Synthesis, structure analysis and activity against breast and cervix cancer cells of a triterpenoid thiazole derived from ochraceolide A

Publication date: 15 March 2020Source: Journal of Molecular Structure, Volume 1204Author(s): A.D. Herrera-España, J. Us-Martín, S. Hernández-Ortega, G. Mirón-López, L. Quijano, J.R. Villanueva-Toledo, G.J. Mena-RejónAbstractThe structural modification of natural products has shown to be a remarkable tool in the generation of novel bioactive molecules. Herein, the synthesis, structural analysis and anticancer activity of the novel triterpenoid thiazole 3 is reported. The synthesis was carried out through the bromination of ochraceolide A (1) and the subsequent heterocyclic condensation with thiourea (overall yield of 80%). The bromination reaction of 1 led to obtain a diastereomeric mixture of 2α- and 2β-bromo ochraceolide A in a ratio of 6:4 (2a and 2b, respectively). Compound 3 was fully characterized by 1D and 2D NMR spectroscopy, FT-IR, HR-MS and single-crystal X-ray diffraction analysis. The triterpenoid thiazole crystallized as an ethyl acetate hemisolvate in the orthorhombic space group P212121 with one molecule of 3 in the asymmetric unit. In the crystal, the molecules interact mainly through N–H⋯N and N–H⋯S hydrogen bonds via a R22 (8) synthon. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (69.5%), H⋯O/O⋯H (16.4%), H⋯C/C⋯H (5.5%), H⋯S/S⋯H (4.6%) and H⋯N/N⋯H (3.5%) interactions. The cytotoxicity and antiproliferative ac...
Source: Journal of Molecular Structure - Category: Molecular Biology Source Type: research

Related Links:

A new detection method rolled out last month looks for traces of the human papillomavirus (HPV), which cause nearly all cervical tumours.
Source: the Mail online | Health - Category: Consumer Health News Source Type: news
CERVICAL cancer could be ­eliminated thanks to an improved screening method, health chiefs have revealed. In the past, screening samples have been examined and those that showed possible cell changes tested for the human papillomavirus viral infection, that causes the cancer.
Source: Daily Express - Health - Category: Consumer Health News Source Type: news
ConclusionPost-RT persistent lymphopenia could be a poor prognostic factor for patients with cervical cancer who receive RT.
Source: International Journal of Clinical Oncology - Category: Cancer & Oncology Source Type: research
We report a unique case of a 60-year-old woman developing endometrial cancer in a uterine deposit 18 years after she had undergone laparoscopic subtotal hysterectomy with morcellation for benign pathology. She had used unopposed estrogen as menopausal hormone therapy. She presented with a pelvic mass that was causing pressure symptoms. On imaging, the mass had an enhancing vascular nodular component and appeared to abut normal ovaries and the residual cervix. She proceeded to laparotomy, where a 12 cm pelvic mass was found morbidly adherent to the bladder anteriorly and to the cervical stump. The pelvic mass was excise...
Source: Case Reports in Womens Health - Category: OBGYN Source Type: research
This study investigated the relationship between the regulation of SEMA4C on TGF-ß1-induced p38 mitogen-activated protein kinase (MAPK) activation and invasion and metastasis of cervical cancer. MATERIAL AND METHODS Hela-shSEMA4C cell line was established and the success of transfection was confirmed with fluorescence intensity. Cell experiments were divided into 2 groups. Group 1 was Hela, Hela-shNC, and Hela-shSEMA4C; and Group 2 was Hela, Hela-shNC, Hela-shSEMA4C, Hela+TGF-ß1, Hela-shNC+TGF-ß1, and Hela-shSEMA4C+TGF-ß1. Group 1 was detected for SEMA4C mRNA expression by real-time polymerase chain...
Source: Medical Science Monitor - Category: Research Tags: Med Sci Monit Source Type: research
ConclusionsShort ‐term surgical complications develop in 35% of the women after radical hysterectomy for early‐stage cervical cancer in the Netherlands, a nation with centralised surgical care. Comorbidities predict surgical complications and open surgery is associated with excessive perioperative blood loss.
Source: Acta Obstetricia et Gynecologica Scandinavica - Category: OBGYN Authors: Tags: ORIGINAL RESEARCH ARTICLE Source Type: research
We describe three new settings in which ASE improves the detection of a variety of antibodies applied on long-time stored non-human primate brain sections, cell culture monolayers and on squamous carcinomas retrieved from cervical cancer patients. The significant improvement of ASE over optimized immunohistochemical protocols used in clinical practice (i.e. cancer detection) combined with its simplicity and low cost makes it an attractive method for biomedical applications.
Source: Neuroscience - Category: Neuroscience Source Type: research
AbstractPurposeTo evaluate radiotherapy-induced changes in the expression of programmed death ligand  1 (PD-L1), programmed death 1 (PD-1), and human leukocyte antigen class I (HLA-1) in patients with uterine cervical cancer, as well as infiltration of CD8+ and Forkhead box P3+ (FoxP3+) T lymphocytes into tumor tissue and the prognostic value of these parameters.Materials and methodsWe performed immunohistochemical analysis of pre-radiotherapy biopsies and corresponding post-radiotherapy resected tissues in 104 uterine cervical cancer patients undergoing preoperative chemoradiotherapy or radiothera...
Source: Strahlentherapie und Onkologie - Category: Cancer & Oncology Source Type: research
The outcome of locally advanced cervical cancer (LACC) is dismal. Biomarkers are needed to individualize treatments and to improve patient outcomes. Here, we investigated whether coexpression of epidermal growth factor receptor (EGFR) and human epidermal growth factor receptor 3 (HER3) could be an outcome prognostic biomarker, and whether targeting both EGFR and HER3 with a dual antibody (MEHD7945A) enhanced ionizing radiation (IR) efficacy.
Source: International Journal of Radiation Oncology * Biology * Physics - Category: Radiology Authors: Tags: Biology Contribution Source Type: research
In this study, we investigated the microtubule polymerization effects and apoptosis signaling mechanism of BF12. BF12 showed a potent efficiency against cervical cancer cells, SiHa and HeLa, with IC 50 values of 1.10 and 1.06 μM, respectively. The cellular mechanism studies revealed that BF12 induced G2/M phase arrest and apoptosis in SiHa and HeLa cells, which were associated with alterations in the expression of the cell G2/M cycle checkpoint- related proteins (cyclin B1 and cdc2) and alterations in the levels of apoptosis-related proteins (P53, caspase-3, Bcl-2, and Bax) of these cells, respectively. Western blot ana...
Source: Chemistry and Biodiversity - Category: Biochemistry Authors: Tags: Chem Biodivers Source Type: research
More News: Cancer | Cancer & Oncology | Cervical Cancer | Men | Molecular Biology