Synthetic Strategy and Anti-Tumor Activities of Macrocyclic Scaffolds Based on 4-Hydroxyproline.

Abstract

A series of novel 13- to 15-member hydroxyproline-based macrocycles, which contain alkyl-alkyl ether and alkyl-aryl ether moieties, have been synthesized by the strategy of macrocyclization utilising azide-alkyne cycloaddition, Mitsunobu protocol and amide formation. Their anti-tumor activities towards A549, MDA-MB-231 and Hep G2 cells were screened in vitro by an MTT assay. The results indicated that 13-member macrocycle 33 containing alkene chain showed the best results, exhibiting the highest inhibitory effects towards lung cancer cell line A549, which was higher than that of the reference cisplatin (IC50 value = 2.55 µmol/L).

• Authors: Guorui Cao, Kun Yang, Yue Li, Longjiang Huang, Dawei Teng
• Journal: Molecules (Basel, Switzerland) (Molecules) Vol. 21 Issue 2 (Feb 15 2016) ISSN: 1420-3049 [Electronic] Switzerland
• PMID: 26891283 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antineoplastic Agents
• Macrocyclic Compounds
• Cisplatin
• Hydroxyproline

Topics

• Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
• Cell Line, Tumor
• Cell Proliferation (drug effects)
• Cell Survival (drug effects)
• Cisplatin (pharmacology)
• Cycloaddition Reaction
• Hep G2 Cells
• Humans
• Hydroxyproline (chemistry)
• Macrocyclic Compounds (chemical synthesis, chemistry, pharmacology)
• Molecular Structure