Interference with Mitosis (tubulin)
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5 Terms
cell division overview
as parent cell and chromosomes divide, a mitotic spindle is generated that links the 2 daughter cells
major structural elements of the spindle are microtubule polymers formed from tubulin proteins
vinca alkaloids: vinblastine and vincristine 1950s
first anti-cancer natural products found to interfere with tubulin process
bind tubulin and prevent its polymerisation to form microtubules, cell division arrested
widely used in anti-cancer chemo
taxol (isolated 1960s)
stabilises the microtubule polymer and protects it from disassembly so cell division is prevented further down the line
effective against solid tumours and revolutionary against hormone reactive breast cancer
marketed as paclitaxel in 1993
supply problem of paclitaxel
not sustainable (pacific yew tree)
European yew needles contain closely related compound, sustainable and can be used to synthesise taxol
how is 10-decateylbaccatin from European yew converted to paclitaxel
2OH groups must be protected
leftmost OH group undergoes esterification with the left hand side of taxol as an acyl chloride
Note 
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