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Model of the 10′-fluoro binding site of 10′-fluorovinblastine (R = F, top) generated by adding the fluorine substituent to the X-ray structure of tubulin-bound vinblastine67 (R = H, bottom).64 Modeled complexes with larger substituents (R = Cl, Me, Br, I) exhibited increasingly larger destabilizing steric interactions as the substituent size progressively increased.
