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J. Biol. Chem., Vol. 277, Issue 43, 40544-40548, October 25, 2002
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From the Vacuolar-type ATPase (V-ATPase) purified
from the midgut of the tobacco hornworm Manduca
sexta is inhibited 50% by 10 nM of the
plecomacrolide concanamycin A, the specific inhibitor of V-ATPases. To
determine the binding site(s) of that antibiotic in the enzyme complex,
labeling with the semisynthetic
9-O-[p-(trifluoroethyldiazirinyl)-benzoyl]-21,23-dideoxy-23-[125I]iodo-concanolide
A (J-concanolide A) was performed, which still inhibits the V-ATPase
50% at a concentration of 15-20 µM. Upon treatment with
UV light, a highly reactive carbene is generated from this concanamycin
derivative, resulting in the formation of a covalent bond to the
enzyme. In addition, the radioactive tracer 125I makes the
detection of the labeled subunit(s) feasible. Treatment of the
V1/Vo holoenzyme, the Vo complex,
and the V-ATPase containing goblet cell apical membranes with
concanolide resulted in the labeling of only the proteolipid, subunit
c, of the proton translocating Vo complex. Binding of
J-concanolide A to subunit c was prevented in a
concentration-dependent manner by concanamycin A,
indicating that labeling was specific. Binding was also prevented by
the plecomacrolides bafilomycin A1 and B1,
respectively, but not by the benzolactone enamide salicylihalamide, a
member of a novel class of V-ATPase inhibitors.
Concanamycin A, the Specific Inhibitor of V-ATPases, Binds to the
Vo Subunit c*
§,
,§§,¶¶,, and§
Universität Osnabrück,
Fachbereich Biologie/Chemie, § Abteilung
Tierphysiologie, and Abteilung
Mikrobiologie, 49069 Osnabrück, Germany, the
¶ Universität Göttingen, Fakultät für
Chemie, Institut für Organische Chemie,
37077 Göttingen, Germany, and the
** Universität Münster, Interdisziplinäres
Zentrum für Klinische Forschung, Integrierte Funktionelle
Genomik, 48149 Münster, Germany
*
This work was supported by grants from the Deutsche
Forschungsgemeinschaft Sonderforschungsbereich 431 (to H. W. and
K. A.), the Fonds der Chemischen Industrie (to K. A. and A. Z.), and
the Dept. of Research and Technology in Germany, Nos. 01KX9820/B and 01KS9604/0 (to S. K.).The costs of publication of this
article were defrayed in part by the
payment of page charges. The article must therefore be hereby marked
"advertisement" in
accordance with 18 U.S.C. Section
1734 solely to indicate this fact.
Present address: School of Pharmacy, University of Wisconsin,
Madison, WI 53705.
§§
Present address: Deutsches Krebsforschungszentrum, 69120 Heidelberg, Germany.
¶¶
Present address: Universitätsklinikum Frankfurt,
Institut für Biochemie I, 60590 Frankfurt, Germany.
To whom correspondence should be addressed:
Universität Osnabrück, Fachbereich Biologie/Chemie,
Abteilung Tierphysiologie, 49069 Osnabrück, Germany. Tel.:
49-541-9693501; Fax: 49-541-9693503; E-mail:
wieczorek@biologie.uni-osnabrueck.de.
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