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Dolastatin 11 conformations, analogues and pharmacophore.

Abstract：

:Twenty analogues of the natural antitumor agent dolastatin 11, including majusculamide C, were synthesized and tested for cytotoxicity against human cancer cells and stimulation of actin polymerization. Only analogues containing the 30-membered ring were active. Molecular modeling and NMR evidence showed the low-energy conformations. The amide bonds are all trans except for the one between the Tyr and Val units, which is cis. Since an analogue restricted to negative 2-3-4-5 angles stimulated actin polymerization but was inactive in cells, the binding conformation (most likely the lowest-energy conformation in water) has a negative 2-3-4-5 angle, whereas a conformation with a positive 2-3-4-5 angle (most likely the lowest energy conformation in chloroform) goes through cell walls. The highly active R alcohol from borohydride reduction of dolastatin 11 is a candidate for conversion to prodrugs.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Ali MA,Bates RB,Crane ZD,Dicus CW,Gramme MR,Hamel E,Marcischak J,Martinez DS,McClure KJ,Nakkiew P,Pettit GR,Stessman CC,Sufi BA,Yarick GV

doi

10.1016/j.bmc.2005.04.040

subject

Has Abstract

pub_date

2005-07-01 00:00:00

pages

4138-52

issue

13

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(05)00340-8

journal_volume

13

pub_type

杂志文章

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