Synthesis, characterization and biological evaluation of bile acid-aromatic/heteroaromatic amides linked via amino acids as anti-cancer agents

Agarwal, Devesh S.; Anantaraju, Hasitha Shilpa; Sriram, Dharmarajan; Yogeeswari, Perumal; Nanjegowda, Shankara H.; Mallu, P.; Sakhuja, Rajeev

doi:10.1016/j.steroids.2015.12.022

Cited by 32 publications

(31 citation statements)

References 44 publications

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“…Bile acids are water-soluble steroids formed during the catabolism of cholesterol to primary bile acids, i.e. cholic acids and chenodeoxycholic acids 34 and show anticancer and antibacterial activities 35 , 36 . Cholesterol was previously reported from Onchidium reevesii (Gray, 1850) 17 , octocorals 37 , and sponges 38 , while there are only a few reports of bile acids and derivatives in other marine invertebrates.…”

Section: Discussionmentioning

confidence: 99%

From Persian Gulf to Indonesia: interrelated phylogeographic distance and chemistry within the genus Peronia (Onchidiidae, Gastropoda, Mollusca)

Maniei

Moghaddam

Crüsemann

et al. 2020

Sci Rep

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the knowledge of relationships between taxa is essential to understand and explain the chemical diversity of the respective groups. Here, twelve individuals of the panpulmonate slug Peronia persiae from two localities in persian Gulf, and one animal of P. verruculata from Bangka island, indonesia, were analyzed in a phylogenetic and chemotaxonomic framework. Based on the ABGD test and haplotype networking using coi gene sequences of Peronia specimens, nine well-supported clades were found. Haplotype network analysis highlighted a considerable distance between the specimens of P. persiae and other clades. Metabolomic analysis of both species using tandem mass spectrometrybased GnpS molecular networking revealed a large chemical diversity within Peronia of different clades and localities. While P. persiae from different localities showed a highly similar metabolome, only few identical chemical features were found across the clades. the main common metabolites in both Peronia species were assigned as polypropionate esters of onchitriols and ilikonapyrones, and osmoprotectant amino acid-betaine compounds. On the other hand, the isoflavonoids genistein and daidzein were exclusively detected in P. persiae, while cholesterol and conjugated chenodeoxycholic acids were only found in P. verruculata. flavonoids, bile acids, and amino acid-betaine compounds were not reported before from onchidiidae, some are even new for panpulmonates. our chemical analyses indicate a close chemotaxonomic relation between phylogeographically distant Peronia species. Peronia Fleming, 1822, a panpulmonate slug genus, is typically distributed in tropical and subtropical regions of the Indo-Pacific ocean 1. The genus Peronia, with ten acknowledged species, has been reported from many localities ranging from the Indo-Pacific to the East Coast of Africa and to Hawaii 2-4. Due to undetected cryptic speciation, species diversity is often underestimated while the widespread distributions attributed to species is often overestimated 5. The integration of molecular and morphological methods has led to numerous discoveries of cryptic species complexes 6. This is also true for the genus Peronia, as was shown by Maniei et al. 3. To date, only three Peronia species are well investigated by molecular and/or morphology data, i.e.

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Section: Discussionmentioning

confidence: 99%

From Persian Gulf to Indonesia: interrelated phylogeographic distance and chemistry within the genus Peronia (Onchidiidae, Gastropoda, Mollusca)

Maniei

Moghaddam

Crüsemann

et al. 2020

Sci Rep

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“…[51] BA-Aryl/heteroaryl Condensation MDA-MB-231, U87. Comparable/better cytotoxicity than Cisplatin and Doxorubicin [52] Upon irradiation with visible light, 1-nitro-2-(trifluoromethyl)aniline alkyne, a nitic oxide (NO) photodonor molecule, is able to generate NO radicals [48]. NO can be used as an anticancer agent or as a chemosensitizer to enhance the effect of traditional cancer therapies [53,54].…”

Section: Hybridmentioning

confidence: 99%

“…Another study reported on the cytotoxicity of BA-based aryl/heteroaryl hybrids linked through α-amino acids [52]. The synthetic strategy involved the coupling of L-aminoacyl aromatic and heteroaromatic amides with CA and DCA using EDC•HCl/HOBt in DMF at room temperature (Scheme 10).…”

Section: Ic50 µM Compound K562 Htc116 Fibroblastmentioning

confidence: 99%

Bile Acid Conjugates with Anticancer Activity: Most Recent Research

2020

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The advantages of a treatment modality that combines two or more therapeutic agents in cancer therapy encourages the study of hybrid functional compounds for pharmacological applications. In light of this, we reviewed recent works on hybrid molecules based on bile acids. Due to their biological properties, as well as their different chemical/biochemical reactive moieties, bile acids can be considered very interesting starting molecules for conjugation with natural or synthetic bioactive molecules.

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“…[48][49][50] Within this context heteroaromatic amino acids have been shown to be valuable building blocks for the synthesis of many biologically active compounds. [51][52][53] The Negishi cross-coupling is one way in which heteroaromatic-appended amino acids can be synthesised in relatively few steps with great modularity.…”

Section: Synthesis Of Heteroaromatic Amino Acidsmentioning

confidence: 99%