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https://www.readbyqxmd.com/read/28342744/synthesis-and-anti-cancer-activity-of-chiral-tetrahydropyrazolo-1-5-a-pyridine-fused-steroids
#1
Susana M M Lopes, Emanuel P Sousa, Luísa Barreira, Cátia Marques, Maria João Rodrigues, Teresa M V D Pinho E Melo
Regio- and stereoselective synthesis of novel chiral 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-fused steroids via [8π+2π] cycloaddition of diazafulvenium methides with steroidal scaffolds is reported. The biological evaluation of the new family of hexacyclic steroids as anti-cancer agents was also carried out. Hexacyclic steroids bearing a benzyl group at C-22, derived from 16-dehydropregnenolone and 16-dehydroprogesterone, show considerable cytotoxicity against EL4 (murine T-lymphoma) in contrast with the corresponding C-22-unsubstituted derivatives showing low cytotoxicity...
March 22, 2017: Steroids
https://www.readbyqxmd.com/read/28327355/cytotoxic-and-apoptosis-inducing-activity-of-c21-steroids-from-the-roots-of-cynanchum-atratum
#2
Jian Zhang, Lin Ma, Zheng-Feng Wu, Shu-Le Yu, Lei Wang, Wen-Cai Ye, Qing-Wen Zhang, Zhi-Qi Yin
Two new(1-2) and two known C21steroids (3-4) were isolated from the roots of Cynanchum atratum. Their structures were elucidated by detailed 1D and 2D spectroscopic.The MTT assay showed that compounds 1-4 displayed obvious cytotoxic activities against HepG2 cells with IC50 values ranging from 10.19μM to 76.12μM. Compounds 1-3 also exhibited cytotoxic effects in A549 cells with IC50 values of 30.87-95.39 μM. Compound 3 showed the antiproliferative activity via G0/G1 cell cycle arrest and proapoptosis in HepG2 cells by Flowcytometry analysis...
March 18, 2017: Steroids
https://www.readbyqxmd.com/read/28322864/water-soluble-derivatives-of-25-och3-ppd-and-their-anti-proliferative-activities
#3
Wu-Xi Zhou, Yuan-Yuan Sun, Wei-Hui Yuan, Yu-Qing Zhao
(20R)-25-Methoxyl-dammarane-3β,12β,20-triol (25-OCH3-PPD, AD-1) is a dammarane-type sapogenin showing anti-tumor potential. In the search for new anti-tumor agents with higher potency than our previously identified compound 25-OCH3-PPD, 11 novel sulfamic acid and diacid derivatives that could improve water solubility and contribute to good drug potency and pharmacokinetic profiles were designed and synthesized. Their in vitro anti-tumor activities in MCF-7, A-549, HCT-116, and BGC-823 cell lines and one normal cell line were tested by standard MTT assay...
March 18, 2017: Steroids
https://www.readbyqxmd.com/read/28300584/synthesis-of-side-chain-oxysterols-and-their-enantiomers-through-cross-metathesis-reactions-of-%C3%AE-22-steroids
#4
David P Brownholland, Douglas F Covey
A synthetic route that utilizes a cross-metathesis reaction with Δ(22) steroids has been developed to prepare sterols with varying C-27 side-chains. Natural sterols containing hydroxyl groups at the 25 and (25R)-26 positions were prepared. Enantiomers of cholesterol and (3β,25R)-26-hydroxycholesterol (27-hydroxycholesterol) trideuterated at C-19 were prepared for future biological studies.
March 12, 2017: Steroids
https://www.readbyqxmd.com/read/28300583/synthesis-of-new-c-25-and-c-26-steroidal-acids-as-potential-ligands-of-the-nuclear-receptors-daf-12-lxr-and-gr
#5
María V Dansey, María C Del Fueyo, Adriana S Veleiro, Pablo H Di Chenna
A new methodology to obtain C-25 and C-26 steroidal acids starting from pregnenolone is described. Construction of the side chain was achieved by applying the Mukaiyama aldol reaction with a non-hydrolytic work-up to isolate the trapped silyl enol ether with higher yields. Using this methodology we synthesized three new steroidal acids as potential ligands of DAF-12, Liver X and Glucocorticoid nuclear receptors and studied their activity in reporter gene assays. Our results show that replacement of the 21-CH3 by a 20-keto group in the side chains of the cholestane scaffold of DAF-12 or Liver X receptors ligands causes the loss of the activity...
