The curiosity and attention that researchers have devoted to alkaloids are due to their bioactivities, structural diversity, and intriguing chemistry. Marine-derived macrocyclic alkaloids (MDMAs) are considered to be a potential source of drugs. Trabectedin, a tetrahydroisoquinoline derivative, has been approved for the treatment of metastatic soft tissue sarcoma and ovarian cancers. MDMAs displayed potent activities that enabled them to be used as anticancer, anti-invasion, antimalarial, antiplasmodial, and antimicrobial. This review presents the reported chemical structures, biological activities, and structure-activity relationships of macrocyclic alkaloids from marine organisms that have been published since their discovery until May 2020. This includes 204 compounds that are categorized under eight subclasses: pyrroles, quinolines, bis-quinolizidines, bis-1-oxaquinolizidines, 3-alkylpiperidines, manzamines, 3-alkyl pyridinium salts, and motuporamines.
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http://dx.doi.org/10.3390/md18070368 | DOI Listing |
ACS Appl Mater Interfaces
December 2024
China National Institute for Food and Drug Control, Institute of Chemical Drug Control, HuaTuo Road 29, Beijing 100050, China.
Maximizing drug cargo carrying capacity in blood circulation, controlling the fate of nanoparticles, and precisely drug release to tumor targets are the main aims of multifunctional nanomedicine-based antitumor therapy. Here we combined macrocyclic polyamine di(triazole-[12]aneN) () and chemical drug camptothecin (CPT, ) through photosensitizer 1,1-dicyano-2-phenyl-2-(4-diphenylamino) phenyl-ethylene () containing the cleavable disulfide () linkage as an all-in-one theranostic nanoprodrug, . The corresponding compound with carbon chain () linkage, , was also prepared for a comparison study.
View Article and Find Full Text PDFJ Am Chem Soc
December 2024
Department of Chemistry, University of California, Berkeley, Berkeley, California 94720, United States.
In this report, we detail two distinct synthetic approaches to calyciphylline A-type alkaloids himalensine A and daphenylline, which are inspired by our analysis of the structural complexity of these compounds. Using MolComplex, a Python-based web application that we have developed, we quantified the structural complexity of all possible precursors resulting from one-bond retrosynthetic disconnections. This led to the identification of transannular bonds as especially simplifying to the molecular graph, and, based on this analysis, we pursued a total synthesis of himalensine A from macrocyclic intermediates with planned late-stage transannular ring formations.
View Article and Find Full Text PDFPhytomedicine
December 2024
Department of Nutrition and Health, Beijing Advanced Innovation Center for Food Nutrition and Human Health, China Agricultural University, Beijing 100080, PR China; Beijing Life Science Academy, Beijing 102209, PR China; Flavour Science Research Center, Food Laboratory of Zhongyuan, Zhengzhou University, Zhengzhou 450001, PR China. Electronic address:
J Mater Chem B
November 2024
College of Materials Science and Technology, Nanjing University of Aeronautics and Astronautics, Nanjing 211106, China.
The antibiotic resistance of bacterial membranes poses a significant threat to global public health, highlighting the urgent need for novel therapeutic agents and strategies to combat bacterial membranes. In response, we have developed a novel macrocyclic host molecule (GCPCB) based on guanidiniocarbonyl-pyrrole (GCP) functionalized cucurbit[7]uril with an aggregation-induced luminescence effect. GCPCB exhibits high antimicrobial potency against bacterial membranes, particularly demonstrating strong antibacterial activity against Gram-positive strains of and Gram-negative strains of .
View Article and Find Full Text PDFAngew Chem Int Ed Engl
September 2024
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871, People's Republic of China.
The bisbenzylisoquinoline alkaloids (bisBIAs) have attracted tremendous attention from the synthetic community due to their diverse and intriguing biological activities. Herein, we report the convergent and modular chemoenzymatic syntheses of eight bisBIAs bearing various substitutes and linkages in 5-7 steps. The gram-scale synthesis of various well-designed enantiopure benzylisoquinoline monomers was accomplished through an enzymatic stereoselective Pictet-Spengler reaction, followed by regioselective enzymatic methylation or chemical functionalization in a sequential one-pot process.
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