Synthesis, Antimicrobial and Antineoplastic Activities for Agelasine and Agelasimine Analogs with a β‐Cyclocitral Derived Substituent

Proszenyák, Ágnes; Charnock, Colin; Hedner, Erik; Larsson, Rolf; Bohlin, Lars; Gundersen, Lise‐Lotte

doi:10.1002/ardp.200700137

Cited by 35 publications

(34 citation statements)

References 38 publications

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“…These compounds have gained attention because of their biological activity to confer cytotoxicity towards cancer cell lines (minimal inhibitory concentrations of ca. 1 μM; for review see [45]), as well as their anti-bacterial, anti-fungal and anti-protozoal properties [46][47][48][49]. New analogues have been synthesized with activities against Mycobacterium tuberculosis , protozoa such as Plasmodium falciparum and Leishmania infantum as well as against drug-resistant cancer cell lines [50].…”

Section: Discussionmentioning

confidence: 99%

Natural compounds with P2X7 receptor-modulating properties

Fischer

Urban

Immig

et al. 2013

Purinergic Signalling

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The adenosine 5′-triphosphate (ATP)-gated P2X7 receptor is a membrane-bound, non-selective cation channel, expressed in a variety of cell types. The P2X7 senses high extracellular ATP concentrations and seems to be implicated in a wide range of cellular functions as well as pathophysiological processes, including immune responses and inflammation, release of gliotransmitters and cytokines, cancer cell growth or development of neurodegenerative diseases. In the present study, we identified natural compounds and analogues that can block or sensitize the ATP (1 mM)-induced Ca 2+ response using a HEK293 cell line stably expressing human P2X7 and fluorometric imaging plate reader technology. For instance, teniposide potently blocked the human P2X7 at sub-miromolar concentrations, but not human P2X4 or rat P2X2. A marked block of ATPinduced Ca 2+ entry and Yo-Pro-1 uptake was also observed in human A375 melanoma cells and mouse microglial cells, both expressing P2X7. On the other hand, agelasine (AGL) and garcinolic acid (GA) facilitated the P2X7 response to ATP in all three cell populations. GA also enhanced the YO-PRO-1 uptake, whereas AGL did not affect the ATP-stimulated intracellular accumulation of this dye. According to the pathophysiological role of P2X7 in various diseases, selective modulators may have potential for further development, e.g. as neuroprotective or antineoplastic drugs.

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Section: Discussionmentioning

confidence: 99%

Natural compounds with P2X7 receptor-modulating properties

Fischer

Urban

Immig

et al. 2013

Purinergic Signalling

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“…Furthermore, determination of the mechanism by which these substances act as antibiotics and further functionalization of the agelasine analogs may also result in substances with more specific antimicrobial activity [87]. Recently, Proszenyák and colleagues [88] synthesized structurally simplified analogs of these natural products (agelasines and agelasimines) starting fromcyclocitral. The novel substances were found to be strong inhibitors of a wide variety of pathogenic microorganisms, including M. tuberculosis.…”

Section: Antibacterial Activitymentioning

confidence: 99%

“…castellanii and A. polyphaga [88] CvL Lectin Cliona varians L. chagasi [55] Diisocyanoadociane Tetracyclic diterpene Cymbastela hooperi P. falciparum [193] Halichondramide Macrolide P. falciparum [192] Kalihinol A Kalihinane diterpenoids Acanthella sp. P. falciparum [195] Manzamine A Alkaloid several sponge species T. gondii, P. berghei, P. falciparum [166,[187][188][189] Mirabilin B Alkaloid Monanchora unguifera L. donovani [167] Pachymatismin Glycoprotein Pachymatisma johnstonii Leishmania sp.…”

Section: Antiprotozoal Activitymentioning

confidence: 99%

Marine Sponges: Potential Sources of New Antimicrobial Drugs

Laport¹,

Santos²,

Muricy³

2009

CPB

254

191

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Sponges (phylum Porifera) are sessile marine filter feeders that have developed efficient defense mechanisms against foreign attackers such as viruses, bacteria, or eukaryotic organisms. Marine sponges are among the richest sources of pharmacologically-active chemicals from marine organisms. It is suggested that (at least) some of the bioactive secondary metabolites isolated from sponges are produced by functional enzyme clusters, which originated from the sponges and their associated microorganisms. More than 5,300 different products are known from sponges and their associated microorganisms, and more than 200 new metabolites from sponges are reported each year. As infectious microorganisms evolve and develop resistance to existing pharmaceuticals, the marine sponge provides novel leads against bacterial, viral, fungal and parasitic diseases. Many marine natural products have successfully advanced to the late stages of clinical trials, as for example ara-A (vidarabine), an anti-viral drug used against the herpes simplex encephalitis virus. This substance is in clinical use for many years. Moreover, a growing number of candidates have been selected as promising leads for extended preclinical assessment, including manzamine A (activity against malaria, tuberculosis, HIV, and others), lasonolides (antifungal activity) and psammaplin A (antibacterial activity). In this review we have surveyed the discoveries of products derived from marine sponges and associated bacteria that have shown in vivo efficacy or potent in vitro activity against infectious and parasitic diseases, including bacterial, viral, fungal and protozoan infections. Our objective was to highlight the substances that have the greatest potential to lead to clinically useful treatments.

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“…Several adenine derivatives have been reported for antimicrobial agent (Ashour et al, 2012;Hirokawa et al, 2009;Proszenyak et al, 2007;Tunçbilek et al, 2009). Additionally, these antimicrobial agents are more effective when compared to our adenine derivatives.…”

Section: Antimicrobial Activitymentioning

confidence: 88%

Synthesis of some novel purine derivatives incorporating tetrazole ring and investigation of their antimicrobial activity and DNA interactions

2014

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This work describes a novel purine derivatives incorporating tetrazole ring for biological applications. Initially, (6-aminopurin-9-yl)alkanenitrile compounds were synthesized. Then, 9-((1H-tetrazol-5-yl)alkyl)-9H-purin-6-amine compounds were synthesized via the addition of sodium azide to nitrile group. These novel purine analogues incorporating tetrazole ring were characterized by Fourier transform infrared, nuclear magnetic resonance and mass spectroscopic techniques. All the synthesized compounds were screened for their antibacterial activities against Gram-positive and Gram-negative bacteria and for their antifungal activities against yeast strains. The effect of the compounds on pBR322 plasmid DNA was studied by gel electrophoretic mobility measurements. The antibacterial activities and plasmid DNA interaction studies suggest that purine derivatives incorporating tetrazole ring cause DNA damages, and higher antibacterial activities than other derivatives.

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Synthesis, Antimicrobial and Antineoplastic Activities for Agelasine and Agelasimine Analogs with a β‐Cyclocitral Derived Substituent

Cited by 35 publications

References 38 publications

Natural compounds with P2X7 receptor-modulating properties

Natural compounds with P2X7 receptor-modulating properties

Marine Sponges: Potential Sources of New Antimicrobial Drugs

Synthesis of some novel purine derivatives incorporating tetrazole ring and investigation of their antimicrobial activity and DNA interactions

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