title: Structure, synthesis and biological properties of the pentacyclic guanidinium alkaloids.
abstract: The pentacyclic guanidinium alkaloids (PGAs) are a family of marine natural products that possess a polycyclic guanidine-containing core and a long alkyl chain tethered spermidine-derived tail that is rarely observed in other natural products. These natural products exhibit potent activities on a wide range of organisms and therefore have attracted the attention of many synthetic chemists; however, the structure-activity relationships and mechanisms of action of PGAs remain largely elusive. Herein we summarize the structure, synthesis, toxicity and mechanisms of action of PGAs and highlight their potential as chemical probes and/or therapeutic leads.
authors.affiliation: Department of Chemistry, NC State University, Raleigh, NC 27695, United States.
authors.forename: Yunlong
authors.initials: Y
authors.lastname: Shi
authors.affiliation: Department of Chemistry, NC State University, Raleigh, NC 27695, United States.
authors.forename: Yasamin
authors.initials: Y
authors.lastname: Moazami
authors.affiliation: Department of Chemistry, NC State University, Raleigh, NC 27695, United States; Comparative Medicine Institute, NC State University, Raleigh, NC 27695, United States. Electronic address: jgpierce@ncsu.edu.
authors.forename: Joshua G
authors.initials: JG
authors.lastname: Pierce
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000981:Antiprotozoal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D019791:Guanidine / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D000470:Alkaloids; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D000981:Antiprotozoal Agents; D000998:Antiviral Agents; D019791:Guanidine
keywords: Chemical probe; Guanidinium alkaloids; Marine natural products; Mechanism of action; Structure-activity relationship