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Steroid Compounds with Potential Biological Activity

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

Deadline for manuscript submissions: closed (30 September 2023) | Viewed by 31531

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Special Issue Editors

Dr. Marina Savić

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Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, University of Novi Sad, 21000 Novi Sad, Serbia
Interests: Organic synthesis; androstane derivatives; biologically active compounds

Dr. Erzsébet Mernyák

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Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary
Interests: steroid synthesis; core modification; secosteroids; homosteroids; molecular mechanics; molecular dynamics; drug design
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Dr. Jovana Ajdukovic

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Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, University of Novi Sad, 21000 Novi Sad, Serbia
Interests: medicinal chemistry; organic chemistry; organic synthesis; steroids

Prof. Dr. Suzana Jovanović-Šanta

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Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, University of Novi Sad, 21000 Novi Sad, Serbia
Interests: study of the biological activity of modified steroids and other compounds in vitro on cell cultures and animal tissues and in vivo on animal models: testing of antiestrogenic, anticancer, antioxidant activity, measuring the effect on steroid-converting enzymes

Special Issue Information

Dear Colleagues,

We warmly invite you to contribute to this Special Issue of Molecules entitled “Steroid Compounds with Potential Biological Activity”.

Steroids are a large group of compounds whose structure is based on a 17-carbon skeleton, with a specific cyclopentanoperhydrophenanthrene ring system. Natural steroids have been fine-tuned through evolution to build membranes, to act as chemical messengers that regulate metabolic, immune, and reproductive functions in animals, as well as to stimulate growth or protect animal organisms. The steroid core represents a suitable motive for structural modifications. Therefore, a large group of semi-synthetic steroid derivatives have occupied the attention of synthetic chemists as well as medicinal chemists due to their potential biological activity, including anticancer, antibacterial, anti-inflammatory, (anti)hormonal and other activities.

This Special Issue is dedicated to both experimental and theoretical studies on steroid chemistry, structural biology, biosynthesis, metabolism, and pharmacology. The Issue focuses on the isolation and synthesis of steroid compounds, diverse in origin, as well as their structural characterization and identification. Manuscripts relating to in vitro, in vivo or in silico studies of pharmacological properties, molecular biology, biochemistry, and structural biology of steroids are encouraged.

We look forward to the submission of original research papers or reviews to this Special Issue of Molecules entitled “Steroid Compounds with Potential Biological Activity”.

Dr. Marina Savić
Dr. Erzsébet Mernyák
Dr. Jovana Ajdukovic
Prof. Dr. Suzana Jovanović-Šanta
Guest Editors

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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.

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Keywords

natural steroid compounds
semi-synthetic steroid compounds
isolation
structure elucidation
bioactive steroids
physiological activity
metabolism
medicinal chemistry of steroids

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Published Papers (12 papers)

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Research

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19 pages, 9971 KiB

Open AccessArticle

New Steroidal Selenides as Proapoptotic Factors

by Izabella Jastrzebska, Natalia Wawrusiewicz-Kurylonek, Paweł A. Grześ, Artur Ratkiewicz, Ewa Grabowska, Magdalena Czerniecka, Urszula Czyżewska and Adam Tylicki

Molecules 2023, 28(22), 7528; https://doi.org/10.3390/molecules28227528 - 10 Nov 2023

Viewed by 1231

Abstract

Cytostatic and pro-apoptotic effects of selenium steroid derivatives against HeLa cells were determined. The highest cytostatic activity was shown by derivative 4 (GI₅₀ 25.0 µM, almost complete growth inhibition after three days of culture, and over 97% of apoptotic and dead cells at 200 µM). The results of our study (cell number measurements, apoptosis profile, relative expression of apoptosis-related APAF1, BID, and mevalonate pathway-involved HMGCR, SQLE, CYP51A1, and PDHB genes, and computational chemistry data) support the hypothesis that tested selenosteroids induce the extrinsic pathway of apoptosis by affecting the cell membrane as cholesterol antimetabolites. An additional mechanism of action is possible through a direct action of derivative 4 to inhibit PDHB expression in a way similar to steroid hormones. Full article

