DNA-binding studies of the natural β-carboline eudistomin U

Abstract

Eudistomin U is a member of the β-carboline class of heterocyclic amine-containing molecules that are capable of binding to DNA. The structure of eudistomin U is unique since it contains an indole ring at the 1-position of the pyridine ring. While simple β-carbolines are reported to intercalate DNA, an examination of the mode of binding of eudistomin U has been lacking. We report preliminary spectroscopic (UV-Vis, thermal denaturation, CD) and calorimetric (DSC) data on the binding of eudistomin U to DNA, which suggest that eudistomin U binds weakly according to a mechanism that is more complicated than other members of its class.

Occurrence, Formation from d-Fructose and 3-Deoxyglucosone, and Activity of the Carbohydrate-Derived β-Carbolines in Foods

“…The βCs have been previously reported to interact with DNA. 32 The interaction of βCs 1–4 with DNA was studied by spectrophotometry UV–vis following standard procedures. 31 None of the compounds showed a relevant interaction or intercalation with calf thymus DNA evidenced by changes in UV–vis spectra compared with DNA and compounds alone ( Figure 9 C).…”

“…The carbohydrate βCs had almost no antioxidant activity compared with ascorbic acid, catechin, or quercetin (Figure B). The βCs have been previously reported to interact with DNA . The interaction of βCs 1–4 with DNA was studied by spectrophotometry UV–vis following standard procedures .…”

“…THβCs and βCs exhibit antioxidant effects and react with hydroxyl radicals. , However, compounds 1 – 4 had poor antioxidant activity compared with ascorbic acid or phenolic compounds (quercetin and catechin). This agrees with the relatively low antioxidant activity reported for 1a/b and with the fact that aromatic βCs have low antioxidant activity compared to THβCs , On the other hand, it has been reported that the aromatic βCs could interact with DNA. , Results of this work suggest that the carbohydrate βCs 1–4 have no relevant activity of direct interaction with DNA. However, as the compounds with a β-carboline residue are bioactive substances and their activity depends on the specific structure of β-carboline, it is likely that the carbohydrate-derived βCs have other activities and act on different targets.…”

Ascidian Toxins with Potential for Drug Development

“…These compounds, originally isolated by Rinehart’s group [ 107 ], display a variety of biological activities with the oxathiazepino-eudistomins having strong antiviral properties [ 82 ]. DNA binding studies have been conducted with Eudistomin U ( Figure 7 ) [ 108 ]. The structure of this alkaloid differs from other eudistomins, in that it contains an indole ring at the 1-position of the pyridine ring.…”

New β-carboline derivatives containing imidazolium as potential VEGFR2 inhibitors: synthesis, X-ray structure, antiproliferative evaluations, and molecular modeling

“…14–16 In recent decades, there have been intense research efforts in the design and development of β-carbolines as a new class of antitumor agents, and a large number of β-carboline derivatives have been prepared in search of agents that are more potent. The results indicate that this class of compounds exert antitumor effects through various mechanisms of action, including intercalating with DNA, 17,18 and by inhibition of cyclin-dependent kinase (CDK), 19 topoisomerases I and II, 20 polo-like kinase 1 (PLK1), 21,22 and IκB kinase. 23…”