Pyridine peptidomimetics (I) [L is selected from the group consisting of thiol, organo-​sulfur groups, such as sulfide, disulfide, thioesters, and dithiocarbammates , Y is selected from -​(CH2)​n- and -​(OCH2CH2)​m-​, where n is between 7 and 13 and m is 10 between 2 and 6] are developed as compds. useful as nanosensors for the rapid and specific detn. of the FKBP12 protein. Thus, N-​Boc-​L-​pipecolinic acid (Boc-​tert-​butoxycarbonyl) was coupled with 3-​phenylpropyl-​1-​amine in the presence of DIPEA and HATU in anhyd. DMF, following by reaction with freshly prepd. 4-​hydroxy phenylglyoxalic acid to give (S)​-​4-​(2-​oxo-​2-​(2-​(3-​phenylpropylcarbamoyl)​piperidin-​1-​yl)​acetyl)​phenyl acetate intermediate, which was reacted with 11-​(tritylthio)​undecanoic acid to give (S)​-​4-​(2-​oxo-​2-​(2-​((3-​phenylpropyl)​carbamoyl)​piperidin-​1-​yl) acetyl)​phenyl 11-​(tritylthio) undecanoate. The latter was deprotected and compd. I [L= SH, Y = (CH2)​8] was isolated in the form of a light yellow oil and characterized by NMR, IR and MS. The prepd. compd. can be useful as diagnostic agent for detn. of the levels of the FKBP12 protein which in the biol. fluids of a subject change if the subject is affected by pathol. conditions, in particular neurodegenerative diseases, such as the Parkinson's disease and the Alzheimer's syndrome, tumor pathologies, autoimmune diseases, or if that subject is in a phase of acute rejection after organ transplantation.

A compound for the determination of the protein FKBP12 and a sensor unit comprising it / Caminati, Gabriella; Procacci, Piero; Menichetti, Stefano; Martina, Maria Raffaella; Marsili, Laura. - (2020).

A compound for the determination of the protein FKBP12 and a sensor unit comprising it

Caminati, Gabriella
;
Procacci, Piero;Menichetti, Stefano;Martina, Maria Raffaella;
2020

Abstract

Pyridine peptidomimetics (I) [L is selected from the group consisting of thiol, organo-​sulfur groups, such as sulfide, disulfide, thioesters, and dithiocarbammates , Y is selected from -​(CH2)​n- and -​(OCH2CH2)​m-​, where n is between 7 and 13 and m is 10 between 2 and 6] are developed as compds. useful as nanosensors for the rapid and specific detn. of the FKBP12 protein. Thus, N-​Boc-​L-​pipecolinic acid (Boc-​tert-​butoxycarbonyl) was coupled with 3-​phenylpropyl-​1-​amine in the presence of DIPEA and HATU in anhyd. DMF, following by reaction with freshly prepd. 4-​hydroxy phenylglyoxalic acid to give (S)​-​4-​(2-​oxo-​2-​(2-​(3-​phenylpropylcarbamoyl)​piperidin-​1-​yl)​acetyl)​phenyl acetate intermediate, which was reacted with 11-​(tritylthio)​undecanoic acid to give (S)​-​4-​(2-​oxo-​2-​(2-​((3-​phenylpropyl)​carbamoyl)​piperidin-​1-​yl) acetyl)​phenyl 11-​(tritylthio) undecanoate. The latter was deprotected and compd. I [L= SH, Y = (CH2)​8] was isolated in the form of a light yellow oil and characterized by NMR, IR and MS. The prepd. compd. can be useful as diagnostic agent for detn. of the levels of the FKBP12 protein which in the biol. fluids of a subject change if the subject is affected by pathol. conditions, in particular neurodegenerative diseases, such as the Parkinson's disease and the Alzheimer's syndrome, tumor pathologies, autoimmune diseases, or if that subject is in a phase of acute rejection after organ transplantation.
Caminati, Gabriella; Procacci, Piero; Menichetti, Stefano; Martina, Maria Raffaella; Marsili, Laura
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2158/1285092
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