New pyridoacridine alkaloids from the purple morph of the ascidian Cystodytes dellechiajei

Bry, Delphine; Banaigs, Bernard; Long, Christophe; Bontemps, Nataly

doi:10.1016/j.tetlet.2011.04.005

Cited by 31 publications

(34 citation statements)

References 14 publications

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“…Subsequent research has been more thorough, and several potently antibacterial alkaloid monomers (MICs ≤10 µg/mL) have been identified in the aaptamine [46], indole [47][48][49][50][51][52], indolizidine [53], isoquinoline [54][55][56][57][58][59], piperazine [60], quinoline [61,62], quinolone [63], agelasine [64,65], and polyamine [32] classes. Alkaloid dimers with similar levels of activity have been found in the aaptamine-indole [66], bisindole [67,68], indole-quinoline [69,70], pyridoacridine [71,72], bispyrrole [73][74][75], and pyrrole-imidazole [76] classes. A list of compounds with the lowest recorded MICs is presented in Table 1.…”

Section: Naturally Occurring Alkaloidsmentioning

confidence: 70%

Alkaloids: An overview of their antibacterial, antibiotic-enhancing and antivirulence activities

Cushnie¹,

Cushnie²,

Lamb³

2014

International Journal of Antimicrobial Agents

702

374

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With reports of pandrug-resistant bacteria causing untreatable infections, the need for new antibacterial therapies is more pressing than ever. Alkaloids are a large and structurally diverse group of compounds that have served as scaffolds for important antibacterial drugs such as metronidazole and the quinolones. In this review, we highlight other alkaloids with development potential. Natural, semisynthetic and synthetic alkaloids of all classes are considered, looking first at those with direct antibacterial activity and those with antibiotic-enhancing activity. Potent examples include CJ-13,136, a novel actinomycete-derived quinolone alkaloid with a minimum inhibitory concentration of 0.1 ng/mL against Helicobacter pylori, and squalamine, a polyamine alkaloid from the dogfish shark that renders Gram-negative pathogens 16- to >32-fold more susceptible to ciprofloxacin. Where available, information on toxicity, structure-activity relationships, mechanisms of action and in vivo activity is presented. The effects of alkaloids on virulence gene regulatory systems such as quorum sensing and virulence factors such as sortases, adhesins and secretion systems are also described. The synthetic isoquinoline alkaloid virstatin, for example, inhibits the transcriptional regulator ToxT in Vibrio cholerae, preventing expression of cholera toxin and fimbriae and conferring in vivo protection against intestinal colonisation. The review concludes with implications and limitations of the described research and directions for future research.

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Section: Naturally Occurring Alkaloidsmentioning

confidence: 70%

Alkaloids: An overview of their antibacterial, antibiotic-enhancing and antivirulence activities

Cushnie¹,

Cushnie²,

Lamb³

2014

International Journal of Antimicrobial Agents

702

374

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“…Moderate cytotoxicity towards the HCT-116 human colon tumor cell line with IC 50 values of 33, 89, 2.6 and 1.6 µM were observed for each of 12 – 15 respectively. Styelsamine D is considered to play a central role in the biogenesis of many pyridoacridine alkaloids [7], though no definitive biosynthetic studies have been reported to date [8]. …”

Section: Introductionmentioning

confidence: 99%

Synthesis, DNA Binding and Antitumor Evaluation of Styelsamine and Cystodytin Analogues

Fong

Copp

2013

Marine Drugs

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A series of N-14 sidechain substituted analogues of styelsamine (pyrido[4,3,2-mn]acridine) and cystodytin (pyrido[4,3,2-mn]acridin-4-one) alkaloids have been prepared and evaluated for their DNA binding affinity and antiproliferative activity towards a panel of human tumor cell lines. Overall it was found that styelsamine analogues were stronger DNA binders, with the natural products styelsamines B and D having particularly high affinity (Kapp 5.33 × 106 and 3.64 × 106 M−1, respectively). In comparison, the cystodytin iminoquinone alkaloids showed lower affinity for DNA, but were typically just as active as styelsamine analogues at inhibiting proliferation of tumor cells in vitro. Sub-panel selectivity towards non-small cell lung, melanoma and renal cancer cell lines were observed for a number of the analogues. Correlation was observed between whole cell activity and clogP, with the most potent antiproliferative activity being observed for 3-phenylpropanamide analogues 37 and 41 (NCI panel average GI50 0.4 μM and 0.32 μM, respectively) with clogP ~4.0–4.5.

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“…Delfourne’s first total synthesis of demethyldeoxyamphimedine ( 56 ), which is illustrated in Scheme 10 , was published in 2002 [ 12 ], years before this compound was identified as a natural product [ 27 ]. This approach started with a hetero-Diels-Alder cycloaddition of isoquinoline-5,8-dione ( 10 ) and 1-azadieene 57 , both of them not commercially available.…”

Section: Amphimedine-type Pyridoacridinesmentioning

confidence: 99%

New Perspectives in the Chemistry of Marine Pyridoacridine Alkaloids

Plodek

Bracher

2016

Marine Drugs

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Secondary metabolites from marine organisms are a rich source of novel leads for drug development. Among these natural products, polycyclic aromatic alkaloids of the pyridoacridine type have attracted the highest attention as lead compounds for the development of novel anti-cancer and anti-infective drugs. Numerous sophisticated total syntheses of pyridoacridine alkaloids have been worked out, and many of them have also been extended to the synthesis of libraries of analogues of the alkaloids. This review summarizes the progress in the chemistry of pyridoacridine alkaloids that was made in the last one-and-a-half decades.

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New pyridoacridine alkaloids from the purple morph of the ascidian Cystodytes dellechiajei

Cited by 31 publications

References 14 publications

Alkaloids: An overview of their antibacterial, antibiotic-enhancing and antivirulence activities

Alkaloids: An overview of their antibacterial, antibiotic-enhancing and antivirulence activities

Synthesis, DNA Binding and Antitumor Evaluation of Styelsamine and Cystodytin Analogues

New Perspectives in the Chemistry of Marine Pyridoacridine Alkaloids

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