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Novel Therapeutic Agents for Bone Resorption. Part 1. Synthesis and Protonation Thermodynamics of Poly(amido-Amine)s Containing Bis-Phosphonate Residues

Novel Therapeutic Agents for Bone Resorption. Part 1. Synthesis and Protonation Thermodynamics of Poly(amido-Amine)s Containing Bis-Phosphonate Residues

Mario Casolaro, Ilaria Casolaro, Adriano Spreafico, Caterina Capperucci, Bruno Frediani, Roberto Marcolongo, Nicola Margiotta, Rosa Ostuni, Raniero Mendichi, Filippo Samperi, Takehiko Ishii, Yoshihiro Ito

Biomacromolecules. 2006 Dec;7(12):3417-27.

PMID: 17154470

Abstract:

Two poly(amido-amine)s (oligoPAM and oligoNER) containing bis-phosphonate residues were obtained by a Michael-type polyaddition of pamidronate and neridronate to 1,4-bis(acryloyl)piperazine. The SEC (size-exclusion chromatography) and the MALDI-TOF (matrix assisted laser desorption ionization) analyses were consistent with the presence of oligomeric species (2-3 kDa) and with a narrow polydispersity index. The thermodynamic results (log Ks, -DeltaH(o) , and DeltaS(o) obtained at 25 degrees C in 0.15 M NaCl) of both the oligomers and the corresponding low molecular weight precursors were in line with a cluster structure formed during the protonation of the basic nitrogen in the pamidronate. The solubility of the oligoNER with a longer aliphatic chain was improved at high pHs, allowing the evaluation of their solution properties. Preliminary biological results show that both the oligomers do not negatively affect the in vitro viability, proliferation, and cellular activity of either normal animal or human osteoblasts.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP6342172-A	1,4-Bis(acryloyl)piperazine		6342-17-2	Price

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