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Synthesis, Anion-Binding Properties, and In Vitro Anticancer Activity of Prodigiosin Analogues

✍ Scribed by Jonathan L. Sessler; Leah R. Eller; Won-Seob Cho; Sergios Nicolaou; Apolonio Aguilar; Jeong Tae Lee; Vincent M. Lynch; Darren J. Magda

Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
127 KB
Volume
44
Category
Article
ISSN
0044-8249

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✦ Synopsis

Prodigiosins, for example, 1 and 2, are a family of naturally occurring tripyrrolic red pigments that were first isolated in the 1930s from microorganisms including Serratia and Streptomyces and are characterized by a common pyrrolylpyrromethene skeleton. [1] These molecules, especially prodigiosin 25-C (1) but also synthetic analogues such as 3, [2,3] have been studied extensively for their promising immunosuppressive [4] and anticancer activities. [5,6] To date, two very different modes of action have been put forward to explain their anticancer activity. One suggestion, proposed by Manderville, Melvin, and co-workers, [7] and further supported by FΓΌrstner and Grabowski, [8] is that prodigiosin mediates its anticancer effect through coppermediated cleavage of double-stranded DNA. The second

[*] Prof.

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## Abstract A series of novel compounds **7–43** were prepared __via__ the condensation of enaminones **4a–h** and the guanidines carbonate **6a–f**. The structures of these newly synthesized compounds were confirmed by ^1^H‐NMR, MS, EA and IR. All the compounds were tested for their cytotoxic acti