Photoaffinity labelling of submitochondrial membranes with the 3-azido analogue of 9-amino-3-chloro-7-methoxyacridine

Kopacz, Stephan J.; Mueller, David M.; Lee, C.P.

doi:10.1016/0005-2728(85)90121-5

Cited by 11 publications

(7 citation statements)

References 31 publications

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“…Other important derivatives are 9-aminoacridine. This class of molecules is the object of extensive investigations due to a biological activity that ranges from anti-malarial properties [117], enzyme inhibition [118][119][120], anticancer activity [121] that led to chemotherapeutics development, photo-affinity labels [122] and fluorescent probes for cancer cell detection [123]. Despite the numerous studies on aminoacridine derivatives, mechanistic aspects of these molecules binding to polynucleotides have been seldom analysed.…”

Section: Proflavine Derivative Binding Modesmentioning

confidence: 99%

Mechanistic aspects of the interaction of intercalating metal complexes with nucleic acids

Biver

Secco

Venturini

2008

Coordination Chemistry Reviews

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Section: Proflavine Derivative Binding Modesmentioning

confidence: 99%

Mechanistic aspects of the interaction of intercalating metal complexes with nucleic acids

Biver

Secco

Venturini

2008

Coordination Chemistry Reviews

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“…In the first set of entries (1-15) the synthesized 9-chloroacridines were coupled with commercially available sidechain 9{1,9}, while in the second set of entries (16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31), the commercially available 9-chloroacridine heterocycle 7{4,6} of quinacrine was coupled with the set of synthesized diamines. Yields and purities of the coupled products were highly variable.…”

Section: Proof-of-concept Librarymentioning

confidence: 99%

Parallel synthesis of 9-aminoacridines and their evaluation against chloroquine-resistant Plasmodium falciparum

Anderson

Sherrill

Madrid

et al. 2006

Bioorganic & Medicinal Chemistry

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A parallel synthetic strategy to the 9-aminoacridine scaffold of the classical anti-malarial drug quinacrine (2) is presented. The method features a new route to 9-chloroacridines that utilizes triflates of salicylic acid derivatives, which are commercially available in a variety of substitution patterns. The route allows ready variation of the two diversity elements present in this class of molecules: the tricyclic aromatic heterocyclic core, and the disubstituted diamine sidechain. In this study, a library of 175 compounds was designed, although only 93 of the final products had purities acceptable for screening. Impurity was generally due to incomplete removal of 9-acridones (18), a degradation product of the 9-chloroacridine synthetic intermediates. The library was screened against two strains of Plasmodium falciparum, including a model of the drug-resistant parasite, and six novel compounds were found to have IC 50 values in the low nanomolar range.

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“…We have used two different aminoacridine fluorescent dyes, quinacrine and ACMA, to monitor Suc-induced proton movements and membrane energization (Kraayenhof, 1970(Kraayenhof, , 1980Huang et al, 1983), but only quinacrine fluorescence responded to pH changes in media devoid of any membranes (results not shown) and could be used as a pH indicator (Huang et al, 1977(Huang et al, , 1983Kopacz et al, 1985). ACMA, a pH-dependent fluorescent dye of high sensitivity (Dufour et al, 1982;Greutert and Keller, 1993), exhibited a significant fluorescence quench in the presence of membranes as a response to changing energization states of the membranes (Huang et al, 1983; this report, "Results").…”

Section: Monitoring Of H+ Pump Activitymentioning

confidence: 99%

Characteristics of Sucrose Transport and Sucrose-Induced H+ Transport on the Tonoplast of Red Beet (Beta vulgaris L.) Storage Tissue

Getz

Klein

1995

Plant Physiol.

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Sucrose-induced changes of the energization state of the red beet root (Beta vulgaris L. ssp. conditiva) vacuolar membrane were observed with the fluorescent dyes 6-chloro-9-{[4-(diethylamino)-1 -methylbutyll-aminol-2-methoxyacridine dihydrochloride, as a pH monitor, and 9-amino-6-chloro-2-methoxyacridine (ACMA). Consequently, transient acidification of the surrounding suspension medium could be measured with a pH electrode. This signal was specific for Suc and was not seen for sorbitol, mannitol, or maltose. Sucrose-induced medium acidification was sensitive to the same inhibitors that were efficient i n inhibiting sucrose transport, including the monoclonal antibodies TNP, , -, , and C50-5.3. It was seen with vacuoles and vesicles energized with MgATP before sucrose was added but also with vacuoles not artificially energized previously. Using bafilomycin A, for the inhibition of the vacuolar ATPase of vacuoles previously energized by MgATP, apparent K, values for H + export from the vacuoles to the medium could be calculated taking into account the passive proton leak. Apparent K, values for H + export determined from data obtained with pH measurements in the medium and with ACMA corresponded to those obtained previously for sucrose uptake. Comparing sucrose uptake rates with corresponding H+ export rates at the respective sucrose concentrations and at K , , a stoichiometry of approximately one proton per transported sucrose was estimated.

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Photoaffinity labelling of submitochondrial membranes with the 3-azido analogue of 9-amino-3-chloro-7-methoxyacridine

Cited by 11 publications

References 31 publications

Mechanistic aspects of the interaction of intercalating metal complexes with nucleic acids

Mechanistic aspects of the interaction of intercalating metal complexes with nucleic acids

Parallel synthesis of 9-aminoacridines and their evaluation against chloroquine-resistant Plasmodium falciparum

Characteristics of Sucrose Transport and Sucrose-Induced H+ Transport on the Tonoplast of Red Beet (Beta vulgaris L.) Storage Tissue

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