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.
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(alpha)-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.
Kasser
Johanna
J
University of Vienna, Institute of Inorganic Chemistry, Vienna, Austria.
Nazarov
Alexey A
AA
Hartinger
Christian G
CG
Wdziekonski
Brigitte
B
Dani
Christian
C
Kuznetsov
Maxim L
ML
Arion
Vladimir B
VB
Keppler
Bernhard K
BK
D050156:Adipogenesis / Q000187:drug effects*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002454:Cell Differentiation / Q000187:drug effects; D002478:Cells, Cultured; D006801:Humans; D059630:Mesenchymal Stem Cells / Q000166:cytology / Q000187:drug effects* / Q000378:metabolism; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D010012:Osteogenesis / Q000187:drug effects*; D014961:X-Ray Diffraction
D000596:Amino Acids; D009943:Organophosphorus Compounds