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Frontiers in Bile Acid Chemistry and Applications
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Frontiers in Bile Acid Chemistry and Applications

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (31 December 2022) | Viewed by 15347

Special Issue Editors

Dr. Daniela Perrone

E-Mail Website
Guest Editor
Department of Environmental and Prevention Sciences, University of Ferrara, Via Fossato di Mortara 17, 44121 Ferrara, Italy
Interests: organic synthesis; synthetic bioactive compounds; bile acid derivatives; modified oligonucleotides
Special Issues, Collections and Topics in MDPI journals
Dr. Maria Luisa Navacchia

E-Mail Website
Guest Editor
Institute of Organic Synthesis and Photoreactivity, National Research Council, via Piero Gobetti 101, 40129 Bologna, Italy
Interests: organic synthesis; rational drug design; liquid chromatography-mass spectrometry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

It is our great pleasure to announce the launch of a new Special Issue on Frontiers in Bile Acid Chemistry and Applications.

Since the beginning of the 20th century, bile acids have attracted a great deal of attention in medicine, biochemistry, and drug delivery research thanks to their physical-chemical and biological properties, and biocompatibility, together with the fact that chemical modifications of the bile acid scaffold are easy to carry out. This Special Issue of Molecules will cover the major advancements and challenges toward synthetic bile acid derivatives and their potent and attractive use in the fields of chemistry, biochemistry, biomaterials, and delivery of drugs and biomolecules. This issue will be of interest to researchers working on the chemistry and medicinal chemistry of bile acid derivatives, biomaterials, and drug delivery and to chemical biologists, pharmacologists, and clinicians interested in drug discovery.

We cordially invite researchers working in this field to contribute original research articles, short communications, and review articles. Short papers on one compound will also be welcome.

Dr. Daniela Perrone
Dr. Maria Luisa Navacchia
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • bile acid derivatives
  • bile acid medicinal chemistry
  • bile acid drug discovery
  • bile acid conjugates
  • bile acid applications
  • bile acid drug delivery
  • bile acid biomaterials
  • bile acid supramolecular chemistry
  • bile acid in biochemistry

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Published Papers (5 papers)

