A revised structure of sibiromycin

Leber, Jack D.; Hoover, John R. E.; Holden, Kenneth G.; Johnson, Randall K.; Hecht, Sidney M.

doi:10.1021/ja00217a061

Cited by 43 publications

(20 citation statements)

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“…Facile oxidation of the dihydropyrrole under the harsh acidic degradation conditions used resulted in the incorrect assignment. 1D and 2D NMR studies of sibiromycin lead to the final assignment of the aglycone of the sibiromycin with a hydropyrrole moiety (Fig. ).…”

Section: Isolation and Characterization Of Naturally Produced Pyrrolomentioning

confidence: 99%

Biosynthesis, synthesis, and biological activities of pyrrolobenzodiazepines

Gerratana

2010

Medicinal Research Reviews

115

142

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Pyrrolobenzodiazepines (PBDs) are sequence selective DNA alkylating agents with remarkable antineoplastic activity. They are either naturally produced by actinomycetes or synthetically produced. The remarkable broad spectrum of activities of the naturally produced PBDs encouraged the synthesis of several PBDs, including dimeric and hybrid PBDs yielding to an improvement in the DNA binding sequence specificity and in the potency of this class of compounds. However, limitation in the chemical synthesis prevented the testing of one of the most potent PBDs, sibiromycin, a naturally produced glycosylated PBDs. Only recently the biosynthetic gene clusters for PBDs have been identified opening the doors to the production of glycosylated PBDs by mutasynthesis and biosynthetic engineering. The present review describes the recent studies on the biosynthesis of naturally produced pyrrolobenzodiazepines. In addition, it provides an overview on the isolation and characterization of naturally produced PBDs, on the chemical synthesis of PBDs, on the mechanism of DNA alkylation, and on the DNA binding affinity and cytotoxic properties of both naturally produced and synthetic pyrrolobenzodiazepines.

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Section: Isolation and Characterization Of Naturally Produced Pyrrolomentioning

confidence: 99%

Biosynthesis, synthesis, and biological activities of pyrrolobenzodiazepines

Gerratana

2010

Medicinal Research Reviews

115

142

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“…One can see that, even after correction, the wire does not have perfect cylindrical symmetry. The texture, which causes strong maxima, can be explained by a typical arrangement of orientations called 'circular' or 'cyclic' fibre texture by Stiiwe (1961) and Leber (1961), respectively. We have observed that this texture is always encountered at all steps of the drawing process of b.c.c, iron wire (whether thick or thin wires) (Montesin, 1991), it is located at about 0.8R and its extent depends on the drawing conditions.…”

Section: Experimental Checking Of N(qo Jl)mentioning

confidence: 99%

Evolution of crystallographic texture in thin wires

Montésin¹,

Heizmann

1992

J Appl Cryst

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An X-ray diffraction procedure has been developed to measure accurately the textures of thin wires so that the texture variation across the wire radius may be obtained. Since X-rays penetrate no further than the surface of most metals, X-ray examination can be considered to be superficial for large wires but by thinning the wire it is possible to obtain the texture variation across its radius. When the diameter is very small, X-rays can penetrate a significant proportion of the wire. In these cases a new technique using the texture changes between several thinning procedures allows a precise understanding of the texture variation between the surface and the core of the wire. To illustrate the application of this procedure, some examples are given for 175 ~tm steel cord.

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“…[17][18] PBD dimers were designed from monomeric natural products [19][20][21][22] which include anthramycin 1, sibiromycin 2 and tomaymycin 3 Figure 1. These natural products are DNA minor groove binders with GC sequence specificity and potent cytotoxic activity in the nM IC 50 range.…”

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confidence: 99%