Balanol
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| Formula | C28H26N2O10 |
| Molar mass | 551.17 g/mol |
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Balanol is a fungal metabolite produced by the fungus Verticillium balanoides. It is a potent inhibitor of the serine/threonine kinases protein kinase A (PKA) and protein kinase C (PKC), binding in a similar manner with that of ATP. Balanol was discovered in 1993 in the search for novel inhibitors of PKC, a member of a family of serine/threonine kinases whose overactivation is associated with numerous human diseases of signal transduction including cancer. However, much of the research on balanol focuses on how chemical modifications of the molecular structure affect binding to PKA. Indeed, balanol, its chemically altered analogs, and their interactions with PKA in particular are used to illuminate the roles of selectivity and protein flexibility in the inhibition of kinases. For instance, the X-ray crystal structure of balanol in complex with PKA was used in order to confer selectivity and to improve pharmacological efficacy of inhibitors of the H. sapiens Akt (PKB), another serine/threonine protein kinase implicated in the proper functioning of many cellular processes.
The chemical structure was initially characterized through a combination of IR spectroscopy, hydrogen-1 NMR, carbon-13 NMR, and 2D NMR spectra data, and the crystal structure of balanol in complex with PKA was solved in 1999. The balanol molecule consists of three regions: a benzophenone, hexahydroazepane, and 4-hydroxy benzoyl moiety. The benzophenone and hexahydroazepane moieties are connected via an ester linkage, and the azepane and benzoyl moieties are connected through an amide linkage. Furthermore, balanol is sometimes referred to as ophiocordin, an antifungal agent produced by the fungus Cordyceps ophioglossoides whose structure is regioisometric to that of balanol; that is, in ophiocordin, the benzophenone is linked to the hexahydroazepane instead via an amide; the 4-hydroxy benzoyl group and hexahydroazepane are connected with an ester linkage.
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