53733-98-5Relevant articles and documents
Structure-Activity Relationship of 18F-Labeled Phosphoramidate Peptidomimetic Prostate-Specific Membrane Antigen (PSMA)-Targeted Inhibitor Analogues for PET Imaging of Prostate Cancer
Dannoon, Shorouk,Ganguly, Tanushree,Cahaya, Hendry,Geruntho, Jonathan J.,Galliher, Matthew S.,Beyer, Sophia K.,Choy, Cindy J.,Hopkins, Mark R.,Regan, Melanie,Blecha, Joseph E.,Skultetyova, Lubica,Drake, Christopher R.,Jivan, Salma,Barinka, Cyril,Jones, Ella F.,Berkman, Clifford E.,Vanbrocklin, Henry F.
, p. 5684 - 5694 (2016/07/06)
A series of phosphoramidate-based prostate specific membrane antigen (PSMA) inhibitors of increasing lipophilicity were synthesized (4, 5, and 6), and their fluorine-18 analogs were evaluated for use as positron emission tomography (PET) imaging agents for prostate cancer. To gain insight into their modes of binding, they were also cocrystallized with the extracellular domain of PSMA. All analogs exhibited irreversible binding to PSMA with IC50 values ranging from 0.4 to 1.3 nM. In vitro assays showed binding and rapid internalization (80-95%, 2 h) of the radiolabeled ligands in PSMA(+) cells. In vivo distribution demonstrated significant uptake in CWR22Rv1 (PSMA(+)) tumor, with tumor to blood ratios of 25.6:1, 63.6:1, and 69.6:1 for [18F]4, [18F]5, and [18F]6, respectively, at 2 h postinjection. Installation of aminohexanoic acid (AH) linkers in the phosphoramidate scaffold improved their PSMA binding and inhibition and was critical for achieving suitable in vivo imaging properties, positioning [18F]5 and [18F]6 as favorable candidates for future prostate cancer imaging clinical trials.
In situ formation of N-trifluoroacetoxy succinimide (TFA-NHS): One-pot formation of succinimidyl esters, N-trifluoroacetyl amino acid succinimidyl esters, and N-maleoyl amino acid succinimidyl esters
Leonard, Nicholas M.,Brunckova, Jarmila
experimental part, p. 9169 - 9174 (2011/12/16)
A method for the in situ formation of N-trifluoroacetoxy succinimide (TFA-NHS) and its application in the formation of succinimidyl esters is presented. The developed method provides N-trifluoroacetyl and N-maleoyl amino acid succinimidyl esters from a variety of amino acids using a one-pot, high-yielding protocol. Investigations into the formation of an N-maleoyl amino acid succinimidyl ester supported the proposal of a revised reaction mechanism, and contributed to the optimization of the reaction conditions.
Branched supramolecular polymers formed by bifunctional cyclodextrin derivatives
Miyawaki, Atsuhisa,Takashima, Yoshinori,Yamaguchi, Hiroyasu,Harada, Akira
, p. 8355 - 8361 (2008/12/22)
Branched supramolecular polymers have been prepared from the mixture of 3-cinnamamide-α-CD (1) and 3-Nα-cinnamamidehexancarbonyl-Nε-cinnamamide-lysinamide-α-CD (3) and from the mixture of 3-cinnamamidehexanamide-α-CD (2) and 3. Compo