Rhodamine 101 Conjugates of Triterpenoic Amides Are of Comparable Cytotoxicity as Their Rhodamine B Analogs

Molecules

Daniel Major¹  Marie Kozubek¹  Niels V. Heise¹  Sophie Hoenke¹  Immo Serbian¹  René Csuk¹ 

[1] Department of Organic Chemistry, Martin-Luther University Halle-Wittenberg, Kurt-Mothes Str. 2, D-06120 Halle (Saale), Germany;

关键词: triterpenoic acid;    ursolic acid;    oleanolic acid;    betulinic acid;    rhodamine B;    rhodamine 101;   

DOI  :  10.3390/molecules27072220

来源: DOAJ

【 摘 要 】

Pentacyclic triterpenoic acids (betulinic, oleanolic, ursolic, and platanic acid) were selected and subjected to acetylation followed by the formation of amides derived from either piperazine or homopiperazine. These amides were coupled with either rhodamine B or rhodamine 101. All of these compounds were screened for their cytotoxic activity in SRB assays. As a result, the cytotoxicity of the parent acids was low but increased slightly upon their acetylation while a significant increase in cytotoxicity was observed for piperazinyl and homopiperazinyl amides. A tremendous improvement in cytotoxicity was observed; however, for the rhodamine B and rhodamine 101 conjugates, and compound 27, an ursolic acid derived homopiperazinyl amide holding a rhodamine 101 residue showed an EC₅₀ = 0.05 µM for A2780 ovarian cancer cells while being less cytotoxic for non-malignant fibroblasts. To date, the rhodamine 101 derivatives presented here are the first examples of triterpene derivatives holding a rhodamine residue different from rhodamine B.

【 授权许可】

Unknown