A porphyrin/β-cyclodextrin conjugated nano-system having a pan-lid molecular structure for smart drug carrier applications.
In this study, 5,10,15-tri[p(9-methoxy-triethyleneoxy)phenyl]-20-[p-phenylisophthalate-β-cyclodextrin]porphyrin, a compound containing a porphyrin and a β-cyclodextrin unit covalently linked by means of an isophthalic bridge, was synthesized and characterized by NMR, MALDI-TOF mass spectrometry and UV-vis and circular dichroism spectroscopies. This porphyrin/β-cyclodextrin system, with the porphyrin unit connected to the lower rim (OH-2) of the cyclodextrin structure, is water-soluble and no evidence of a self-assembly arrangement between the porphyrin and cyclodextrin units appears. In this way, the β-cyclodextrin cavities remain free, retaining their potential ability of drug-delivery, with the spectroscopic advantage induced by the high absorbance of the porphyrin unit. Furthermore, the porphyrin unit, interacting with the guest and acting as a lid, could have a role in the controlled release process of the drug.
Dipartimento di Scienze Chimiche and I.N.S.T.M. UdR of Catania, Università di Catania, Viale A. Doria, 6, 95125 Catania, Italy. gmineo@unict.it.
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D002942:Circular Dichroism; D004126:Dimethylformamide / Q000737:chemistry; D004337:Drug Carriers / Q000737:chemistry*; D008958:Models, Molecular; D053758:Nanoparticles / Q000737:chemistry*; D011166:Porphyrins / Q000138:chemical synthesis / Q000737:chemistry*; D066244:Proton Magnetic Resonance Spectroscopy; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013056:Spectrophotometry, Ultraviolet; D047392:beta-Cyclodextrins / Q000138:chemical synthesis / Q000737:chemistry*
D004337:Drug Carriers; D011166:Porphyrins; D047392:beta-Cyclodextrins; D004126:Dimethylformamide; C031215:betadex