Squalamine

• CAT Number: I001823
• CAS Number: 148717-90-2
• Molecular Formula: C34H65N3O5S
• Molecular Weight: 627.96
• Purity: ≥95%
• Solubility: DMSO
• Storage: -20°C
• InChI: InChI=1S/C34H65N3O5S/c1-23(2)31(42-43(39,40)41)12-9-24(3)27-10-11-28-32-29(14-16-34(27,28)5)33(4)15-13-26(21-25(33)22-30(32)38)37-20-8-19-36-18-7-6-17-35/h23-32,36-38H,6-22,35H2,1-5H3,(H,39,40,41)/t24-,25-,26+,27-,28+,29+,30-,31-,32+,33+,34-/m1/s1
• InChIKey: UIRKNQLZZXALBI-MSVGPLKSSA-N
• SMILES: CC(C)C(CCC(C)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)NCCCNCCCCN)C)O)C)OS(=O)(=O)O

Squalamine (CAT: I001823) is an aminosterol compound that exhibits potent broad-spectrum antimicrobial activity. It was initially discovered in the tissues of the dogfish shark (Squalus acanthias). The identification of squalamine in sharks suggests that steroids could serve as host-defense agents in vertebrates and provides valuable insights into the development of a class of antibiotics with broad-spectrum activity. Squalamine’s antimicrobial properties make it a potential candidate for combating a range of infections caused by bacteria, fungi, and viruses. Further research is being conducted to explore its therapeutic applications and potential as a novel antimicrobial agent.

Reference

1. Curr Med Chem. 2010;17(32):3909-17.

Squalamine as an example of a new potent antimicrobial agents class: a critical
review.

Alhanout K(1), Rolain JM, Brunel JM.

Author information:
(1)Unité de Recherche sur les Maladies Infectieuses et Tropicales émergentes
(URMITE), UMR 6236 CNRS, Faculté de Pharmacie et de Médecine, Université de la
Méditerranée, 27 boulevard Jean Moulin, 13385 Marseille 05, France.

An important strategy to circumvent the problem of antimicrobial resistance is to
search for new compounds with antimicrobial activity. In this context,
aminosterols, which include squalamine-like compounds and ceragenins, have gained
interest due to their wide spectrum of antibacterial and antifungal properties.
In light of recently reported data, we decided to analyze the mechanism of action
of these compounds as well as their antimicrobial properties. Aminosterols are
active against both bacterial reference strains and multidrug-resistant
antibiotics as they disrupt the integrity of the bacterial membrane. Thus, these
compounds could be useful in the development of new topical decontaminants or
disinfecting agents.

2. Ophthalmol Clin North Am. 2006 Sep;19(3):381-91, vi.

Squalamine lactate for exudative age-related macular degeneration.

Connolly B(1), Desai A, Garcia CA, Thomas E, Gast MJ.

Author information:
(1)Retina Associates of Western New York, 890 Westfall Road, Suite D, Rochester,
NY 14618, USA.

Squalamine lactate inhibits angiogenesis by a long-lived, intracellular mechanism
of action. The drug is taken up into activated endothelial cells through
caveolae, small invaginations in the cellular membrane. Subsequently, the drug
binds to and /chaperones/ calmodulin to an intracellular membrane compartment and
blocks angiogenesis at several levels. A series of basic investigations,
preclinical studies, and human clinical trials have begun to establish the proof
of concept, efficacy, and safety parameters for use of squalamine lactate as a
therapeutic agent for exudative age-related macular degeneration and several
types of malignancies.

3. Curr Cancer Drug Targets. 2005 Jun;5(4):267-72.

Squalamine: a polyvalent drug of the future?

Brunel JM(1), Salmi C, Loncle C, Vidal N, Letourneux Y.

Author information:
(1)Laboratoire SESNAB Faculté de St Jérôme, Université Paul Cézanne, Av.
Escadrille Normandie Niemen, 13397 Marseille, Cedex 20, France.

The purpose of this mini-review is to summarize and highlight the different
advances in our understanding of the antimicrobial and antiangiogenic activity of
squalamine, a cationic steroid isolated in 1993 from the dogfish shark Squalus
Acanthias. Indeed, squalamine has shown to be useful for the treatment of
important diseases such as cancers (lung, ovarian, brain and others), age-related
macular degeneration (AMD) and the control of body weight in man. All these
results led to a question: could we consider squalamine as a polyvalent drug of
the future?