(This article belongs to the Special Issue Steroid Compounds with Potential Biological Activity)

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18 pages, 1834 KiB

Open AccessArticle

Aza Analogs of the TRPML1 Inhibitor Estradiol Methyl Ether (EDME)

by Philipp Rühl and Franz Bracher

Molecules 2023, 28(21), 7428; https://doi.org/10.3390/molecules28217428 - 4 Nov 2023

Cited by 1 | Viewed by 1511

Abstract

Estradiol methyl ether (EDME) has recently been described by us as a very potent and subtype-specific inhibitor of the lysosomal cation channel TRPML1. Following the principle of bioisosteres, we worked out efficient synthetic approaches to ring-A aza-analogs of EDME, namely a methoxypyridine and a methoxypyrimidine analog. Both target compounds were obtained in good overall yields in six and eight steps starting from 19-nortestosterone via the oxidative cleavage of ring A followed over several intermediates and with the use of well-selected protective groups by re-cyclization to provide the desired hetero-analogs. The methoxypyridine analog largely retained its TRPML1-inhibitory activity, whereas the methoxypyrimidine analog significantly lost activity. Full article

(This article belongs to the Special Issue Steroid Compounds with Potential Biological Activity)

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14 pages, 3945 KiB

Open AccessArticle

Montmorillonite Catalyzed Synthesis of Novel Steroid Dimers

by Aneta M. Tomkiel, Adam D. Majewski, Leszek Siergiejczyk and Jacek W. Morzycki

Molecules 2023, 28(20), 7068; https://doi.org/10.3390/molecules28207068 - 13 Oct 2023

Cited by 2 | Viewed by 1286

Abstract

The reactions of sterols (androst-5-en-3β-ol-17-one, diosgenin, and cholesterol) and their tosylates with hydroquinone aimed at the synthesis of O,O-1,4-phenylene-linked steroid dimers were studied. The reaction course strongly depended on the conditions used. The study has shown that the major reaction products are the elimination products and unusual steroid dimers resulting from the nucleophilic attack of the hydroquinone C2 carbon atom on the steroid C3 position, followed by an intramolecular addition to the C5–C6 double bond. A different reaction course was observed when montmorillonite K10 was used as a catalyst. The reaction of androst-5-en-3β-ol-17-one under the promotion of this catalyst afforded the O,O-1,4-phenylene-linked steroid dimer in addition to the disteroidal ether. The formation of the latter compound was suppressed by using 3-tosylate as a substrate instead of the free sterol. The reactions of androst-5-en-3β-ol-17-one tosylate and cholesteryl tosylate with hydroquinone catalyzed by montmorillonite K10 carried out under optimized conditions afforded the desired dimers in 31% and 67% yield, respectively. Full article

(This article belongs to the Special Issue Steroid Compounds with Potential Biological Activity)

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26 pages, 4435 KiB

Open AccessArticle

Exploration of Binding Affinities of a 3β,6β-Diacetoxy-5α-cholestan-5-ol with Human Serum Albumin: Insights from Synthesis, Characterization, Crystal Structure, Antioxidant and Molecular Docking

by Mahboob Alam

Molecules 2023, 28(16), 5942; https://doi.org/10.3390/molecules28165942 - 8 Aug 2023

