《ESI-MS Study of the Interaction of Potential Oxidovanadium(IV) Drugs and Amavadin with Model Proteins》 was published in Inorganic Chemistry in 2020. These research results belong to Ugone, Valeria; Sanna, Daniele; Sciortino, Giuseppe; Crans, Debbie C.; Garribba, Eugenio. Synthetic Route of C6H5NO2 The article mentions the following:
In this study, the binding to lysozyme (Lyz) of four important VIV compounds with antidiabetic and/or anticancer activity, [VIVO(pic)2(H2O)], [VIVO(ma)2], [VIVO(dhp)2], and [VIVO(acac)2], where pic-, ma-, dhp-, and acac- are picolinate, maltolate, 1,2-dimethyl-3-hydroxy-4(1H)-pyridinonate, and acetylacetonate anions, and of the vanadium-containing natural product amavadin ([VIV(hidpa)2]2-, with hidpa3-N-hydroxyimino-2,2′-diisopropionate) was investigated by ElectroSpray Ionization-Mass Spectrometry (ESI-MS). Moreover, the interaction of [VIVO(pic)2(H2O)], chosen as a representative VIVO2+ complex, was examined with two addnl. proteins, myoglobin (Mb) and ubiquitin (Ub), to compare the data. The examined vanadium concentration was in the range 15-150 μM, i.e., very close to that found under physiol. conditions. With pic-, dhp-, and hidpa3-, the formation of adducts n[VIVOL2]-Lyz or n[VIVL2]-Lyz is favored, while with ma- and acac- the species n[VIVOL]-Lyz are detected, with n dependent on the exptl. VIV/protein ratio. The behavior of the systems with [VIVO(pic)2(H2O)] and Mb or Ub is very similar to that of Lyz. The results suggested that under physiol. conditions, the moiety cis-VIVOL2 (L = pic-, dhp-) is bound by only one accessible side-chain protein residue that can be Asp, Glu, or His, while VIVOL+ (L = ma-, acac-) can interact with the two equatorial and axial sites. If the VIV complex is thermodynamically stable and does not have available coordination positions, such as amavadin, the protein cannot interact with it through the formation of coordination bonds and, in such cases, noncovalent interactions are predicted. The formation of the adducts is dependent on the thermodn. stability and geometry in aqueous solution of the VIVO2+ complex and affects the transport, uptake, and mechanism of action of potential V drugs. The potentiality of ElectroSpray Ionization-Mass Spectrometry (ESI-MS) to determine the number and composition of adducts formed by labile V complexes with potential pharmacol. application and the natural product amavadin with some proteins was examined ESI-MS allows the study of vanadium concentrations close to those found under physiol. conditions. The nature of the adducts-which could be related to the transport, uptake, and mechanism of action of potential V drugs-depends on the structure and thermodn. stability at concentrations around micromolar. In the experiment, the researchers used Picolinic acid(cas: 98-98-6Synthetic Route of C6H5NO2)
Picolinic acid(cas: 98-98-6) is used in the preparation of 2-Aminodihydro[1,3]thiazines as BACE 2 inhibitors and their preparation and use in the treatment of diabetes.Synthetic Route of C6H5NO2