Stability and biocompatibility of a library of polyester dendrimers in comparison to polyamidoamine dendrimers

Biomaterials

Volumn 33, Issue 7, 2012, Pages 1970-1981

  Feliu, Neus ^a   Walter, Marie V ^b   Montañez, Maria I ^b   Kunzmann, Andrea ^a   Hult, Anders ^b   Nyström, Andreas ^a   Malkoch, Michael ^b   Fadeel, Bengt ^a  

^a KAROLINSKA INSTITUTE   (Sweden)

^b ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

Biocompatibility; Cytokine secretion; Degradation; Dendrimer; Macrophage

Indexed keywords

2 ,2-BIS(METHYLOL)PROPIONIC ACID; ACIDIC PH; ALIPHATIC POLYESTER; BIOMEDICAL APPLICATIONS; CELL LINES; CELL VIABILITY; CERVICAL CANCERS; CHEMICAL SURFACES; CYTOKINE SECRETIONS; DENDRONS; DOSE-DEPENDENT; END GROUPS; HUMAN CELL LINES; HUMAN MONOCYTE-DERIVED MACROPHAGES; HYDROXYL END GROUP; IN-VITRO; LEUKEMIA CELLS; MACROPHAGE-LIKE CELLS; MATERIAL STABILITY; POLYAMIDOAMINE DENDRIMERS; POLYESTER DENDRIMERS; PRIMARY CELLS; STRUCTURAL FRAGMENTS; WELL-DEFINED STRUCTURES;

BIOCOMPATIBILITY; CELL CULTURE; CYTOTOXICITY; DEGRADATION; DENDRIMERS; DISEASES; ESTERS; FATTY ACIDS; MACROPHAGES; MEDICAL APPLICATIONS;

FUNCTIONAL POLYMERS;

DENDRIMER; GRANULOCYTE MACROPHAGE COLONY STIMULATING FACTOR; INTERLEUKIN 10; INTERLEUKIN 6; MACROPHAGE INFLAMMATORY PROTEIN 1BETA; POLYAMIDOAMINE; POLYESTER; TUMOR NECROSIS FACTOR ALPHA; ZINC OXIDE;

ARTICLE; BIOCOMPATIBILITY; CELL DIFFERENTIATION; CELL VIABILITY; COMPARATIVE STUDY; CONTROLLED STUDY; CYTOKINE RELEASE; CYTOTOXICITY; FEMALE; HELA CELL; HUMAN; HUMAN CELL; IN VITRO STUDY; LEUKEMIA CELL; MACROPHAGE; MOLECULAR LIBRARY; MOLECULAR STABILITY; MONOCYTE; PH MEASUREMENT; POLYMER PRODUCTION; PRIORITY JOURNAL; TEMPERATURE DEPENDENCE;

BIOCOMPATIBLE MATERIALS; CATIONS; CELL LINE; CYTOKINES; DENDRIMERS; HELA CELLS; HUMANS; HYDROGEN-ION CONCENTRATION; MACROPHAGES; MATERIALS TESTING; MOLECULAR STRUCTURE; POLYESTERS; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; TEMPERATURE;

EID: 84855729574     PISSN: 01429612     EISSN: 18785905     Source Type: Journal    
DOI: 10.1016/j.biomaterials.2011.11.054     Document Type: Article

References (50)

