Reaction participants Show >> << Hide
- Name help_outline doxorubicin Identifier CHEBI:64816 Charge 1 Formula C27H30NO11 InChIKeyhelp_outline AOJJSUZBOXZQNB-TZSSRYMLSA-O SMILEShelp_outline COc1cccc2C(=O)c3c(O)c4C[C@](O)(C[C@H](O[C@H]5C[C@H]([NH3+])[C@H](O)[C@H](C)O5)c4c(O)c3C(=O)c12)C(=O)CO 2D coordinates Mol file for the small molecule Search links Involved in 3 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:35079 | RHEA:35080 | RHEA:35081 | RHEA:35082 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Mechanism of recognition of compounds of diverse structures by the multidrug efflux pump AcrB of Escherichia coli.
Takatsuka Y., Chen C., Nikaido H.
The AcrB trimeric multidrug efflux transporter of Escherichia coli pumps out a very wide spectrum of compounds. Although minocycline and doxorubicin have been cocrystallized within the large binding pocket in the periplasmic domain of the binding protomer, nothing is known about the binding of man ... >> More
The AcrB trimeric multidrug efflux transporter of Escherichia coli pumps out a very wide spectrum of compounds. Although minocycline and doxorubicin have been cocrystallized within the large binding pocket in the periplasmic domain of the binding protomer, nothing is known about the binding of many other ligands to this protein. We used computer docking to evaluate the interaction of about 30 compounds with the binding protomer and found that many of them are predicted to bind to a narrow groove at one end of the pocket whereas some others prefer to bind to a wide cave at the other end. Competition assays using nitrocefin efflux and covalent labeling of Phe615Cys mutant AcrB with fluorescein-5-maleimide showed that presumed groove-binders competed against each other, but cave-binders did not compete against groove-binders, although the number of compounds tested was limited. These results give us at least a hypothesis to be tested by more biochemical and genetic experiments in the future. << Less
Proc Natl Acad Sci U S A 107:6559-6565(2010) [PubMed] [EuropePMC]
This publication is cited by 7 other entries.