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Novel dithiane analogues of tiapamil with high activity to overcome multidrug resistance in vitro

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Novel dithiane analogues of tiapamil with high activity to overcome multidrug resistance in vitro

Auteurs : James F. Eliason [Japon] ; Henri Ramuz [Suisse] ; Takashi Yoshikubo [Japon] ; Tohru Ishikawa [Japon] ; Taeko Yamamoto [Japon] ; Takashi Tsuruo [Japon]

Source :

Biochemical Pharmacology [ 0006-2952 ] ; 1995.

RBID : ISTEX:EBDC38881AF85441604401B03D6CE66649D76B0D

English descriptors

KwdEn :
- 5-fura, 5′-dfurd, ABC, CDDP, DOX, ELISA, FCS, MDR, MTT, P-glycoprotein, PAGE, RM, RMI, SDS, VCR, cell lines, doxorubicin, multiple drug resistance, tiapamil analogues, vincristine.
Teeft :
- Active reference compounds, Analogue, Aortic rings, Assay, Azidopine binding, Bacterial transport proteins, Biochem biophys, Biochem pharmacol, Biol chem, Calcium antagonists, Calcium channel blockers, Cancer cells, Cell line, Cell lines, Cell proliferation, Cepharanthine, Colorectal, Colorectal cell lines, Compound, Control cultures, Cyclosporin, Cytotoxicity, Detectable levels, Dipyridamole, Distinct patterns, Dithiane, Dithiane analogue, Dithiane analogues, Dithiane tetraoxide, Dithianes, Dos, Doxorubicin, Doxorubicin resistance, Drug accumulation, Drug resistance, Eliason, Enantiomer, Gottesman, Higher doses, Increases daunorubicin uptake, Krebshenseleit solution, Large number, Lcso values, Lower doses, Membrane vesicles, Methyl group, Multidrug, Multidrug resistance, Parental cells, Parental line, Pglycoprotein, Plasma membrane, Plasma membrane fractions, Plasma membranes, Regression lines, Reserpine, Resistance modification index, Resistant cells, Reversal, Several analogues, Structural features, Tiapamil, Tiapamil analog, Tsuruo, Tumor cells, Verapamil, Vesicle, Vincristine, Vincristine resistance.

Abstract

Abstract: Dithiane analogues of tiapamil are highly active as modifiers of P-glycoprotein mediated multidrug resistance (MDR) in vitro. In an assay using the P-glycoprotein over-expressing cell line KB-8-5, the most active analogues for decreasing vincristine resistance were the racemate Ro 11-5160 and its two enantiomers, Ro 44-5911 (R) and Ro 44-5912 (S). In the KB-8-5 assay, the resistance modification index (RMI) of Ro 11-5160 was approximately 12-fold higher than those of the most active reference compounds tested, dipyridamole, cepharanthine, reserpine and cyclosporin A, when compared at concentrations equal to one-tenth of the ic50 of each compound (RMI0.1). The enantiomers have similar resistance modifying activities, but the (S) enantiomer Ro 44-5912 is somewhat more active, fully reverting the vincristine sensitivity of KB-8-5 cells to the level of the parental KB-3-1 cells at a concentration of 2 μM. The (R) enantiomer attained this level of modification at a concentration of 3.5 μM. These concentrations are both well below their ic50 values for KB-8-5 cells (150 μM). The enantiomers appear to interact with P-glycoprotein because they inhibited [3H]azidopine and [3H]-vinblastine binding to plasma membrane fractions prepared from resistant K562/ADR cells. However, in addition to their resistance modifying activities with KB-8-5 cells, these compounds also decreased the ic50 values of vincristine and doxorubicin with KB-3-1 cells that do not express detectable levels of P-glycoprotein. Ro 44-5911 overcame doxorubicin and vincristine resistance in three colorectal cancer cell lines (DLD-1, WiDr and COLO 201) that express P-glycoprotein. No effect was seen with the 3 colorectal cell lines on the ic50 values of three drugs not related to the MDR phenotype, 5-fluorouracil, 5′-deoxy-5-fluorouridine and cis-diaminodichloroplatinum(II). The in vitro vasodilatory activity of these dithianes, measured with strips of rat aorta contracted with KCl, was about 5% of that of verapamil. These results suggest that dithianes could be useful agents for MDR modification in vivo.

Url:

https://api.istex.fr/ark:/67375/6H6-ML8DGPW5-H/fulltext.pdf

DOI: 10.1016/0006-2952(95)00115-G

Affiliations:

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Le document en format XML

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<term>CDDP</term>
<term>DOX</term>
<term>ELISA</term>
<term>FCS</term>
<term>MDR</term>
<term>MTT</term>
<term>P-glycoprotein</term>
<term>PAGE</term>
<term>RM</term>
<term>RMI</term>
<term>SDS</term>
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<term>cell lines</term>
<term>doxorubicin</term>
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<term>tiapamil analogues</term>
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<term>Biol chem</term>
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<term>Control cultures</term>
<term>Cyclosporin</term>
<term>Cytotoxicity</term>
<term>Detectable levels</term>
<term>Dipyridamole</term>
<term>Distinct patterns</term>
<term>Dithiane</term>
<term>Dithiane analogue</term>
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<front><div type="abstract" xml:lang="en">Abstract: Dithiane analogues of tiapamil are highly active as modifiers of P-glycoprotein mediated multidrug resistance (MDR) in vitro. In an assay using the P-glycoprotein over-expressing cell line KB-8-5, the most active analogues for decreasing vincristine resistance were the racemate Ro 11-5160 and its two enantiomers, Ro 44-5911 (R) and Ro 44-5912 (S). In the KB-8-5 assay, the resistance modification index (RMI) of Ro 11-5160 was approximately 12-fold higher than those of the most active reference compounds tested, dipyridamole, cepharanthine, reserpine and cyclosporin A, when compared at concentrations equal to one-tenth of the ic50 of each compound (RMI0.1). The enantiomers have similar resistance modifying activities, but the (S) enantiomer Ro 44-5912 is somewhat more active, fully reverting the vincristine sensitivity of KB-8-5 cells to the level of the parental KB-3-1 cells at a concentration of 2 μM. The (R) enantiomer attained this level of modification at a concentration of 3.5 μM. These concentrations are both well below their ic50 values for KB-8-5 cells (150 μM). The enantiomers appear to interact with P-glycoprotein because they inhibited [3H]azidopine and [3H]-vinblastine binding to plasma membrane fractions prepared from resistant K562/ADR cells. However, in addition to their resistance modifying activities with KB-8-5 cells, these compounds also decreased the ic50 values of vincristine and doxorubicin with KB-3-1 cells that do not express detectable levels of P-glycoprotein. Ro 44-5911 overcame doxorubicin and vincristine resistance in three colorectal cancer cell lines (DLD-1, WiDr and COLO 201) that express P-glycoprotein. No effect was seen with the 3 colorectal cell lines on the ic50 values of three drugs not related to the MDR phenotype, 5-fluorouracil, 5′-deoxy-5-fluorouridine and cis-diaminodichloroplatinum(II). The in vitro vasodilatory activity of these dithianes, measured with strips of rat aorta contracted with KCl, was about 5% of that of verapamil. These results suggest that dithianes could be useful agents for MDR modification in vivo.</div>
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Novel dithiane analogues of tiapamil with high activity to overcome multidrug resistance in vitro

Novel dithiane analogues of tiapamil with high activity to overcome multidrug resistance in vitro

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Abstract

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