1. Padilla De Jesús O.L., Ihre H.R., Gagne L., Fréchet J.M.J., Szoka F.C. Polyester dendritic systems for drug delivery applications: invitro and invivo evaluation. Bioconjug Chem 2002, 13:453-461.
2. Lee C.C., MacKay J.A., Frechet J.M.J., Szoka F.C. Designing dendrimers for biological applications. Nat Biotech 2005, 23:1517-1526.
3. Carlmark A., Hawker C., Hult A., Malkoch M. New methodologies in the construction of dendritic materials. Chem Soc Rev 2009, 38:352-362.
4. Ihre H.R., Padilla De Jesús O.L., Szoka F.C., Fréchet J.M.J. Polyester dendritic systems for drug delivery applications: design, synthesis, and characterization. Bioconjug Chem 2002, 13:443-452.
5. Gajbhiye V., Jain N.K. The treatment of glioblastoma xenografts by surfactant conjugated dendritic nanoconjugates. Biomaterials 2011, 32:6213-6225.
6. Wang Y., Guo R., Cao X., Shen M., Shi X. Encapsulation of 2-methoxyestradiol within multifunctional poly(amidoamine) dendrimers for targeted cancer therapy. Biomaterials 2011, 32:3322-3329.
7. Luo K., Liu G., She W., Wang Q., Wang G., He B., et al. Gadolinium-labeled peptide dendrimers with controlled structures as potential magnetic resonance imaging contrast agents. Biomaterials 2011, 32:7951-7960.
8. Wijagkanalan W., Kawakami S., Hashida M. Designing dendrimers for drug delivery and imaging: pharmacokinetic considerations. Pharmaceut Res 2011, 28:1500-1519.
9. Mintzer M.A., Grinstaff M.W. Biomedical applications of dendrimers: a tutorial. Chem Soc Rev 2011, 40:173-190.
10. 1H NMR self-diffusion studies of dendritic aliphatic polyesters based on 2,2-bis(hydroxymethyl)propionic acid and 1,1,1-Tris(hydroxyphenyl)ethane. JAm Chem Soc 1996, 118:6388-6395.
11. Almutairi A., Akers W.J., Berezin M.Y., Achilefu S., Fréchet J.M. Monitoring the biodegradation of dendritic near-infrared nanoprobes by invivo fluorescence imaging. Mol Pharm 2008, 5:1103-1110.
12. Almutairi A., Rossin R., Shokeen M., Hagooly A., Ananth A., Capoccia B., et al. Biodegradable dendritic positron-emitting nanoprobes for the noninvasive imaging of angiogenesis. Proc Natl Acad Sci U S A 2009, 106:685-690.
13. Lee C.C., Gillies E.R., Fox M.E., Guillaudeu S.J., Fréchet J.M.J., Dy E.E., et al. Asingle dose of doxorubicin-functionalized bow-tie dendrimer cures mice bearing C-26 colon carcinomas. Proc Natl Acad Sci U S A 2006, 103:16649-16654.
14. Shen Y., Ma X., Zhang B., Zhou Z., Sun Q., Jin E., et al. Degradable dual pH- and temperature-responsive photoluminescent dendrimers. Chemistry 2011, 17:5319-5326.
15. Mukherjee S.P., Lyng F.M., Garcia A., Davoren M., Byrne H.J. Mechanistic studies of invitro cytotoxicity of poly(amidoamine) dendrimers in mammalian cells. Toxicol Appl Pharmacol 2010, 248:259-268.
16. Mukherjee S.P., Davoren M., Byrne H.J. Invitro mammalian cytotoxicological study of PAMAM dendrimers - towards quantitative structure activity relationships. Toxicol Vitro 2010, 24:169-177.
17. Jevprasesphant R., Penny J., Jalal R., Attwood D., McKeown N.B., D'Emanuele A. The influence of surface modification on the cytotoxicity of PAMAM dendrimers. Int J Pharmaceut 2003, 252:263-266.
18. 125I-labelled polyamidoamine dendrimers invivo. JControl Rel 2000, 65:133-148.
19. Duncan R., Izzo L. Dendrimer biocompatibility and toxicity. Adv Drug Deliv Rev 2005, 57:2215-2237.
20. Nyitrai G, Kékesi O, Pál I, Keglevich P, Csíki Z, Fügedi P, et al. Assessing toxicity of polyamidoamine dendrimers by neuronal signaling functions. Nanotoxicology. doi:10.3109/17435390.2011.591511. doi:10.3109/17435390.2011.591511.
21. Shah N., Steptoe R.J., Parekh H.S. Low-generation asymmetric dendrimers exhibit minimal toxicity and effectively complex DNA. JPept Sci 2011, 17:470-478.
22. Parrott M.C., Benhabbour S.R., Saab C., Lemon J.A., Parker S., Valliant J.F., et al. Synthesis, radiolabeling, and bio-imaging of high-generation polyester dendrimers. JAm Chem Soc 2009, 131:2906-2916.
23. Dobrovolskaia M.A., McNeil S.E. Immunological properties of engineered nanomaterials. Nat Nanotech 2007, 2:469-478.
24. Fadeel B., Garcia-Bennett A.E. Better safe than sorry: understanding the toxicological properties of inorganic nanoparticles manufactured for biomedical applications. Adv Drug Deliv Rev 2010, 62:362-374.
25. Witasp E., Kupferschmidt N., Bengtsson L., Hultenby K., Smedman C., Paulie S., et al. Efficient internalization of mesoporous silica particles of different sizes by primary human macrophages without impairment of macrophage clearance of apoptotic or antibody-opsonized target cells. Toxicol Appl Pharmacol 2009, 239:306-319.
26. Cory A.H., Owen T.C., Barltrop J.A., Cory J.G. Use of an aqueous soluble tetrazolium/formazan assay for cell growth assays in culture. Cancer Commun 1991, 3:207-212.
27. Cheng Y., Zhao L., Li Y., Xu T. Design of biocompatible dendrimers for cancer diagnosis and therapy: current status and future perspectives. Chem Soc Rev 2011, 40:2673-2703.