Cited by 7 | Viewed by 1821

Abstract

The present study describes the synthesis, characterization, and in vitro molecular interactions of a steroid 3β,6β-diacetoxy-5α-cholestan-5-ol. Through conventional and solid-state methods, a cholestane derivative was successfully synthesized, and a variety of analytical techniques were employed to confirm its identity, including high-resolution mass spectrometry (HRMS), Fourier transforms infrared (FT-IR), nuclear magnetic resonance (NMR), elemental analysis, and X-ray single-crystal diffraction. Optimizing the geometry of the steroid was undertaken using density functional theory (DFT), and the results showed great concordance with the data from the experiments. Fluorescence spectral methods and ultraviolet–vis absorption titration were employed to study the in vitro molecular interaction of the steroid regarding human serum albumin (HSA). The Stern-Volmer, modified Stern-Volmer, and thermodynamic parameters’ findings showed that steroids had a significant binding affinity to HSA and were further investigated by molecular docking studies to understand the participation of active amino acids in forming non-bonding interactions with steroids. Fluorescence studies have shown that compound 3 interacts with human serum albumin (HSA) through a static quenching mechanism. The binding affinity of compound 3 for HSA was found to be 3.18 × 10⁴ mol⁻¹, and the Gibbs free energy change (ΔG) for the binding reaction was −9.86 kcal mol⁻¹ at 298 K. This indicates that the binding of compound 3 to HSA is thermodynamically favorable. The thermodynamic parameters as well as the binding score obtained from molecular docking at various Sudlow’s sites was −8.2, −8.5, and −8.6 kcal/mol for Sites I, II, and III, respectively, supporting the system’s spontaneity. Aside from its structural properties, the steroid demonstrated noteworthy antioxidant activity, as evidenced by its IC₅₀ value of 58.5 μM, which is comparable to that of ascorbic acid. The findings presented here contribute to a better understanding of the pharmacodynamics of steroids. Full article

(This article belongs to the Special Issue Steroid Compounds with Potential Biological Activity)

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17 pages, 1665 KiB

Open AccessArticle

Synthesis and Antiproliferative Activity of Steroidal Diaryl Ethers

by Édua Kovács, Hazhmat Ali, Renáta Minorics, Péter Traj, Vivien Resch, Gábor Paragi, Bella Bruszel, István Zupkó and Erzsébet Mernyák

Molecules 2023, 28(3), 1196; https://doi.org/10.3390/molecules28031196 - 25 Jan 2023

Cited by 11 | Viewed by 2569

Abstract

Novel 13α-estrone derivatives have been synthesized via direct arylation of the phenolic hydroxy function. Chan–Lam couplings of arylboronic acids with 13α-estrone as a nucleophilic partner were carried out under copper catalysis. The antiproliferative activities of the newly synthesized diaryl ethers against a panel of human cancer cell lines (A2780, MCF-7, MDA-MB 231, HeLa, SiHa) were investigated by means of MTT assays. The quinoline derivative displayed substantial antiproliferative activity against MCF-7 and HeLa cell lines with low micromolar IC₅₀ values. Disturbance of tubulin polymerization has been confirmed by microplate-based photometric assay. Computational calculations reveal significant interactions of the quinoline derivative with the taxoid binding site of tubulin. Full article

(This article belongs to the Special Issue Steroid Compounds with Potential Biological Activity)

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20 pages, 3075 KiB

Open AccessArticle

An Exemestane Derivative, Oxymestane-D1, as a New Multi-Target Steroidal Aromatase Inhibitor for Estrogen Receptor-Positive (ER⁺) Breast Cancer: Effects on Sensitive and Resistant Cell Lines

by Cristina Amaral, Georgina Correia-da-Silva, Cristina Ferreira Almeida, Maria João Valente, Carla Varela, Elisiário Tavares-da-Silva, Anne Marie Vinggaard, Natércia Teixeira and Fernanda M. F. Roleira

Molecules 2023, 28(2), 789; https://doi.org/10.3390/molecules28020789 - 12 Jan 2023

