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51.
Sophia Grigoropoulou Dimitra Manou Antonia I. Antoniou Artemis Tsirogianni Carlo Siciliano Achilleas D. Theocharis Constantinos M. Athanassopoulos 《Molecules (Basel, Switzerland)》2022,27(11)
Dehydroabietic Acid (DHA, 1) derivatives are known for their antiproliferative properties, among others. In the context of this work, DHA was initially modified to two key intermediates bearing a C18 methyl ester, a phenol moiety at C12, and an acetyl or formyl group at C13 position. These derivatives allowed us to synthesize a series of DHA-chalcone hybrids, suitable for structure–activity relationship studies (SARS), following their condensation with a variety of aryl-aldehydes and methyl ketones. The antiproliferative evaluation of the synthesized DHA-chalcone hybrids against three breast cancer cell lines (the estrogen-dependent MCF-7 and the estrogen-independent MDA-MB-231 and Hs578T) showed that eight derivatives (33, 35, 37, 38, 39, 41, 43, 44) exhibit low micromolar activity levels (IC50 2.21–11.5 μΜ/MCF-7). For instance, some of them showed better activity compared to the commercial anticancer drug 5-FU against MCF-7 cells (33, 41, 43, 44) and against MDA-MB231 (33 and 41). Hybrid 38 is a promising lead compound for the treatment of MCF-7 breast cancer, exhibiting comparable activity to 5-FU and being 12.9 times less toxic (SI = 22.7). Thus, our findings suggest that DHA-chalcone hybrids are drug candidates worth pursuing for further development in the search for novel breast cancer therapies. 相似文献
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To derive accurately the thermodynamic parameters governing the hydrolysis of the lactone ring at physiological pH, a derivative spectrophotometric technique was used for the simultaneous estimation of lactone and carboxylate forms of the 10-hydroxy-camptothecin (10-HC). Validation of the analytical method was done with respect to reproducibility, percent recovery, and level of detection. Hydrolysis of the lactone ring of 10-HC followed a 1st order decay with a rate constant equal to (0.0281 ± 0.001) min−1 in PBS at pH 7.4 and at a temperature of 310 K. The activation energy for the hydrolysis reaction as calculated from the Arrhenius equation was (79.41 ± 0.92) kJ · mol−1, whereas the enthalpy and entropy of hydrolysis of 10-hydroxy-camptothecin were on average 12.45 kJ · mol−1 and 52.37 J · K−1 · mol−1, respectively. The positive enthalpy and entropy values of the 10-HC-lactone hydrolysis indicate that the reaction is endothermic and entropically driven. 相似文献
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Loukiani Savva Dr. Mathieu Fossépré Odysseas Keramidas Alexandros Themistokleous Natalia Rizeq Dr. Nikos Panagiotou Dr. Maxime Leclercq Eliana Nicolaidou Dr. Mathieu Surin Dr. Sophia C. Hayes Dr. Savvas N. Georgiades 《Chemistry (Weinheim an der Bergstrasse, Germany)》2022,28(54):e202201497
Organometallic molecules offer some of the most promising scaffolds for interaction with G-quadruplex nucleic acids. We report the efficient synthesis of a family of organoplatinum(II) complexes, featuring a 2-([2,2′-bipyridin]-6-yl)phenyl tridentate (N∧N∧C) ligand, that incorporates peripheral side-chains aiming at enhancing and diversifying its interaction capabilities. These include a di-isopropyl carbamoyl amide, a morpholine ethylenamide, two enantiomeric proline imides and an oxazole. The binding affinities of the Pt-complexes were evaluated via UV-vis and fluorescence titrations, against 5 topologically-distinct DNA structures, including c-myc G-quadruplex, two telomeric (22AG) G-quadruplexes, a duplex (ds26) and a single-stranded (polyT) DNA. All compounds exhibited binding selectivity in favour of c-myc, with association constants (Ka) in the range of 2–5×105 M−1, lower affinity for both folds of 22AG and for ds26 and