International Journal of Organic Chemistry, 2019, 9, 47-66
http://www.scirp.org/journal/ijoc
ISSN Online: 2161-4695
ISSN Print: 2161-4687
DOI: 10.4236/ijoc.2019.91005 Mar. 15, 2019 47 International Journal of Organic Chemistry
Synthesis of Folate-Appended β-Cyclodextrin
Using Phenanthroline as Linker for Cancer
Targeting Drug Delivery
Nadim S. Russel
1
, Punam K. Paul
1
, Mohammad Karim
1*
, Byeongwoon Song
2*
1
Department of Chemistry, Tennessee State University, Nashville, USA
2
Department of Microbiology, Immunology, and Physiology, Meharry Medical College, Nashville, USA
Abstract
Here we have synthesized cancer targeting drug delivery system that contains
β-cyclodextrin as a drug carrier and folic acid as a targeting ligand. Folic acid
was selected as a cancer targeting ligand because folic acid receptors are
highly expressed in a variety of tumor types. β-cyclodextrin and folic acid
were connected through a linker [1,10-phenanthroline or 5-(hydroxymethyl)
furfural]. β-cyclodextrin and folic acid were attached to the linker by forma-
tion of Schiffbase and ester, respectively. Our targeted synthetic products
were confirmed by NMR, Mass and IR spectroscopy. We anticipate that our
synthetic products can confer cancer cell-specific drug delivery as well as de-
sired properties such as nanoparticle formation.
Keywords
Schiff Base, β-Cyclodextrin, p-Toluenesulfonylchloride, Ethylenediamine,
Folic Acid, 2,9-Dimethyl-1,10-Phenanthroline Hemi-Hydrate,
5-(Hydroxymethyl-2-Furaldehyde)
1. Introduction
Cyclodextrins (CDs) are cyclic oligosaccharides generated from starch (e.g. corn,
potato) and β-cyclodextrin is one type of cyclodextrin that contains 7 glucose
units in its structure [1]. The hydrophobic central cavity and the hydrophilic
outer surface allow CDs to form water-soluble inclusion complexes with several
drug molecules or compounds and help to protect the guest molecules from
oxidation and degradation and to increase their solubility and bioavailability.
Thus, CDs are frequently used as a drug carrier.
Hybrid delivery system for effective transportation of temoporfin was sug-
How to cite this paper: Russel, N.S., Paul,
P.K., Karim, M. and Song, B. (2019) Syn-
thesis of Folate-Appended β-Cyclodextrin
Using Phenanthroline as Linker for Cancer
Targeting Drug Delivery. International Jour-
nal of Organic Chemistry, 9, 47-66.
https://doi.org/10.4236/ijoc.2019.91005
Received: January 24, 2019
Accepted: March 12, 2019
Published: March 15, 2019
Copyright © 2019 by author(s) and
Scientific Research Publishing Inc.
This work is licensed under the Creative
Commons Attribution International
License (CC BY 4.0).
http://creativecommons.org/licenses/by/4.0/
Open Access