Functionalization of PEGylated Fe3O4 magnetic nanoparticles with tetraphosphonate cavitand for biomedical application.
In this contribution, Fe3O4 magnetic nanoparticles (MNPs) have been functionalized with a tetraphosphonate cavitand receptor (Tiiii), capable of complexing N-monomethylated species with high selectivity, and polyethylene glycol (PEG) via click-chemistry. The grafting process is based on MNP pre-functionalization with a bifunctional phosphonic linker, 10-undecynylphosphonic acid, anchored on an iron surface through the phosphonic group. The Tiiii cavitand and the PEG modified with azide moieties have then been bonded to the resulting alkyne-functionalized MNPs through a "click" reaction. Each reaction step has been monitored by using X-ray photoelectron and FTIR spectroscopies. PEG and Tiiii functionalized MNPs have been able to load N-methyl ammonium salts such as the antitumor drug procarbazine hydrochloride and the neurotransmitter epinephrine hydrochloride and release them as free bases. In addition, the introduction of PEG moieties promoted biocompatibility of functionalized MNPs, thus allowing their use in biological environments.
Dipartimento di Scienze Chimiche, Università di Catania and INSTM UdR di Catania, v.le A. Doria 6, 95125 Catania, Italy. guido.condorelli@unict.it.
C
C
Tudisco
F
F
Bertani
M T
MT
Cambria
F
F
Sinatra
E
E
Fantechi
C
C
Innocenti
C
C
Sangregorio
E
E
Dalcanale
G G
GG
Condorelli
D000480:Alkynes / Q000737:chemistry; D000970:Antineoplastic Agents / Q000737:chemistry / Q000633:toxicity; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D057930:Click Chemistry; D004337:Drug Carriers / Q000737:chemistry; D004837:Epinephrine / Q000737:chemistry / Q000494:pharmacology; D004988:Ethers, Cyclic / Q000737:chemistry*; D052203:Ferrosoferric Oxide / Q000737:chemistry*; D006801:Humans; D058185:Magnetite Nanoparticles / Q000737:chemistry* / Q000633:toxicity; D059630:Mesenchymal Stem Cells / Q000166:cytology / Q000187:drug effects / Q000378:metabolism; D018377:Neurotransmitter Agents / Q000737:chemistry / Q000494:pharmacology; D011092:Polyethylene Glycols / Q000737:chemistry*; D011344:Procarbazine / Q000737:chemistry / Q000633:toxicity; D012118:Resorcinols / Q000737:chemistry*; D013696:Temperature
D000480:Alkynes; D000970:Antineoplastic Agents; D004337:Drug Carriers; D004988:Ethers, Cyclic; D058185:Magnetite Nanoparticles; D018377:Neurotransmitter Agents; D012118:Resorcinols; C442939:cavitand; D011344:Procarbazine; D011092:Polyethylene Glycols; D052203:Ferrosoferric Oxide; D004837:Epinephrine