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Frederick A Meece, Gulzar Ahmed, Hareesh Nair, Bindu Santhamma, Rajeshwar R Tekmal, Chumang Zhao, Nicole E Pollok, Julia Lara, Ze'ev Shaked, Klaus Nickisch
An effort with the goal of discovering single-dose, long-lasting (>6 months) injectable contraceptives began using levonorgestrel (LNG)-17-β esters linked to a sulfonamide function purposed as human carbonic anhydrase II (hCA 2) ligands. One single analog from this first series showed noticeably superior anti-ovulatory activity in murine models, and a subsequent structure-activity relationship (SAR, the relationship between a compound's molecular structure and its biological activity) study based on this compound identified a LNG-phenoxyacetic acid ester analog exhibiting longer anti-ovulatory properties using the murine model at 2 and 4 mg dose than medroxyprogesterone acetate (MPA)...
August 4, 2018: Steroids
Sen Liu, Ying Wang, Mingzhi Su, Shao-Jiang Song, Jongki Hong, Suhkmann Kim, Dong Soon Im, Jee H Jung
During our search for bioactive secondary metabolites in the jellyfish-derived fungus Penicillium chrysogenum J08NF-4, several bile acid derivatives (2-6) were isolated along with a new steroidal artifact (1). An in vitro anti-inflammatory assay showed that pretreatment with 1 suppressed NO production and the gene expressions of the pro-inflammatory mediators iNOS and TNF-α in LPS-induced RAW 264.7 macrophages. Docking analysis of 1 revealed that it might bind to the ligand binding domain (LBD) of PPARγ in a manner similar to that of the synthetic steroid mifepristone (7), which is used clinically to treat hypercortisolism and was recently reported to be a PPARγ agonist...
August 4, 2018: Steroids
Ana Carolina Momentti, Débora Estadella, Luciana Pellegrini Pisani
There is a growing concern about the impacts of hypovitaminosis D on the health of pregnant woman, fetal development, childhood, and adult life. Variations in maternal nutrition during gestation and/or lactation play a critical role in the physiological and metabolic development of the fetus and neonate, which can induce phenotypic changes and trigger important consequences throughout life, such as type 2 diabetes, cardiovascular disease, obesity, and hypertension. Vitamin D plays a role in regulating cell proliferation and differentiation and in modulating the innate and adaptive immune response...
July 29, 2018: Steroids
Mehri Javid, Bahman Nickavar, Hossein Vahidi, Mohammad Ali Faramarzi
Microbial transformations are capable of producing steroid substances difficult to synthesize by chemical methods. Strains belonging to the genus Aspergillus are effective facilitators of microbial biotransformations due to their enzymatic diversity. In this study, the biotransformation of progesterone by the fungus Aspergillus sojae (A. sojae) PTCC 5196 was examined. Analysis of the bioconversion process revealed that progesterone was converted to testololactone through a three-step pathway (17β-acetyl side chain cleavage, 17β-hydroxyl oxidation, and oxygenative lactonization of 17-ketone), indicating the presence of Baeyer-Villiger monooxygenase (BVMO) activity in the fungal strain...
July 25, 2018: Steroids
Soumya Salas, Kajal Chakraborty
Two unusual △5 sterols with unprecedented skeletons were isolated from the organic extract of muricid gastropod Chicoreus ramosus collected off the Gulf of Mannar Coast. This is the first report of isolation of bioactive sterols endowed with anti-inflammatory potentials from this species. The compounds were characterized as (5Z)-24a-homocholesta-5,24a1 (24a2 ) dien-3β-ol (1) and 27(25→23)-abeo-(5Z)-3β-hydroxy-24-isopropyl cholesteno-26,23-lactone (2) by the interpretation of a series of spectroscopic techniques involving two-dimensional nuclear magnetic resonance and mass spectral data...
July 25, 2018: Steroids
Shardool Nair, Geetanjali Sachdeva
Metastatic cancer cells meet several physical, biochemical and immunological barriers before colonizing a new territory. Cancerous cells turn invasive, mobile and eventually disengage from their native niche. This is followed by their intravasation, extravasation, survival, proliferation, and colonization into distant organs. Unlike well-confined tumors, which respond favorably to anti-cancer therapeutics, metastatic tumors are life-threatening and incurable. More than 90% of cancer-related mortality is caused by metastases, hence the emphasis is now on developing the strategies to block or reverse the process of metastasis...
July 20, 2018: Steroids
Ligia R Gomes, John N Low, Alan B Turner, James L Wardell
The crystal structures and Hirshfeld surface analyses of two hemi-solvates of 3α-hydroxy-16α-bromoandrostan-17-one, 3, namely [(3)2 .(H2 O)] and [(3)2 .(MeOH)], are reported. Both solvates crystallize in the monoclinic space group, P21 , with Z = 4.. The asymmetric unit of the hemi-hydrate [(3)2 .(H2 O)] contains two independent but similar steroid molecules and a water molecule, while that of the hemi-methanoate [(3)2 .(MeOH)] has four similar but independent steroid molecules and two methanol molecules...