March 11, 2017: Steroids
https://www.readbyqxmd.com/read/28288896/age-and-menopause-related-differences-in-subcutaneous-adipose-tissue-estrogen-receptor-mrna-expression
#6
Young-Min Park, Christopher Erickson, Dan Bessesen, Rachael E Van Pelt, Kimberly Cox-York
OBJECTIVES: Changes in estrogen receptor (ER) expression likely underlie differential metabolic effects of estrogen in pre- and postmenopausal women. The aim of the current study was to determine whether ER gene expression in abdominal and femoral subcutaneous adipose tissue (SAT) was associated with age, menopause, or regional adiposity. METHODS: We studied pre- and post-menopausal (n=23 and 22, respectively; age 35-65y) normal weight (mean±SD; BMI 23.7±2.5kg/m(2)) women with similar total fat mass...
March 10, 2017: Steroids
https://www.readbyqxmd.com/read/28267564/development-of-17%C3%AE-hydroxysteroid-dehydrogenase-type-3-as-a-target-in-hormone-dependent-prostate-cancer-therapy
#7
REVIEW
Xiaohui Ning, Yan Yang, Hong Deng, Qihao Zhang, Yadong Huang, Zhijian Su, Yongmei Fu, Qi Xiang, Shu Zhang
17β-Hydroxysteroid dehydrogenase type 3 (17β-HSD3) is expressed almost exclusively in the testes and specifically converts the weak androgenic androstenedione to active testosterone (T) in the presence of NADPH. Additionally, studies have demonstrated that 17β-HSD3 is over-expressed in hormone-dependent prostate cancer. T, which interacts with the androgen receptor (AR), eventually stimulates the growth of prostate cancer cells. Defects in T synthesis or action impair the development of the male phenotype during embryogenesis and cause the autosomal recessive disorder male pseudohermaphroditism...
March 4, 2017: Steroids
https://www.readbyqxmd.com/read/28237768/steroidal-saponins-from-datura-metel
#8
Nguyen Thi Mai, Nguyen Thi Cuc, Hoang Le Tuan Anh, Nguyen Xuan Nhiem, Bui Huu Tai, Chau Van Minh, Tran Hong Quang, Kwan Woo Kim, Youn-Chul Kim, Hyuncheol Oh, Phan Van Kiem
Datura metel L. (Solanaceae) is an annual herb that has been widely used in the traditional medicine for the treatment of coughs, bronchial asthma, and rheumatism. Chemical investigation of an acidic methanol extract of the whole plants of D. metel resulted in the isolation of five new steroidal saponins (1-3, 5, and 6), named metelosides A-E, and four known compounds (4, 7-9). Their structures were elucidated by extensive spectroscopic methods, including 1D and 2D NMR and MS spectra. The structures of metelosides A and B were found to be unusual among the reported spirostane-type steroidal saponins due to the presence of the acetamide groups in the molecules...
February 22, 2017: Steroids
https://www.readbyqxmd.com/read/28143704/-22%C3%AE-25r-3%C3%AE-hydroxy-spirost-5-en-7-iminoxy-heptanoic-acid-exhibits-anti-prostate-cancer-activity-through-caspase-pathway
#9
A A Hamid, Tanu Kaushal, Raghib Ashraf, Arjun Singh, Amit Chand Gupta, Om Prakash, Jayanta Sarkar, Debabrata Chanda, D U Bawankule, Feroz Khan, Karuna Shanker, O O Aiyelaagbe, Arvind S Negi
Prostate cancer is one of the most common cancers in men. Diosgenin and related compounds are potential cytotoxic agents. Twelve diverse analogues of long chain fatty acid/ester of diosgenin-7-ketoxime have been prepared. Six of the analogues exhibited significant anticancer activity against a panel of human cancer cell lines with IC50 ranging from 12 to 35μM. Compound 16, the best representative of the series exerted S phase arrest in DU145 prostate cancer cells and induced apoptosis through caspase pathway...
January 28, 2017: Steroids
https://www.readbyqxmd.com/read/28119082/a-hydroxylated-flavonol-fisetin-inhibits-the-formation-of-a-carcinogenic-estrogen-metabolite
#10
Xin Meng, Hui Sun, Lianrong Yang, Rui Yin, Lehui Qi
Fisetin can be found in a wide variety of plants and possesses strong efficacy against many cancers. 17β-Estradiol (E2) is hydrolyzed to 4-hydroxy-E2 (4-OHE2) via cytochrome P450 (CYP) 1B1 in vivo. In estrogen target tissues including the mammary gland, ovaries, and uterus, CYP1B1 is highly expressed, and 4-OHE2 is predominantly formed in cancerous tissues. Herein, we investigated the inhibitory activity of fisetin and flavone against CYP1B1 using estrogen E2 as substrate in vitro to reveal structure-activity relationship between structure of flavonoids and inhibition...
