Dioxopiperazines: Chemistry and biology

Witiak, Donald T.; Wei, Yong

doi:10.1007/978-3-0348-7133-4_7

Cited by 17 publications

(31 citation statements)

References 380 publications

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“…As predicted, the bis(2,6-dioxopiperazine)s did have anticancer activity (1)(2)(3)(4) and were shown to selectively inhibit DNA synthesis in cultured cells while having little effect on RNA or protein synthesis (5). However, there is also evidence that metal chelation plays little, if any, role in their anticancer activity (2).…”

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confidence: 87%

“…However, there is also evidence that metal chelation plays little, if any, role in their anticancer activity (2). Numerous bis(dioxopiperazine)s have been studied for anticancer activity and for interactions with other anticancer drugs and radiation (1)(2)(3)(4). (I)-4,4Ј-(1,2-propanediyl)-bis-(4-piperazine-2,6-dione) (ICRF⅐159, NSC 129943) has pronounced effects on tumor vasculature, and it has been claimed that this is the basis of its antimetastatic activity (3,6).…”

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confidence: 99%

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Topoisomerase II Poisoning by ICRF-193

Huang¹,

Gao²,

Yamasaki³

et al. 2001

Journal of Biological Chemistry

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Antineoplastic bis(dioxopiperazine)s, such as meso-2,3-bis(2,6-dioxopiperazin-4-yl)butane (ICRF-193), are widely believed to be only catalytic inhibitors of topoisomerase II. However, topoisomerase inhibitors have little or no antineoplastic activity unless they are topoisomerase poisons, a special subclass of topoisomerasetargeting drugs that stabilize topoisomerase-DNA strand passing intermediates and thus cause the topoisomerase to become a cytotoxic DNA-damaging agent.

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confidence: 87%

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confidence: 99%

Topoisomerase II Poisoning by ICRF-193

Huang¹,

Gao²,

Yamasaki³

et al. 2001

Journal of Biological Chemistry

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“…These metabolites possess a broad spectrum of biological activities, including antibacterial, antiviral and antifungal activities (Witiak and Wei, 1990;Gardiner et al, 2005;Borthwick, 2012). Several naturally occurring ETPs, such as gliotoxin (antitumor activity) (Cole and Cox, 1981), chaetocin (antimyeloma activity) (Isham et al, 2007), and acetylaranotin (pro-apoptotic activity) (Neuss et al, 1968;Choi et al, 2011) have attracted considerable attention in recent years due to their pronounced cytotoxic activities against various human cancer cell lines (Dubey et al, 2013;Boyer et al, 2013;Reece et al, 2014).…”

Section: Introductionmentioning

confidence: 99%

Pretrichodermamide C and N-methylpretrichodermamide B, two new cytotoxic epidithiodiketopiperazines from hyper saline lake derived Penicillium sp.

Orfali

Aly

Ebrahim

et al. 2015

Phytochemistry Letters

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“…Witiak and Wei (1990) have reviewed the chemistry and biology of 2,5-dioxopiperazines. These compounds have shown e.g.…”

Section: Discussionmentioning

confidence: 99%

Anthelmintic activity of 3,6-dibenzyl-2,5-dioxopiperazine, cyclo(L-Phe-L-Phe)

Walchshofer

Sarciron²,

Garnier

et al. 1997

Amino Acids

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Summary.After oral administration, dipeptide Phe-Phe-OMe 1 exhibits anthelmintic activity against Echinococcus multilocularis larvae, cestoda, in mongolian gerbils (intraperitoneal localization), but not against Hymenolepis nana, cestoda, in fasted mice (gastro-intestinal localization). This compound rapidly provides its cyclization product dioxopiperazine 2 in pH 7.4 buffer at 37°C, but was stable at pH 2.4 during 16h at 30°C. It was postulated that dipeptide 1 could act as a prodrug of 2. Initial pharmacokinetics studies were carried out in mice and dogs. After oral administration, biotransformation of 1 into 2 occurred to some extent in mice but not in fasted dogs. Results of these studies did not allow to ascertain that 1 is a prodrug of 2. Compound 2 has been tested in mice against H. nana and Schistosoma rnansoni, a gastrointestinal trematoda. Albeit less active than the reference compound praziquantel, 2 has shown a good activity against both worms. 2,5-dioxopiperazines represent therefore a new class of anthelmintics.

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Dioxopiperazines: Chemistry and biology

Cited by 17 publications

References 380 publications

Topoisomerase II Poisoning by ICRF-193

Topoisomerase II Poisoning by ICRF-193

Pretrichodermamide C and N-methylpretrichodermamide B, two new cytotoxic epidithiodiketopiperazines from hyper saline lake derived Penicillium sp.

Anthelmintic activity of 3,6-dibenzyl-2,5-dioxopiperazine, cyclo(L-Phe-L-Phe)

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