Selective killing of cancer cells with triterpenoic acid amides - The substantial role of an aromatic moiety alignment

Sommerwerk, Sven; Heller, Lucie; Kuhfs, Julia; Csuk, René

doi:10.1016/j.ejmech.2016.06.053

Cited by 36 publications

(20 citation statements)

References 29 publications

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“…Acetylation of 1 with acetic anhydride (Scheme 1) yielded the tri-acetate 2 whose acetate groups were detected in the 1 H N.M.R. spectrum 35 Previous studies showed chloro-acetylated compounds are of higher cytotoxicity than their acetylated analogs [37][38][39] . Thus, 3,9,10-tri-Ochloroacetyl-brazilin (4) was prepared from 1 and chloroacetyl chloride in 66% isolated yield, while from 1 and 4-chlorobutyryl chloride 5 was obtained in 51% yield.…”

Section: Resultsmentioning

confidence: 99%

“…were used employing several malignant cell lines and nonmalignant fibroblasts (N.I.H. 3T3) 38,39 . The results from these assays are compiled in Table 1 and depicted in Figure 2.…”

Section: Resultsmentioning

confidence: 99%

“…The compounds ' cytotoxicity was evaluated using the sulforhodamine-B (Kiton-Red S, A.B.C.R.) microculture colorimetric assay, as previously reported using confluent cells [37][38][39] .The EC50 values were averaged from three independent experiments performed each in triplicate calculated from semilogarithmic dose-response curves applying a nonlinear Hills-slope equation (GraphPad Prism5; variables top and bottom were set to 100 and 0, respectively).…”

Section: Cytotoxic Evaluationmentioning

confidence: 99%

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The cytotoxicity of brazilin and derivatives might be due to an inhibition of the c-Src-kinase

et al. 2020

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In this study, several derivatives of brazilin with different lipophilicity were synthesized. The cytotoxic potential of these substances was evaluated in S.R.B. assays. A triacetylated brazilin reaction with PBr3 or PCl3 and a subsequent aqueous workup led to the formation of a phosphorous ester containing two triacetylated brazilin subunits. This compound held unexpected high cytotoxicity. In this study, Brazilin-derived triacetate showed good cytotoxic activity (EC50 = 5.2 M) concerning A2780 carcinoma cells. The results from docking studies suggest that brazilin's cytotoxicity might be due to an inhibition of a tyrosine kinase in an ATP-competitive manner.

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Section: Resultsmentioning

confidence: 99%

“…were used employing several malignant cell lines and nonmalignant fibroblasts (N.I.H. 3T3) 38,39 . The results from these assays are compiled in Table 1 and depicted in Figure 2.…”

Section: Resultsmentioning

confidence: 99%

Section: Cytotoxic Evaluationmentioning

confidence: 99%

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The cytotoxicity of brazilin and derivatives might be due to an inhibition of the c-Src-kinase

et al. 2020

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“…Oleanolic acid (OA) and ursolic acid (UA) exert weak cytotoxicity; previous studies showed an increase in cytotoxicity upon their acetylation [18][19][20] . Also, OA and UA derived amides holding an additional amino group attached distally to an alkyl group (or a cyclic amine) were shown to be higher cytotoxic than their parent compounds [18][19][20][21][22][23] .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of amide-spacered dimers of ursolic and oleanolic acid

et al. 2019

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Transdermal therapeutic systems can release drug substances slowly and in a controlled manner from a drug depot. To provide a slow-release form of ursolic and oleanolic acid amide-spacered dimers were synthesized from the parent acids and diamines of variable chain lengths. These dimers were assayed in sulforhodamine B (SRB) assays for their cytotoxicity since as a pre-requisite for their use in slow-release forms these substances must not exert any unfavorable side-effects such as cytotoxicity. As a result of long term incubation up to 96 hours, none of these compounds showed any significant cytotoxicity in sulforhodamine B assays.

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“…There are roughly 3000 approved drugs available, that is 3000 targets for a possible repurposing, and nowadays big‐data analytics and high‐throughput screening systems are used to find new targets for old drugs . During our own search for cytotoxic or cytostatic compounds, we became aware of the anti‐proliferative effect of isoquinoline‐substituted triterpenoic acids and the inhibitory activity of the isoquinoline alkaloid papaverin (Fig. ) onto telomerase .…”

Section: Introductionmentioning

confidence: 99%

Drotaverine – a Concealed Cytostatic!

Pavel

Heller

Sommerwerk

et al. 2016

Archiv der Pharmazie

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Drotaverine (also known as dihydroperparine or No-Spa ) is an antispasmodic drug closely related to papaverin. Drotaverin also acts as a cytostatic compound for several human tumor cell lines and nonmalignant mouse fibroblasts, and EC values as low as 3.0 μM were observed in SRB assays for HT-29 human colorectal carcinoma cells. Small structural changes (e.g., aromatization, benzylic oxidation) led to a reduced activity or a complete loss of cytotoxicity. Staining of the cells with acridine orange showed the cell membrane of the dead cells to be still intact, and a slight G1/G0 arrest in the treated cells was observed after 24 h. Extra annexin V-FITC/PI assays and flow cytometry revealed drotaverine mainly to act as a cytostatic and only to a minor extent as cytotoxic agent.

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Selective killing of cancer cells with triterpenoic acid amides - The substantial role of an aromatic moiety alignment

Cited by 36 publications

References 29 publications

The cytotoxicity of brazilin and derivatives might be due to an inhibition of the c-Src-kinase

The cytotoxicity of brazilin and derivatives might be due to an inhibition of the c-Src-kinase

Synthesis of amide-spacered dimers of ursolic and oleanolic acid

Drotaverine – a Concealed Cytostatic!

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