Mitocanic Di- and Triterpenoid Rhodamine B Conjugates |
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Authors: | Sophie Hoenke Immo Serbian Hans-Peter Deigner Ren Csuk |
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Institution: | 1.Organic Chemistry, Martin-Luther University Halle-Wittenberg, Kurt-Mothes Street 2, D-06120 Halle, Germany; (S.H.); (I.S.);2.Medical and Life Science Faculty, Institute of Precision Medicine, Furtwangen University, Jakob–Kienzle–Street 17, D-78054 Villigen–Schwenningen, Germany; |
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Abstract: | The combination of the “correct” triterpenoid, the “correct” spacer and rhodamine B (RhoB) seems to be decisive for the ability of the conjugate to accumulate in mitochondria. So far, several triterpenoid rhodamine B conjugates have been prepared and screened for their cytotoxic activity. To obtain cytotoxic compounds with EC50 values in a low nano-molar range combined with good tumor/non-tumor selectivity, the Rho B unit has to be attached via an amine spacer to the terpenoid skeleton. To avoid spirolactamization, secondary amines have to be used. First results indicate that a homopiperazinyl spacer is superior to a piperazinyl spacer. Hybrids derived from maslinic acid or tormentic acid are superior to those from oleanolic, ursolic, glycyrrhetinic or euscaphic acid. Thus, a tormentic acid-derived RhoB conjugate 32, holding a homopiperazinyl spacer can be regarded, at present, as the most promising candidate for further biological studies. |
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Keywords: | triterpenoic acid maslinic acid tormentic acid betulinic acid oleanolic acid rhodamine B cytotoxicity |
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