemical Society, Vol. 138, Issue 38
Biocompatible and biodegradable polymersomes as delivery vehicles in biomedical applications
journal, January 2012
- Liu, Gong-Yan; Chen, Chao-Jian; Ji, Jian
- Soft Matter, Vol. 8, Issue 34
Thermo-responsive block copolymers with multiple phase transition temperatures in aqueous solutions
journal, March 2015
- Strandman, S.; Zhu, X. X.
- Progress in Polymer Science, Vol. 42
Simulating Induced Interdigitation in Membranes
journal, September 2004
- Kranenburg, Marieke; Vlaar, Martin; Smit, Berend
- Biophysical Journal, Vol. 87, Issue 3
Tweaking dendrimers and dendritic nanoparticles for controlled nano-bio interactions: potential nanocarriers for improved cancer targeting
journal, September 2015
- Bugno, Jason; Hsu, Hao-jui; Hong, Seungpyo
- Journal of Drug Targeting, Vol. 23, Issue 7-8
Gel permeation chromatography of poly(styrene-co-divinylbenzene) microgels. Effect of electrolyte concentration in the solvent system dimethylformamide plus lithium bromide
journal, January 1980
- Booth, C.; Forget, J. -L.; Georgii, I.
- European Polymer Journal, Vol. 16, Issue 3
Organocatalytic Ring-Opening Polymerization
journal, December 2007
- Kamber, Nahrain E.; Jeong, Wonhee; Waymouth, Robert M.
- Chemical Reviews, Vol. 107, Issue 12
Polymeric Systems for Controlled Drug Release
journal, November 1999
- Uhrich, Kathryn E.; Cannizzaro, Scott M.; Langer, Robert S.
- Chemical Reviews, Vol. 99, Issue 11
Equilibrium Chain Exchange Kinetics of Diblock Copolymer Micelles: Tuning and Logarithmic Relaxation
journal, June 2006
- Lund, Reidar; Willner, Lutz; Richter, Dieter
- Macromolecules, Vol. 39, Issue 13
Synthesis and Characterization of Linear-Dendron-like Poly(ε-caprolactone)- b -poly(ethylene oxide) Copolymers via the Combination of Ring-Opening Polymerization and Click Chemistry
journal, September 2008
- Hua, Chong; Peng, Song-Ming; Dong, Chang-Ming
- Macromolecules, Vol. 41, Issue 18
Structural and thermodynamic aspects of the cylinder-to-sphere transition in amphiphilic diblock copolymer micelles
journal, January 2011
- Lund, Reidar; Pipich, Vitaliy; Willner, Lutz
- Soft Matter, Vol. 7, Issue 4
Mechanism for Rapid Self-Assembly of Block Copolymer Nanoparticles
journal, September 2003
- Johnson, Brian K.; Prud’homme, Robert K.
- Physical Review Letters, Vol. 91, Issue 11
Organic Catalysis for Ring-Opening Polymerization
journal, November 2012
- Dove, Andrew P.
- ACS Macro Letters, Vol. 1, Issue 12
Particle size distribution from small-angle X-ray scattering data
journal, August 1985
- Walter, G.; Kranold, R.; Gerber, T.
- Journal of Applied Crystallography, Vol. 18, Issue 4
Synthesis and characterization of multi-functional linear-dendritic block copolymer for intracellular delivery of antitumor drugs
journal, August 2013
- Qiao, Hongzhi; Li, Juan; Wang, Yang
- International Journal of Pharmaceutics, Vol. 452, Issue 1-2
Synthesis and properties of novel linear-dendritic block copolymers. Reactivity of dendritic macromolecules toward linear polymers
journal, October 1993
- Gitsov, Ivan; Wooley, Karen L.; Hawker, Craig J.