January 22, 2017: Steroids
https://www.readbyqxmd.com/read/28119080/allopregnanolone-promotes-proliferation-and-differential-gene-expression-in-human-glioblastoma-cells
#11
Carmen J Zamora-Sánchez, Valeria Hansberg-Pastor, Ivan Salido-Guadarrama, Mauricio Rodríguez-Dorantes, Ignacio Camacho-Arroyo
Allopregnanolone (3α-THP) is one of the main reduced progesterone (P4) metabolites that is recognized as a neuroprotective and myelinating agent. 3α-THP also induces proliferation of different neural cells. It has been shown that P4 favors the progression of glioblastomas (GBM), the most common and aggressive primary brain tumors. However, the role of 3α-THP in the growth of GBMs is unknown. Here, we studied the effects of 3α-THP on the number of cells, proliferation and gene expression in U87 cell line derived from a human GBM...
January 22, 2017: Steroids
https://www.readbyqxmd.com/read/28089927/metabolism-of-selective-20-epi-vitamin-d3-analogs-in-rat-osteosarcoma-umr-106-cells-isolation-and-identification-of-four-novel-c-1-fatty-acid-esters-of-1%C3%AE-25-dihydroxy-16-ene-20-epi-vitamin-d3
#12
Caroline Ceailles Flarakos, Andrew Weiskopf, Matthew Robinson, Guoshun Wang, Paul Vouros, Gino J Sasso, Milan R Uskokovic, G Satyanarayana Reddy
Analogs of 1α,25-dihydroxyvitamin D3 (S1) with 20-epi modification (20-epi analogs) possess unique biological properties. We previously reported that 1α,25-dihydroxy-20-epi-vitamin D3 (S2), the basic 20-epi analog is metabolized into less polar metabolites (LPMs) in rat osteosarcoma cells (UMR-106) but not in a perfused rat kidney. Furthermore, we also noted that only selective 20-epi analogs are metabolized into LPMs. For example, 1α,25-dihydroxy-16-ene-20-epi-vitamin D3 (S4), but not 1α,25-dihydroxy-16-ene-23-yne-20-epi-vitamin D3 (S5) is metabolized into LPMs...
January 12, 2017: Steroids
https://www.readbyqxmd.com/read/28063793/interleukin-6-increases-the-expression-of-key-proteins-associated-with-steroidogenesis-in-human-nci-h295r-adrenocortical-cells
#13
Janae Strickland, Stephen McIlmoil, Brice J Williams, Dennis C Seager, James P Porter, Allan M Judd
Mechanisms of interleukin-6 (IL-6)-induced cortisol release (CR) were investigated by exposing H295R cells to IL-6 and determining mRNA/protein expression (PCR/western blots) for steroidogenic enzymes (SE), steroidogenic acute regulatory protein (StAR), steroidogenic factor-1 (SF-1) (enhances SE/StAR expression), activator protein 1 (AP-1) (regulates SE/StAR expression) and adrenal hypoplasia congenita-like protein (DAX-1) (inhibits SE/StAR expression). Promoter activity of StAR (SPA) was measured by a luciferase-coupled promoter...
January 4, 2017: Steroids
https://www.readbyqxmd.com/read/28063792/syntheses-and-antiproliferative-activities-of-novel-phosphatidylcholines-containing-dehydroepiandrosterone-moieties
#14
Marek Kłobucki, Aleksandra Grudniewska, Damian A Smuga, Małgorzata Smuga, Joanna Jarosz, Joanna Wietrzyk, Gabriela Maciejewska, Czesław Wawrzeńczyk
Dehydroepiandrosterone (DHEA) is a natural hormone with many beneficial properties including an anticancer activity. Unfortunately, DHEA is unstable in the body and exhibits cytotoxicity against healthy cells. In this study, a series of new phosphocholines containing DHEA at sn-1 and/or sn-2 positions were prepared. Succinic acid was used as a linker between the active drug and sn-glycero-3-phosphocholine. All the compounds were evaluated in vitro for their antiproliferative activities against four cell lines: Balb/3T3, HL-60, B16, and LNCaP...
January 4, 2017: Steroids
https://www.readbyqxmd.com/read/28041953/synthetic-approaches-towards-the-multi-target-drug-spironolactone-and-its-potent-analogues-derivatives
#15
REVIEW
Fayaz Ali Larik, Aamer Saeed, Danish Shahzad, Muhammad Faisal, Hesham El-Seedi, Haroon Mehfooz, Pervaiz Ali Channar
Spironolactone is a well-known multi-target drug and is specifically used for the treatment of high blood pressure and heart failure. It is also used for the treatment of edema, cirrhosis of the liver, malignant, pediatric, nephrosis and primary hyperaldosteronism. Spironolactone in association with thiazide diuretics treats hypertension and in association with furosemide treats bronchopulmonary dyspepsia. The therapeutic mechanism of action of spironolactone involves binding to intracellular mineralocorticoids receptors (MRs) in kidney epithelial cells, thereby inhibiting the binding of aldosterone...