Cited by 10 | Viewed by 3183

Abstract

Around 70–85% of all breast cancer (BC) cases are estrogen receptor-positive (ER⁺). The third generation of aromatase inhibitors (AIs) is the first-line treatment option for these tumors. Despite their therapeutic success, they induce several side effects and resistance, which limits their efficacy. Thus, it is crucial to search for novel, safe and more effective anti-cancer molecules. Currently, multi-target drugs are emerging, as they present higher efficacy and lower toxicity in comparison to standard options. Considering this, this work aimed to investigate the anti-cancer properties and the multi-target potential of the compound 1α,2α-epoxy-6-methylenandrost-4-ene-3,17-dione (Oxy), also designated by Oxymestane-D1, a derivative of Exemestane, which we previously synthesized and demonstrated to be a potent AI. For this purpose, it was studied for its effects on the ER⁺ BC cell line that overexpresses aromatase, MCF-7aro cells, as well as on the AIs-resistant BC cell line, LTEDaro cells. Oxy reduces cell viability, impairs DNA synthesis and induces apoptosis in MCF-7aro cells. Moreover, its growth-inhibitory properties are inhibited in the presence of ERα, ERβ and AR antagonists, suggesting a mechanism of action dependent on these receptors. In fact, Oxy decreased ERα expression and activation and induced AR overexpression with a pro-death effect. Complementary transactivation assays demonstrated that Oxy presents ER antagonist and AR agonist activities. In addition, Oxy also decreased the viability and caused apoptosis of LTEDaro cells. Therefore, this work highlights the discovery of a new and promising multi-target drug that, besides acting as an AI, appears to also act as an ERα antagonist and AR agonist. Thus, the multi-target action of Oxy may be a therapeutic advantage over the three AIs applied in clinic. Furthermore, this new multi-target compound has the ability to sensitize the AI-resistant BC cells, which represents another advantage over the endocrine therapy used in the clinic, since resistance is a major drawback in the clinic. Full article

(This article belongs to the Special Issue Steroid Compounds with Potential Biological Activity)

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18 pages, 4124 KiB

Open AccessArticle

A Study on the Chemistry and Biological Activity of 26-Sulfur Analogs of Diosgenin: Synthesis of 26-Thiodiosgenin S-Mono- and Dioxides, and Their Alkyl Derivatives

by Aneta M. Tomkiel, Dorota Czajkowska-Szczykowska, Ewa Olchowik-Grabarek, Lucie Rárová, Szymon Sękowski and Jacek W. Morzycki

Molecules 2023, 28(1), 189; https://doi.org/10.3390/molecules28010189 - 26 Dec 2022

Viewed by 2192

Abstract

A chemoselective procedure for MCPBA oxidation of 26-thiodiosgenin to corresponding sulfoxides and sulfone was elaborated. An unusual equilibration of sulfoxides in solution was observed. Moreover, α-alkylation of sulfoxide and sulfone was investigated. Finally, the biological activity of obtained compounds was examined. Full article

(This article belongs to the Special Issue Steroid Compounds with Potential Biological Activity)

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18 pages, 682 KiB

Open AccessFeature PaperArticle

The Isolation, Structure Elucidation and Bioactivity Study of Chilensosides A, A₁, B, C, and D, Holostane Triterpene Di-, Tri- and Tetrasulfated Pentaosides from the Sea Cucumber Paracaudina chilensis (Caudinidae, Molpadida)

by Alexandra S. Silchenko, Sergey A. Avilov, Pelageya V. Andrijaschenko, Roman S. Popov, Ekaterina A. Chingizova, Boris B. Grebnev, Anton B. Rasin and Vladimir I. Kalinin

Molecules 2022, 27(21), 7655; https://doi.org/10.3390/molecules27217655 - 7 Nov 2022

