Abstract
This review comprehensively describes the recent advances in the synthesis and pharmacological evaluation of steroid polyamines squalamine, trodusquemine, ceragenins, claramine, and their diverse analogs and derivatives, with a special focus on their complete synthesis from cholic acids, as well as an antibacterial and antiviral, neuroprotective, antiangiogenic, antitumor, antiobesity and weight-loss activity, antiatherogenic, regenerative, and anxiolytic properties. Trodusquemine is the most-studied small-molecule allosteric PTP1B inhibitor. The discovery of squalamine as the first representative of a previously unknown class of natural antibiotics of animal origin stimulated extensive research of terpenoids (especially triterpenoids) comprising polyamine fragments. During the last decade, this new class of biologically active semisynthetic natural product derivatives demonstrated the possibility to form supramolecular networks, which opens up many possibilities for the use of such structures for drug delivery systems in serum or other body fluids.
Highlights
Biogenic polymethylene polyamines are found in all living cells in significant quantities and are involved in many important biological processes [1,2]
Dimeric and tetrameric analogs in which two or four subunits were linked by a side chain to putrescine or spermine “head-to-head” or “tail-to-tail” demonstrated high antibacterial activity [108], Chen et al became interested in conducting a detailed study structures-activity using linked sterol-polyamine conjugates, i.e., covalently linked dimers and tetramers
Multi-resistant strains of bacteria that are susceptible to ceragenins include S. aureus, S. pneumoniae, S. pyogenes, H. influenza, P. aeruginosa, N. meningitides, L. pneumophila etc., Candida, C. neoformans, and A. fumigatus fungi, trypanosomes, as well as the vaccinia virus in 5 μM concentration [222,223,224]
Summary
Biogenic polymethylene polyamines are found in all living cells in significant quantities and are involved in many important biological processes [1,2]. Squalamine was isolated from other organs of the shark (spleen, intestines, ovaries) [7,8,9], its maximum content was noted in the liver and gallbladder It was identified in the blood cells of the sea lamprey. Seven other amino sterols 2–8 (Figure 1) with antibacterial activity, structurally similar to squalamine, were isolated from the liver of the shark S. acanthias [3]. They contain a cholestan skeleton conjugated to spermidine or spermine at the C3 position, while the side chain can be sulfated.
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