In vitro antiproliferative activity of 2?-(2-hydroxyphenyl)-2?-thiazoline-4?-carboxylic acid and its methyl ester of L1210 and P388 murine neoplasms

Gt, Elliot; Kf, Kelly; Rl, Bonna; Tr, Wardlaw; Er, Burns

doi:10.1007/bf00262776

Cited by 9 publications

(9 citation statements)

References 16 publications

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“…Cell accumulation at the G 1-S boundary was described in terms of growth of KB cells treated by acyclic analogs of bromotubericidin, known to be potent inhibitors of human cytomegalovirus [19]. The same cell cycle perturbation was encountered with iron chelators which displayed antiproliferative activity on L1210 and P388 murine neoplasms [20] by interference with ribonucleotide reductase and hence DNA synthesis. On the contrary, other compounds are acting on the G1 phase leading to G2M phase accumulation.…”

Section: Discussionmentioning

confidence: 98%

In vitro effect of fungal cyclodepsipeptides on leukemic cells: study of destruxins A, B and E

Odier

Vey²,

Bureau³

1992

Biology of the Cell

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The activities of three mycotoxins isolated from the hyphomycete Metarhizium anisopliae: destruxin A, B, and E (DA, DB and DE) are described and compared in vitro on leukemic cells. Their antitumor effect was investigated by flow cytometry on growth, cell viability and cell cycle perturbation 48 h after destruxin exposure. Against P388 leukemic cells, DE displayed greater antiproliferative activity than DA and DB. The minimum concentration required to inhibit 50% of cell proliferation is 0.33 microgram/ml for DE, 11.7 micrograms/ml for DA and 9.4 micrograms/ml for DB. Cell cycle modifications were only observed with DE at 50 and 10 micrograms/ml and consisted in an accumulation of the cells in G0/1 phase. DA and DB did not modify the number of cells in G0/1 of the cell cycle. Nevertheless a decrease in the number of cells in G2+M phase was induced by the three destruxins.

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Section: Discussionmentioning

confidence: 98%

In vitro effect of fungal cyclodepsipeptides on leukemic cells: study of destruxins A, B and E

Odier

Vey²,

Bureau³

1992

Biology of the Cell

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“…The antifungal properties have not been defined chemically; they might be related to Dha production. Furthermore, Dha is an Fe(III) chelator and inhibitor of DNA replication at the level of ribonucleotide reductase, resulting in a cytostatic effect on murine neoplasms (18). It may be worthwhile to test whether Dha, like salicylate and pyochelin (9,36), can act as a siderophore in Pseudomonas spp.…”

Section: Discussionmentioning

confidence: 99%

Biosynthesis of pyochelin and dihydroaeruginoic acid requires the iron-regulated pchDCBA operon in Pseudomonas aeruginosa

et al. 1997

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The high-affinity siderophore salicylate is an intermediate in the biosynthetic pathway of pyochelin, another siderophore and chelator of transition metal ions, in Pseudomonas aeruginosa. The 2.5-kb region upstream of the salicylate biosynthetic genes pchBA was sequenced and found to contain two additional, contiguous genes, pchD and pchC, having the same orientation. The deduced amino acid sequence of the 60-kDa PchD protein was similar to those of the EntE protein (2,3-dihydroxybenzoate-AMP ligase) of Escherichia coli and other adenylate-forming enzymes, suggesting that salicylate might be adenylated at the carboxyl group by PchD. The 28-kDa PchC protein showed similarities to thioesterases of prokaryotic and eukaryotic origin and might participate in the release of the product(s) formed from activated salicylate. One potential product, dihydroaeruginoate (Dha), was identified in culture supernatants of iron-limited P. aeruginosa cells. The antifungal antibiotic Dha is thought to arise from the reaction of salicylate with cysteine, followed by cyclization of cysteine. Inactivation of the chromosomal pchD gene by insertion of the transcription and translation stop element ⍀Sm/Sp abolished the production of Dha and pyochelin, implying that PchD-mediated activation of salicylate may be a common first step in the synthesis of both metabolites. Furthermore, the pchD::⍀Sm/Sp mutation had a strong polar effect on the expression of the pchBA genes, i.e., on salicylate synthesis, indicating that the pchDCBA genes constitute a transcriptional unit. A full-length pchDCBA transcript of ca. 4.4 kb could be detected in iron-deprived, growing cells of P. aeruginosa. Transcription of pchD started at tandemly arranged promoters, which overlapped with two Fur boxes (binding sites for the ferric uptake regulator) and the promoter of the divergently transcribed pchR gene encoding an activator of pyochelin biosynthesis. This promoter arrangement allows tight iron-mediated repression of the pchDCBA operon.

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“…23 While pyochelin is better characterized, physiochemical and biological properties of these simpler biosynthetic shunt products are largely unknown. Dha (1) was initially characterized as an iron-chelating, antiproliferative compound; 24 however, these iron-chelating properties were not extensively investigated. Dha was also found to have modest antifungal and antibacterial activity, although the scope of microbes tested was quite limited.…”

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confidence: 99%

Pyochelin Biosynthetic Metabolites Bind Iron and Promote Growth in Pseudomonads Demonstrating Siderophore-like Activity

2021

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Pseudomonads employ several strategies to sequester iron vital for their survival including the use of siderophores such as pyoverdine and pyochelin. Similar in structure but significantly less studied are pyochelin biosynthetic byproducts, dihydroaeruginoic acid, aeruginoic acid, aeruginaldehyde (IQS), and aeruginol, along with two other structurally related molecules, aerugine and pyonitrins A−D, which have all been isolated from numerous Pseudomonad extracts. Because of the analogous substructure of these compounds to pyochelin, we hypothesized that they may play a role in iron homeostasis or have a biological effect on other bacterial species. Herein, we discuss the physiochemical evaluation of these molecules and disclose, for the first time, their ability to bind iron and promote growth in Pseudomonads.

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In vitro antiproliferative activity of 2?-(2-hydroxyphenyl)-2?-thiazoline-4?-carboxylic acid and its methyl ester of L1210 and P388 murine neoplasms

Cited by 9 publications

References 16 publications

In vitro effect of fungal cyclodepsipeptides on leukemic cells: study of destruxins A, B and E

In vitro effect of fungal cyclodepsipeptides on leukemic cells: study of destruxins A, B and E

Biosynthesis of pyochelin and dihydroaeruginoic acid requires the iron-regulated pchDCBA operon in Pseudomonas aeruginosa

Pyochelin Biosynthetic Metabolites Bind Iron and Promote Growth in Pseudomonads Demonstrating Siderophore-like Activity

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