negligible affinity for polyT. Remarkable emission enhancements (up to 200-fold) upon addition of excess DNA were demonstrated by a subset of the compounds with c-myc, providing a basis for optical selectivity, since optical response to all other tested DNAs was low. A c-myc DNA-melting experiment showed significant stabilizing abilities for all compounds, with the most potent binder, the morpholine-Pt-complex, exhibiting a ΔTm>30 °C, at 1 : 5 DNA-to-ligand molar ratio. The same study implied contributions of the diverse side-chains to helix stabilization. To gain direct evidence of the nature of the interactions, mixtures of c-myc with the four most promising compounds were studied via UV Resonance Raman (UVRR) spectroscopy, which revealed end-stacking binding mode, combined with interactions of side-chains with loop nucleobase residues. Docking simulations were conducted to provide insights into the binding modes for the same four Pt-compounds, suggesting that the binding preference for two alternative orientations of the c-myc G-quadruplex thymine ‘cap’ (‘open’ vs. ‘closed’), as well as the relative contributions to affinity from end-stacking and H-bonding, are highly dependent on the nature of the interacting Pt-complex side-chain. 相似文献
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Gourbatsis Sotiris Hadjiliadis Nick Perlepes Spyros P. Garoufis Achilleas Butler Ian S. 《Transition Metal Chemistry》1998,23(5):599-604
Cu(NO3)2·3H2O reacts with 1 equiv. of the tetradentate Schiff base N,N-bis[1–(2–pyridyl)ethylidene]ethane-1,2–diamine (LA) in refluxing acetone to yield the [CuLA(ONO2)(H2O)](NO3) complex in ca. 80% yield. The structure of this salt has been determined by single-crystal X-ray crystallography. The copper is six-coordinated with the LA ligand in the equatorial plane and weakly bonded aqua and nitrato ligands above and below this plane. The complex cation is hydrogen-bonded to the nitrate counter-ion. The complex was also characterized by elemental analyses, molar conductivity, room-temperature magnetic susceptibility and spectroscopic (i.r., far-i.r., u.v.–vis, e.s.r.) studies. The data are discussed in terms of the nature of bonding and the known structure. 相似文献
60.
Efstathios A. Sinouris Spyros S. Skandalis Virginia Kilia Achilleas D. Theocharis Dimitrios A. Theocharis Panagiota Ravazoula Demitrios H. Vynios Nickoletta Papageorgakopoulou 《Biomedical chromatography : BMC》2009,23(5):455-463
Proteoglycans (PGs) are widely expressed in all areas of the brain. In this study, the keratan sulfate‐containing PGs (KS‐PGs) from cerebrum (CB), cerebellum (CL) and brainstem (BS) of young sheep brain were isolated, purified and characterized. The amount of KS‐PGs in CL was significantly lower than that in CB and BS. KS‐PGs were characterized by increased extent of glycosylation and heterogeneity of KS chains in CL. Western blot analyses demonstrated the presence of the KS‐PGs phosphacan, SV2A and SV2B isoforms of synaptic vesicle proteoglycan in all three areas of the young sheep brain. Phosphacan predominated in BS and CB, showing significant molecular heterogeneity. SV2A and SV2B were found in two forms of high and low molecular sizes according to their extent of glycosylation in sheep brain. SV2A predominated in CL, where forms with very high molecular sizes were detected. Immunohistochemical examination revealed that SV2A was localized in the extracellular matrix of both gray and white matter. In contrast, phosphacan and SV2B were mainly localized in the white matter in all brain regions. The results of the present study demonstrated that KS‐PGs are present in the three areas of the sheep brain, showing significant variations in their content, structure and localization among the distinct areas. These differences may be important for the physiology of the brain. Copyright © 2008 John Wiley & Sons, Ltd. 相似文献