Duocarmycin-based prodrugs for cancer prodrug monotherapy

Tietze, Lutz F.; Schuster, Heiko; Schmuck, Kianga; Schuberth, Ingrid; Alves, Frauke

doi:10.1016/j.bmc.2008.05.009

Cited by 52 publications

(21 citation statements)

References 51 publications

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“…A prodrug of CBI (Fig. 38) where the phenol is derivatised as the corresponding glucuronide for application as monotherapy in -glucuronidase overexpressing tumours has been reported [119]. Both the free acid 71a and ester 71b (a double prodrug since the methyl ester is cleaved by carboxypeptidases to give 71a) showed potential as prodrugs with an impressive in vitro differential in activity in the presence/absence of -glucuronidase.…”

Section: Figure (37) Activity Against L1210 Cellsmentioning

confidence: 99%

Chemical and Biological Explorations of the Family of CC-1065 and the Duocarmycin Natural Products

Ghosh¹,

Sheldrake²,

Searcey³

et al. 2009

CTMC

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CC-1065, the duocarmycins and yatakemycin are members of a family of ultrapotent antitumour antibiotics that have been the subject of extensive investigations due to their mode of action and potential in the design of new anticancer therapeutics. The natural products and their analogues exert their effects through a sequence selective alkylation of duplex DNA in the minor groove at the N3 of adenine. An understanding of their structure and its effect on biological activity has been derived through chemical synthesis and has also generated new potential lead compounds. These studies form the first section of the review. The desire to progress these compounds to clinic has also led to studies of bioconjugation and prodrug formation and this is discussed in the second section of the review. The combination of synthesis with key biological experiments is a powerful tool to define the requirements for the development of natural products as potential therapeutic agents. The studies described herein form an excellent paradigm for the study and development of other natural products

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Section: Figure (37) Activity Against L1210 Cellsmentioning

confidence: 99%

Chemical and Biological Explorations of the Family of CC-1065 and the Duocarmycin Natural Products

Ghosh¹,

Sheldrake²,

Searcey³

et al. 2009

CTMC

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“…26 Two other condensed pyrrolic compounds 2k and 2l, 4,5-dihydrobenz[e]indole and 4,5-dihydrobenz[g]indole, now also accessible via the method here reported, are potential drug precursors possessing antiarrhythmic, central nervous system depressant, anti-inflammatory and antihypertensive activity. 27,28 …”

Section: Tetrahedronmentioning

confidence: 98%

Expedient one-pot synthesis of pyrroles from ketones, hydroxylamine, and 1,2-dichloroethane

et al. 2015

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“…Other relatively frequently used drugs include the natural antibiotic duocarmycin SA, member of the CC-1065 family (72), which is a tremendously powerful cytostatic compound against different cancer cell lines and hence one of the most powerful anticancer agents known so far (73). Mithramycin (MTR) and chromomycine ( Figure 9) have a similar mode of binding to GC-rich DNA sequences in the minor groove and belong to the aureolic acid group of anticancer drugs (66).…”

Section: Dna Groove Bindersmentioning

confidence: 99%

Antineoplastic DNA-Binding Compounds: Intercalating and Minor Groove Binding Drugs

Mišković

Bujak

Lončar

et al. 2013

Archives of Industrial Hygiene and Toxicology

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DNA intercalating and minor groove binding compounds are new weapons in the battle against malignant diseases. These antineoplastic agents target the DNA molecule and interfere with the cell cycle leading to rapidly proliferating cell death. They are mainly derivates of a naturally occurring organic compound derived from a microorganism or plant. Intercalators usually act as topoisomerase I and/or II poisons, while the mechanisms of DNA minor groove binders are a combination of several steps including topoisomerase poisoning. This paper gives an overview of some of the developed DNA intercalating and minor groove binding compounds, as well as an explanation of their chemical structures, origins, and application in chemotherapy.

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Duocarmycin-based prodrugs for cancer prodrug monotherapy

Cited by 52 publications

References 51 publications

Chemical and Biological Explorations of the Family of CC-1065 and the Duocarmycin Natural Products

Chemical and Biological Explorations of the Family of CC-1065 and the Duocarmycin Natural Products

Expedient one-pot synthesis of pyrroles from ketones, hydroxylamine, and 1,2-dichloroethane

Antineoplastic DNA-Binding Compounds: Intercalating and Minor Groove Binding Drugs

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