Marine-Derived Natural Lead Compound Disulfide-Linked Dimer Psammaplin A: Biological Activity and Structural Modification

Abstract

Marine natural products are considered to be valuable resources that are furnished with diverse chemical structures and various bioactivities. To date, there are seven compounds derived from marine natural products which have been approved as therapeutic drugs by the U.S. Food and Drug Administration. Numerous bromotyrosine derivatives have been isolated as a type of marine natural products. Among them, psammaplin A, including the oxime groups and carbon–sulfur bonds, was the first identified symmetrical bromotyrosine-derived disulfide dimer. It has been found to have a broad bioactive spectrum, especially in terms of antimicrobial and antiproliferative activities. The highest potential indole-derived psammaplin A derivative, UVI5008, is used as an epigenetic modulator with multiple enzyme inhibitory activities. Inspired by these reasons, psammaplin A has gradually become a research focus for pharmacologists and chemists. To the best of our knowledge, there is no systematic review about the biological activity and structural modification of psammaplin A. In this review, the pharmacological effects, total synthesis, and synthesized derivatives of psammaplin A are summarized.

Two New Cytotoxic Compounds from a Deep-Sea Penicillum citreonigrum XT20-134

“…The diversity of sulfur-containing chemical structures leads to their various bioactivities [29]. Among them, psammaplin A, has been found to have a broad bioactive spectrum, especially in terms of antimicrobial and antiproliferative activities [30]. With a sulfur atom, compound 2 exhibited potent cytotoxic activity.…”

Biomaterials from the sea: Future building blocks for biomedical applications

“…Marine-derived chitinous skeletons have long been identified as excellent three-dimensional biomaterials-based matrices [ 311 ]. Bromotyrosines possess multitarget activities including antimicrobial, anti-cancer, antiviral as well as cytotoxic traits [ 312 ]. In the chitin-bromotyrosine hybrid scaffolds, chitin is used as drug delivery vehicles because of its mesh-like structure and capillary network [ 313 ].…”

Perspectives and controversies regarding the use of natural products for the treatment of lung cancer

“…In 1999, psammaplin A was found to exert significant in vitro antibacterial activity against Staphylococcus aureus (SA) and methicillin‐resistant Staphylococcus aureus (MRSA) 105 . The pharmacological activities of psammaplin A and its derivatives include anticancer, antiviral, and insecticidal effects, as well as the promotion of embryonic development and chemical defensive encryption 106 . It has also been reported to be an effective inhibitor of two epigenetic enzymes, histone deacetylase, and DNA methyltransferase 107 …”

“…For example, CPT, curcumin, GA, tanshinone, TPL, EGCG, resveratrol, artemisinin, and other compounds have poor water solubility, low biocompatibility, low oral bioavailability, instability, and poor pharmacokinetic properties, which hinder their clinical application 21,130,204,261‐265 . In addition, the yield of natural separation from natural products is low 106 …”