Studying Histone Deacetylase Inhibition and Apoptosis Induction of Psammaplin A Monomers with Modified Thiol Group

Bao, Yu; Xu, Qihao; Wang, Lin; Wei, Yunfei; Hu, Baichun; Wang, Jian; Liu, Dan; Zhao, Liang; Jing, Yongkui

doi:10.1021/acsmedchemlett.0c00369

Cited by 13 publications

(14 citation statements)

References 33 publications

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“…Previous studies revealed that psammaplin A is a natural prodrug that inhibits class I histone deacetylase [ 88 ]. In fact, the monomeric thiol form of psammaplin A was found to be exquisitely potent against HDAC1 in vitro with IC 50 of 0.9 nM [ 89 ]. Based on preliminary molecular docking simulations, we hypothesize that psammaplin A could be reduced to the active monomeric thiol form in the bacterial cell and binds to the LBD of LasR, preventing the binding of the native autoinducer, N -3-oxo-dodecanoyl-L-homoserine lactone.…”

Section: Resultsmentioning

confidence: 99%

Inhibition of the Quorum Sensing System, Elastase Production and Biofilm Formation in Pseudomonas aeruginosa by Psammaplin A and Bisaprasin

Oluwabusola¹,

Katermeran

Poh

et al. 2022

Molecules

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Natural products derived from marine sponges have exhibited bioactivity and, in some cases, serve as potent quorum sensing inhibitory agents that prevent biofilm formation and attenuate virulence factor expression by pathogenic microorganisms. In this study, the inhibitory activity of the psammaplin-type compounds, psammaplin A (1) and bisaprasin (2), isolated from the marine sponge, Aplysinellarhax, are evaluated in quorum sensing inhibitory assays based on the Pseudomonas aeruginosa PAO1 lasB-gfp(ASV) and rhlA-gfp(ASV) biosensor strains. The results indicate that psammaplin A (1) showed moderate inhibition on lasB-gfp expression, but significantly inhibited the QS-gene promoter, rhlA-gfp, with IC50 values at 14.02 μM and 4.99 μM, respectively. In contrast, bisaprasin (2) displayed significant florescence inhibition in both biosensors, PAO1 lasB-gfp and rhlA-gfp, with IC50 values at 3.53 μM and 2.41 μM, respectively. Preliminary analysis suggested the importance of the bromotyrosine and oxime functionalities for QSI activity in these molecules. In addition, psammaplin A and bisaprasin downregulated elastase expression as determined by the standard enzymatic elastase assay, although greater reduction in elastase production was observed with 1 at 50 μM and 100 μM. Furthermore, the study revealed that bisaprasin (2) reduced biofilm formation in P. aeruginosa.

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Section: Resultsmentioning

confidence: 99%

Inhibition of the Quorum Sensing System, Elastase Production and Biofilm Formation in Pseudomonas aeruginosa by Psammaplin A and Bisaprasin

Oluwabusola¹,

Katermeran

Poh

et al. 2022

Molecules

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“…Recent studies of BTA compounds have shown this class of compounds as being promising candidates within the preclinical pipeline [ 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 ]. Despite this, the large majority of BTAs from Verongiida sponges have been understudied when it comes to biological activity and function, leaving a potentially untapped resource for drug development.…”

Section: Resultsmentioning

confidence: 99%

“…Notable examples include the disulphide-linked psammaplins, first isolated from an unidentified specimen of Psammaplysilla Keller, 1889 (= Pseudoceratina Carter, 1885), in 1987 [ 24 ]. These compounds have inspired further studies of Verongiid sponges as well as the design of synthetically targeted anti-cancer drug libraries [ 25 , 26 , 27 ]. The BTA compounds from the Verongiid sponges show enormous pharmaceutical potential, with many viewed as being promising targets within the preclinical pipeline.…”

Section: Introductionmentioning

confidence: 99%

Application of Networking Approaches to Assess the Chemical Diversity, Biogeography, and Pharmaceutical Potential of Verongiida Natural Products

et al. 2021

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This study provides a review of all isolated natural products (NPs) reported for sponges within the order Verongiida (1960 to May 2020) and includes a comprehensive compilation of their geographic and physico-chemical parameters. Physico-chemical parameters were used in this study to infer pharmacokinetic properties as well as the potential pharmaceutical potential of NPs from this order of marine sponge. In addition, a network analysis for the NPs produced by the Verongiida sponges was applied to systematically explore the chemical space relationships between taxonomy, secondary metabolite and drug score variables, allowing for the identification of differences and correlations within a dataset. The use of scaffold networks as well as bipartite relationship networks provided a platform to explore chemical diversity as well as the use of chemical similarity networks to link pharmacokinetic properties with structural similarity. This study paves the way for future applications of network analysis procedures in the field of natural products for any order or family.

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“…In bromotyrosine derivatives, such as psammaplin A monomers ( 102 ) and its analogs ( 103 ) (Baud et al 2012 ; Bao et al 2021 ), significance for the cytotoxicity effect of the free ketoxime group over the dimethylamine on 37 and 38 is evident. Besides the free ketoxime group, the cytotoxicity against the A549 cell line also leans towards a more straightforward structure of bromophenol in comparison to dibromomethoxyphenol moiety as present on 31 and 32 .…”

Section: Discussionmentioning

confidence: 99%

Structure–Activity Relationship of Cytotoxic Natural Products from Indonesian Marine Sponges

Panggabean

Adiguna

Murniasih³

et al. 2022

Rev. Bras. Farmacogn.

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Graphical abstract Indonesian marine natural products have been one of the most promising sources in the race to obtain potential drugs for cancer treatment. One of the primary producers of cytotoxic compounds is sponges. However, there are still limited sources of comprehensive reviews related to the relationship between the structure of isolated compounds and their cytotoxic activity. This review remarks the attempt to provide a preliminary guidance from the perspective of structure–activity relationship and its participation on marine natural products research. This guidance is segregated by the compound’s classes and their cytotoxic targets to obtain and organized a reliable summary of inter-study of the isolated compounds and their cytotoxicity. Structure–activity relationship is well-known for its ability to tune the bioactivity of a specific compound, especially on synthetic organic chemistry and in silico study but rarely used on natural product chemistry. The present review is intended to narrow down the endless possibilities of cytotoxicity by giving a predictable structure–activity relationship for active compounds. In addition, bioactive framework leads were selected by uncovering a noticeable structure–activity relationship with the intervention of cytotoxic agents from natural sources, especially Indonesian marine sponge.

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Studying Histone Deacetylase Inhibition and Apoptosis Induction of Psammaplin A Monomers with Modified Thiol Group

Cited by 13 publications

References 33 publications

Inhibition of the Quorum Sensing System, Elastase Production and Biofilm Formation in Pseudomonas aeruginosa by Psammaplin A and Bisaprasin

Inhibition of the Quorum Sensing System, Elastase Production and Biofilm Formation in Pseudomonas aeruginosa by Psammaplin A and Bisaprasin

Application of Networking Approaches to Assess the Chemical Diversity, Biogeography, and Pharmaceutical Potential of Verongiida Natural Products

Structure–Activity Relationship of Cytotoxic Natural Products from Indonesian Marine Sponges

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