A new non-protein enediyne antibiotic N1999A2: Unique enediyne chromophore similar to neocarzinostatin and DNA cleavage feature

Ando, Toshihiko; Ishii, Makoto; Kajiura, Takayuki; Kameyama, T; Miwa, Kiyoshi; Sugiura, Yukio

doi:10.1016/s0040-4039(98)01383-5

Cited by 54 publications

(27 citation statements)

References 5 publications

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“…The metabolites, belonging to a steadily growing enediyne family, now comprise nine natural products: neocarzinostatin (137), which was isolated from S. carzinostaticus (207)(208)(209)(210)(211)(212)(213), kedarcidin (138) from Actinomycete L585-6 (214-218), maduropeptin (139) from Actinomadura madurea (219,220), and N1999A2 (140) from Streptomyces sp. AJ9493 (221)(222)(223). The representatives of this group are probably the most potent anticancer agents discovered.…”

Section: Bacterial and Cyanobacterial Acetylenic Metabolitesmentioning

confidence: 99%

Anticancer activity of natural and synthetic acetylenic lipids

Dembitsky¹

2006

Lipids

129

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This review is a comprehensive survey of acetylenic lipids and their derivatives, obtained from living organisms, that have anticancer activity. Acetylenic metabolites belong to a class of molecules containing triple bond(s). They are found in plants, fungi, microorganisms, and marine invertebrates. Although acetylenes are common as components of terrestrial plants, fungi, and bacteria, it is only within the last 30 years that biologically active polyacetylenes having unusual structural features have been reported from plants, cyanobacteria, algae, invertebrates, and other sources. Naturally occurring aquatic acetylenes are of particular interest since many of them display important biological activities and possess antitumor, antibacterial, antimicrobial, antifouling, antifungal, pesticidal, phototoxic, HIV-inhibitory, and immunosuppressive properties. There is no doubt that they are of great interest, especially for the medicinal and/or pharmaceutical industries. This review presents structures and describes cytotoxic and anticancer activities only for more than 300 acetylenic lipids and their derivatives isolated from living organisms.

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Section: Bacterial and Cyanobacterial Acetylenic Metabolitesmentioning

confidence: 99%

Anticancer activity of natural and synthetic acetylenic lipids

Dembitsky¹

2006

Lipids

129

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“…Similar substituted naphthoate fragments are found in the enediyne DNA-cleaving agents neocarzinostatin chromophore (105; Scheme 11.14) [157,158] and N1999A2 (106) [159]. The neocarzinostatin biosynthetic gene cluster in Streptomyces carzinostaticus has recently been sequenced [160], revealing the existence of an iterative Type I polyketide synthase believed to be required for synthesis of the naphthoate fragment.…”

Section: Biosynthesismentioning

confidence: 89%

Aziridine Natural Products – Discovery, Biological Activity and Biosynthesis

Lowden

2006

Aziridines and Epoxides in Organic Synthesis

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“…A novel and unstable nine-membered epoxyenediyne, N1999-A2 ( 96 ), was reported to exhibit extremely potent cytotoxicity toward cultured cancer cells in 1998 by Ando and coworkers at Ajinomoto Co. Ltd. 116) The structure of 96 is very similar to that of the aglycon of neocarzinostatin chromophore ( 95 ) but lacks a stabilizing carrier apoprotein. Since the stereochemistry of 96 was unknown, we synthesized its stereoisomers through C7,C8- or C5,C6-cyclization using cerium acetylide (Scheme 11).…”

Section: Stereocontrolled Syntheses Of Chromoprotein Enediyne Antitummentioning

confidence: 99%

Total synthesis and related studies of large, strained, and bioactive natural products

Hirama

2016

Proceedings of the Japan Academy. Ser. B: Physical and Biologic

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Our chemical syntheses and related scientific investigations of natural products with complex architectures and powerful biological activities are described, focusing on the very large 3 nm-long polycyclic ethers called the ciguatoxins, highly strained and labile chromoprotein antitumor antibiotics featuring nine-membered enediyne cores, and extremely potent anthelmintic macrolides called the avermectins.

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A new non-protein enediyne antibiotic N1999A2: Unique enediyne chromophore similar to neocarzinostatin and DNA cleavage feature

Cited by 54 publications

References 5 publications

Anticancer activity of natural and synthetic acetylenic lipids

Anticancer activity of natural and synthetic acetylenic lipids

Aziridine Natural Products – Discovery, Biological Activity and Biosynthesis

Total synthesis and related studies of large, strained, and bioactive natural products

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