Synthesis and biological evaluation of novel cytotoxic phospholipids for prostate cancer

Gududuru, Veeresa; Hurh, Eunju; Durgam, Gangadhar G.; Hong, Seoung Soo; Sardar, Vineet M.; Xu, Huiping; Dalton, James T.; Miller, Duane D.

doi:10.1016/j.bmcl.2004.07.026

Cited by 17 publications

(7 citation statements)

References 17 publications

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“…However, while optimisation identified inhibitor leads (e.g. 43) in multiple prostate cancer cell-lines, high toxicity to non-tumour cell-lines was also observed [69]. Meanwhile SAR studies conducted on separated stereoisomers from Darmstoff racemate 44 (a dual LPA 1 /LPA 3 -R antagonist, in contrast to the agonist character of 35) revealed LPA 3 -Rsubtype specificity in isomers (S)-44, which was transformed to pan-agonist behaviour for LPA 1-3 -R (selective for the LPA 3 subtype) in their (S)-45 thiophosphate analogues -all Darmstoff derivatives inhibiting ATX.…”

Section: Lpa-receptor Ligandsmentioning

confidence: 86%

Organophosphorus Compounds: Intervention in Mechanisms of Signal Transduction Relevant to Proliferative, Immunological and Circulatory Disorders

Wardle¹,

Bligh²,

Hudson³

2008

CMC

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Literature publications reporting the development of organophosphorus compounds, targeting aspects of signal transduction to the titled therapeutic ends, are reviewed. With respect to extracellular targets, the development of ligands to purinergic (P2), and endothelial differentiation-gene receptors (of S1P- and LPA-receptor subtypes) is charted, along with inhibitors of the production and release of tumour necrosis factor-alpha (TNF-alpha). Reported also are inhibitors of the ectoenzymes aminopeptidase N, aminopeptidase A and dipeptidyl peptidase IV, the proteolytic enzyme thrombin, ligands to "apoptosis-receptors" and gammadelta T-cell activators. In addition, disruption of intracellular signalling chains mediated through reversible coupling of proteins via phosphorylation of Tyr residues and docking of pTyr residues in SH2-binding domains is covered. In particular, the development of ligands to SH2-binding domains in tyrosine kinases Src and lck, adaptor protein Grb2, and also ZAP70 protein are reported along with inhibitors to relevant phosphatases. SAR studies of ligands to Ins(1,4,5)-P3- and ryanodine-type receptors of intracellular Ca2+-storage organelles are described including analogues to secondary messengers cyclic-ADP-ribose (cADPR) and myo-inositol-1,4,5-triphosphate. Inhibitors of phosphatidyl inositol 3-kinase (PI3K) and sphingomyelinase are also reported, as are inhibitors of farnesyl transferase, the enzyme involved in protein-prenylation.

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Section: Lpa-receptor Ligandsmentioning

confidence: 86%

Organophosphorus Compounds: Intervention in Mechanisms of Signal Transduction Relevant to Proliferative, Immunological and Circulatory Disorders

Wardle¹,

Bligh²,

Hudson³

2008

CMC

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“…5,6 The authors, who rst generated serine phosphate amides as lysophosphatidic acid analogues to treat prostate cancer, noted their poor selectivity due to the possible hydrolysis of the phosphate group present in their structures. 7 To circumvent this issue, they chose to work with 4thiazolidinone derivatives 8 because this cycle is described as a phosphate biomimetic. 9 To optimize their cytotoxicity results the authors then developed thiazolidine compounds, and subsequently discovered their promising apoptotic property.…”

Section: Introductionmentioning

confidence: 99%

3-Propionyl-thiazolidine-4-carboxylic acid ethyl esters: a family of antiproliferative thiazolidines

et al. 2015

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“…Biological activity of the prepared amidophosphates is among the valuable properties of the derivatives. In particular, many of the substituted amidophosphates exhibited antifungal [60,61], antibacterial [61], or antitumor [62][63][64] activity. The reported results and our earlier studies of phosphorylation of polyene macrolide antibiotics [40][41][42][43][65][66][67][68] attracted our interest to investigation of medicinal and biological properties of the prepared derivatives I-V.…”

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confidence: 99%

Chemical modification of heptaene macrolide antibiotic Amphotericin B under conditions of the Atherton-Todd reaction

2014

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Chemical modification of heptaene macrolide antibiotic Amphotericin B with dialkyl(diaryl)phosphites has been performed under conditions of the Atherton-Todd reaction. As a result, the corresponding dialkyl(aryl)amidophosphonate derivatives of Amphotericin B have been formed. The prepared derivatives have been characterized by their physicochemical properties, toxicity, and antifungal activity against a set of test cultures of pathogenic fungi and yeast-like fungi of the Candida species.

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Synthesis and biological evaluation of novel cytotoxic phospholipids for prostate cancer

Cited by 17 publications

References 17 publications

Organophosphorus Compounds: Intervention in Mechanisms of Signal Transduction Relevant to Proliferative, Immunological and Circulatory Disorders

Organophosphorus Compounds: Intervention in Mechanisms of Signal Transduction Relevant to Proliferative, Immunological and Circulatory Disorders

3-Propionyl-thiazolidine-4-carboxylic acid ethyl esters: a family of antiproliferative thiazolidines

Chemical modification of heptaene macrolide antibiotic Amphotericin B under conditions of the Atherton-Todd reaction

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