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  1. 6 Acta Biochimica Polonica

  2. 6 Cellular and Molecular Biology Letters

  3. 3 Folia Histochemica et Cytobiologica

  4. 2 Archivum Immunologiae et Therapiae Experimentalis

  5. 1 Current Topics in Biophysics

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  1. 5 Jozwiak Z.

  2. 3 Kania K.

  3. 2 Gwozdzinski K.

  4. 2 Koceva-Chyla A.

  5. 2 Priebe W.

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  1. 1 2020

  2. 1 2013

  3. 2 2012

  4. 1 2009

  5. 1 2007

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1

Synthesis and conformational preference of novel 8-fluoroanthracyclines

100%
Lombardi P., Animati F., Cipollone A., Giannini G., Monteagudo E., Arcamone F.
Acta Biochimica Polonica
|
1995
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tom 42
|
nr 4
Analogues of daunorubicin possessing a fluorine atom at position C(8) of ring A have been synthesized with the aim of comparing their DNA-drug interaction and antitumour properties with those of the clinically useful anthracyclines doxorubicin and idarubicin. The synthesis of (8S)-8-fluoro-4-demethoxydaunorubicin, 1, is reported and molecular mechanics and NMR studies which guided towards the synthesis of the epimeric (8R)-8-fluoro-4-demethoxydaunorubicin, 2, are discussed. Both compounds were prepared by divergent routes starting from the common intermediate, 6, obtained via the Diels-Alder cyclisation between quinizarin diquinone, 3, and 2-(l-hydroxyethyl)-l,3-butadiene, 4. The synthesis of the (8S)-fluoroepimer proceeded via epoxidation of the C(8)-C(9) olefinic bond of 6, oxidation, oxirane cleavage by BF3 • Et20 to give the fluorohydroxyketone, 9, followed by the introduction of the hydroxyl moiety at C(7) and glycosylation. Conversely, the synthesis of the (8R)-fluoroepimer involved the fluorobromination of the C(8)-C(9) olefinic bond of 6, formation of the C(9)-C(13) epoxide, 20 which, after regioselective hydrolysis and oxidation of the resulting fluorodiol to the epimeric fluoro­hydroxyketone, 21, similarly gave the desired fluoroaglycone, 25 and, hence, the corresponding glycoside, 2. The cytotoxic properties of the two 8-fluoroanthracycline analogues, 1 and 2, were markedly affected by the stereochemistry of the fluorine substituent.
2

Cytotoxicity and inhibitory properties against topoisomerase II of doxorubicin and its formamidine derivatives

86%
Kik K., Studzian K., Wasowska-Lukawska M., Oszczapowicz I., Szmigiero L.
Acta Biochimica Polonica
|
2009
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tom 56
|
nr 1
135-142
 This work was undertaken to compare cytotoxicity, DNA damaging properties and effect on DNA cleavage by topoisomerase II of the anthracycline drug doxorubicin (DOX) and its two derivatives with a formamidino group containing a cyclic amine moiety such as morpholine (DOXM) or hexamethyleneimine (DOXH). The tetrazolium dye colorimetric assay was used to determine the cytotoxic activity of anthracyclines toward L1210 leukemia cells. DNA damage was measured by alkaline elution technique. The effect of anthracyclines on DNA cleavage was studied in a cell-free system containing supercoiled pBR322 DNA and purified human topoisomerase II. The cytotoxicity data and the results of studies on the mechanism of DNA break formation by anthracyclines at the cellular level and in the cell-free system showed that the presence of the formamidino group in the doxorubicin molecule reduced its ability to stimulate DNA cleavage by DNA topoisomerase II. Conclusion: DNA topoisomerase II is not a primary cellular target for DOXM or DOXH. An advantageous feature of formamidinoanthracyclines is their mechanism of cytotoxic action which is not related to the inhibition of DNA topoisomerase II. Therefore this class of anthracyclines seems to be a good source for selection of an anticancer drug directed toward cancer cells with the developed multidrug resistance attributed to the presence of altered DNA topoisomerase II.
3

