Synthesis and biological properties of novel sphingosine derivatives

Murakami, Taku; Furusawa, Kazuya; Tamai, Tadakazu; Yoshikai, Kazuyoshi; Nishikawa, Masazumi

doi:10.1016/j.bmcl.2004.12.010

Cited by 20 publications

(17 citation statements)

References 38 publications

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“…The threo analogs (57−58) have been found not only to inhibit Ca 2+ ion mobilization in HL60 leukemia cells but also to produce no Ca 2+ ion increasing activity comparable to natural S1P (6) [107]. The presence and configuration of the amino alcohol moiety seemed to be a very important factor in the inhibitory effect.…”

Section: Sphingosine-1-phosphate and Analogsmentioning

confidence: 98%

Sphingolipids in Anticancer Therapy

Padrón

2006

CMC

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Sphingolipids constitute a broad class of compounds with many biological functions. The sphingolipid metabolites ceramide and sphingosine are potent apoptosis inducers and produce cell cycle arrest, whereas sphingosine-1-phosphate promotes cellular growth and differentiation. Herein, the effects of sphingolipids and their analogs on diverse signaling pathways implicated in the apoptotic process are highlighted. The relatively simple chemical structure of these compounds has led to several strategies for their total synthesis. Those methods have contributed to the development and biological study of several analogs that present diverse degree of modification from the original structure. This article catalogues many of the recently developed synthetic analogs that act on diverse aspects of sphingolipid metabolism. A description of known enzyme inhibitors of the sphigolipids pathway is also given. Finally, diverse new sphingolipid-like antitumor agents isolated from marine sources are presented. This contribution opens the way for future development of new sphingolipid analogs that might be useful in cancer chemotherapy.

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Section: Sphingosine-1-phosphate and Analogsmentioning

confidence: 98%

Sphingolipids in Anticancer Therapy

Padrón

2006

CMC

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“…However, they did not show activities. Their results indicated that the presence and configuration of the amino alcohol moiety appeared to be very important for the antagonist inhibitory effect [83].…”

Section: For Preparing Antagonists Of Edg/s-1p Receptorsmentioning

confidence: 98%

An Overview of Highly Optically Pure Chloramphenicol Bases: Applications and Modifications

Yang

Fang²,

Gong³

et al. 2009

MRMC

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“…N-Pr derivatisation, however, was not tolerated [82]. Ca 2+ -mobilisation studies in HL60 cells demonstrated agonist activity in D-erythrosphingosines 63 and the antagonist potential of (2S,3S,4E)-L-threo-sphingosines 64 [87].…”

Section: S1p-receptor Ligandsmentioning

confidence: 99%

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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Synthesis and biological properties of novel sphingosine derivatives

Cited by 20 publications

References 38 publications

Sphingolipids in Anticancer Therapy

Sphingolipids in Anticancer Therapy

An Overview of Highly Optically Pure Chloramphenicol Bases: Applications and Modifications

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

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