Novel potential inhibitors for adenylylsulfate reductase to control souring of water in oil industries

Santos, E. S.; Souza, Leila Cristiane Virgens de; Assis, Patrícia Nascimento de; Almeida, Paulo Fernando de; Ramos-de-Souza, Elias

doi:10.1080/07391102.2013.834850

Cited by 13 publications

(5 citation statements)

References 41 publications

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“…The RMSD values for hdz-NO 2 in gas (0.431 Å) and water (0.405 Å) phases were lower than the respective values for hdz-CH 3 (0.648 Å in the gas phase and 0.623 Å in water). However, the small RMSD values in all cases showed that the calculated structures correlated pretty well with the respective experimental ones [45,46]. The biggest differences between the theoretical structures and the experimental data corresponded to the aldehyde-derived ring, containing the -CH 3 (or -NO 2 ) substituents, an effect which is more explicit in hdz-NO 2 , probably due to the intrinsic disorder observed in its structure.…”

Section: Tures (Figures S2b and S3b In Supporting Information File 1)...mentioning

confidence: 55%

Effects of the aldehyde-derived ring substituent on the properties of two new bioinspired trimethoxybenzoylhydrazones: methyl vs nitro groups

Martins,

Lamosa,

da Silva

et al. 2023

Beilstein J. Org. Chem.

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N-Acylhydrazones are a versatile class of organic compounds with a diversity of potential applications. In this study, two new structure-related 3,4,5-trimethoxybenzoyl-containing N-acylhydrazones were synthesized and fully characterized, both in solution and in the solid state. The compounds differ with respect to the carbonyl precursors, i.e., 3-substituted salicylaldehydes with either a methyl or a nitro group. Single crystals of both compounds were isolated from the respective mother liquors and, in both cases, XRD confirmed the obtention of the (E)-isomer, in an anti-conformation. Computational calculations (gas and water phases) were performed in order to confirm some of the structural and vibrational aspects of the compounds. An important intramolecular H bond involving the phenolic hydroxy group and the azomethine nitrogen was identified in the solid state and seems to be maintained in solution. Moreover, the presence of the electron-withdrawing nitro substituent makes this interaction stronger. However, the contact should probably not subsist for the nitro compound under physiological conditions since the presence of this substituent significantly affects the pKa of the phenol: an apparent value of 5.68 ± 0.02 was obtained. This also impacts the basicity of the azomethine nitrogen and, as a consequence, increases the hydrazone’s susceptibility to hydrolysis. Nevertheless, both compounds are stable at physiological-like conditions, especially the methyl-derived one, which qualifies them for further toxicological and activity studies, such as those involving trivalent metal ions sequestering in the context of neurodegenerative diseases.

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Section: Tures (Figures S2b and S3b In Supporting Information File 1)...mentioning

confidence: 55%

Effects of the aldehyde-derived ring substituent on the properties of two new bioinspired trimethoxybenzoylhydrazones: methyl vs nitro groups

Martins,

Lamosa,

da Silva

et al. 2023

Beilstein J. Org. Chem.

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“…There is a dearth of literature using this approach in reducing sulfur production in oil fields. A relatively recent work screened about 15 compounds to find potential inhibitors for Archaeoglobus fulgidus , which though not a bacterium but is also a sulfate-reducing organism. However, the number of compounds screened was quite small and this reduced the possibility of finding an effective compound that will be able inhibit the enzymes responsible for sulfate reduction.…”