Cited by 3 | Viewed by 2267

Abstract

Five new triterpene (4,4,14-trimethylsterol) di-, tri- and tetrasulfated pentaosides, chilensosides A (1), A₁ (2), B (3), C (4), and D (5) were isolated from the Far-Eastern sea cucumber Paracaudina chilensis. The structures were established on the basis of extensive analysis of 1D and 2D NMR spectra and confirmed by HR-ESI-MS data. The structural variability of the glycosides concerned the pentasaccharide chains. Their architecture was characterized by the upper semi-chain consisting of three sugar units and the bottom semi-chain of two sugars. Carbohydrate chains of compounds 2–5 differed in the quantity and positions of sulfate groups. The interesting structural features of the glycosides were: the presence of two sulfate groups at C-4 and C-6 of the same glucose residue in the upper semi-chain of 1, 2, 4, and 5 and the sulfation at C-3 of terminal glucose residue in the bottom semi-chain of 4 that makes its further elongation impossible. Chilensoside D (5) was the sixth tetrasulfated glycoside found in sea cucumbers. The architecture of the sugar chains of chilensosides A–D (1–5), the positions of sulfation, the quantity of sulfate groups, as well as the aglycone structures, demonstrate their similarity to the glycosides of the representatives of the order Dendrochirotida, confirming the phylogenetic closeness of the orders Molpadida and Dendrochirotida. The cytotoxic activities of the compounds 1–5 against human erythrocytes and some cancer cell lines are presented. Disulfated chilensosides A₁ (2) and B (3) and trisulfated chilensoside C (4) showed significant cytotoxic activity against human cancer cells. Full article

(This article belongs to the Special Issue Steroid Compounds with Potential Biological Activity)

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18 pages, 3592 KiB

Open AccessArticle

Novel 4-Azapregnene Derivatives as Potential Anticancer Agents: Synthesis, Antiproliferative Activity and Molecular Docking Studies

by Vanessa Brito, Adriana Oliveira Santos, Gilberto Alves, Paulo Almeida and Samuel Silvestre

Molecules 2022, 27(18), 6126; https://doi.org/10.3390/molecules27186126 - 19 Sep 2022

Cited by 4 | Viewed by 2480

Abstract

A series of novel 21E-arylidene-4-azapregn-5-ene steroids has been successfully designed, synthesized and structurally characterized, and their antiproliferative activity was evaluated in four different cell lines. Within this group, the 21E-(pyridin-3-yl)methylidene derivative exhibited significant cytotoxic activity in hormone-dependent cells LNCaP (IC₅₀ = 10.20 µM) and T47-D cells (IC₅₀ = 1.33 µM). In PC-3 androgen-independent cells, the steroid 21E-p-nitrophenylidene-4-azapregn-5-ene was the most potent of this series (IC₅₀ = 3.29 µM). Considering these results, the 21E-(pyridin-3-yl)methylidene derivative was chosen for further biological studies on T47-D and LNCaP cells, and it was shown that this azasteroid seems to lead T47-D cells to apoptotic death. Finally, molecular docking studies were performed to explore the affinity of these 4-azapregnene derivatives to several steroid targets, namely 5α-reductase type 2, estrogen receptor α, androgen receptor and CYP17A1. In general, compounds presented higher affinity to 5α-reductase type 2 and estrogen receptor α. Full article

(This article belongs to the Special Issue Steroid Compounds with Potential Biological Activity)

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Review

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53 pages, 10056 KiB

Open AccessReview

Fascinating Furanosteroids and Their Pharmacological Profile

by Valery M. Dembitsky

Molecules 2023, 28(15), 5669; https://doi.org/10.3390/molecules28155669 - 26 Jul 2023

Cited by 7 | Viewed by 2628

Abstract

This review article delves into the realm of furanosteroids and related isoprenoid lipids derived from diverse terrestrial and marine sources, exploring their wide array of biological activities and potential pharmacological applications. Fungi, fungal endophytes, plants, and various marine organisms, including sponges, corals, molluscs, and other invertebrates, have proven to be abundant reservoirs of these compounds. The biological activities exhibited by furanosteroids and related lipids encompass anticancer, cytotoxic effects against various cancer cell lines, antiviral, and antifungal effects. Notably, the discovery of exceptional compounds such as nakiterpiosin, malabaricol, dysideasterols, and cortistatins has revealed their potent anti-tuberculosis, antibacterial, and anti-hepatitis C attributes. These compounds also exhibit activity in inhibiting protein kinase C, phospholipase A2, and eliciting cytotoxicity against cancer cells. This comprehensive study emphasizes the significance of furanosteroids and related lipids as valuable natural products with promising therapeutic potential. The remarkable biodiversity found in both terrestrial and marine ecosystems offers an extensive resource for unearthing novel biologically active compounds, paving the way for future drug development and advancements in biomedical research. This review presents a compilation of data obtained from various studies conducted by different authors who employed the PASS software 9.1 to evaluate the biological activity of natural furanosteroids and compounds closely related to them. The utilization of the PASS software in this context offers valuable advantages, such as screening large chemical libraries, identifying compounds for subsequent experimental investigations, and gaining insights into potential biological activities based on their structural features. Nevertheless, it is crucial to emphasize that experimental validation remains indispensable for confirming the predicted activities. Full article