- Macromolecules, Vol. 26, Issue 21
New Paradigms for Organic Catalysts: The First Organocatalytic Living Polymerization
journal, July 2001
- Nederberg, Fredrik; Connor, Eric F.; Möller, Michael
- Angewandte Chemie International Edition, Vol. 40, Issue 14
Dynamic phase diagram of soft nanocolloids
journal, January 2015
- Gupta, Sudipta; Camargo, Manuel; Stellbrink, Jörg
- Nanoscale, Vol. 7, Issue 33
“Janus” dendrimers: syntheses and properties
journal, January 2012
- Caminade, Anne-Marie; Laurent, Régis; Delavaux-Nicot, Béatrice
- New J. Chem., Vol. 36, Issue 2
Polymersome Formation from AB 2 Type 3-Miktoarm Star Copolymers
journal, October 2009
- Yin, Haiqing; Kang, Sun-Woong; Bae, You Han
- Macromolecules, Vol. 42, Issue 19
Dendrimers for drug delivery
journal, January 2014
- Caminade, Anne-Marie; Turrin, Cédric-Olivier
- J. Mater. Chem. B, Vol. 2, Issue 26
Self-assembly of amphiphilic Janus dendrimers into uniform onion-like dendrimersomes with predictable size and number of bilayers
journal, June 2014
- Zhang, S.; Sun, H. -J.; Hughes, A. D.
- Proceedings of the National Academy of Sciences, Vol. 111, Issue 25
Initiators for the stereoselective ring-opening polymerization of meso-lactide
journal, January 2011
- Buffet, Jean-Charles; Okuda, Jun
- Polymer Chemistry, Vol. 2, Issue 12
Nika : software for two-dimensional data reduction
journal, March 2012
- Ilavsky, Jan
- Journal of Applied Crystallography, Vol. 45, Issue 2
A Small-Angle Neutron and X-ray Contrast Variation Scattering Study of the Structure of Block Copolymer Micelles: Corona Shape and Excluded Volume Interactions
journal, January 2003
- Pedersen, Jan Skov; Svaneborg, Carsten; Almdal, Kristoffer
- Macromolecules, Vol. 36, Issue 2
PAMAM Dendrimers: Destined for Success or Doomed to Fail? Plain and Modified PAMAM Dendrimers in the Context of Biomedical Applications
journal, January 2015
- Labieniec-Watala, Magdalena; Watala, Cezary
- Journal of Pharmaceutical Sciences, Vol. 104, Issue 1
Impact of PEGylated Nanoparticles on Tumor Targeted Drug Delivery
journal, December 2018
- Mozar, Fitya Syarifa; Chowdhury, Ezharul Hoque
- Current Pharmaceutical Design, Vol. 24, Issue 28
Linear–dendritic block copolymers: The state of the art and exciting perspectives
journal, January 2011
- Wurm, Frederik; Frey, Holger
- Progress in Polymer Science, Vol. 36, Issue 1
Syntheses of biodegradable (multi) block copolymers, star-shaped polyesters and networks via ring-expansion polymerization
journal, October 2002
- Kricheldorf, Hans R.
- Polymers for Advanced Technologies, Vol. 13, Issue 10-12
Predicting the Size and Properties of Dendrimersomes from the Lamellar Structure of Their Amphiphilic Janus Dendrimers
journal, December 2011
- Peterca, Mihai; Percec, Virgil; Leowanawat, Pawaret
- Journal of the American Chemical Society, Vol. 133, Issue 50
Poly(amidoamine) (PAMAM) dendrimers: from biomimicry to drug delivery and biomedical applications
journal, April 2001
- Esfand, Roseita; Tomalia, Donald A.
- Drug Discovery Today, Vol. 6, Issue 8
Dendrimers and supramolecular chemistry
journal, April 2002
- Frechet, J. M. J.
- Proceedings of the National Academy of Sciences, Vol. 99, Issue 8
PEGylated PAMAM dendrimers: Enhancing efficacy and mitigating toxicity for effective anticancer drug and gene delivery
journal, October 2016
- Luong, Duy; Kesharwani, Prashant; Deshmukh, Rahul
- Acta Biomaterialia, Vol. 43
Supramolecular Architectures of Dendritic Amphiphiles in Water
journal, December 2015
- Thota, Bala N. S.; Urner, Leonhard H.; Haag, Rainer
- Chemical Reviews, Vol. 116, Issue 4
Nanoprecipitation process: From encapsulation to drug delivery
journal, October 2017
- Martínez Rivas, Claudia Janeth; Tarhini, Mohamad; Badri, Waisudin
- International Journal of Pharmaceutics, Vol. 532, Issue 1
Soft Interaction in Liposome Nanocarriers for Therapeutic Drug Delivery
journal, June 2016
- Lombardo, Domenico; Calandra, Pietro; Barreca, Davide
- Nanomaterials, Vol. 6, Issue 7
Review of Matrix-Assisted Laser Desorption Ionization-Imaging Mass Spectrometry for Lipid Biochemical Histopathology
journal, June 2015
- Yalcin, Emine B.; de la Monte, Suzanne M.
