Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials

• Jessica Villegas,
• Bryce C. Ball,
• Katelyn M. Shouse,
• Caleb W. VanArragon,
• Ashley N. Wasserman,
• Hannah E. Bhakta,
• Allen G. Oliver,
• Danielle A. Orozco-Nunnelly and
• Jeffrey M. Pruet

Beilstein J. Org. Chem. 2023, 19, 1511–1524, doi:10.3762/bjoc.19.108

• with associated standard error (n = 5). Vancomycin, streptomycin, and/or fluconazole were used as positive controls, and solvents were used as negative controls and showed no zones of inhibition. X-ray crystal structures of the oxidation byproducts a) B4 (CCDC 2271457) and b) B6 (CCDC 2271458; one

• shown with the associated standard error (n = 3–6). Vancomycin, streptomycin, and/or fluconazole were used as positive controls, and solvents alone were used as negative controls and showed no zones of inhibition. Kirby–Bauer zones of inhibition for variants C1–C4 compared to original chelerythrine (C

• ). Mean zones of inhibition using 0.12 mg of each compound tested against 12 unique microbial species shown with the associated standard error (n = 3–6). Vancomycin, streptomycin, and/or fluconazole were used as positive controls, and solvents were used as negative controls and showed no zones of

A Streptomyces P450 enzyme dimerizes isoflavones from plants

• Run-Zhou Liu,
• Shanchong Chen and
• Lihan Zhang

Beilstein J. Org. Chem. 2022, 18, 1107–1115, doi:10.3762/bjoc.18.113

• Experimental section, 254 nm). b) Chemical genetics experiments indicated three P450 inhibitors could reduce the production of dimers derived from 4 (analytical method B to better analyze the isoflavone region, 254 nm). CTA: clotrimazole (2.5 µM), FCA: fluconazole (1000 µM), RVT: resveratrol (100 µM). CYP158C1

Biological properties and conformational studies of amphiphilic Pd(II) and Ni(II) complexes bearing functionalized aroylaminocarbo-N-thioylpyrrolinate units

• Samet Poyraz,
• Samet Belveren,
• Sabriye Aydınoğlu,
• Mahmut Ulger,
• Abel de Cózar,
• Maria de Gracia Retamosa,
• Jose M. Sansano and
• H. Ali Döndaş

Beilstein J. Org. Chem. 2021, 17, 2812–2821, doi:10.3762/bjoc.17.192

• Ankara, Turkey) with respect to the standard document (M27-A2) of NCCLS [33]. As a reference antifungal agent fluconazole (Sigma, F8929) was used (Table 2). As mentioned in the M27-A2 document, experiments were performed in RPMI 1640 medium adjusted to pH 7.0 with 0.165 M 3-(N-morpholino)-propane

• sulfonic acid (MOPS, Sigma, M1254). With dissolving the tested compounds in DMSO, an initial concentration of 1000 μg/mL was prepared. After this, serial twofold dilutions of the compounds and fluconazole in 100 μL of RPMI 1640 medium were prepared in the plates. Working suspensions of the standard Candida

• growth of the standard Candida strain was determined as the MIC value, which detected visually. Fluconazole (Sigma, F8929) showed activity with a range of 3.90–31.25 μg/mL when tested against the indicated yeast. Main geometrical features and the relative energies (in kcal·mol–1) of (A) ligand L1, (B

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

• Nikita Brodyagin,
• Martins Katkevics,
• Venubabu Kotikam,
• Christopher A. Ryan and
• Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

• Guido Gambacorta,
• James S. Sharley and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

• Shivani Gulati,
• Stephy Elza John and
• Nagula Shankaraiah

Beilstein J. Org. Chem. 2021, 17, 819–865, doi:10.3762/bjoc.17.71

β-Cyclodextrin- and adamantyl-substituted poly(acrylate) self-assembling aqueous networks designed for controlled complexation and release of small molecules

• Liang Yan,
• Duc-Truc Pham,
• Philip Clements,
• Stephen F. Lincoln,
• Jie Wang,
• Xuhong Guo and
• Christopher J. Easton

Beilstein J. Org. Chem. 2017, 13, 1879–1892, doi:10.3762/bjoc.13.183

• , fluconazole [40] and curcumin [37], along with larger species exemplified by RNA and DNA segments [26][32][33][36][39][47]. Some systems are designed to target specific tissues [26][35]. We are particularly interested in the extent to which small molecule guest complexation and release characteristics may be

