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. 2023 Nov 13;29(12):370.
doi: 10.1007/s00894-023-05780-5.

Electronic structure and molecular properties of nitisinone and mesotrione in water

Richard Imrich  1 , Juraj Štofko  1 , Roman Boča  2 , Cyril Rajnák  3
Affiliations

Electronic structure and molecular properties of nitisinone and mesotrione in water

Richard Imrich et al. J Mol Model. .

Abstract

Context: Nitisinone is a medium-sized organic molecule that is used in treating hereditary tyrosinemia type 1 (HT-1). The structurally analogous mesotrione, however, is used as a pesticide/herbicide. What molecular properties are responsible for the similarity/dissimilarity of these molecules is investigated here. The solvent effect reduces the electron affinity to rather negative values and causes the negative electron affinity which manifests itself in a very high positive absolute reduction potential.

Methods: B3LYP method was utilized for a geometry optimization of nitisinone and mesotrione in their neural and ionized (L0, L+, L-) forms of 6 structures. The calculations were conducted in water as a solvent using conductor-like polarizable continuum model (CPCM), nitisinone also in vacuo. The complete vibrational analysis at the true energy minimum allows evaluating the thermodynamic functions with focus to the zero-point energy and overall entropic term. The change of the Gibbs energy on reductions and/or oxidation facilitates evaluating the absolute reduction and absolute oxidation potentials. Also, DLPNO-CCSD(T) method that involves the major part of the correlation energy has been applied to nitisinone and mesotrione and their molecular ions.

Keywords: Ab initio calculations; Electronic structure; Mesotrione; Molecular properties; Nitisinone.

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Conflict of interest statement

The authors declare no competing interests.

Figures

Fig. 1
Fig. 1
Structural formula of nitisinone (left) and mesotrione (right)
Fig. 2
Fig. 2
The optimized molecular structure (by B3LYP) and 3D mapped isosurface of the molecular electrostatic potential (by AM1 method); contours 0.03 ea0−1, a0 bohr unit. Color scale: blue, negative; red, positive. Left, nitisinone; right, mesotrione
Fig. 3
Fig. 3
Calculated IR spectrum for nitisinone in water (102 transitions)
Fig. 4
Fig. 4
Calculated IR spectrum (bottom panel, in water, 93 transitions) in comparison with reported significant transitions for solid-state mesotrione (top panel, data collected above 500 cm−1 [20])
See this image and copyright information in PMC

References

    1. Hajji H, Imbard A, Spraul A, Taibi L, Barbier V, Habes D, Brassier A, Arnoux J-B, Bouchereau J, Pichard S, Sissaoui S, Lacaille F, Girard M, Debray D, de Lonlay P, Schigg M. Mol Genet Metab Rep. 2022;33:10. - PMC - PubMed
    1. Ranganath LR, Psarelli EE, Arnoux JB, Braconi D, Briggs M, Bröijersén A, Loftus N, Bygott H, Cox TF, Davison AS, Dillon JP, Fisher M, FitzGerald R, Genovese F, Glasova H, Hall AK, Hughes AT, Hughes JH, Imrich R, Jarvis JC, Khedr M, Laan D, Le Quan Sang KH, Luangrath E, Lukáčová O, Milan AM, Mistry A, Mlynáriková V, Norman BP, Olsson B, Rhodes NP, Rovenský J, Rudebeck M, Santucci A, Shweihdi E, Scott C, Sedláková J, Sireau N, Stančík R, Szamosi J, Taylor S, van Kan C, Vinjamuri S, Vrtíková E, Webb C, West E, Záňová E, Zatkova A, Gallagher JA. Lancet Diabetes Endocrinol. 2020;8:762. doi: 10.1016/S2213-8587(20)30228-X. - DOI - PubMed
    1. Davison AS, Hughes G, Harrold JA, Clarke P, Griffin R, Ranganath LR. JIMD Rep. 2022;63:221. doi: 10.1002/jmd2.12272. - DOI - PMC - PubMed
    1. Teke Kisa P, Eroglu Erkmen S, Bahceci H, Arslan Gulten Z, Aydogan A, Karalar Pekuz OK, Yuce Inel T, Ozturk T, Uysal S, Arslan N. Ann Nutr Metab. 2022;78:48. doi: 10.1159/000519813. - DOI - PubMed
    1. Ranganath LR, Hughes AT, Davison AS, Khedr M, Olsson B, Rudebeck M, Imrich R, Norman BP, Bou-Gharios G, Gallagher JA, Milan AM (2022) Temporal adaptations in the phenylalanine/tyrosine pathway and related factors during nitisinone-induced tyrosinaemia in alkaptonuria. Mol Genet Metab 1:S1096–7192(22)00325–0. 10.1016/j.ymgme.2022.05.006 - PubMed

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