Novel bisphosphonates near infrared fluorescent and non-fluorescent nanoparticles of narrow size distribution for bone targeting

Bisphosphonates (BPs) are a group of organophosphorus compounds which are used in the treatment of various bone related diseases. BPs possess a high affinity to the calcium in bone and thus can be used for bone targeting. Nanoparticles (NPs) are being developed as in-vivo targeted drug delivery syst...

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Bibliographic Details
Published in:Polymer (Guilford) 2017-12, Vol.132, p.188-192
Main Authors: Tal, Nimrod, Rudnick-Glick, Safra, Margel, Shlomo
Format: Article
Language:English
Subjects:
Affinity
Amino groups
Biomedical materials
Bisphosphonates
Bone diseases
Calcium
Calcium targeting
Conjugation
Copolymerization
Crosslinking
Drug delivery
Drug delivery systems
Ethylene glycol
Fluorescence
Hydroxyapatite
Infrared radiation
Medical treatment
Methacrylamide
Monomers
Nanoparticles
Organophosphorus compounds
Polymerization
Size distribution
Studies
Surgical implants
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Summary:Bisphosphonates (BPs) are a group of organophosphorus compounds which are used in the treatment of various bone related diseases. BPs possess a high affinity to the calcium in bone and thus can be used for bone targeting. Nanoparticles (NPs) are being developed as in-vivo targeted drug delivery systems. In this article, we report the synthesis and characterization of a new bisphosphonate vinylic monomer MA-Glu-BP (methacrylate glutamate bisphosphonate) prepared by interacting methacryloyl chloride with γ-Glu-BP. Non-fluorescent crosslinked bisphosphonate NPs of narrow size distribution were then prepared by dispersion co-polymerization of MA-Glu-BP with a vinylic monomer containing primary amino group, N-(3-aminopropyl) methacrylamide (APMA) and a crosslinker vinylic monomer, tetra ethylene glycol diacrylate (TTEGDA). Near infra-red (NIR) fluorescent crosslinked bisphosphonate NPs were then prepared by covalent conjugation of the NIR dye Cy-7 to the primary amino groups belonging to the APMA monomeric units of the non-fluorescent bisphosphonate NPs. The affinity of the poly(MA-Glu-BP) NPs to calcium was illustrated by interacting the NIR fluorescent poly(MA-Glu-BP) NPs with hydroxyapatite. [Display omitted] •Synthesis of new bisphosphonate compounds N-Pht-Glu-BP, γ-Glu-BP and vinylic monomer MA-Glu-BP.•Near infrared (NIR) fluorescent and non-fluorescent crosslinked poly(MA-Glu-BP) nanoparticles for bone targeting.•The affinity of the poly(MA-Glu-BP) NPs to calcium was illustrated.
ISSN:0032-3861
1873-2291
DOI:10.1016/j.polymer.2017.11.003