Cation ion specifically induces a conformational change in trans-dehydroandrosterone – A solid-state NMR study

Solid‐state nuclear magnetic resonance investigation of neurosteroid compounds and magnesium interactions

“…We here show that the Mg 2+ binding sites of DHEA analogs are different from those previously observed for DHEA . In the case of DHEA, the most perturbed CSD value was detected at C17, indicating that C17–O is involved in the Mg 2+ interaction, whereas in the case of 1 and 2 the greatest perturbations in terms of CSD value were detected at C5 and C6 (see Table ), suggesting that Mg 2+ prefers to interact with C5–C6, albeit weakly, mediated by a π‐electron pair.…”

“…In our previous solid‐state NMR study, we demonstrated that Mg 2+ is capable of inducing a conformational change in DHEA . It was suggested that Mg 2+ may associate with the oxygen atom attached to C17 through a lone pair of electrons.…”

“…Investigation of DHEA analogs/Mg 2+ interaction by solid‐state NMR spectroscopy. The 13 C intensity ratios of the C17 signals of DHEA (▴) and C6 signals of compounds 1 (♦) and 2 (×) are plotted as a function of Mg 2+ concentration. The signal intensities were calculated with reference to that of the C14 signal.…”

“…High‐resolution 1 H– 13 C CP/MAS spectra of a variety of steroids, including testosterone, hydrocortisone, DHEA, spironolactone, vitamin D, deflazacort, and Prd tert ‐butyl acetate, show multiplet patterns with splittings of 0.2–2.1 ppm, which are indicative of different steroidal conformations . In our previous study of steroid–cation interaction, we demonstrated by solid‐state NMR spectroscopy that the DHEA molecule is able to interact with Mg 2+ and Ca 2+ . The cation interaction induces different conformational changes in DHEA.…”

New Polymorph of Dehydroepiandrosterone Obtained via Cryomodification

“…However, the antiaging action of DHEA was claimed in 1990s together with therapeutic benefits in many medical conditions. It was shown that DHEA and its derivatives are efficient neuromodulators in the central nervous system and in peripheral tissues, and all these discoveries help to understand why DHEA still remains in the focus of scientific investigations. − Six crystalline forms of DHEA (FI–FVI) and four forms of its solvates (S1–S4) were described, − and crystal structures for some of them were reported, namely, for FI, FII, FVI, S1, S2, and S4 . Our attempts to synthesize nanoparticles of DHEA with the use of the cryochemical technology involved characterization of the obtained powder samples by X-ray powder diffraction (XRPD) immediately after the synthesis.…”