July 20, 2018: Steroids
Yury V Kuznetsov, Inna S Levina, Alexander M Scherbakov, Olga E Andreeva, Andrey S Dmitrenok, Oleg R Malyshev, Igor V Zavarzin
New 3,20-dihydroxy-13α-19-norpregna-1,3,5(10)-trienes were synthesized. The effects of these compounds on breast cancer cells and ERα activation were investigated. The scaffold of compounds containing the six-membered ring D' annulated at 16α,17α-positions was constructed via the Lewis acid catalyzed Diels-Alder reaction of butadiene with 3-methoxy-13α-19-norpregna-1,3,5(10),16-tetraen-20-one 5 under a pressure of 600 MPa. The hydrogenation of primary cyclohexene adduct 6 followed by the one-pot reduction-demethylation (DIBAH) gave target epimeric 3,20-dihydroxy steroids 8a and 8b...
July 20, 2018: Steroids
Aymen Ben Nejma, Mansour Znati, Adam Daich, Mohamed Othman, Ata Martin Lawson, Hichem Ben Jannet
Interesting biological activities (anti-inflammatory, anticancer, antiviral, antioxidant, antidiabetic…) have been reported for maslinic acid (MA) and MA-based compounds. In continuation of our previous work on MA, herbicide potential of Tunisian plant extracts and 1,4-triazolyl derivatives of MA, we now wish to report semisynthesis of new MA-based triazole hybrid compounds with herbicide potential. These compounds were synthesized through Cu-catalyzed azide-alkyne cycloaddition (CuAAC) under microwave irradiation conditions between propargylated MA and a series of phthalimide azides...
July 19, 2018: Steroids
Cheryl S Watson, Luke Koong, Yow-Jiun Jeng, Rene Vinas
Rapid nongenomic signaling by estrogens (Es), initiated near the cell membrane, provides new explanations for the potent actions of environmental chemicals that imperfectly mimic physiological Es. These pathways can affect tumor growth, stabilization, or shrinkage via a number of signaling streams such as activation/inactivation of mitogen-activated protein kinases and caspases, generation of second messengers, and phospho-triggering of cyclin instability. Though prostate cancers are better known for their responsiveness to androgen deprivation, ∼17% of late stage tumors regress in response to high dose natural or pharmaceutical Es; however, the mechanisms at the cellular level are not understood...
July 19, 2018: Steroids
Veronika M Gebhart, Jack D Caldwell, Andrea Rodewald, Konstantina Kalyvianaki, Marilena Kampa, Gustav F Jirikowski
Estrogens exert a critical influence on neuronal tissues and cells. As demonstrated in many clinical studies, estrogens are neuroprotective to the extent that they improve prognosis for women with neurodegenerative diseases. Unfortunately, we still do not know exactly how these effects are mediated. Fifty years ago the first estrogen receptor was found, but since then many other new pathways of estrogen action have been identified. This review describes several of these pathways of estrogen effects and provides some conclusions and correlations about these as determined by recent studies with nerve growth factor differentiated rat pheochromocytoma cell line...
July 18, 2018: Steroids
Romain Jouve, Vincent Thery, Sylvie Ducki, Julie Helfenbein, Jean-Christophe Thiery, Aurélie Job, Elodie Picard, Christophe Mallet, Isabelle Ripoche, Khalil Bennis
A short and efficient synthesis, based on a one-step double elimination, of a key intermediate in the synthesis of various glucocorticosteroids has been developed. This method can be carried out on large scale for further industrial applications. The synthesis allowed us to identify a novel prednisolone derivative 10 and its anti-inflammatory activity was determined in an in vivo model of inflammation. In order to understand the regioselectivity of the double elimination under various conditions, mechanistic studies were undertaken and confirmed the experimental results...
July 12, 2018: Steroids
Nur Siti Khadijah Ramli, Nelli Giribabu, Naguib Salleh
Effects of testosterone on expression and functional activity of ENaC, CFTR and NHE in vas deferens were investigated. METHODS: Orchidectomized, adult male rats were given 125 and 250 μg/kg/day testosterone subcutaneously, with or without flutamide and finasteride for seven consecutive days. At the end of the treatment, rats were anesthetized and vas deferens were perfused. Changes in vas deferens fluid secretion rate, pH, HCO3 - , Cl- and Na+ concentrations were recorded in the presence of amiloride and Cftr inh-172...
July 10, 2018: Steroids
Marcos Vinícius de Moura Ribeiro, Nivaldo Boralle, Lidiane Gaspareto Felippe, Helena Redigolo Pezza, Leonardo Pezza
Counterfeiting and adulteration of pharmaceuticals is a prevalent problem worldwide and represents a major health risk to the population, with anabolic steroids being one of the main classes of drugs consumed and obtained from dubious sources. In this work, we propose the use of the 1 H NMR technique to evaluate formulations containing anabolic steroids, with analysis of 40 samples of anabolic drugs that are used in injectable and capsule forms. The samples analyzed presented the following active ingredients: testosterone propionate, testosterone phenylpropionate, testosterone isocaproate, testosterone decanoate, testosterone cypionate, testosterone undecanoate, stanozolol, drostanolone propionate, trenbolone acetate, oxymetholone, and methandrostenolone...
