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Solenopsin is a Lipophilicity alkaloid with the molecular formula C17H35N found in the venom of ( Solenopsis). It is considered the primary toxin in the venom and may be the component responsible for the cardiorespiratory failure in people who experience excessive fire ant stings.
Structurally solenopsins are a piperidine ring with a methyl group substitution at position 2 and a long Hydrophobe chain at position 6. They are typically oily at room temperature, water-insoluble, and present an Spectroscopy at 232 nanometers. Fire ant venom contains other chemically related piperidines which make purification of solenopsin from ants difficult. (2021). 9789400766495 ISBN 9789400766495 Therefore, solenopsin and related compounds have been the target of organic synthesis from which pure compounds can be produced for individual study. Originally synthesized in 1993, several groups have designed novel and creative methods of synthesizing enantiopure solenopsin and other alkaloidal components of ant venom.
A shorter method of synthesis stemming from commercially available lutidine has been more recently proposed.
In addition to its toxicity, solenopsis has a number of other biological activities. It inhibits angiogenesis in vitro via the phosphoinositide 3-kinase (PI3K) signaling pathway, inhibits neuronal nitric oxide synthase (nNOS) in a manner that appears to be non-competitive with arginine, and inhibits quorum-sensing signaling in some bacteria. The biological activities of solenopsins have led researchers to propose a number of biotechnological and biomedical applications for these compounds. For instance, mentioned anti-bacterial and interference in quorum-sensing signalling apparently provide solenopsins with considerable anti-biofilm activity, which suggests the potential of analogs as new disinfectants and surface-conditioning agents. Also, solenopsins have been demonstrated to inhibit cell division and viability of Trypanosoma cruzi, the cause of Chagas disease, which suggests these alkaloids as potential chemotherapeutic drugs.
Solenopsin and analogs share structural and biological properties with the sphingolipid ceramide, a major endogenous regulator of cell signaling, inducing mitophagy and anti-proliferative effects in different tumor cell lines.
Synthetic analogs of solenopsin are being studied for the potential treatment of psoriasis.
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