A simple model for predicting the free energy of binding between anthracycline antibiotics and DNA

86%
Rudnicki W. R., Kurzepa M., Szczepanik T., Priebe W., Lesyng B.
Acta Biochimica Polonica
|
2000
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tom 47
|
nr 1
A theoretical model for predicting the free energy of binding between anthracycline antibiotics and DNA was developed using the electron density functional (DFT) and molecular mechanics (MM) methods. Partial DFT-ESP charges were used in calculating the MM binding energies for complexes formed between anthracycline antibiotics and oligodeoxynucleotides. These energies were then compared with experimental binding free energies. The good correlation between the experimental and theoretical energies allowed us to propose a model for predicting the binding free energy for derivatives of anthracycline antibiotics and for quickly screening new anthracycline derivatives.
4

A transferrin conjugate of adriamycin-synthesis and potential chemotherapeutic efficacy

86%
Lubgan D., Jozwiak Z.
Cellular and Molecular Biology Letters
|
2002
|
tom 07
|
nr Suppl.
5

The nitroxides pirolin and pirolid protect the plasma membrane of rat cardiomiocytes against damage induced by anthracyclines

86%
Koceva-Chyla A., Sokal A., Kania K., Gwozdzinski K., Jozwiak Z.
Cellular and Molecular Biology Letters
|
2002
|
tom 07
|
nr Suppl.
6

Plarosomes - a new concept for anthracycline drug delivery

86%
Gubernator J., Przeworska E., Kozubek A.
Cellular and Molecular Biology Letters
|
1999
|
tom 04
|
nr 2
7
Content available remote

Resveratrol protects against acute chemotherapy toxicity induced by doxorubicin in rat erythrocyte and plasma

72%
Hamlaoui S., Mokni M., Limam N., Carrier A., Limam F., Amri M., Marzouki L., Aouani E.
Journal of Physiology and Pharmacology
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2012
|
tom 63
|
nr 3
8

Study of DNA topoisomerase IIalpha expression in canine lymphomas and its potential role as a marker of sensitivity to anthracycline-based chemotherapy in dogs

72%
Klimiuk P., Lopuszynski W., Bulak K., Smiech A., Brzana A.
Folia Histochemica et Cytobiologica
|
2020
|
tom 58
|
nr 1
9

Pretreatment levels of vascular endothelial growth factor in plasma predict a complete remission rate and time to relapse or progression in patients with diffuse large B-cell lymphoma

72%
Lech-Maranda E., Bienvenu J., Broussais-Guillaumot F., Michallet A.-S., Warzocha K., Bilinski P., Boyle P., Coiffier B., Salles G.
Archivum Immunologiae et Therapiae Experimentalis
|
2013
|
tom 61
|
nr 2
10

Correlation of histopathological and biochemical appraisal of anthracyclin-induced myocardium damage

72%
Dziegiel P., Surowiak P., Zabel M.
Folia Histochemica et Cytobiologica
|
2002
|
tom 40
|
nr 2
11

Chemiluminescence measurement of reactive oxygen species [ROS] in eukaryotic cells

72%
Rozga B., Furmanczyk M., Jozwiak Z.
Cellular and Molecular Biology Letters
|
2002
|
tom 07
|
nr Suppl.
12

Molecular modeling of singlet-oxygen binding to anthraquinones in relation to the peroxidating activity of antitumor anthraquinone drugs

72%
Liwo A., Jeziorek D., Ossowski T., Dyl D., Tempczyk A., Tarasiuk J., Nowacka M., Borowski E., Woznicki W.
Acta Biochimica Polonica
|
1995
|
tom 42
|
nr 4
Anthraquinone derivatives are important anti-cancer drugs possessing, however, undesirable peroxidating and, in consequence, cardiotoxic properties. This results from the mediation by these compounds of the one-electron reduction processes of the oxygen molecule, which produces the highly toxic superoxide anion radical and other active oxygen species. This article summarizes the results of our studies on the molecular aspects of the mechanism of anthraquinone-mediated peroxidation which were carried out using enzymatic-assay, electrochemical, and quantum-mechanical methods.
13

