Int. J. Mol. Sci. 2008, 9(5), 821-837; doi:10.3390/ijms9050821
Article

Synthesis and Biological Evaluation of a Novel Pentagastrin- Toxin Conjugate Designed for a Targeted Prodrug Monotherapy of Cancer

Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen, Tammannstraße 2, D-37077 Göttingen, Germany
* Author to whom correspondence should be addressed.
Received: 25 April 2008; in revised form: 15 May 2008 / Accepted: 16 May 2008 / Published: 20 May 2008
(This article belongs to the Special Issue Natural Compounds for Cancer Treatment and Prevention)
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Abstract: A novel carbamate prodrug 2 containing a pentagastrin moiety was synthesized. 2 was designed as a detoxified analogue of the highly cytotoxic natural antibiotic duocarmycin SA (1) for the use in a targeted prodrug monotherapy of cancers expressing cholecystokinin (CCK-B)/gastrin receptors. The synthesis of prodrug 2 was performed using a palladium-catalyzed carbonylation of bromide 6, followed by a radical cyclisation to give the pharmacophoric unit 10, coupling of 10 to the DNA-binding subunit 15 and transformation of the resulting seco-drug 3b into the carbamate 2 via addition of a pentagastrin moiety.
Keywords: antibiotics; antitumor agents; pentagastrin; prodrug; prodrug monotherapy

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MDPI and ACS Style

Tietze, L.F.; Panknin, O.; Krewer, B.; Major, F.; Schuberth, I. Synthesis and Biological Evaluation of a Novel Pentagastrin- Toxin Conjugate Designed for a Targeted Prodrug Monotherapy of Cancer. Int. J. Mol. Sci. 2008, 9, 821-837.

AMA Style

Tietze LF, Panknin O, Krewer B, Major F, Schuberth I. Synthesis and Biological Evaluation of a Novel Pentagastrin- Toxin Conjugate Designed for a Targeted Prodrug Monotherapy of Cancer. International Journal of Molecular Sciences. 2008; 9(5):821-837.

Chicago/Turabian Style

Tietze, Lutz F.; Panknin, Olaf; Krewer, Birgit; Major, Felix; Schuberth, Ingrid. 2008. "Synthesis and Biological Evaluation of a Novel Pentagastrin- Toxin Conjugate Designed for a Targeted Prodrug Monotherapy of Cancer." Int. J. Mol. Sci. 9, no. 5: 821-837.

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