2008
DOI: 10.1016/j.bbrc.2008.06.056
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Ageladine A, a pyrrole–imidazole alkaloid from marine sponges, is a pH sensitive membrane permeable dye

Abstract: a b s t r a c tThe alkaloid ageladine A, a pyrrole-imidazole alkaloid isolated from marine Agelas sponges shows fluorescence in the blue-green range during excitation with UV light with the highest absorption at 370 nm. The fluorescence of this alkaloid is pH dependent. Highest fluorescence is observed at pH 4, lowest at pH 9 with the largest fluorescence changes between pH 6 and 7. Ageladine A is brominated, which facilitates membrane permeation and therefore allows for easy staining of living cells and even … Show more

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Cited by 32 publications
(20 citation statements)
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“…For Ageladine-A (Fujita et al, 2003), this was done following a previously described method (Bickmeyer et al, 2008;Bickmeyer, 2012) in which the average values obtained for each of the treatments are expressed as a proportion of the control values, and by assuming that non-specialized cells under these control conditions would present a putative pH i of 7.3-7.4. In contrast, as BCECF fluorescence intensity at 490nm linearly increases between pH6.4 and 7.8 (Silver, 2003), BCECF results were converted to pH i by constructing a calibration curve using the nigericin technique (nigericin sodium salt, 5mg, N7143, Sigma-Aldrich, St Louis, MO, USA) described previously (Thomas et al, 1979).…”
Section: Optical Measurementsmentioning
confidence: 99%
“…For Ageladine-A (Fujita et al, 2003), this was done following a previously described method (Bickmeyer et al, 2008;Bickmeyer, 2012) in which the average values obtained for each of the treatments are expressed as a proportion of the control values, and by assuming that non-specialized cells under these control conditions would present a putative pH i of 7.3-7.4. In contrast, as BCECF fluorescence intensity at 490nm linearly increases between pH6.4 and 7.8 (Silver, 2003), BCECF results were converted to pH i by constructing a calibration curve using the nigericin technique (nigericin sodium salt, 5mg, N7143, Sigma-Aldrich, St Louis, MO, USA) described previously (Thomas et al, 1979).…”
Section: Optical Measurementsmentioning
confidence: 99%
“…Ageladine A has been reported to be a moderate inhibitor of matrix metalloproteases and to be intensely fluorescent [13]. This fluorescence is pH dependent as it is stronger under acidic conditions and barely detectable in alkaline solutions [15]. The synthesis of ageladine A has been described by several groups [16,17,18,19], which provides a ready source of this compound and a viable alternative to isolation from natural sources.…”
Section: Introductionmentioning
confidence: 99%
“…The synthesis of ageladine A has been described by several groups [16,17,18,19], which provides a ready source of this compound and a viable alternative to isolation from natural sources. As ageladine A is pH sensitive and a useful dye for isolated cells as well as transparent whole animals [15] we postulated that the dye might be useful for staining acidic vesicles inside cells.…”
Section: Introductionmentioning
confidence: 99%
“…These small compounds in prey and food may be secondary metabolites produced in algae or sponges which show in part feeding deterrence (Pawlik et al, 1995;Assmann et al, 2000) as well as disturbance of neuronal and hormonal signalling in mammalian endocrine cells (Bickmeyer et al, 2004;Bickmeyer, 2005;Hassenklöver et al, 2006). Some of these natural products seem to be not expelled from living tissues and cells and are therefore under suspicion to inhibit-beside other effects-xenobiotic transporters (Bickmeyer et al, 2008b). In the investigated midgut glands only H. gammarus showed increased dye accumulation in the presence of MK571.…”
Section: Discussionmentioning
confidence: 99%