- Journal of Histochemistry & Cytochemistry, Vol. 63, Issue 10
The effect of particle design on cellular internalization pathways
journal, August 2008
- Gratton, S. E. A.; Ropp, P. A.; Pohlhaus, P. D.
- Proceedings of the National Academy of Sciences, Vol. 105, Issue 33, p. 11613-11618
The role of surface charge in cellular uptake and cytotoxicity of medical nanoparticles
journal, November 2012
- Fröhlich, Eleonore
- International Journal of Nanomedicine
Synthesis and Unimolecular Micelles of Amphiphilic Dendrimer-like Star Polymer with Various Functional Surface Groups
journal, March 2011
- Cao, Weiqiang; Zhu, Lei
- Macromolecules, Vol. 44, Issue 6
The effect of surface charge on the uptake and biological function of mesoporous silica nanoparticles in 3T3-L1 cells and human mesenchymal stem cells
journal, July 2007
- Chung, Tsai-Hua; Wu, Si-Han; Yao, Ming
- Biomaterials, Vol. 28, Issue 19
Effects of Vesicle Size and Shape on Static and Dynamic Light Scattering Measurements
journal, September 2003
- Pencer, Jeremy; Hallett, F. Ross
- Langmuir, Vol. 19, Issue 18
Disulfide Cross-Linked Phosphorylcholine Micelles for Triggered Release of Camptothecin
journal, June 2013
- McRae Page, Samantha; Martorella, Molly; Parelkar, Sangram
- Molecular Pharmaceutics, Vol. 10, Issue 7
Polylactide-Based Amphiphilic Block Copolymers: Crystallization-Induced Self-Assembly and Stereocomplexation
journal, October 2018
- Noack, Sebastian; Schanzenbach, Dirk; Koetz, Joachim
- Macromolecular Rapid Communications, Vol. 40, Issue 1
Biomedical applications of biodegradable polymers
journal, May 2011
- Ulery, Bret D.; Nair, Lakshmi S.; Laurencin, Cato T.
- Journal of Polymer Science Part B: Polymer Physics, Vol. 49, Issue 12
Effects of Size and Surface Charge of Polymeric Nanoparticles on <i>in Vitro</i> and <i>in Vivo</i> Applications
journal, January 2016
- Sadat, Sams M. A.; Jahan, Sheikh Tasnim; Haddadi, Azita
- Journal of Biomaterials and Nanobiotechnology, Vol. 07, Issue 02
Cooperation of Amphiphilicity and Crystallization for Regulating the Self-Assembly of Poly(ethylene glycol)- block -poly(lactic acid) Copolymers
journal, August 2016
- Wang, Zhen; Cao, Yuanyuan; Song, Jiaqi
- Langmuir, Vol. 32, Issue 37
Analytical strategy for the molecular weight determination of random copolymers of poly(methyl methacrylate) and poly(methacrylic acid)
journal, June 2010
- Giordanengo, Rémi; Viel, Stéphane; Hidalgo, Manuel
- Journal of the American Society for Mass Spectrometry, Vol. 21, Issue 6
Concerning the ring-opening polymerization of lactide and cyclic esters by coordination metal catalysts
journal, June 2010
- Chisholm, Malcolm H.
- Pure and Applied Chemistry, Vol. 82, Issue 8
New Paradigms for Organic Catalysts: The First Organocatalytic Living Polymerization
journal, July 2001
- Nederberg, Fredrik; Connor, Eric F.; Möller, Michael
- Angewandte Chemie, Vol. 113, Issue 14
Synthesis and Characterization of Linear-Dendron-like Poly(ε-caprolactone)- b -poly(ethylene oxide) Copolymers via the Combination of Ring-Opening Polymerization and Click Chemistry
journal, March 2009
- Hua, Chong; Peng, Song-Ming; Dong, Chang-Ming
- Macromolecules, Vol. 42, Issue 7
Mass Spectroscopy
journal, October 1958
- Duckworth, Henry E.; Seth, Kamal K.
- Physics Today, Vol. 11, Issue 10