2. Academic Validation
  3. Combination of amino acid/dipeptide with nitric oxide donating oleanolic acid derivatives as PepT1 targeting antitumor prodrugs

Combination of amino acid/dipeptide with nitric oxide donating oleanolic acid derivatives as PepT1 targeting antitumor prodrugs

  • J Med Chem. 2014 Feb 13;57(3):1116-20. doi: 10.1021/jm401634d.
Lei Fang 1,  Meng Wang,  Shaohua Gou,  Xuying Liu,  Huan Zhang,  Feng Cao
Affiliations

Affiliation

  • 1 Pharmaceutical Research Center and Jiangsu Province Hi-Tech Key Laboratory for Bio-Medical Research, School of Chemistry and Chemical Engineering, Southeast University , Nanjing 211189, China.
PMID: 24422538 DOI: 10.1021/jm401634d
Abstract

By taking advantage of the cytotoxic effect of nitric oxide (NO) and PepT1 for molecule-targeted drug delivery, a series of amino acid/dipeptide diester prodrugs of NO-donating oleanolic acid derivatives were designed and synthesized. Two prodrugs 6a and 8a showed potent cytotoxcity, which is probably due to their high PepT1 affinity and NO-releasing ability. Furthermore, the aqueous solubility of the prodrugs was also significantly enhanced because of the hydrophilic amino acid/dipeptide promoiety.

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