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Iron Complexation to Oxygen Rich Marine Natural Products: A Computational Study
Chemistry Department, Valdosta State University, Valdosta, GA 31698, USA
* Author to whom correspondence should be addressed.
Received: 4 December 2009; in revised form: 12 December 2009 / Accepted: 28 December 2009 / Published: 4 January 2010
Abstract: The natural products kahalalide F, halichondrin B, and discodermolide are relatively large structures that were originally harvested from marine organisms. They are oxygen rich structures that, to varying degrees, should have the ability to bind iron (II or III) by Fe-O and/or Fe-N bonds. In this semi empirical study, the binding of these natural products to iron (II) is studied and the aqueous stability factor (ASF) is used to determine which bonding configuration is most stable. The energy, the complex charge (+1), the average Fe-O (or Fe-N) bond distances and the dipole moments are used to calculate the ASF. The ASF provides insight to which complex will be the most stable and water soluble, important for a medicinal application. The ability of a molecule with a more than six oxygen and/or nitrogen atoms to bind iron (hexavalent, octahedral) by shifting which six atoms (O/N) are bound to the iron qualifies it as a polarity adaptive molecule.
Keywords: kahalalide F; halichondrin B; discodermolide; marine natural product; aqueous stability factor; computational
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MDPI and ACS Style
Manning, T.J.; Williams, J.; Jarrard, J.; Gorman, T. Iron Complexation to Oxygen Rich Marine Natural Products: A Computational Study. Mar. Drugs 2010, 8, 1-23.
Manning TJ, Williams J, Jarrard J, Gorman T. Iron Complexation to Oxygen Rich Marine Natural Products: A Computational Study. Marine Drugs. 2010; 8(1):1-23.
Manning, Thomas J.; Williams, Jimmy; Jarrard, Joey; Gorman, Teresa. 2010. "Iron Complexation to Oxygen Rich Marine Natural Products: A Computational Study." Mar. Drugs 8, no. 1: 1-23.