Partitioning of poly(amidoamine) dendrimers between n-octanol and water.
Dendritic nanomaterials are emerging as key building blocks for a variety of nanoscale materials and technologies. Poly(amidoamine) (PAMAM) dendrimers were the first class of dendritic nanomaterials to be commercialized. Despite numerous investigations, the environmental fate, transport, and toxicity of PAMAM dendrimers is still not well understood. As a first step toward the characterization of the environmental behavior of dendrimers in aquatic systems, we measured the octanol-water partition coefficients (logK(ow)) of a homologous series of PAMAM dendrimers as a function of dendrimer generation (size), terminal group and core chemistry. We find that the logK(ow) of PAMAM dendrimers depend primarily on their size and terminal group chemistry. For G1-G5 PAMAM dendrimers with terminal NH2 groups, the negative values of their logK(ow) indicate that they prefer to remain in the water phase. Conversely, the formation of stable emulsions at the octanol-water (O/ W) interface in the presence of G6-NH2 and G8-NH2 PAMAM dendrimers suggest they prefer to partition at the O/W interface. In all cases, published studies of the cytotoxicity of Gx-NH2 PAMAM dendrimers show they strongly interact with the lipid bilayers of cells. These results suggest that the logK(ow) of a PAMAM dendrimer may not be a good predictor of its affinity with natural organic media such as the lipid bilayers of cell membranes.
Giri
Jyotsnendu
J
Materials and Process Simulation Center, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA, USA.
Diallo
Mamadou S
MS
Goddard
William A
WA
Dalleska
Nathan F
NF
Fang
Xiangdong
X
Tang
Yongchun
Y
D020003:1-Octanol / Q000737:chemistry*; D002462:Cell Membrane / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D050091:Dendrimers / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D008051:Lipid Bilayers / Q000737:chemistry; D018625:Microscopy, Atomic Force; D008956:Models, Chemical; D008968:Molecular Conformation; D036103:Nanotechnology / Q000379:methods*; D011073:Polyamines / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
D050091:Dendrimers; D008051:Lipid Bilayers; C104700:PAMAM Starburst; D011073:Polyamines; D014867:Water; D020003:1-Octanol