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Research

13 pages, 1971 KiB  
Article
N-methyl Benzimidazole Tethered Cholic Acid Amphiphiles Can Eradicate S. aureus-Mediated Biofilms and Wound Infections
by Himanshu Kakkar, Nalini Chaudhary, Devashish Mehta, Varsha Saini, Shallu Maheshwari, Jitender Singh, Preeti Walia and Avinash Bajaj
Molecules 2022, 27(11), 3501; https://doi.org/10.3390/molecules27113501 - 30 May 2022
Cited by 3 | Viewed by 1971
Abstract
Infections associated with Gram-positive bacteria like S. aureus pose a major threat as these bacteria can develop resistance and thereby limit the applications of antibiotics. Therefore, there is a need for new antibacterials to mitigate these infections. Bacterial membranes present an attractive therapeutic [...] Read more.
Infections associated with Gram-positive bacteria like S. aureus pose a major threat as these bacteria can develop resistance and thereby limit the applications of antibiotics. Therefore, there is a need for new antibacterials to mitigate these infections. Bacterial membranes present an attractive therapeutic target as these membranes are anionic in nature and have a low chance of developing modifications in their physicochemical features. Antimicrobial peptides (AMPs) can disrupt the microbial membranes via electrostatic interactions, but the poor stability of AMPs halts their clinical translation. Here, we present the synthesis of eight N-methyl benzimidazole substituted cholic acid amphiphiles as antibacterial agents. We screened these novel heterocyclic cholic acid amphiphiles against different pathogens. Among the series, CABI-6 outperformed the other amphiphiles in terms of bactericidal activity against S. aureus. The membrane disruptive property of CABI-6 using a fluorescence-based assay has also been investigated, and it was inferred that CABI-6 can enhance the production of reactive oxygen species. We further demonstrated that CABI-6 can clear the pre-formed biofilms and can mitigate wound infection in murine models. Full article
(This article belongs to the Special Issue Frontiers in Bile Acid Chemistry and Applications)
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12 pages, 6917 KiB  
Article
Deoxycholic Acid Modulates Cell-Junction Gene Expression and Increases Intestinal Barrier Dysfunction
by Huawei Zeng, Bryan D. Safratowich, Wen-Hsing Cheng, Kate J. Larson and Mary Briske-Anderson
Molecules 2022, 27(3), 723; https://doi.org/10.3390/molecules27030723 - 22 Jan 2022
Cited by 17 | Viewed by 4296
Abstract
Diet-related obesity is associated with increased intestinal hyperpermeability. High dietary fat intake causes an increase in colonic bile acids (BAs), particularly deoxycholic acid (DCA). We hypothesize that DCA modulates the gene expression of multiple cell junction pathways and increases intestinal permeability. With a [...] Read more.
Diet-related obesity is associated with increased intestinal hyperpermeability. High dietary fat intake causes an increase in colonic bile acids (BAs), particularly deoxycholic acid (DCA). We hypothesize that DCA modulates the gene expression of multiple cell junction pathways and increases intestinal permeability. With a human Caco-2 cell intestinal model, we used cell proliferation, PCR array, biochemical, and immunofluorescent assays to examine the impact of DCA on the integrity of the intestinal barrier and gene expression. The Caco-2 cells were grown in monolayers and challenged with DCA at physiological, sub-mM, concentrations. DCA increased transcellular and paracellular permeability (>20%). Similarly, DCA increased intracellular reactive oxidative species production (>100%) and accompanied a decrease (>40%) in extracellular signal-regulated kinase 1/2 (ERK1/2) signaling pathways. Moreover, the mRNA levels of 23 genes related to the epithelial barrier (tight junction, focal adhesion, gap junction, and adherens junction pathways) were decreased (>40%) in (0.25 mM) DCA-treated Caco-2 cells compared to untreated cells. Finally, we demonstrated that DCA decreased (>58%) the protein content of occludin present at the cellular tight junctions and the nucleus of epithelial cells. Collectively, DCA decreases the gene expression of multiple pathways related to cell junctions and increases permeability in a human intestinal barrier model. Full article
(This article belongs to the Special Issue Frontiers in Bile Acid Chemistry and Applications)
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15 pages, 2003 KiB  
Article
Synthesis and Biological Investigation of Bile Acid-Paclitaxel Hybrids
by Elisabetta Melloni, Elena Marchesi, Lorenzo Preti, Fabio Casciano, Erika Rimondi, Arianna Romani, Paola Secchiero, Maria Luisa Navacchia and Daniela Perrone
Molecules 2022, 27(2), 471; https://doi.org/10.3390/molecules27020471 - 12 Jan 2022
Cited by 12 | Viewed by 2850
Abstract
Chenodeoxycholic acid and ursodeoxycholic acid (CDCA and UDCA, respectively) have been conjugated with paclitaxel (PTX) anticancer drugs through a high-yield condensation reaction. Bile acid-PTX hybrids (BA-PTX) have been investigated for their pro-apoptotic activity towards a selection of cancer cell lines as well as [...] Read more.
