Solid-Phase Library Synthesis of Bi-Functional Derivatives of Oleanolic and Maslinic Acids and Their Cytotoxicity on Three Cancer Cell Lines

A wide set of 264 compounds has been semisynthesized with high yields and purities. These compounds have been obtained through easy synthetic processes based on a solid-phase combinatorial methodology. All the members of this library have one central core of a natural pentacyclic triterpene (oleanolic or maslinic acid) and differ by 6 amino acids, coupled with the carboxyl group at C-28 of the triterpenoid skeleton, and by 10 different acyl groups attached to the hydroxyl groups of the A-ring of these molecules. According to the literature on the outstanding and promising pharmacological activities of other similar terpene derivatives, some of these compounds have been tested for their cytotoxic effects on the proliferation of three cancer cell lines: B16–F10, HT29, and Hep G2. In general, we have found that around 70% of the compounds tested show cytotoxicity in all three of the cell lines selected; around 60% of the cytotoxic compounds are more effective than their corresponding precursors, that is, oleanolic (OA) or maslinic (MA) acids; and nearly 50% of the cytotoxic derivatives have IC₅₀ values between 2- to 320-fold lower than their corresponding precursor (OA or MA)

Modulating Anticancer Potential by Modifying the Structural Properties of a Family of Zinc Metal–Organic Chains Based on 4‑Nitro‑1<i>H</i>‑pyrazole

We have synthesized a novel family of metal–organic chains based on 4-nitro-1<i>H</i>-pyrazole linker and zinc as metal center. We report the formation of these coordination polymers using hydrothermal routes with water as solvent. These materials display one-dimensional structures with major structural modifications from minimal synthetic variations. What is more interesting, we have carried out antitumor measurements, and we have related these properties with the structural networks. To the best of our knowledge, these materials constitute the first examples of polymeric structures for 4-NO₂-pz ligands. NMR and MS spectrometry were used to verify the characterization of the metal complexes in solution to corroborate that these materials are present in the biological assays