Section: Introductionmentioning

confidence: 99%

Computational Screening of Potential Inhibitors of Desulfobacter postgatei for Pyrite Scale Prevention in Oil and Gas Wells

et al. 2021

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Sulfate-reducing bacteria (SRB), such as Desulfobacter postgatei are found in oil wells. However, they lead to the release of hydrogen sulfide. This in turn leads to the iron sulfide scale formation (pyrite). ATP sulfurylase is an enzyme present in SRB, which catalyzes the formation of adenylyl sulfate (APS) and inorganic pyrophosphatase (PPi) from ATP and sulfate. This reaction is the first among many in hydrogen sulfide production by D. postgatei . Consensus scoring using molecular docking and machine learning was used to identify three potential inhibitors of ATP sulfurylase from a database of about 40 million compounds. These selected hits (( S , E )-1-(4-methoxyphenyl)-3-(9-(( m -tolylimino)methyl)-9,10-dihydroanthracen-9-yl)pyrrolidine-2,5-dione; methyl 2-[[(1 S )-5-cyano-2-imino-1-(4-phenylthiazol-2-yl)-3-azaspiro[5.5]undec-4-en-4-yl]sulfanyl]acetate; and (4 S )-4-(3-chloro-4-hydroxy-phenyl)-1-(6-hydroxypyridazin-3-yl)-3-methyl-4,5-dihydropyrazolo[3,4-b]pyridin-6-ol), known as A, B, and C, respectively) all had good binding affinities with ATP sulfurylase and were further analyzed for their toxicological properties. Compound A had the highest docking score. However, based on the physicochemical and toxicological properties, only compound C was predicted to be both safe and effective as a potential inhibitor of ATP sulfurylase, hence the preferred choice. The molecular interactions of compound C revealed favorable interactions with the following residues: LEU213, ASP308, ARG307, TRP347, LEU224, GLN212, MET211, and HIS309.

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“…Another remarkable advantage using in silico approach is the opportunity for preparing simulations based on difficult experimental maneuvers. For this reason, simulations emerge as a useful approach to provide insight into the intermolecular complex structure constituted by target and ligand, predicting both mode and free energy bindings by assuming scoring functions [8][9]. In this context, computer experiments were successfully used to investigate protein interactions with aqueous solution elements at different physicochemical conditions [10,11].…”

Section: Introductionmentioning

confidence: 99%

Aqueous solution interactions with sex hormone-binding globulin and estradiol: a theoretical investigation

Silva

Santos

2018

J Biol Phys

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Sex hormone-binding globulin (SHBG) is a binding protein that regulates the availability of steroid hormones in the plasma. Although best known as a steroid carrier, recent studies have associated SHBG in modulating behavioral aspects related to sexual receptivity. Among steroids, estradiol (17β-estradiol, oestradiol or E2), documented as the most active endogenous female hormone, exerts important physiological roles in both reproductive and non-reproductive functions. In this framework, we employed molecular dynamics (MD) and docking techniques for quantifying the interaction energy between a complex aqueous solution, composed by different salts, SHBG and E2. As glucose concentration resembles measured levels in diabetes, special emphasis was devoted to analyzing the interaction energy between this carbohydrate, SHBG and E2 molecules. The calculations revealed remarkable interaction energy between glucose and SHBG surface. Surprisingly, a movement of solute components toward SHBG was observed, yielding clusters surrounding the protein. The high energy and short distance between glucose and SHBG suggests a possible scenario in favor of a detainment state between the sugar and the protein. In this context, we found that glucose clustering does not insert modification on binding site area nor over binding energy SHBG-E2 complex, in spite of protein superficial area increment. The calculations also point to a more pronounced interaction between E2 and glucose, considering the hormone immersed in the solution. In summary, our findings contribute to a better comprehension of both SHBG and E2 interplay with aqueous solution components.

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Novel potential inhibitors for adenylylsulfate reductase to control souring of water in oil industries

Cited by 13 publications

References 41 publications

Effects of the aldehyde-derived ring substituent on the properties of two new bioinspired trimethoxybenzoylhydrazones: methyl vs nitro groups

Effects of the aldehyde-derived ring substituent on the properties of two new bioinspired trimethoxybenzoylhydrazones: methyl vs nitro groups

Computational Screening of Potential Inhibitors of Desulfobacter postgatei for Pyrite Scale Prevention in Oil and Gas Wells

Aqueous solution interactions with sex hormone-binding globulin and estradiol: a theoretical investigation

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