July 10, 2018: Steroids
Guo-Mei Hou, Xiu-Mei Xu, Qian Wang, Dan-Yi Li, Zhan-Lin Li
A new hybrid of dehydroergosterol and nitrogenous alternariol derivative, pestauvicomorpholine A (1), and three alternariol analogues (2-4) including a new aminated one, pestauvicolactone A (2), were isolated from the fermentation product of the fungus Pestalotiopsis uvicola on rice media. Compounds 1 and 2 represent the first example of aza-alternariol and aza-alternariol-steroid derived from transamination followed by intermolecular hetero-Diels-Alder reaction.
July 10, 2018: Steroids
Alexander M Scherbakov, Igor V Zavarzin, Svetlana K Vorontsova, Alakananda Hajra, Olga E Andreeva, Anton V Yadykov, Inna S Levina, Yulia A Volkova, Valerii Z Shirinian
Novel benzylidenes (chalcones) of the 16-dehydroprogesterone series have been characterized and their antitumor activity against two breast cancer cell lines was evaluated. Benzylidenes exhibit significant antiproliferative effect on cells and inhibit cell growth in hormone-dependent MCF-7 and hormone-independent MDA-MB-231 breast cancer cell lines. Compound 3d exhibits the highest activity against two breast cancer cell lines, with the IC50 value of about 2 µM. Compounds 3e,m,n display considerable selectivity for hormone-dependent breast cancer cells, with the IC50 value lower than 6 µM...
July 8, 2018: Steroids
Elena Moreno-Castillo, Daniel P Ramírez-Echemendía, Giselle Hernández-Campoalegre, Dayana Mesa-Tejeda, Francisco Coll-Manchado, Yamilet Coll-García
Brassinosteroids (BRs) are hormones found in a wide range of plant species, they are synthesized at low concentrations and are essential for normal growth and development. These phytohormones are recognized by the Leucine-rich-repeat ectodomain of the receptor-like-kinase BRI1 which leads to subsequent downstream signaling mediating plant growth/development. In spite of the advantages that BRs offer, their extraction from natural sources is highly expensive, which constitutes one of its major limitations. Thus, the design and synthesis of structural and/or functional analogues of BRs with higher activity and lower cost has a great practical significance in world agriculture...
July 8, 2018: Steroids
Vladimir A Zolottsev, Gelii V Ponomarev, Maria O Taratynova, Galina E Morozevich, Roman A Novikov, Vladimir P Timofeev, Pavel N Solyev, Maria G Zavialova, Olga V Zazulina, Yaroslav V Tkachev, Alexander Y Misharin
Conjugates of 17α-substituted testosterone (1 and 2) and 17β-substituted epitestosterone (3 and 4) with pyropheophorbide a were synthesized. The scheme consisted of synthesis of 17α-hydroxy-3-oxopregn-4-en-21-oic and 17β-hydroxy-3-oxopregn-4-en-21-oic acids, and their coupling with pyropheophorbide a by means of either ethylene diamine, or 1,5-diamino pentane linkers. Mutual influence of steroidal and macrocyclic fragments in conjugates molecules was dependent on configuration of C17 and length of linker, that was established by analysis of 1 H NMR spectra and molecular models of conjugates...
July 7, 2018: Steroids
Nury Pérez-Hernández, Elvia Becerra-Martínez, Pedro Joseph-Nathan
The 750 MHz 1 H NMR spectrum of cholesteryl benzoate (1b) could be assigned completely, which means all chemical shifts and all coupling constants, including some long-range values, were established. This task was possible by extracting many approximate coupling constant values in the overlapped spectrum region from an HSQC experiment, and using these values in the 1 H iterative full spin analysis integrated in the PERCH NMR software. The task was facilitated using our published data for 3β-acetoxypregna-5,16-dien-20-one (3), the assignment data of the sesquiterpene benzoquinone dihydroperezone (2), also performed in the present study, which contains the same carbon atoms chain than cholesterol (1a), and an HSQC study of (25R)-27-deuteriocholesterol (1c) we prepared some 40 years ago...
July 7, 2018: Steroids
Jumpei Fujiki, Naoyuki Maeda, Michiko Sato, Takahiro Ieko, Hiroki Inoue, Tomohito Iwasaki, Hidetomo Iwano, Hiroshi Yokota
Corticosterone (CORT), the major glucocorticoid in rodents, is secreted from the adrenal gland, affects various organs in the body and regulates energy metabolism as a stress response. Although local steroidogenesis of androgens and estrogens in skeletal muscles has been previously reported, local CORT synthesis in skeletal muscle remains unconfirmed. In the present study, we investigated steroidogenic activities in a clonal myoblastic cell line, C2C12 cells. Three enzymes involved in CORT synthesis, 3ß-hydroxysteroid dehydrogenase (3ß-HSD), cytochrome P450c21 and cytochrome P45011ß, were identified in C2C12 cells by detecting the enzymatic reaction products with LC-MS/MS analysis...
July 7, 2018: Steroids
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