Erratum to “Discovery, design, and synthesis of anti-metastatic lead phenylmethylene hydantoins inspired by marine natural products” [Bioorg. Med. Chem. 17 (2009) 1731–1738]

Mudit, Mudit; Khanfar, Monther A.; Anbalagan, Muralidharan; Thomas, Shibu; Shah, Girish V.; Soest, R.W.M. van; Sayed, Khalid A. El

doi:10.1016/j.bmc.2008.12.073

Cited by 14 publications

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“…A 50 mm dose of PMH 1 significantly increased transepithelial resistance (TER) of diluent and CT-(calcitonin)-treated PC-3M cell cultures, suggesting that 1 promotes tight junctions (TJs) formation and completely reverses the action of CT on TER [6] [7]. PMH 1 decreased baseline paracellular permeability and also abolished CT-induced increase in paracellular permeability of polarized PC-3M cell layers [6] [7]. This effect further supported the fact that 1 promotes TJs formation.…”

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“…(Phenylmethylidene)-hydantoins (PMHs) are marine-derived compounds reported earlier from the Red Sea sponge Hemimycale arabica and showed good in vitro and in vivo activities against the highly metastatic androgen-independent human prostate cancer cells [6] [7]. Several synthetic analogues related to the natural PMH 1 ( Table 1) [29] were also reported to show significant activities [6].…”

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“…Several synthetic analogues related to the natural PMH 1 ( Table 1) [29] were also reported to show significant activities [6]. The natural PMH 1 and the synthetic (5Z)-5-[4-(ethylsulfanyl)benzylidene]imidazolidine-2,4-dione (2) showed potent anti-invasive and anti-migratory properties against PC-3M prostate cancer cells in various pharmacological assays including the spheroid disaggregation assay [6] [7]. A 50 mm dose of PMH 1 significantly increased transepithelial resistance (TER) of diluent and CT-(calcitonin)-treated PC-3M cell cultures, suggesting that 1 promotes tight junctions (TJs) formation and completely reverses the action of CT on TER [6] [7].…”

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confidence: 99%

“…The natural PMH 1 and the synthetic (5Z)-5-[4-(ethylsulfanyl)benzylidene]imidazolidine-2,4-dione (2) showed potent anti-invasive and anti-migratory properties against PC-3M prostate cancer cells in various pharmacological assays including the spheroid disaggregation assay [6] [7]. A 50 mm dose of PMH 1 significantly increased transepithelial resistance (TER) of diluent and CT-(calcitonin)-treated PC-3M cell cultures, suggesting that 1 promotes tight junctions (TJs) formation and completely reverses the action of CT on TER [6] [7]. PMH 1 decreased baseline paracellular permeability and also abolished CT-induced increase in paracellular permeability of polarized PC-3M cell layers [6] [7].…”

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Optimization of (Phenylmethylidene)‐hydantoins as Prostate Cancer Migration Inhibitors: SAR‐Directed Design, Synthesis, and Pharmacophore Modeling

Mudit

Sayed

2011

Chemistry & Biodiversity

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Prostate cancer is one of the most common cancer forms among males of Western countries. Natural products proved to be an unparalleled source of molecular diversity. The 4-(hydroxyphenylmethylidene)hydantoin (PMH; 1), (5Z)-5-(4-hydroxybenzylidene)imidazolidine-2,4-dione, was isolated from the Red Sea sponge Hemimycale arabica, and recently showed junctional complexes stabilization, antiinvasive, and antimetastatic activities in vitro and in vivo. The related synthetic analogue, (5Z)-5-[4-(ethylsulfanyl)benzylidene]imidazolidine-2,4-dione (2), showed several-fold-improved in vivo antimetastatic properties against the highly invasive prostate cancer. To further optimize the activity of PMHs, various ligand-based strategies were used including the extension of the structure, structural simplification, linker extension, and computer-assisted CoMFA (Comparative Molecular Field Analysis) results. These strategies yielded thirty 2nd-generation PMHs, designed based on the 1st-generation PMHs, such as 1 and 2. Wound-healing assay was selected to evaluate the in vitro anti-migratory potential of these new PMHs against the PC-3 cell line. Several active PMHs, including 10, 13, 24, 29, with nearly twelvefold enhancement of activity vs. 2, were identified. Active compounds were then used to build a pharmacophore model using the SYBYLs DIStance COmparison technique (DISCOtech). Active PMHs were also screened for fragment-based drug likeness using the OSIRIS program, and an overall drug score was also calculated. Interestingly, the overall drug scores of 24 and 29 along with their antimigratory activity were significantly greater than those of 1 and 2. In conclusion, PMHs can be the appropriate scaffolds for the urgently needed drug candidates for the control of androgen independent prostate cancer.

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Optimization of (Phenylmethylidene)‐hydantoins as Prostate Cancer Migration Inhibitors: SAR‐Directed Design, Synthesis, and Pharmacophore Modeling

Mudit

Sayed

2011

Chemistry & Biodiversity

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In Silico‐Guided Strategies for the Discovery and Rationalization of Bioactive Natural Products

Pfisterer

Schuster

Rollinger

et al. 2014

Encyclopedia of Analytical Chemistry

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The identification of bioactive natural products is a multidisciplinary research field. One methodology used in this research environment is the application of computational (virtual) screening. In silico screening allows for focusing experimental efforts on promising plant material and constituents. Starting from the chemical structures of natural products in the form of 3D multiconformational databases, virtual screening methods predict potentially active compounds within the screened database. For this task docking, pharmacophore‐based screening, 2D similarity searches, quantitative structure–activity relationship (QSAR) modeling, and neural networks can be employed. A procedure for selecting the most promising virtual hits for further analyses is described. In addition, bioactivity profiling and activity rationalization strategies are shown. Finally, also the limits of the virtual approaches are discussed. This chapter gives an overview of virtual screening applications in the field of natural product research. In addition, selected examples and strategies are described in detail.

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Reaction of Hydantoin with Boronic Acids

Gwynne¹,

Holt²,

Dwan³

et al. 2010

Helvetica Chimica Acta

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We have examined the reaction of hydantoin (¼ imidazolidine-2,4-dione) with (formylphenyl)boronic acids, where the addition of a boronic acid group is hoped to increase bioactivities. Addition of (2-formylphenyl)boronic acid to hydantoin gave an unexpected azaborine compound, which presumably arises by initial formation of the (phenylmethylidene)hydantoin, with subsequent loss of H 2 O to give the cyclized product. Reactions of (3-formylphenyl)-and (4-formylphenyl)boronic acids with hydantoin gave the corresponding [(Z)-phenylmethylidene]hydantoins in good-to-excellent yields. Attempts to use (3-formylthiophen-2-yl)boronic acid gave a product where the boronic acid group has been cleaved.

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Erratum to “Discovery, design, and synthesis of anti-metastatic lead phenylmethylene hydantoins inspired by marine natural products” [Bioorg. Med. Chem. 17 (2009) 1731–1738]

Cited by 14 publications

References 0 publications

Optimization of (Phenylmethylidene)‐hydantoins as Prostate Cancer Migration Inhibitors: SAR‐Directed Design, Synthesis, and Pharmacophore Modeling

Optimization of (Phenylmethylidene)‐hydantoins as Prostate Cancer Migration Inhibitors: SAR‐Directed Design, Synthesis, and Pharmacophore Modeling

In Silico‐Guided Strategies for the Discovery and Rationalization of Bioactive Natural Products

Reaction of Hydantoin with Boronic Acids

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