A one step/one pot synthesis of N,N-bis(phosphonomethyl)amino acids and their effects on adipogenic and osteogenic differentiation of human mesenchymal stem cells
- Author(s)
- Johanna Hubinger-Kasser, Alexey Nazarov, Christian Hartinger, Brigitte Wdziekonski, Christian Dani, Maxim L. Kuznetsov, Vladimir Arion, Bernhard Keppler
- Abstract
The one pot reaction of amino acids with diethylphosphite and formaldehyde yielded N,N-bis(phosphonomethyl)amino acids. This synthetic route does not require harsh reagents to cleave the ester group. The molecular structures of the new compounds were determined by X-ray diffraction methods. By employing DFT calculations the hydrolysis of the intermediate phosphonic esters to the respective acids could be explained by the decreasing P-OEt bond strength for C?-bisalkylated amino acids. Biological evaluation on the adipogenic and osteogenic differentiation of mesenchymal stem cells revealed no modification of the adipocyte differentiation, but inhibition of osteoblast formation at concentrations without detectable cytotoxicity.
- Organisation(s)
- Department of Inorganic Chemistry
- External organisation(s)
- Université Nice-Sophia-Antipolis, Universidade Técnica de Lisboa
- Journal
- Bioorganic & Medicinal Chemistry
- Volume
- 17
- Pages
- 3388-3393
- No. of pages
- 6
- ISSN
- 0968-0896
- DOI
- https://doi.org/10.1016/j.bmc.2009.03.039
- Publication date
- 2009
- Peer reviewed
- Yes
- Austrian Fields of Science 2012
- 104015 Organic chemistry, 301303 Medical biochemistry
- Portal url
- https://ucrisportal.univie.ac.at/en/publications/3553f86b-1100-42eb-8463-da4dc24e566c