Purification and functional reconstitution of intact ral-binding GTPase activating protein, RLIP76, in artificial liposomes

72%
Singhal S. S., Singhal J., Cheng J., Pikula S., Sharma R., Zimniak P., Awasthi Y. C., Awasthi S.
Acta Biochimica Polonica
|
2001
|
tom 48
|
nr 2
We have recently shown that RLIP76, a ral-bind ing GTPase ac ti vat ing pro tein, me­diates ATP-dependent transport of glutathione-conjugates (GS-E) and doxorubicin (DOX) (S. Awasthi eta/., Biochemistry39l9327l2000).TransportfunctionofRLIP76 was found to be in tact de spite con sid er able proteolytic frag men ta tion in prep a ra tions used for those stud ies, sug gest ing ei ther that the re sid ual in tact RLIP76 was re spon si ble for trans port ac tiv ity, or that the trans port ac tiv ity could be re con sti tuted by frag­ments of RLIP76. If the for mer were true, in tact RLIP76 would have a much higher spe cific ac tiv ity for ATP-hydrolysis than the frag mented pro tein. We have ad dressed this ques tion by com par ing trans port prop er ties of re com bi nant RLIP76 and hu man eryth ro cyte mem brane RLIP76 pu ri fied in buff ers treated with either 100 or 500uM serine pro te ase in hib i tor, PMSF. The pu rity and iden tity of re com bi nant and hu man eryth ro cyte RLIP76 was es tab lished by SDS/PAGE and West ern-blot anal y sis. These studies con firmed the or i gin of the 38 kDa pro tein, pre vi ously re ferred to as DNP-SG ATPase, from RLIP76. Higher PMSF con cen tra tion re sulted in lower yield of the 38 kDa band and higher yield of in tact RLIP76 from both hu man and re com bi nant source. In con trast, the sub strate-stimulated ATPase ac tiv ity in pres ence of DNP-SG, doxorubicin, daunorubicin, or colchicine were un af fected by in creased PMSF; similarly, ATP-dependent trans port of doxorubicin in proteo liposomes re con sti tuted with RLIP76 was un af fected by higher PMSF. These re sults in di cated that lim ited proteolysis by serine pro teas es does not ab ro gate the trans port func tion of RLIP76. Com parison of trans port ki net ics for daunorubicin be tween re com bi nant vs hu man erythrocyte RLIP76 re vealed higher spe cific ac tiv ity of trans port for tis sue pu ri fied RLIP76, in di cat ing that ad di tional fac tors pres ent in tis sue pu ri fied RLIP76 can mod u late its transport activity.
14

Morphological and biochemical changes in human fibroblast lines induced by anthracyclines during apoptosis

72%
Kania K., Dragojew S., Jozwiak Z.
Cellular and Molecular Biology Letters
|
2003
|
tom 08
|
nr 1
We show that treating human trisomie fibroblasts with anthracyclines - aclarubicin, daunorubicin and idarubicin - leads to certain changes in these cells; namely the activation of caspase 3, morphological changes and an increase in the level of intracellular calcium. These results suggest that anthracycline drugs are also able to induce apoptosis in pathological, trisomic cells.
15

Effect of structural modification at the 4,3', and 2' positions of doxorubicin on topoisomerase II poisoning, apoptosis, and cytotoxicity in human melanoma cells

72%
Gruber B. M., Anuszewska E. L., Bubko I., Gozdzik A., Fokt I., Priebe W.
Archivum Immunologiae et Therapiae Experimentalis
|
2007
|
tom 55
|
nr 3
16

