Brominated pyrrole alkaloids from marine Agelas sponges reduce depolarization-induced cellular calcium elevation

Bickmeyer, Ulf; Drechsler, Christoph; Köck, Matthias; Assmann, Michael

doi:10.1016/j.toxicon.2004.04.001

Cited by 53 publications

(53 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Other brominated pyrrole alkaloids, especially some of the dimeric molecules, are known to have antibiotic, antiparasitic and cytotoxic effects [9,14,29], interact with membrane ion channel function [30] and therefore ionic trans-membrane transport processes [11] and inhibit cell motility in a variety of cancer cell lines [31]. As sensory and olfactory neurones of predators are primarily exposed to sponge compounds [11] and are equipped with numerous ion channel and cellular signal chains it seems plausible that these alkaloids serve as feeding deterrents as described by several authors [6,7,8].…”

Section: Discussionmentioning

confidence: 99%

“…For example, sponges are well known to produce a large number of bioactive compounds such as brominated pyrrole imidazoles as feeding deterrents against predatory fishes [6,7,8]. Some brominated pyrrole imidazole alklaloids are known to be cytotoxic [9] and to interact with ion channels and be involved in cellular signalling in mammalian and invertebrate cells [10,11,12].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Tracking of fast moving neuronal vesicles with ageladine A

Bickmeyer¹,

Heisenberg²,

Podbielski³

et al. 2010

Biochemical and Biophysical Research Communications

Self Cite

View full text Add to dashboard Cite

This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. Tracking of fast moving neuronal vesicles with ageladine A

show abstract

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Tracking of fast moving neuronal vesicles with ageladine A

Bickmeyer¹,

Heisenberg²,

Podbielski³

et al. 2010

Biochemical and Biophysical Research Communications

Self Cite

View full text Add to dashboard Cite

show abstract

“…Receptor neurons within the rhinophore epithelium of Archidoris may not be very sensitive to stimulation with amino acids. Responses to tactile stimuli and other chemical substances such as alkaloids used in Aplysia (Bickmeyer et al 2004) need to be investigated in the future to clarify this issue.…”

Section: Discussionmentioning

confidence: 99%

Functional neuroanatomy of the rhinophore of Archidoris pseudoargus

et al. 2007

Self Cite

View full text Add to dashboard Cite

For sea slugs, chemosensory information represents an important sensory modality, because optical and acoustical information are limited. In the present study, we focussed on the neuroanatomy of the rhinophores and processing of olfactory stimuli in the rhinophore ganglion of Archidoris pseudoargus, belonging to the order of Nudibranchia in the subclass of Opisthobranchia. Histological techniques, Xuorescent markers, and immunohistochemistry were used to analyse neuroanatomical features of the rhinophore. A large ganglion and a prominent central lymphatic channel are surrounded by longitudinal muscles. Many serotonin-immunoreactive (IR) processes were found around the centre and between the ganglion and the highly folded lobes of the rhinophore, but serotonin-IR cell bodies were absent inside the rhinophore. In contrast to the conditions recently found in Aplysia punctata, we found no evidence for the presence of olfactory glomeruli within the rhinophore. Using calcium-imaging techniques with Fura II as a calcium indicator, we found diVerential calcium responses in various regions within the ganglion to stimulation of the rhinophore with diVerent amino acids. The lack of glomeruli in the rhinophores induces functional questions about processing of chemical information in the rhinophore.

show abstract

“…Especially, the degree of bromination and the guanidine moieties have shown to be important for the alkaloids efficacy to disturb cellular calcium ion entry via voltage operated channels in neuroendocrine cells [10][11][12], which possess mainly L-and N-type calcium channels common in neuronal cells. During these fluorescence measurements of cellular effects by pyrrole-imidazole alkaloids, ageladine A was noticed to show fluorescence during UV excitation [12], which was also described earlier by Fujita et al [1].…”

Section: Introductionmentioning

confidence: 99%

Ageladine A, a pyrrole–imidazole alkaloid from marine sponges, is a pH sensitive membrane permeable dye

Bickmeyer

Grube

Klings

et al. 2008

Biochemical and Biophysical Research Communications

Self Cite

View full text Add to dashboard Cite

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 whole transparent animal staining. To calculate the exact pH in solutions, cells, and tissues, the actual concentration of the alkaloid has to be known. A ratiometric measurement at the commonly used excitation wavelengths at 340/380 nm allows pH measurements in living tissues with an attenuated influence of the ageladine A concentration on calculated values. The fluorescence changes report small intracellular pH changes induced by extracellular acidification and alkalization as well as intracellular alkalization induced by ammonium chloride.Ó 2008 Elsevier Inc. All rights reserved.The pyrrole-imidazole alkaloid ageladine A was first isolated and described by Fujita et al.[1] using bioassay guided fractionation of extracts of the marine sponge Agelas nakamurai.The alkaloid showed biological effects such as the inhibition of matrix metallo-proteinases and the inhibition of cell migration of bovine endothelial cells. In 2006 the total synthesis of ageladine A was completed by the groups of Weinreb and Karuso [2,3] and later optimized [4,5].Brominated pyrrole-imidazole alkaloids are known to be fish feeding deterrent against the reef fish Thalassoma bifasciatum [6,7] and demonstrate antibiotic activity [8] even against pathogens like Helicobacter pylori [9]. Especially, the degree of bromination and the guanidine moieties have shown to be important for the alkaloids efficacy to disturb cellular calcium ion entry via voltage operated channels in neuroendocrine cells [10][11][12], which possess mainly L-and N-type calcium channels common in neuronal cells. During these fluorescence measurements of cellular effects by pyrrole-imidazole alkaloids, ageladine A was noticed to show fluorescence during UV excitation [12], which was also described earlier by Fujita et al. [1]. We demonstrate here other surprising properties of ageladine A such as its sensitivity to pH changes covering a wide range and because of its high membrane permeability an easy whole animal pH sensitive staining. Material and methodsCulture methods. PC12 cells from the DSMZ (Deutsche Sammlung von Mikroorganismen und Zellkulturen GmbH, Braunschweig, Germany) were kept in culture medium containing RPMI 1640, 10% fetal calf serum, 5% horse serum, and 100 U penicillin/streptomycin per milliliter. Cells were cultivated in an incubator at 37°C, 90% humidity and 5% CO 2 with regular medium changes twice a week or when additionally necessary. Cells grew in culture flasks and 1-2 days prior to the experiments were seeded into petri dishes coated with coll...

show abstract

Brominated pyrrole alkaloids from marine Agelas sponges reduce depolarization-induced cellular calcium elevation

Cited by 53 publications

References 24 publications

Tracking of fast moving neuronal vesicles with ageladine A

Tracking of fast moving neuronal vesicles with ageladine A

Functional neuroanatomy of the rhinophore of Archidoris pseudoargus

Ageladine A, a pyrrole–imidazole alkaloid from marine sponges, is a pH sensitive membrane permeable dye

Contact Info

Product

Resources

About