(This article belongs to the Special Issue Steroid Compounds with Potential Biological Activity)

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53 pages, 13822 KiB

Open AccessReview

Biological Activity and Structural Diversity of Steroids Containing Aromatic Rings, Phosphate Groups, or Halogen Atoms

by Valery M. Dembitsky

Molecules 2023, 28(14), 5549; https://doi.org/10.3390/molecules28145549 - 20 Jul 2023

Cited by 22 | Viewed by 4636

Abstract

This review delves into the investigation of the biological activity and structural diversity of steroids and related isoprenoid lipids. The study encompasses various natural compounds, such as steroids with aromatic ring(s), steroid phosphate esters derived from marine invertebrates, and steroids incorporating halogen atoms (I, Br, or Cl). These compounds are either produced by fungi or fungal endophytes or found in extracts of plants, algae, or marine invertebrates. To assess the biological activity of these natural compounds, an extensive examination of referenced literature sources was conducted. The evaluation encompassed in vivo and in vitro studies, as well as the utilization of the QSAR method. Numerous compounds exhibited notable properties such as strong anti-inflammatory, anti-neoplastic, anti-proliferative, anti-hypercholesterolemic, anti-Parkinsonian, diuretic, anti-eczematic, anti-psoriatic, and various other activities. Throughout the review, 3D graphs illustrating the activity of individual steroids are presented alongside images of selected terrestrial or marine organisms. Additionally, the review provides explanations for specific types of biological activity associated with these compounds. The data presented in this review hold scientific interest for academic science as well as practical implications in the fields of pharmacology and practical medicine. The analysis of the biological activity and structural diversity of steroids and related isoprenoid lipids provides valuable insights that can contribute to advancements in both theoretical understanding and applied research. Full article

(This article belongs to the Special Issue Steroid Compounds with Potential Biological Activity)

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32 pages, 5139 KiB

Open AccessReview

The Structural Diversity and Biological Activity of Steroid Oximes

by Ana R. Gomes, Ana S. Pires, Fernanda M. F. Roleira and Elisiário J. Tavares-da-Silva

Molecules 2023, 28(4), 1690; https://doi.org/10.3390/molecules28041690 - 10 Feb 2023

Cited by 8 | Viewed by 4019

Abstract

Steroids and their derivatives have been the subject of extensive research among investigators due to their wide range of pharmacological properties, in which steroidal oximes are included. Oximes are a chemical group with the general formula R₁R₂C=N−OH and they exist as colorless crystals and are poorly soluble in water. Oximes can be easily obtained through the condensation of aldehydes or ketones with various amine derivatives, making them a very interesting chemical group in medicinal chemistry for the design of drugs as potential treatments for several diseases. In this review, we will focus on the different biological activities displayed by steroidal oximes such as anticancer, anti-inflammatory, antibacterial, antifungal and antiviral, among others, as well as their respective mechanisms of action. An overview of the chemistry of oximes will also be reported, and several steroidal oximes that are in clinical trials or already used as drugs are described. An extensive literature search was performed on three main databases—PubMed, Web of Science, and Google Scholar. Full article

(This article belongs to the Special Issue Steroid Compounds with Potential Biological Activity)

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