28. Reul R., Renette T., Bege N., Kissel T. Nanoparticles for paclitaxel delivery: a comparative study of different types of dendritic polyesters and their degradation behavior. Int J Pharmaceut 2011, 407:190-196.
29. Demaurex N. pH Homeostasis of cellular organelles. News Physiol Sci 2002, 17:1-5.
30. Seib F.P., Jones A.T., Duncan R. Comparison of the endocytic properties of linear and branched PEIs, and cationic PAMAM dendrimers in B16f10 melanoma cells. JControl Rel 2007, 117:291-300.
31. Lee I., Athey B.D., Wetzel A.W., Meixner W., Baker J.R. Structural molecular dynamics studies on polyamidoamine dendrimers for a therapeutic application: effects of pH and generation. Macromolecules 2002, 35:4510-4520.
32. Perumal O.P., Inapagolla R., Kannan S., Kannan R.M. The effect of surface functionality on cellular trafficking of dendrimers. Biomaterials 2008, 29:3469-3476.
33. Albertazzi L., Serresi M., Albanese A., Beltram F. Dendrimer internalization and intracellular trafficking in living cells. Mol Pharmaceut 2010, 7:680-688.
34. Vallhov H., Qin J., Johansson S.M., Ahlborg N., Muhammed M.A., Scheynius A., et al. The importance of an endotoxin-free environment during the production of nanoparticles used in medical applications. Nano Lett 2006, 6:1682-1686.
35. Dobrovolskaia M.A., Neun B.W., Clogston J.D., Ding H., Ljubimova J., McNeil S.E. Ambiguities in applying traditional Limulus Amebocyte Lysate tests to quantify endotoxin in nanoparticle formulations. Nanomedicine 2010, 5:555-562.
36. Lesniak A., Campbell A., Monopoli M.P., Lynch I., Salvati A., Dawson K.A. Serum heat inactivation affects protein corona composition and nanoparticle uptake. Biomaterials 2010, 31:9511-9518.
37. Lundqvist M., Stigler J., Elia G., Lynch I., Cedervall T., Dawson K.A. Nanoparticle size and surface properties determine the protein corona with possible implications for biological impacts. Proc Natl Acad Sci U S A 2008, 105:14265-14270.
38. Leroueil P.R., Hong S., Mecke A., Baker J.R., Orr B.G., Banaszak Holl M.M. Nanoparticle interaction with biological membranes: does nanotechnology present a Janus face?. Acc Chem Res 2007, 40:335-342.
39. Kunzmann A., Andersson B., Thurnherr T., Krug H., Scheynius A., Fadeel B. Toxicology of engineered nanomaterials: focus on biocompatibility, biodistribution and biodegradation. Biochim Biophy Acta 2011, 1810:361-373.
40. Dobrovolskaia M.A., Aggarwal P., Hall J.B., McNeil S.E. Preclinical studies to understand nanoparticle interaction with the immune system and its potential effects on nanoparticle biodistribution. Mol Pharm 2008, 5:487-495.
41. Thakor A.S., Luong R., Paulmurugan R., Lin F.I., Kempen P., Zavaleta C., et al. The fate and toxicity of Raman-active silica-gold nanoparticles in mice. Sci Transl Med 2011, 3:79ra33.
42. Kunzmann A., Andersson B., Vogt C., Feliu N., Ye F., Gabrielsson S., et al. Efficient internalization of silica-coated iron oxide nanoparticles of different sizes by primary human macrophages and dendritic cells. Toxicol Appl Pharmacol 2011, 253:81-93.
43. Wu Z., Zeng X., Zhang Y., Feliu N., Lundberg P., Fadeel B., et al. Linear-dendritic polymeric amphiphiles as carriers of doxorubicin - invitro evaluation of biocompatibility and drug delivery. JPolym Sci A Polym Chem 2011, 10.1002/pola.25008.
44. Diallo M.S., Christie S., Swaminathan P., Balogh L., Shi X., Um W., et al. Dendritic chelating agents. 1. Cu(II) binding to ethylene diamine core poly(amidoamine) dendrimers in aqueous solutions. Langmuir 2004, 20:2640-2651.
45. Choi Y.J., Kang S.J., Kim Y.J., Lim Y., Chung H.W. Comparative studies on the genotoxicity and cytotoxicity of polymeric gene carriers polyethylenimine (PEI) and polyamidoamine (PAMAM) dendrimer in Jurkat T-cells. Drug Chem Toxicol 2010, 33:357-366.
46. Dobrovolskaia M.A., Patri A., Simak J., Hall J., Semberova J., de Paoli Lacerda S., et al. Nanoparticle size and surface charge determine effects of PAMAM dendrimers on human platelets invitro. Mol Pharm 2011, 10.1021/mp200463e.
47. Wang B., Navath R.S., Menjoge A.R., Balakrishnan B., Bellair R., Dai H., et al. Inhibition of bacterial growth and intramniotic infection in a guinea pig model of chorioamnionitis using PAMAM dendrimers. Int J Pharmaceut 2010, 395:298-308.
48. Khandare J., Mohr A., Calderon M., Welker P., Licha K., Haag R. Structure-biocompatibility relationship of dendritic polyglycerol derivatives. Biomaterials 2010, 31:4268-4277.
49. Naha P.C., Davoren M., Lyng F.M., Byrne H.J. Reactive oxygen species (ROS) induced cytokine production and cytotoxicity of PAMAM dendrimers in J774A.1 cells. Toxicol Appl Pharmacol 2010, 246:91-99.
50. Kitchens K.M., Kolhatkar R.B., Swaan P.W., Eddington N.D., Ghandehari H. Transport of pol(amidoamine) dendrimers across Caco-2 cell monolayers: influence of size, charge and fluorescent labeling. Pharm Res 2006, 23:2818-2826.