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Special Issue "Synthesis and Bioanalysis of Steroids and Steroid Biosynthesis Inhibitors"

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Medicinal Chemistry".

Deadline for manuscript submissions: 15 June 2021.

Special Issue Editors

Prof. Dr. Franz Bracher
E-Mail Website
Guest Editor
Department of Pharmacy, Center for Drug Research, Ludwig-Maximilians University Munich, Butenandtstraße 5-13, 81377 Munich, Germany
Interests: medicinal chemistry; steroids; natural products; antifungals; epigenetic targets; cation channels
Dr. Christoph Müller
E-Mail Website
Guest Editor
Department of Pharmacy-Center for Drug Research, Ludwig-Maximilians University Munich, Butenandtstraße 5-13, 81377 Munich, Germany
Interests: analytical chemistry; cholesterol/ergosterol biosynthesis; antifungal resistance; GC-MS

Special Issue Information

Dear Colleagues,

Steroids are a versatile and structurally diverse class of molecules widespread in nature. They are known as cell-building material and as signaling molecules. In recent years, our understanding of the role of steroids and steroid biosynthesis enzymes has significantly evolved. Recent studies have shown that steroids have diverse and hitherto unknown physiological functions. They are involved in the pathomechanisms of diseases or play a role in the inflammatory process in humans. Furthermore, the main target of antifungal therapy is the ergosterol biosynthesis or directly ergosterol, and related mechanisms have been found in other pathogenic organisms such as protozoa. Thus, the function of the steroids, the enzymes involved in their biosynthesis, as well as inhibitors of these enzymes as drug candidates are of great interest. Hence, the demand for authentic steroid standards for their use in bioassays and for analytical approaches cannot be met by simply extraction of steroids from natural sources. Consequently, new methods for isolation and total and partial synthesis of steroids are highly demanded.

This Special Issue is devoted to recent developments in biochemistry, chemistry, and qualitative and quantitative analysis of steroids from different origins to get a better insight into the molecular mechanisms of physiological functions and metabolism of steroids.

This also includes the development of steroid biosynthesis inhibitors as molecular tools for studying pathomechanisms, as novel drugs fighting against upcoming antifungal drug resistance, or as first-in-class drug candidates targeting distinct enzymes in cholesterol biosynthesis, whose enormous therapeutic potential has been highlighted in the past few years.

Prof. Dr. Franz Bracher
Dr. Christoph Müller
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All papers will be peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2000 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Enzyme inhibitors (chemistry and pharmacology)
  • Steroid analysis in diverse samples (tissues, plant material, screening systems)
  • Biological activities and metabolism
  • Steroid biosynthesis
  • Synthesis of steroids and analogues
  • Steroid isolation from diverse sources (mammals, plants, microorganisms)

Published Papers (2 papers)

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Research

Open AccessArticle
New Insights into the Metabolism of Methyltestosterone and Metandienone: Detection of Novel A-Ring Reduced Metabolites
Molecules 2021, 26(5), 1354; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26051354 - 03 Mar 2021
Viewed by 450
Abstract
Metandienone and methyltestosterone are orally active anabolic-androgenic steroids with a 17α-methyl structure that are prohibited in sports but are frequently detected in anti-doping analysis. Following the previously reported detection of long-term metabolites with a 17ξ-hydroxymethyl-17ξ-methyl-18-nor-5ξ-androst-13-en-3ξ-ol structure in the chlorinated metandienone analog dehydrochloromethyltestosterone (“oral [...] Read more.
Metandienone and methyltestosterone are orally active anabolic-androgenic steroids with a 17α-methyl structure that are prohibited in sports but are frequently detected in anti-doping analysis. Following the previously reported detection of long-term metabolites with a 17ξ-hydroxymethyl-17ξ-methyl-18-nor-5ξ-androst-13-en-3ξ-ol structure in the chlorinated metandienone analog dehydrochloromethyltestosterone (“oral turinabol”), in this study we investigated the formation of similar metabolites of metandienone and 17α-methyltestosterone with a rearranged D-ring and a fully reduced A-ring. Using a semi-targeted approach including the synthesis of reference compounds, two diastereomeric substances, viz. 17α-hydroxymethyl-17β-methyl-18-nor-5β-androst-13-en-3α-ol and its 5α-analog, were identified following an administration of methyltestosterone. In post-administration urines of metandienone, only the 5β-metabolite was detected. Additionally, 3α,5β-tetrahydro-epi-methyltestosterone was identified in the urines of both administrations besides the classical metabolites included in the screening procedures. Besides their applicability for anti-doping analysis, the results provide new insights into the metabolism of 17α-methyl steroids with respect to the order of reductions in the A-ring, the participation of different enzymes, and alterations to the D-ring. Full article
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Open AccessArticle
Synthesis of New Brassinosteroid 24-Norcholane Type Analogs Conjugated in C-3 with Benzoate Groups
Molecules 2021, 26(4), 1173; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26041173 - 22 Feb 2021
Cited by 1 | Viewed by 484
Abstract
The metabolism of brassinosteroid leads to structural modifications in the ring skeleton or the side alkyl chain. The esterification and glycosylation at C-3 are the most common metabolic pathways, and it has been suggested that conjugate brassinosteroids are less active or inactive. In [...] Read more.
The metabolism of brassinosteroid leads to structural modifications in the ring skeleton or the side alkyl chain. The esterification and glycosylation at C-3 are the most common metabolic pathways, and it has been suggested that conjugate brassinosteroids are less active or inactive. In this way, plants regulate the content of active brassinosteroids. In this work, the synthesis of brassinosteroid 24-norcholane type analogs conjugated at C-3 with benzoate groups, carrying electron donor and electron attractant substituents on the aromatic ring, is described. Additionally, their growth-promoting activities were evaluated using the Rice Lamina Inclination Test (RLIT) and compared with that exhibited by brassinolide (used as positive control) and non-conjugated analogs. The results indicate that at the lowest tested concentrations (10−8–10−7 M), all analogs conjugated at C-3 exhibit similar or higher activities than brassinolide, and the diasteroisomers with S configuration at C-22 are the more active ones. Increasing concentration (10−6 M) reduces the biological activities of analogs as compared to brassinolide. Full article
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Planned Papers

The below list represents only planned manuscripts. Some of these manuscripts have not been received by the Editorial Office yet. Papers submitted to MDPI journals are subject to peer-review.

Title: Unearthing the sterolome yields suicide antimetabolites of therapeutic significance
Authors: W. David Nes
Affiliation: Texas Tech University, USA
Abstract: Not Ready

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