Magnesium and calcium reveal different chelating effects in a steroid compound: A model study of prednisolone using NMR spectroscopy

Carillo, Kathleen D.; Wu, Danni; Lin, Shio Jean; Tsai, Shen‐Long; Shie, Jiun‐Jie; Tzou, Der‐Lii M.

doi:10.1016/j.steroids.2019.108429

Cited by 6 publications

(3 citation statements)

References 46 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Additionally, coalescing of the H 2 proton signal for 1 relative to HG 2 suggests coordination to the carboxylic acid that results in an even distribution of electron density and subsequent lack of observed splitting. Furthermore, the observation of upfield proton shifting coincides with generalized magnesium coordination and may be observed for the α-proton adjacent to the point of coordination and as far-reaching as the γ-proton. − Conserved integration of the HG 2 proton signals is consistent with no formation of new ligand-based product and is consistent with the 1:1 stoichiometric yield of the previously discussed synthesis.…”

Section: Resultssupporting

confidence: 80%

“…13 C NMR was conducted with the aim of confirming the conclusions derived from infrared and 1 H NMR analyses and is supported as a more sensitive method for determining the mode of magnesium coordination. , The 13 C NMR of 1 was conducted relative to HG 2 . Spectral analysis HG 2 revealed four carbon signals: two signals between the range of 40–50 ppm attributed to the sp 3 -hybridized R–CH 2 –R carbon moieties (C 1 , 40.7 ppm; C 3 , 43.4 ppm) and two signals between 160–180 ppm attributed to the sp 2 -hybridized R–CO–R moieties (C 2 , 167.1 ppm; C 4 , 176.4 ppm) (Figure ).…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis, Characterization, and Cellular Uptake of a Glycylglycine Chelate of Magnesium

Case

Gonzalez²,

Zubieta

et al. 2021

ACS Omega

View full text Add to dashboard Cite

Human chronic latent magnesium deficiency is estimated to impact a substantive portion of the world’s population. A number of magnesium compounds have been developed to combat this deficiency; however, none are ideal due to issues of solubility, absorption, side effects (e.g., laxation) and/or formulation. Here, we describe the pH-dependent synthesis, chemical characterization (inductively coupled plasma and thermal analysis, infrared and nuclear magnetic resonance (1D and 2D) spectroscopies, and electrospray mass spectrometry) and in vitro uptake (in a cell model of the large intestine (CaCo-2 cells)) of a magnesium complex of the glycine dimer (HG 2 ). Results demonstrate that the HG 2 ligand assumes a tridentate coordination mode with an N 2 O donor set and an octahedral coordination sphere completed with coordinated waters. The magnesium:HG 2 complex exhibits significant solubility and cellular uptake.

show abstract

Section: Resultssupporting

confidence: 80%

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization, and Cellular Uptake of a Glycylglycine Chelate of Magnesium

Case

Gonzalez²,

Zubieta

et al. 2021

ACS Omega

View full text Add to dashboard Cite

show abstract

“…It is anticipated that this NMR study approach will have a great impact in the field of steroidal conformational analyses and steroidal drug developments. In the application of steroid/metal ion chelation, we reported previously that ring D is responsible for the metal ion chelation and therefore its conformation is rather sensitive to the presence of metal ions, such as Mg 2+ and Ca 2+ [ 27 ]. By this means, one can probe steroidal conformational change due to the presence the metal ions.…”

Section: Discussionmentioning

confidence: 99%

Resolving Entangled JH-H-Coupling Patterns for Steroidal Structure Determinations by NMR Spectroscopy

Carillo

Shie

et al. 2021

Molecules

Self Cite

View full text Add to dashboard Cite

For decades, high-resolution 1H NMR spectroscopy has been routinely utilized to analyze both naturally occurring steroid hormones and synthetic steroids, which play important roles in regulating physiological functions in humans. Because the 1H signals are inevitably superimposed and entangled with various JH–H splitting patterns, such that the individual 1H chemical shift and associated JH–H coupling identities are hardly resolved. Given this, applications of thess information for elucidating steroidal molecular structures and steroid/ligand interactions at the atomic level were largely restricted. To overcome, we devoted to unraveling the entangled JH–H splitting patterns of two similar steroidal compounds having fully unsaturated protons, i.e., androstanolone and epiandrosterone (denoted as 1 and 2, respectively), in which only hydroxyl and ketone substituents attached to C3 and C17 were interchanged. Here we demonstrated that the JH–H values deduced from 1 and 2 are universal and applicable to other steroids, such as testosterone, 3β, 21-dihydroxygregna-5-en-20-one, prednisolone, and estradiol. On the other hand, the 1H chemical shifts may deviate substantially from sample to sample. In this communication, we propose a simple but novel scheme for resolving the complicate JH–H splitting patterns and 1H chemical shifts, aiming for steroidal structure determinations.

show abstract

1H/13C chemical shifts and cation binding dataset of the corticosteroid Prednisolone titrated with metal cations

Carillo

Lin

et al. 2019

Data in Brief

Self Cite

View full text Add to dashboard Cite

We here reported the 1H/13C chemical shifts, binding affinity and binding free energy of 1,4-pregnadiene-11β,17α,21-triol-3,20-dione (Prednisolone; Prd) interacting with metal cations. Six different Prd/Ni or Co mixtures were examined at different molar ratios (1:0, 1:0.1, 1:0.2, 1:0.3, 1:0.4 and 1:0.5). In this analysis, the 1H and 13C chemical shifts were measured for the Prd/cation mixtures using a Bruker AV 500 MHz spectrometer (Bruker BioSpin GmbH, Rheinstetten, Germany), equipped with a 5 mm z-gradient Prodigy BBO 500 MHz probehead at 298 K, and simulation of the 1H spectra were determined from the Daisy software package (Bruker BioSpin GmbH). Binding affinity and free energy values were deduced from the 13C NMR peak intensities involved in the cation interaction, for more insight on the steroid/cation interactions please see Magnesium and Calcium Reveal Different Chelating Effects in a Steroid Compound: A Model Study of Prednisolone Using NMR Spectroscopy [1].

show abstract

Magnesium and calcium reveal different chelating effects in a steroid compound: A model study of prednisolone using NMR spectroscopy

Cited by 6 publications

References 46 publications

Synthesis, Characterization, and Cellular Uptake of a Glycylglycine Chelate of Magnesium

Synthesis, Characterization, and Cellular Uptake of a Glycylglycine Chelate of Magnesium

Resolving Entangled JH-H-Coupling Patterns for Steroidal Structure Determinations by NMR Spectroscopy

1H/13C chemical shifts and cation binding dataset of the corticosteroid Prednisolone titrated with metal cations

Contact Info

Product

Resources

About