Homologous, Dendritic Amphiphiles
Journal of Medicinal Chemistry, 2007, Vol. 50, No. 7 1649
the lowest concentration completely inhibiting the growth. The
(17) Cardona, C. M.; McCarley, T. D.; Kaifer, A. E. Synthesis, Electro-
chemistry, and Interactions with â-Cyclodextrin of Dendrimers
Containing a Single Ferrocene Subunit Located “Off-Center”. J. Org.
Chem. 2000, 65, 1857-1864.
18) Cardona, C. M.; Alvarez, J.; Kaifer, A. E.; McCarley, T. D.; Pandey,
S.; Baker, G. A.; Bonzagni, N. J.; Bright, F. V. Dendrimers
Functionalized with a Single Fluorescent Dansyl Group Attached “Off
Center”: Synthesis and Photophysical Studies. J. Am. Chem. Soc.
experiments were run in duplicate for the initial cell densities of
7
3
2 to 3.2 × 10 CFU/mL and in single for the initial cell densities
8
of 500 to 5.0 × 10 CFU/mL.
(
Acknowledgment. We gratefully acknowledge financial
support of the Contraceptive Research and Development (CON-
RAD) Program under a cooperative agreement with the U.S.
Agency for International Development (USAID) under sub-
project MSA-03-356. Views expressed in this paper do not
necessarily reflect the views of CONRAD or USAID. We also
gratefully acknowledge DOE for financial support through the
Center for Advanced Separation Technology (DE-FC26-
2
000, 122, 6139-6144.
(
19) Cardona, C. M.; Wilkes, T.; Ong, W.; Kaifer, A. E.; McCarley, T.
D.; Pandey, S.; Baker, G. A.; Kane, M. N.; Baker, S. N.; Bright, F.
V. Dendrimers Functionalized with a Single Pyrene Label: Synthesis,
Photophysics, and Fluorescence Quenching. J. Phys. Chem. B. 2002,
1
06, 8649-8656.
(
20) Ong, W.; Kaifer, A. E. Unusual Electrochemical Properties of
Unsymmetric Viologen Dendrimers. J. Am. Chem. Soc. 2002, 124,
9358-9359.
21) Kellermann, M.; Bauer, W.; Hirsch, A.; Schade, B.; Ludwig, K.;
Bottcher, C. The First Account of a Structurally Persistent Micelle.
Angew. Chem., Int. Ed. Engl. 2004, 43, 2959-2962.
0
1NT41091) at Virginia Tech under subproject VA007. We
(
thank the NSF (Grant CHE-0131128) for funding the purchase
of the Oxford Diffraction Xcalibur2 single-crystal diffractometer.
We thank Ms. Myra D. Williams for her generous help with
the microbial assays. We thank Professor George R. Newkome
for a sample of Weisocyanate. We thank Dr. Victor Seredyuk
for translating ref 39. We gratefully acknowledge reviewers of
this manuscript and an earlier version for helpful comments.
(22) Burghardt, S.; Hirsch, A.; Schade, B.; Ludwig, K.; Bottcher, C.
Switchable Supramolecular Organization of Structurally Defined
Micelles Based on an Amphiphilic Fullerene. Angew. Chem., Int.
Ed. Engl. 2005, 44, 2976-2979.
(23) M u¨ ller, P. U.; Akpo, C. C.; St o¨ ckelhuber, K. W.; Weber, E. Novel
Amphiphiles with Preorganized FunctionalitiessFormation of Lang-
muir-Films and Efficiency in Mineral Flotation. AdV. Colloid
Interface Sci. 2005, 114-115, 291-302.
Supporting Information Available: Experimental procedures
for the synthesis of icosan-1-amine and docosan-1-amine. Char-
acterization data for 2(16)-2(22) and 1(16)-1(22). Description of
a single-crystal X-ray analysis of 2(16). Data from surface-tension
measurements for 1(14)-1(22) in aqueous triethanolamine. This
material is available free of charge via the Internet at http://
pubs.acs.org.
(
24) Williams, A. A.; Day, B. S.; Kite, B. L.; McPherson, M. K.;
Slebodnick, C.; Morris, J. R.; Gandour, R. D. Homologous, Long-
Chain Alkyl Dendrons Form Homologous Thin Films on Silver Oxide
Surfaces. Chem. Commun. 2005, 5053-5055.
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(
(
(
(
26) Hodge, D. J.; Laughlin, R. G.; Ottewill, R. H.; Rennie, A. R.
Micellization of Ultralong Chain Surfactants. Langmuir 1991, 7,
878-884.
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