Synthesis and biological evaluation of enantiomeric rhamnose analogues of the antitumour agent spicamycin - is the mode of action by modification of N-linked glycoproteins?
The synthesis of both enantiomers of dodecyl rhamnospicamycin 2a and 2b, a rhamnose analogue of the naturally occurring combinatorial library spicamycin 1, are derived from L-rhamnose and methyl α-D-mannopyranoside, respectively. The L-(+)-enantiomer 2a containing an L-rhamnose fragment is shown to...
| Main Authors: | , , |
|---|---|
| Format: | Journal article |
| Language: | English |
| Published: |
1999
|
| _version_ | 1797098105819103232 |
|---|---|
| author | Martin, A Butters, T Fleet, G |
| author_facet | Martin, A Butters, T Fleet, G |
| author_sort | Martin, A |
| collection | OXFORD |
| description | The synthesis of both enantiomers of dodecyl rhamnospicamycin 2a and 2b, a rhamnose analogue of the naturally occurring combinatorial library spicamycin 1, are derived from L-rhamnose and methyl α-D-mannopyranoside, respectively. The L-(+)-enantiomer 2a containing an L-rhamnose fragment is shown to be highly cytotoxic towards human myeloma cells with an IC50=120 nM, whereas the D-(-)-enantiomer 2b, based on a D-mannose structure, shows no significant cytotoxicity. The analogue 16, in which the nucleotide base fragment has been replaced by a simple methoxy group, has no cytotoxicity. Initial studies towards clarifying the mechanism of anti-cancer action of spicamycin analogues are reported. |
| first_indexed | 2024-03-07T05:04:54Z |
| format | Journal article |
| id | oxford-uuid:d9966d43-dc30-472d-bea4-401afb6406dd |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T05:04:54Z |
| publishDate | 1999 |
| record_format | dspace |
| spelling | oxford-uuid:d9966d43-dc30-472d-bea4-401afb6406dd2022-03-27T08:56:54ZSynthesis and biological evaluation of enantiomeric rhamnose analogues of the antitumour agent spicamycin - is the mode of action by modification of N-linked glycoproteins?Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:d9966d43-dc30-472d-bea4-401afb6406ddEnglishSymplectic Elements at Oxford1999Martin, AButters, TFleet, GThe synthesis of both enantiomers of dodecyl rhamnospicamycin 2a and 2b, a rhamnose analogue of the naturally occurring combinatorial library spicamycin 1, are derived from L-rhamnose and methyl α-D-mannopyranoside, respectively. The L-(+)-enantiomer 2a containing an L-rhamnose fragment is shown to be highly cytotoxic towards human myeloma cells with an IC50=120 nM, whereas the D-(-)-enantiomer 2b, based on a D-mannose structure, shows no significant cytotoxicity. The analogue 16, in which the nucleotide base fragment has been replaced by a simple methoxy group, has no cytotoxicity. Initial studies towards clarifying the mechanism of anti-cancer action of spicamycin analogues are reported. |
| spellingShingle | Martin, A Butters, T Fleet, G Synthesis and biological evaluation of enantiomeric rhamnose analogues of the antitumour agent spicamycin - is the mode of action by modification of N-linked glycoproteins? |
| title | Synthesis and biological evaluation of enantiomeric rhamnose analogues of the antitumour agent spicamycin - is the mode of action by modification of N-linked glycoproteins? |
| title_full | Synthesis and biological evaluation of enantiomeric rhamnose analogues of the antitumour agent spicamycin - is the mode of action by modification of N-linked glycoproteins? |
| title_fullStr | Synthesis and biological evaluation of enantiomeric rhamnose analogues of the antitumour agent spicamycin - is the mode of action by modification of N-linked glycoproteins? |
| title_full_unstemmed | Synthesis and biological evaluation of enantiomeric rhamnose analogues of the antitumour agent spicamycin - is the mode of action by modification of N-linked glycoproteins? |
| title_short | Synthesis and biological evaluation of enantiomeric rhamnose analogues of the antitumour agent spicamycin - is the mode of action by modification of N-linked glycoproteins? |
| title_sort | synthesis and biological evaluation of enantiomeric rhamnose analogues of the antitumour agent spicamycin is the mode of action by modification of n linked glycoproteins |
| work_keys_str_mv | AT martina synthesisandbiologicalevaluationofenantiomericrhamnoseanaloguesoftheantitumouragentspicamycinisthemodeofactionbymodificationofnlinkedglycoproteins AT butterst synthesisandbiologicalevaluationofenantiomericrhamnoseanaloguesoftheantitumouragentspicamycinisthemodeofactionbymodificationofnlinkedglycoproteins AT fleetg synthesisandbiologicalevaluationofenantiomericrhamnoseanaloguesoftheantitumouragentspicamycinisthemodeofactionbymodificationofnlinkedglycoproteins |