One-step transformation of the marine alkaloid fascaplysin into homofascaplysins B and B-1. The first syntheses of 3-bromohomofascaplysin B and 3–bromohomofascaplysin B-1

Zhidkov, Maxim E.; Sidorova, Maria A.; Lyakhova, Irina

doi:10.1016/j.tetlet.2018.02.070

Cited by 9 publications

(8 citation statements)

References 27 publications

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“…The fraction of live cells after 48 h of observation of compound 26 was 84.0% (1 µM) and 68.2% (1.5 µM). While the results of fascaplysin were 77.7% (1 µM) and 67.4% (1.5 µM) under the same conditions [66].…”

Section: 11one-ring-modified Fascaplysin Derivativesmentioning

confidence: 60%

Marine-Derived Lead Fascaplysin: Pharmacological Activity, Total Synthesis, and Structural Modification

Wang

et al. 2023

Marine Drugs

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Fascaplysin is a planar structure pentacyclic alkaloid isolated from sponges, which can effectively induce the apoptosis of cancer cells. In addition, fascaplysin has diverse biological activities, such as antibacterial, anti-tumor, anti-plasmodium, etc. Unfortunately, the planar structure of fascaplysin can be inserted into DNA and such interaction also limits the further application of fascaplysin, necessitating its structural modification. In this review, the biological activity, total synthesis and structural modification of fascaplysin will be summarized, which will provide useful information for pharmaceutical researchers interested in the exploration of marine alkaloids and for the betterment of fascaplysin in particular.

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Section: 11one-ring-modified Fascaplysin Derivativesmentioning

confidence: 60%

Marine-Derived Lead Fascaplysin: Pharmacological Activity, Total Synthesis, and Structural Modification

Wang

et al. 2023

Marine Drugs

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“…To date, more than ten methods to synthesize fascaplysin and its derivatives and analogs have been reported [ 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 ]. Most of them are based on the high-temperature quaternization of 1-benzoyl-β-carbolines (Stage b , Scheme 1 ), developed by Radchenko et al [ 37 ] and with difference in the method of preparation of necessary β-carbolines.…”

Section: Resultsmentioning

confidence: 99%

Study of Structure–Activity Relationships of the Marine Alkaloid Fascaplysin and Its Derivatives as Potent Anticancer Agents

et al. 2022

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Marine alkaloid fascaplysin and its derivatives are known to exhibit promising anticancer properties in vitro and in vivo. However, toxicity of these molecules to non-cancer cells was identified as a main limitation for their clinical use. Here, for the very first time, we synthesized a library of fascaplysin derivatives covering all possible substituent introduction sites, i.e., cycles A, C and E of the 12H-pyrido[1-2-a:3,4-b’]diindole system. Their selectivity towards human prostate cancer versus non-cancer cells, as well as the effects on cellular metabolism, membrane integrity, cell cycle progression, apoptosis induction and their ability to intercalate into DNA were investigated. A pronounced selectivity for cancer cells was observed for the family of di- and trisubstituted halogen derivatives (modification of cycles A and E), while a modification of cycle C resulted in a stronger activity in therapy-resistant PC-3 cells. Among others, 3,10-dibromofascaplysin exhibited the highest selectivity, presumably due to the cytostatic effects executed via the targeting of cellular metabolism. Moreover, an introduction of radical substituents at C-9, C-10 or C-10 plus C-3 resulted in a notable reduction in DNA intercalating activity and improved selectivity. Taken together, our research contributes to understanding the structure–activity relationships of fascaplysin alkaloids and defines further directions of the structural optimization.

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“…Several groups have synthesized fascaplysin and its naturally occurring analogs and more than 10 syntheses have been reported to date [28,29,30,31,32,33,34,35,36,37,38]. Among them the two-step scheme by Zhu et al is the most suitable for the preparation of the target compounds [36].…”

Section: Resultsmentioning

confidence: 99%

Total Syntheses and Preliminary Biological Evaluation of Brominated Fascaplysin and Reticulatine Alkaloids and Their Analogues

et al. 2019

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A simple approach toward the synthesis of the marine sponge derived pigment fascaplysin was used to obtain the marine alkaloids 3-bromofascaplysin and 3,10-dibromofascaplysin. These compounds were used for first syntheses of the alkaloids 14-bromoreticulatate and 14-bromoreticulatine. Preliminary bioassays showed that 14-bromoreticulatine has a selective antibiotic (to Pseudomonas aeruginosa) activity and reveals cytotoxicity toward human melanoma, colon, and prostate cancer cells. 3,10-Dibromofascaplysin was able to target metabolic activity of the prostate cancer cells, without disrupting cell membrane’s integrity and had a wide therapeutic window amongst the fascaplysin alkaloids.

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One-step transformation of the marine alkaloid fascaplysin into homofascaplysins B and B-1. The first syntheses of 3-bromohomofascaplysin B and 3–bromohomofascaplysin B-1

Cited by 9 publications

References 27 publications

Marine-Derived Lead Fascaplysin: Pharmacological Activity, Total Synthesis, and Structural Modification

Marine-Derived Lead Fascaplysin: Pharmacological Activity, Total Synthesis, and Structural Modification

Study of Structure–Activity Relationships of the Marine Alkaloid Fascaplysin and Its Derivatives as Potent Anticancer Agents

Total Syntheses and Preliminary Biological Evaluation of Brominated Fascaplysin and Reticulatine Alkaloids and Their Analogues

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