December 29, 2016: Steroids
https://www.readbyqxmd.com/read/28041952/synthesis-of-23-deoxy-25-epi-north-unit-of-cephalostatin-1-via-reductive-and-oxidative-modifications-of-hecogenin-acetate
#16
Rayala Naveen Kumar, Seongmin Lee
An efficient synthesis of the 23-deoxy-25-epi north unit of cephalostatin 1 has been achieved in 17 steps via reductive and oxidative functionalizations of hecogenin acetate with an overall yield of 3.8%. This synthesis features transetherification-mediated E-ring opening, D-ring oxidation, hemiketalization-mediated E-ring closure, and stereoselective 5/5-spiroketalization.
December 29, 2016: Steroids
https://www.readbyqxmd.com/read/28192128/antitumor-activity-of-newly-synthesized-oxo-and-ethylidene-derivatives-of-bile-acids-and-their-amides-and-oxazolines
#17
Srđan Bjedov, Dimitar Jakimov, Ana Pilipović, Mihalj Poša, Marija Sakač
Bile acid derivatives with modifications in side chain and modifications on steroid skeleton were synthetized and their antitumor activity against five human cancer cell lines was investigated. Modifications in side chain include amid group, formed in reaction with 2-amino-2-methylpropanol, and 4,4-dimethyloxazoline group, obtained after cyclization of amides. In the steroid skeleton oxo groups were introduced in position 7 (2, 2a, 2b) and 7,12 (3, 3a, 3b). Ethylidene groups were introduced regio- and stereoselectively on C-7, and/or without stereoselectivity on C-3 by Wittig reaction...
April 2017: Steroids
https://www.readbyqxmd.com/read/28192127/long-term-treatment-with-nandrolone-decanoate-impairs-mesenteric-vascular-relaxation-in-both-sedentary-and-exercised-female-rats
#18
Izabela F Caliman, Cristian S Bernabe, Antônio F de Melo, Girlândia A Brasil, Andrews M do Nascimento, Ewelyne M de Lima, Suely G Figueiredo, Tadeu U de Andrade, Nazaré S Bissoli
Nandrolone Decanoate (ND) is an Anabolic Androgenic Steroid (AAS) that under abusive regimen can lead to multiple physiological adverse effects. Studies of AAS-mediated cardiovascular (CV) alterations were mostly taken from male subjects, even though women are also susceptible to the effects of AAS and gender-specific differences in susceptibility to vascular diseases exist. Here we investigate ND-induced vascular reactivity alterations in both sedentary and exercised female rats and whether these alterations depend on endothelium-derived factors...
April 2017: Steroids
https://www.readbyqxmd.com/read/28189541/adhesive-blood-microsampling-systems-for-steroid-measurement-via-lc-ms-ms-in-the-rat
#19
Kirsten Heussner, Manfred Rauh, Nada Cordasic, Carlos Menendez-Castro, Hanna Huebner, Matthias Ruebner, Marius Schmidt, Andrea Hartner, Wolfgang Rascher, Fabian B Fahlbusch
INTRODUCTION: Liquid Chromatography Tandem Mass Spectrometry (LC-MS/MS) allows for the direct analysis of multiple hormones in a single probe with minimal sample volume. Rodent-based animal studies strongly rely on microsampling, such as the dry blood spot (DBS) method. However, DBS suffers the drawback of hematocrit-dependence (non-volumetric). Hence, novel volumetric microsampling techniques were introduced recently, allowing sampling of fixed accurate volumes. We compared these methods for steroid analysis in the rat to improve inter-system comparability...
April 2017: Steroids
https://www.readbyqxmd.com/read/28167101/quinone-related-hexacyclic-by-products-in-the-production-process-of-exemestane
#20
Giovanni Battista Giovenzana, Norberto Masciocchi, Roberto Negri, Giovanni Palmisano, Andrea Penoni, Lucio Toma
Exemestane, a 3rd-generation aromatase inhibitor, is clinically used in the treatment of breast cancer in postmenopausal women. The key step of the industrial synthetic process, i.e., a dehydrogenation to introduce the Δ(1)-unsaturation, is normally performed with quinones such as p-chloranil or DDQ. We observed the formation of two different hexacyclic by-products, depending on the quinone used in the oxidation step. These compounds arise from an initial [4+2] cycloaddition between the precursor 6-methylenandrost-4-ene-3,17-dione and the quinone reagent, followed by a twofold dehydrohalogenation (with p-chloranil) or dehydrogenation (with DDQ)...
April 2017: Steroids
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