Synthesis and evaluation of a photolyzable derivative of sphingosine 1-phosphate-caged SPP

Lixin Qiao; Alan P. Kozikowski; Ana Olivera; Sarah Spiegel

doi:10.1016/S0960-894X(98)00112-7

Synthesis and evaluation of a photolyzable derivative of sphingosine 1-phosphate-caged SPP

Lixin Qiao, Alan P. Kozikowski, Ana Olivera, Sarah Spiegel

Research output: Contribution to journal › Article › peer-review

37 Scopus citations

Abstract

The synthesis of a photolyzable sphingosine 1-phosphate derivative is reported via the reaction of N-(tert-butoxycarbonyl)-2-N,3-O-isopropylidenesphingosine 7 and bis(α-methyl-o-nitrobenzyl) N,N-diisopropylphosphoramidite. Stimulation of DNA synthesis upon illumination of caged SPP-loaded cells is also described.

Original language	English (US)
Pages (from-to)	711-714
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	8
Issue number	7
DOIs	https://doi.org/10.1016/S0960-894X(98)00112-7
State	Published - Apr 7 1998
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/S0960-894X(98)00112-7

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title = "Synthesis and evaluation of a photolyzable derivative of sphingosine 1-phosphate-caged SPP",

abstract = "The synthesis of a photolyzable sphingosine 1-phosphate derivative is reported via the reaction of N-(tert-butoxycarbonyl)-2-N,3-O-isopropylidenesphingosine 7 and bis(α-methyl-o-nitrobenzyl) N,N-diisopropylphosphoramidite. Stimulation of DNA synthesis upon illumination of caged SPP-loaded cells is also described.",

author = "Lixin Qiao and Kozikowski, {Alan P.} and Ana Olivera and Sarah Spiegel",

note = "Funding Information: Acknowledgment. This work was supported by the Department of Defense Research Grant (DAMD17-93-V-3018) to A.P.K. and by Research Grants from the National Institutes of Health (GM43880 and CA61774) to S.S., and by a grant from the American Cancer Society (BE-275) to S.S. We also wish to thank Fidia Pharmaceuticals of Abano Terme, Italy for a generous gift of D-sphingosine sulfate and Margaret E. Schott in the Lombardi Cancer Center of Georgetown University for recording the electrospray mass spectra.",

year = "1998",

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doi = "10.1016/S0960-894X(98)00112-7",

language = "English (US)",

volume = "8",

pages = "711--714",

journal = "Bioorganic and Medicinal Chemistry Letters",

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T1 - Synthesis and evaluation of a photolyzable derivative of sphingosine 1-phosphate-caged SPP

AU - Qiao, Lixin

AU - Kozikowski, Alan P.

AU - Olivera, Ana

AU - Spiegel, Sarah

N1 - Funding Information: Acknowledgment. This work was supported by the Department of Defense Research Grant (DAMD17-93-V-3018) to A.P.K. and by Research Grants from the National Institutes of Health (GM43880 and CA61774) to S.S., and by a grant from the American Cancer Society (BE-275) to S.S. We also wish to thank Fidia Pharmaceuticals of Abano Terme, Italy for a generous gift of D-sphingosine sulfate and Margaret E. Schott in the Lombardi Cancer Center of Georgetown University for recording the electrospray mass spectra.

PY - 1998/4/7

Y1 - 1998/4/7

N2 - The synthesis of a photolyzable sphingosine 1-phosphate derivative is reported via the reaction of N-(tert-butoxycarbonyl)-2-N,3-O-isopropylidenesphingosine 7 and bis(α-methyl-o-nitrobenzyl) N,N-diisopropylphosphoramidite. Stimulation of DNA synthesis upon illumination of caged SPP-loaded cells is also described.

AB - The synthesis of a photolyzable sphingosine 1-phosphate derivative is reported via the reaction of N-(tert-butoxycarbonyl)-2-N,3-O-isopropylidenesphingosine 7 and bis(α-methyl-o-nitrobenzyl) N,N-diisopropylphosphoramidite. Stimulation of DNA synthesis upon illumination of caged SPP-loaded cells is also described.

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JF - Bioorganic and Medicinal Chemistry Letters

IS - 7

ER -

Synthesis and evaluation of a photolyzable derivative of sphingosine 1-phosphate-caged SPP

Abstract

ASJC Scopus subject areas

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