Bedernjak, Alexandre F. Zaytsev, Andrey V. Babolat, Michèle Cellier, Marie James, Arthur L. Orenga, Sylvain Perry, John D. Groundwater, Paul W. Anderson, Rosaleen J. Synthesis and Evaluation of Novel 7- and 8‑Aminophenoxazinones for the Detection of β‑Alanine Aminopeptidase Activity and the Reliable Identification of Pseudomonas aeruginosa in Clinical Samples A series of novel 8-aminophenoxazin-3-one and 7-aminophenoxazin-3-one chromogens and their corresponding β-alanine derivatives were synthesized and evaluated for their ability to detect β-alanyl aminopeptidase activity in bacteria known to hydrolyze β-alanine derivatized substrates. The results provided insight into the structural requirements for effective visualization of enzymatic activity and the mechanism of formation of phenoxazinon-3-ones. 8-Aminophenoxazin-3-one substrates <b>23c</b>, <b>23d</b>, and <b>23e</b> were prepared in good to high overall yield and were selective for β-alanyl aminopeptidase activity in bacteria, producing a lighter agar background coloration facilitating visualization of colored colonies, with variable localization to the colonies, but had lower sensitivities for the detection of Pseudomonas aeruginosa in comparison to the analogous 7-aminophenoxazin-3-one substrates. The synthetic methodology employed here allows the preparation of a range of substrates for evaluation and the establishment of structure–activity relationships. For example, the 2-pentyl substituted aminophenoxazin-3-one <b>22b</b> performed with analogous sensitivity to the corresponding 1-pentyl-7-aminophenoxazin-3-one substrate <b>1</b> used commercially, highlighting that the position of the pentyl substituent can be varied while maintaining detection sensitivity. visualization;alanyl;substrate;aminophenoxazin;alanine;sensitivity;detection;bacteria;aminopeptidase;pentyl;agar background coloration;Pseudomonas aeruginosa 2016-05-04
    https://acs.figshare.com/articles/dataset/Synthesis_and_Evaluation_of_Novel_7_and_8_Aminophenoxazinones_for_the_Detection_of_Alanine_Aminopeptidase_Activity_and_the_Reliable_Identification_of_Pseudomonas_aeruginosa_in_Clinical_Samples/3219364
10.1021/acs.jmedchem.5b01591.s002