Total antioxidant status (TAS) in childhood cancer survivors

58%
Krawczuk-Rybak M., Panasiuk A., Czygier M., Muszynska-Roslan K., Wysocka J., Szmitkowski M.
Folia Histochemica et Cytobiologica
|
2012
|
tom 50
|
nr 3
17

The nitroxides pirolin and pirolid protect the plasma membranes of rat cardiomyocytes against damage induced by anthracyclines

58%
Koceva-Chyla A., Sokal A., Kania K., Gwozdzinski K., Jozwiak Z.
Cellular and Molecular Biology Letters
|
2003
|
tom 08
|
nr 1
This study was performed to evaluate the protective effects of pyrroline and pyrrolidine nitroxides Pirolin, PL, and Pirolid, PD, on the plasma membranes of rat cardiomyocytes treated in vitro with anthracycline drugs aclarubicin (ACL) and doxorubicin (DOX). The influence of two concentrations of drugs (10 and 20 μM) and nitroxides (0.1 and 1 mM) as well as their combinations (a drug and a nitroxide) on membrane fluidity was investigated. The plasma membranes of cardiomyocytes were labelled with a hydrophobic fluorescence probe 12-AS and membrane fluidity was estimated on the basis of the fluorescence anisotropy of the probe. We found that aclarubicin and doxorubicin induced a significant dose-dependent decrease in membrane fluidity, whereas the nitroxides (PL and PD) caused its increase. Preincubation of cardiomyocytes with Pirolin entirely protected plasma membranes of these cells against damage caused by DOX. In the same conditions no protective effect of Pirolid was observed. What is more, Pirolid in combination with DOX caused fluidisation of the plasma membranes of cardiomyocytes. Both nitroxides at low concentration (0.1 mM) protected plasma membranes against rigidification induced by aclarubicin, while high concentration (1 mM) was ineffective and caused fluidisation of the plasma membranes of cardiomyocytes.
18

Sensitivity of trisomic-21 human fibroblasts to gamma-radiation and carminomycin

58%
Rozga B., Duong Thi Bach T.
Current Topics in Biophysics
|
1994
|
tom 18
|
nr 2
19

The influence of intracellular idarubicin and daunorubicin levels on drug cytotoxicity in childhood acute leukemia

58%
Styczynski J., Wysocki M., Debski R., Kurylak A., Balwierz W., Rokicka-Milewska R., Matysiak M., Balcerska A., Kowalczyk J., Wachowiak J., Sonta-Jakimczyk D., Chybicka A.
Acta Biochimica Polonica
|
2002
|
tom 49
|
nr 1
Uptake and efflux of two anthracyclines, idarubicin (IDA) and daunorubicin (DNR), was studied in childhood acute leukemia samples. A comparison of IDA and DNR transport phenomena in relation to drug cytotoxicity and expression of P-glycoprotein (PGP) was made. Intracellular content of IDA/DNR was determined by flow cytometry using the fluorescent properties of the drugs. In vitro drug cytotoxicity was measured by the 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyl tetrazolium bromide (MTT) assay. PGP expression was analysed by flow cytometry. The uptake and efflux rates were non-significantly higher for IDA than DNR. There were no differences between three types of leukemia with respect to drug content during accumulation and retention. After correction for the cell volume, intracellular concentration of both drugs in each moment of uptake and efflux was significantly lower in relapsed ALL and AML samples in comparison with initial ALL cells. Efflux, but not uptake, of both drugs was inversely correlated with PGP expression and IDA, but not DNR, cytotoxicity. The cytotoxicity was correlated with drug accumulation for both drugs and with drug retention for IDA. In conclusion, it seems that (1) intracellular content was related to the lipophilic properties of the drugs rather than to the type of leukemia, (2) decreased intracellular concentration of both drugs might have an impact on compromised therapy results in AML and relapsed ALL children, (3) IDA presents higher cytotoxicity, which possibly might be decreased by the presence of PGP. These results might have a practical impact on the rational design of new chemotherapy protocols.
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