Thiocoraline, a Novel Depsipeptide with Antitumor Activity Produced by a Marine Micromonospora. II. Physico-chemical Properties and Structure Determination.

Baz, Julia Pérez; Cañedo, Librada M.; Puentes, José L. Fernández; Elipe, Maria Victoria Silva

doi:10.7164/antibiotics.50.738

Cited by 114 publications

(42 citation statements)

References 17 publications

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“…89 Thiocoraline differs from the depsipeptide antibiotics discussed above in that it is a thiodepsipeptide, i.e. it incorporates two thioester linkages in place of the ester linkages seen in e.g.…”

Section: Isolation and Structure Elucidation Of Thiocoralinementioning

confidence: 98%

Bisintercalator natural products with potential therapeutic applications: isolation, structure determination, synthetic and biological studies

et al. 2007

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Echinomycin is the prototypical bisintercalator, a molecule that binds to DNA by inserting two planar chromophores between the base-pairs of duplex DNA, placing its cyclic depsipeptide backbone in the minor groove. As such, it has been the focus of an extensive number of investigations into its biological activity, nucleic acid binding and, to some extent, its structure-activity relationships. However, echinomycin is also the parent member of an extended family of natural products that interact with DNA by a similar mechanism of bisintercalation. The structural variety in these compounds leads to changes in sequence selectivity and and biological activity, particularly as anti-tumour and anti-viral agents. One of the more recently identified marine natural products that is moving close to clinical development is thiocoraline, and it therefore seems timely to review the various bisintercalator natural products.

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Section: Isolation and Structure Elucidation Of Thiocoralinementioning

confidence: 98%

Bisintercalator natural products with potential therapeutic applications: isolation, structure determination, synthetic and biological studies

et al. 2007

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“…[11] This compound shows antibacterial activity against Gram-positive bacteria and is a potent antitumor compound active against a variety of human cancer cell lines, due to its DNA bisintercalative properties and its DNA polymerase a inhibition. [12,13] Thiocoraline contains two moieties of the chromophore 3-hydroxy-quinaldic acid (3HQA), which probably acts as a starter unit during biosynthesis. Each of the two symmetrical halves is constituted by 3HQA-D-Cys-Gly-N-methyl-LCys-N,S-dimethyl-L-Cys (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Deciphering the Biosynthesis Pathway of the Antitumor Thiocoraline from a Marine Actinomycete and Its Expression in Two Streptomyces Species

et al. 2006

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Thiocoraline is a thiodepsipeptide antitumor compound produced by two actinomycetes Micromonospora sp. ACM2‐092 and Micromonospora sp. ML1, isolated from two marine invertebrates (a soft coral and a mollusc) found of the Indian Ocean coast of Mozambique. By using oligoprimers derived from nonribosomal peptide synthetase (NRPS) consensus sequences, six PCR fragments containing putative NRPS adenylation domains were amplified from the chromosome of Micromonospora sp. ML1. Insertional inactivation of each adenylation domain showed that two of them generated nonproducing mutants, thereby indicating that these domains were involved in thiocoraline biosynthesis. Sequencing of a 64.6 kbp DNA region revealed the presence of 36 complete open reading frames (ORFs) and two incomplete ones. Heterologous expression of a region of about 53 kbp, containing 26 of the ORFs, in Streptomyces albus and S. lividans led to the production of thiocoraline in these streptomycetes. Surprisingly, the identified gene cluster contains more NRPS modules than expected on the basis of the number of amino acids of thiocoraline. TioR and TioS would most probably constitute the NRPS involved in the biosynthesis of the thiocoraline backbone, according to the colinearity of the respective modules. It is proposed that two other NRPSs, TioY and TioZ, could be responsible for the biosynthesis of a small peptide molecule which could be involved in regulation of the biosynthesis of thicoraline in Micromonospora sp. ML1. In addition, a pathway is proposed for the biosynthesis of the unusual starter unit, 3‐hydroxy‐quinaldic acid.

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“…1a) is a thiodepsipeptide antibiotic produced by some species of actinomycetes Micromonospora. 1,2 Thiocoraline is structurally similar to other natural products such as echinomycin, [3][4][5][6] triostin, 7,8 BE-22179, 9 sandramycin, 10,11 SW-163C-G, [12][13][14][15][16] and luzopeptins 17,18 (Fig. 1a).…”

Section: Introductionmentioning

confidence: 99%

A New Scaffold of an Old Protein Fold Ensures Binding to the Bisintercalator Thiocoraline

Biswas¹,

Zolova²,

Lombó³

et al. 2010

Journal of Molecular Biology

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Thiocoraline, a Novel Depsipeptide with Antitumor Activity Produced by a Marine Micromonospora. II. Physico-chemical Properties and Structure Determination.

Cited by 114 publications

References 17 publications

Bisintercalator natural products with potential therapeutic applications: isolation, structure determination, synthetic and biological studies

Bisintercalator natural products with potential therapeutic applications: isolation, structure determination, synthetic and biological studies

Deciphering the Biosynthesis Pathway of the Antitumor Thiocoraline from a Marine Actinomycete and Its Expression in Two Streptomyces Species

A New Scaffold of an Old Protein Fold Ensures Binding to the Bisintercalator Thiocoraline

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