Chenodeoxycholic acid and ursodeoxycholic acid (CDCA and UDCA, respectively) have been conjugated with paclitaxel (PTX) anticancer drugs through a high-yield condensation reaction. Bile acid-PTX hybrids (BA-PTX) have been investigated for their pro-apoptotic activity towards a selection of cancer cell lines as well as healthy fibroblast cells. Chenodeoxycholic-PTX hybrid (CDC-PTX) displayed cytotoxicity and cytoselectivity similar to PTX, whereas ursodeoxycholic-PTX hybrid (UDC-PTX) displayed some anticancer activity only towards HCT116 colon carcinoma cells. Pacific Blue (PB) conjugated derivatives of CDC-PTX and UDC-PTX (CDC-PTX-PB and UDC-PTX-PB, respectively) were also prepared via a multistep synthesis for evaluating their ability to enter tumor cells. CDC-PTX-PB and UDC-PTX-PB flow cytometry clearly showed that both CDCA and UDCA conjugation to PTX improved its incoming into HCT116 cells, allowing the derivatives to enter the cells up to 99.9%, respect to 35% in the case of PTX. Mean fluorescence intensity analysis of cell populations treated with CDC-PTX-PB and UDC-PTX-PB also suggested that CDC-PTX-PB could have a greater ability to pass the plasmatic membrane than UDC-PTX-PB. Both hybrids showed significant lower toxicity with respect to PTX on the NIH-3T3 cell line. Full article
(This article belongs to the Special Issue Frontiers in Bile Acid Chemistry and Applications)
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15 pages, 1651 KiB  
Article
Glyceric Prodrug of Ursodeoxycholic Acid (UDCA): Novozym 435-Catalyzed Synthesis of UDCA-Monoglyceride
by Federico Zappaterra, Stefania Costa, Daniela Summa, Bruno Semeraro, Virginia Cristofori, Claudio Trapella and Elena Tamburini
Molecules 2021, 26(19), 5966; https://doi.org/10.3390/molecules26195966 - 1 Oct 2021
Cited by 9 | Viewed by 2979
Abstract
Bile acids (BAs) are a family of steroids synthesized from cholesterol in the liver. Among bile acids, ursodeoxycholic acid (UDCA) is the drug of choice for treating primary biliary cirrhosis and dissolving cholesterol gallstones. The clinical effectiveness of UDCA includes its choleretic activity, [...] Read more.
Bile acids (BAs) are a family of steroids synthesized from cholesterol in the liver. Among bile acids, ursodeoxycholic acid (UDCA) is the drug of choice for treating primary biliary cirrhosis and dissolving cholesterol gallstones. The clinical effectiveness of UDCA includes its choleretic activity, the capability to inhibit hydrophobic bile acid absorption by the intestine under cholestatic conditions, reducing cholangiocyte injury, stimulation of impaired biliary output, and inhibition of hepatocyte apoptosis. Despite its clinical effectiveness, UDCA is poorly soluble in the gastro-duodeno-jejunal contents, and pharmacological doses of UDCA are not readily soluble in the stomach and intestine, resulting in incomplete absorption. Indeed, the solubility of 20 mg/L greatly limits the bioavailability of UDCA. Since the bioavailability of drug products plays a critical role in the design of oral administration dosages, we investigated the enzymatic esterification of UDCA as a strategy of hydrophilization. Therefore, we decided to enzymatically synthesize a glyceric ester of UDCA bile acid to produce a more water-soluble molecule. The esterification reactions between UDCA and glycerol were performed with an immobilized lipase B from Candida antarctica (Novozym 435) in solvent-free and solvent-assisted systems. The characterization of the UDCA-monoglyceride, enzymatically synthesized, has been performed by 1H-NMR, 13C-NMR, COSY, HSQC, HMBC, IR, and MS spectroscopy. Full article
(This article belongs to the Special Issue Frontiers in Bile Acid Chemistry and Applications)
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20 pages, 1804 KiB  
Article
Bile-Acid-Appended Triazolyl Aryl Ketones: Design, Synthesis, In Vitro Anticancer Activity and Pharmacokinetics in Rats
by Devesh S. Agarwal, Samrat Mazumdar, Kishan S. Italiya, Deepak Chitkara and Rajeev Sakhuja
Molecules 2021, 26(19), 5741; https://doi.org/10.3390/molecules26195741 - 22 Sep 2021
Cited by 7 | Viewed by 2239
Abstract
A library of bile-acid-appended triazolyl aryl ketones was synthesized and characterized by detailed spectroscopic techniques such as 1H and 13C NMR, HRMS and HPLC. All the synthesized conjugates were evaluated for their cytotoxicity at 10 µM against MCF-7 (human breast adenocarcinoma) [...] Read more.
A library of bile-acid-appended triazolyl aryl ketones was synthesized and characterized by detailed spectroscopic techniques such as 1H and 13C NMR, HRMS and HPLC. All the synthesized conjugates were evaluated for their cytotoxicity at 10 µM against MCF-7 (human breast adenocarcinoma) and 4T1 (mouse mammary carcinoma) cells. In vitro cytotoxicity studies on the synthesized conjugates against MCF-7 and 4T1 cells indicated one of the conjugate 6cf to be most active against both cancer cell lines, with IC50 values of 5.71 µM and 8.71 µM, respectively, as compared to the reference drug docetaxel, possessing IC50 values of 9.46 µM and 13.85 µM, respectively. Interestingly, another compound 6af (IC50 = 2.61 µM) was found to possess pronounced anticancer activity as compared to the reference drug docetaxel (IC50 = 9.46 µM) against MCF-7. In addition, the potent compounds (6cf and 6af) were found to be non-toxic to normal human embryonic kidney cell line (HEK 293), as evident from their cell viability of greater than 86%. Compound 6cf induces higher apoptosis in comparison to 6af (46.09% vs. 33.89%) in MCF-7 cells, while similar apoptotic potential was observed for 6cf and 6af in 4T1 cells. The pharmacokinetics of 6cf in Wistar rats showed an MRT of 8.47 h with a half-life of 5.63 h. Clearly, these results suggest 6cf to be a potential candidate for the development of anticancer agents. Full article
(This article belongs to the Special Issue Frontiers in Bile Acid Chemistry and Applications)
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