Aplyronine A, a potent antitumor substance and the congeners aplyronines B and C isolated from the sea hare Aplysia kurodai

Yamada, Kiyoyuki; Ojika, Makoto; Ishigaki, Takeshi; Yoshida, Yoshitoku; Ekimoto, Hisao; Arakawa, Masayuki

doi:10.1021/ja00076a082

Cited by 151 publications

(81 citation statements)

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“…Many natural macrolides exhibit cytotoxic activities against different cancer cell lines [32,[39][40][41][42][43][44]. This is the case with PTX-2, which displays selective and potent cytotoxicity against human cells of lung, colon and breast cancer [21].…”

Section: Discussionmentioning

confidence: 99%

Lactone Ring of Pectenotoxins: a Key Factor for their Activity on Cytoskeletal Dynamics

Ares

Louzao²,

Espiña³

et al. 2007

Cell Physiol Biochem

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Background: Pectenotoxins are a group of natural products from marine origin that can accumulate in shellfish and intoxicate humans. Recently, novel homologues such as pectenotoxin-11 (PTX-11) and pectenotoxin-2 seco acid (PTX-2SA) have been identified. Their toxic potential towards experimental animals has been evaluated however their interaction with cellular systems is almost unknown. This is the first report showing (i) the biological activity of PTX-11 and PTX-2SA on actin cytoskeleton and morphology of living cells and (ii) the structure- activity relationship for this family of toxic compounds. Methods: Fluorescent phalloidin was utilized to quantify and visualize any modification in polymerized actin. Fluorescence values were obtained with laser-scanning cytometer and cells were imaged through confocal microscopy. For structure-activity evaluations, pectenotoxin-1 (PTX-1) and pectenotoxin-2 (PTX-2) was also analyzed. Results: Data showed that PTX-11 triggered a remarkable depolymerizing effect on actin cytoskeleton and also modifications in the shape of cells. In contrast, PTX-2SA did not evidence the same effects. Conclusion: Our findings point out that (i) the actin cytoskeleton is a common target for PTX-11, PTX-2 and PTX-1, but not for PTX-2SA, and (ii) this difference in activity is related to the presence or absence of an intact lactone ring in their structures.

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Section: Discussionmentioning

confidence: 99%

Lactone Ring of Pectenotoxins: a Key Factor for their Activity on Cytoskeletal Dynamics

Ares

Louzao²,

Espiña³

et al. 2007

Cell Physiol Biochem

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“…The macrocylic ring is attached to a long alycyclic side chain with minor variations occurring either at the macrocylic ring and/or at the side chain. Aplyronines isolated from the Pacific seahare Aplysia kurodai have different macrolide rings but similar side chains (Yamada et al, 1993).…”

Section: Major Classes Of Actin-targeted Drugs Latrunculinsmentioning

confidence: 99%

New anti-actin drugs in the study of the organization and function of the actin cytoskeleton

Spector

Braet²,

Shochet

et al. 1999

Microsc. Res. Tech.

309

245

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“…4) isolated from the sea hare Aplysia kurodai (Yamada et al 1993) exhibited similar effects to those of mycalolide B; it severs F-actin and binds to G-actin with a 1:1 ratio (Saito et al 1996). Although tropomyosin did not prevent the depolymerizing effect of aplyronine A, a stoichiometric (to actin) concentration of phalloidin completely blocked it.…”

Section: Trisoxazole Macrolidesmentioning

confidence: 96%

Developmental Biology of Neoplastic Growth

Macieira‐Coelho¹

2005

Progress in Molecular and Subcellular Biology

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Aplyronine A, a potent antitumor substance and the congeners aplyronines B and C isolated from the sea hare Aplysia kurodai

Cited by 151 publications

References 0 publications

Lactone Ring of Pectenotoxins: a Key Factor for their Activity on Cytoskeletal Dynamics

Lactone Ring of Pectenotoxins: a Key Factor for their Activity on Cytoskeletal Dynamics

New anti-actin drugs in the study of the organization and function of the actin cytoskeleton

Developmental Biology of Neoplastic Growth

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