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Pocket Dendrimers
Pocket Dendrimers
Pocket Dendrimers
A Lost, Forgotten, or Overlooked Science?
Carissa Burton | Monday 15 June 2015 | ChEn 578: Polymer Science | Dr. Pitt
Applications of dendrimers
There are many applications of dendrimers, such as for molecular recognition, catalysts,
and drug delivery. The rigid and patterned structures of dendrimers give them a high
specificity that is extremely useful in biological applications, since they share
similarities with enzymes and can be designed to be compatible with biological
particles. [2]
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Higher generation dendrimers tend to be more effective in catalytic and
biological-mimicking applications due to the higher number of functional groups that
can be designed to have very specific binding capabilities. For example, a thirdgeneration dendrimer designed to catalyze the reduction of carbon dioxide worked
more effectively than the corresponding second-generation dendrimer. However,
fourth-generation dendrimers frequently tend to be much less effective than would be
predicted when looking at the trend of effectiveness. This is often because the steric
hindrance of the dendrons prevents particles from accessing the core of the dendrimer,
which often plays a key role in the necessary reaction. [4]
One specific application of dendrimers is for very specialized drug delivery to
prevent the transmission of HIV. Misumi et. al. [6] performed a study to target M cells
on the mucosal site where HIV begins to infect the body. It was shown that by using a
dendrimer, the drug could be delivered orally and would only react at the mucosal site,
thereby preventing HIV from being able to attach to the mucosal site, which would then
prevent the subject from contracting HIVs.
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functional groups. Creating a pocket like this reduces the steric hindrance around the
core, providing a parking spot for guest molecules to interact with the core.
A study by Imaoka, Tanaka, and Yamamoto [4] showed that a fourth-generation
pocket dendrimer had a similar molecular weight to its third-generation symmetrical
dendrimer counterpart. It also had a similar number of functional groups that aided in
the catalytic reduction of carbon dioxide. However, the accessibility to the core was
much greater, making the dendrimer more effective in its application.
Another study by Shinoda, Ohashi, and Tsukube [5] showed that attaching a
specific dendron that would not grow to one side of the core created two pockets with a
shape and functionality that could accommodate pyridine and thymine guests, with
very specific, if weak, interactions. This pocket dendrimer, with its weak bonding
interactions similar to those used in enzymes and other biological processes, was
particularly useful for drug delivery and enzyme-mimicking applications.
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make it possible to continue using higher-generation dendrimers with reduced steric
hindrance. Using a pocket in a third-generation dendrimer is approximately 40% more
effective than the symmetrical dendrimer counterpart (see Appendix).
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Conclusion
Pocket dendrimers have been proven to be more effective in catalytic, enzymatic, and
drug-delivering applications, yet there seem to have been few cases where pockets have
been put to use between 2007 and 2015. Many dendrimers have been designed for
particular purposes, and have proven useful, but have been stunted in their
effectiveness due to the steric hindrances of high-generation dendrimers. By adding
pockets to some of these dendrimers, it should be possible to make certain dendrimers
more selective and increase the effectiveness of various dendrimers. It may even be
possible to make a fifth-generation dendrimer with pockets, allowing for even more
guest accommodation sites, giving the possibility of more customizable and selective
applications and higher-molecular-weight dendrimers with more functional groups
capable of binding to guest molecules.
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References
[1] Reymond, J., Bergmann, M., and Darbre, T. (2013), Glycopeptide dendrimers as
Pseudomonas aeruginosa biofilm inhibitors. Chem. Soc. Rev., 42: 481422.
<http://pubs.rsc.org.erl.lib.byu.edu/en/content/articlepdf/2013/cs/c3cs35504g>
[2] Shinoda, S. (2007), Nanoscale substrate recognition by porphyrin dendrimers with
patched structures. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 59: 19.
[3] He, X., et. al. (2015), RGD peptide-modified multifunctional dendrimer platform for
drug encapsulation and targeted inhibition of cancer cells. Colloids and Surfaces B:
Biointerfaces, 125: 8289.
<www.sciencedirect.com/science/article/pii/S0927776514006183>
[4] Imaoka, T., Tanaka, R., and Yamamoto, K. (2006), Synergetic Activation of Carbon
Dioxide Molecule Using Phenylazomethine Dendrimers as a Catalyst. Journal of
Polymer Science, 44: 522936.
<http://onlinelibrary.wiley.com.erl.lib.byu.edu/doi/10.1002/pola.21611/epdf>
[5] Shinoda, S., Ohashi, M. and Tsukube, H. (2007), Pocket Dendrimers as Nanoscale
Receptors for Bimolecular Guest Accommodation. Chem. Eur. J., 13: 8189.
<onlinelibrary.wiley.com/store/10.1002/chem.200600076>
[6] Misumi, S., et. al. (2009), Targeted Delivery of Immunogen to Primate M Cells with
Tetragalloyl Lysine Dendrimer. The Journal of Immunology, 182: 606170.