Synthesis and Antiapoptotic Activity of a Novel Analogue of the Neutral Sphingomyelinase Inhibitor Scyphostatin

Claus, Ralf A.; Wüstholz, Annette; Müller, Stefan; Bockmeyer, Clemens L.; Riedel, Norman Hendrik; Kinscherf, Ralf; Deigner, Hans‐Peter

doi:10.1002/cbic.200400228

Cited by 21 publications

(9 citation statements)

References 73 publications

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“…Claus and coworkers recently synthesized a scyphostatin desepoxy analogue (referred to as scyphostatin analogue 14, (Fig. 3C) [96]. This analogue is a chemically and metabolically stabilized compound lacking the epoxy function of the natural congener and carrying a palmitic acid group instead of the native trienoyl residue.…”

Section: (B) Neutral Sphingomyelinase Inhibitorsmentioning

confidence: 98%

“…This analogue is a chemically and metabolically stabilized compound lacking the epoxy function of the natural congener and carrying a palmitic acid group instead of the native trienoyl residue. An evaluation of the biological activity of scyphostatin analogue 14 revealed nSMase inhibition in several in vivo test systems (monocytes, macrophages, hepatocytes) [96]. Arenz and coworkers reported on the synthesis of the spiroepoxide 2 (Fig.…”

Section: (B) Neutral Sphingomyelinase Inhibitorsmentioning

confidence: 99%

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Ceramide Involvement in Apoptosis and Apoptotic Diseases

Thevissen¹,

François²,

Winderickx³

et al. 2006

MRMC

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Apoptosis is implicated in a number of diseases, including neurodegenerative diseases and AIDS. More and more, evidence is accumulating pointing to the critical role of ceramides in the induction of apoptosis. The present review summarizes (i) the molecular basis and regulation of the apoptotic machinery, (ii) the molecular role of ceramides in the induction or execution of apoptotic pathways, and (iii) evidence linking ceramide generation to various apoptotic diseases. Additionally, this review discusses putative therapeutic approaches inhibiting ceramide production in apoptotic diseases.

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Section: (B) Neutral Sphingomyelinase Inhibitorsmentioning

confidence: 98%

Section: (B) Neutral Sphingomyelinase Inhibitorsmentioning

confidence: 99%

Ceramide Involvement in Apoptosis and Apoptotic Diseases

Thevissen¹,

François²,

Winderickx³

et al. 2006

MRMC

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“…In 2005, the enantioselective synthesis of a scyphostatin analogue was reported [149]. As shown in scheme 53, cyclohexanone (316) was coupled with Garner´s aldehyde and then the aldol ob-tained was mesylated to give 317.…”

Section: Syntheses Of Scyphostatinmentioning

confidence: 99%

Enantioselective Synthesis of Natural Epoxyquinoids

Pandolfi

Schapiro²,

Heguaburu³

et al. 2013

COS

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Natural products play an important role as a source not only of potential therapeutic drugs but also of starting materials for semisynthetic new medicines. The epoxyquinoid family, composed by cyclohexane epoxides and related structures, exhibit these characteristics without doubt.Since 2004, significant efforts have been devoted to the stereocontrolled synthesis of these molecules with different and interesting strategies. More than 50 works on this field have been published during this period of time. In addition, many of these polyoxygenated cyclohexenoids exhibit diverse and impressive bioactive shapes. This review aims to analyze the recent advances in the enantioselective processes that have been performed for the total syntheses of these target molecules. It includes a wide range of methodologies for the introduction of chirality either enzymatic or chemical ones. This summarizes microbial preparation of starting materials, lipase kinetic resolutions, use of compounds from the chiral pool, use of chiral auxiliaries and asymmetric catalysis. In a special section, syntheses of scyphostatin are also included.

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“…Also scyphostatin analogs 3a and 3b have inhibitor effects on N-SMase; in particular the primary hydroxy group in compound 2 is important for this activity [35]. Scyphostatin analog 14, a chemically and metabolically stabilized compound lacking the epoxy function of the natural congener and carrying a palmitic acid group instead of the native trienoyl residue induces N-SMase inhibition in several systems (monocytes, macrophages, hepatocytes) [36]. Chlorogentisylquinone, purified from the culture broth of a fungal strain FOM-8108 isolated from a marine environment by solvent extraction, silica gel chromatography and Sephadex LH-20 chromatography, inhibits N-SMase rat brain membranes [37].…”

Section: Inhibitors Of Sphingomyelin Utilizationmentioning

confidence: 99%

Sphingolipid Metabolism Inhibitors and Cell Function

Albi¹,

Magni²

2008

TOEIJ

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It has been widely shown that ceramide, ceramide phosphate, sphingosine and sphingosine-1-phosphate are molecules involved in cell proliferation, differentiation and apoptosis. The regulation of the enzymes that control their metabolism has an important role for cellular fate. Many studies in the field have shed light on sphingolipid metabolism inhibition and on its role in cell processes such as gene expression, DNA duplication and RNA transcription. The aim of this review is to collect, in a systematic way, the recent advances in the field of sphingolipid metabolism inhibitors, with special emphasis on their effects on cell function.

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Synthesis and Antiapoptotic Activity of a Novel Analogue of the Neutral Sphingomyelinase Inhibitor Scyphostatin

Cited by 21 publications

References 73 publications

Ceramide Involvement in Apoptosis and Apoptotic Diseases

Ceramide Involvement in Apoptosis and Apoptotic Diseases

Enantioselective Synthesis of Natural Epoxyquinoids

Sphingolipid Metabolism Inhibitors and Cell Function

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