(−)-Doliculide, a New Macrocyclic Depsipeptide Enhancer of Actin Assembly

Bai, Ruoli; Covell, David G.; Liu, Chunfeng; Ghosh, Arun K.; Hamel, Ernest

doi:10.1074/jbc.m205076200

Cited by 57 publications

(72 citation statements)

References 27 publications

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“…The ''hydrocarbon'' portion is probably crucial in conferring a preorganized bioactive conformation. Hamel and coworkers (30) reported that the cytotoxicity of doliculide was caused by interference with the polymerization of actin in developing cells.…”

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confidence: 99%

Total synthesis of the cytotoxic cyclodepsipeptide (-)-doliculide: The “ester” effect in acyclic 1,3-induction of deoxypropionates

Hanessian

Mascitti

Giroux

2004

Proc. Natl. Acad. Sci. U.S.A.

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The total synthesis of the marine cyclodepsipeptide (؊)-doliculide is described. An acyclic (2S,4S,6R)-trimethyl alkanoic acid precursor to the ''hydrocarbon'' portion of doliculide was synthesized starting with L-ascorbic acid based on a stereocontrolled iterative conjugate addition of lithium dimethylcuprate to acyclic ␦-Cmethyl ␣,␤-unsaturated ester derivatives. syn͞syn selectivity was achieved by relying on 1,3-induction in preferred folded conformations that avoid 1,5-syn-pentane interactions in the transition states. The nature of the ester moiety seems to play an important role in determining the syn͞anti ratios of C-methyl adducts. The 1-methyl-1-cyclopentyl ester group was found to confer the best syn selectivity to the cuprate addition products, especially in seven-carbon enoates.

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confidence: 99%

Total synthesis of the cytotoxic cyclodepsipeptide (-)-doliculide: The “ester” effect in acyclic 1,3-induction of deoxypropionates

Hanessian

Mascitti

Giroux

2004

Proc. Natl. Acad. Sci. U.S.A.

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“…With regard to biochemical studies, Hamel, Ghosh and co-workers reported that doliculide arrested cells at the G2/M phase by enhancing actin assembly [159]. Doliculide is structurally related to cyclodepsipeptides such as jasplakinolide (jaspamide) from the marine sponge Jaspis sp.…”

Section: Peptides and Depsipeptidesmentioning

confidence: 99%

Antitumor Effects of Sea Hare-Derived Compounds in Cancer

Kigoshi

Kita

2014

Handbook of Anticancer Drugs From Marine Origin

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Sea hares (family Aplysiidae) are a rich source of bioactive substances. Especially, over the past 40 years, the genera Aplysia and Dolabella have afforded numerous bioactive secondary metabolites that exhibit antitumor activity. For example, the depsipeptide dolastatin 10 and its analogue are currently in cancer clinical trials. Meanwhile, the chemical probe approach has revealed that the antitumor macrolide aplyronine A inhibits microtubule assembly in association with actin. This article highlights the recent findings regarding the chemical biology of antitumor and antineoplastic compounds from sea hares, as well as molecules that have been discovered and characterized after 2000.Keywords Antitumor · Sea hare · Aplysia · Antitumor · Actin-deplymerization · Cytotoxicity · Tubulin IntroductionSea hares, which belong to the opisthobranch group of mollusks (clade Aplysiomorpha), are shell-less, slow-moving benthic marine mollusks [1]. The order Anaspidea includes two families, Akeridae and Aplysiidae [2]. Almost all chemical studies have focused on Aplysiidae specimens. The family Aplysiidae includes nine genera, Aplysia (Linnaeus 1767), Bursatella (Blainville 1817), Dolabella (Lamarck 1801), Dolabrifera (Gray 1847), Notarchus (Cuvier 1817), Petalifera (Gray 1847), Phyllaplysia (Fischer 1872), Syphonota (Adams 1854), and Stylocheilus (Gould 1852). Sea hares are herbivorous, and are typically found on seaweed in shallow water. They are not eaten by other marine animals and have been postulated to contain chemical defense substances. The poisonous properties of sea hare secretions were known in Roman times. In addition, sea hares release ink from their ink glands, which deter predators. This ink acts as a screen, while at the

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“…Iodide 89 was isolated in fair to very high yields with complete E-selectivity and excellent enantioselectivity (94-98% ee) (Scheme 2.21) [45]. The use of CaH 2 instead of 4Å MS prevented both competing hydrolysis of the silyl ketene acetal (66) and, most importantly, the Lewis-acid-promoted isomerization of the initial E,E-configured vinyl halide (87). The bromide 90 (Scheme 2.21) was used in the total syntheses of (+)-dolastin 19 (91) [46,47] and (−)-auriside A (92) and B (93) [48] (chemical structures, see Scheme 2.22).…”

Section: Ester-derived Silyl Dienol Ethers -Enantioselective Processesmentioning

confidence: 99%

“…VMAR of (6S,7R)-polyketide fragment 146 and (6R,7S)-polyketide fragment ent-146. 6-epi-Chondramide C (originally proposed structure by Gosh)[66], and natural (−)-chondramide C (revised structure). the opening maneuver was the VMAR between aldehyde 149 and l-valine-based silyl N,O-acetal 136.…”

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confidence: 99%