Cyclodextrin–polysaccharide-based, in situ-gelled system for ocular antifungal delivery

• Anxo Fernández-Ferreiro,
• Noelia Fernández Bargiela,
• María Santiago Varela,
• Maria Gil Martínez,
• Maria Pardo,
• Antonio Piñeiro Ces,
• José Blanco Méndez,
• Miguel González Barcia,
• Maria Jesus Lamas and
• Francisco.J. Otero-Espinar

Beilstein J. Org. Chem. 2014, 10, 2903–2911, doi:10.3762/bjoc.10.308

• Pharmacy, University of Santiago de Compostela (USC), Praza Seminario de Estudos Galegos s/n, Santiago de Compostela, 15701, Spain 10.3762/bjoc.10.308 Abstract Fluconazole was studied with two different hydrophilic cyclodextrins (hydroxypropyl-β-cyclodextrin (HPBCD) and sulfobutyl ether-β-cyclodextrin

• (SBECD)) for the formation of inclusion complexes. HPBCD and SBECD showed low cell cytotoxicity in human keratocytes as assessed by the label-free xCELLigence system for real-time monitoring. The fluconazole–HPBCD complex was incorporated into an ion-sensitive ophthalmic gel composed of the natural

• polysaccharides gellan gum and κ-carrageenan. This system showed good bioadhesive properties and effective control of fluconazole release. Keywords: cyclodextrins; eye drops; fluconazole; hydroxypropyl-β-cyclodextrin; sulfobutylether-β-cyclodextrin; Introduction Fungal keratitis is a serious disease that can

ML212: A small-molecule probe for investigating fluconazole resistance mechanisms in Candida albicans

• Willmen Youngsaye,
• Cathy L. Hartland,
• Barbara J. Morgan,
• Amal Ting,
• Partha P. Nag,
• Benjamin Vincent,
• Carrie A. Mosher,
• Joshua A. Bittker,
• Sivaraman Dandapani,
• Michelle Palmer,
• Luke Whitesell,
• Susan Lindquist,
• Stuart L. Schreiber and
• Benito Munoz

Beilstein J. Org. Chem. 2013, 9, 1501–1507, doi:10.3762/bjoc.9.171

• Molecular Libraries and Probe Production Centers Network (NIH-MLPCN) screened >300,000 compounds to evaluate their ability to restore fluconazole susceptibility in resistant Candida albicans isolates. Additional counter screens were incorporated to remove substances inherently toxic to either mammalian or

• fungal cells. A substituted indazole possessing the desired bioactivity profile was selected for further development, and initial investigation of structure–activity relationships led to the discovery of ML212. Keywords: antifungal; Candida albicans; chemosensitizer; fluconazole; Molecular Libraries

• chemosensitizers of the pathogenic fungus Candida albicans [11]. The C. albicans clinical isolates used in this study demonstrate a range of resistance to the widely prescribed triazole antimycotic fluconazole (Flc) [12], and the objective was to identify novel small molecules capable of surmounting this inherent

Chemical–biological characterization of a cruzain inhibitor reveals a second target and a mammalian off-target

• Jonathan W. Choy,
• Clifford Bryant,
• Claudia M. Calvet,
• Patricia S. Doyle,
• Shamila S. Gunatilleke,
• Siegfried S. F. Leung,
• Kenny K. H. Ang,
• Steven Chen,
• Jiri Gut,
• Juan A. Oses-Prieto,
• Jonathan B. Johnston,
• Michelle R. Arkin,
• Alma L. Burlingame,
• Jack Taunton,
• Matthew P. Jacobson,
• James M. McKerrow,
• Larissa M. Podust and
• Adam R. Renslo

Beilstein J. Org. Chem. 2013, 9, 15–25, doi:10.3762/bjoc.9.3

• ) predicted to interact with the tryptophan ring of (R)-5 (Figure 2A). This same hydrophobic site in TcCYP51 binds the fluoroaryl rings of fluconazole and posaconazole in co-crystal structures [14]. The predicted binding mode of the enantiomer (S)-5 was described previously [16] and is distinct from that

Advances in synthetic approach to and antifungal activity of triazoles

• Kumari Shalini,
• Nitin Kumar,
• Sushma Drabu and
• Pramod Kumar Sharma

Beilstein J. Org. Chem. 2011, 7, 668–677, doi:10.3762/bjoc.7.79

• -anxiety agents and sedatives [17]. The most important use, however, is as antimycotics in drugs such as fluconazole, itraconazole and voriconazole [18][19]. The triazole moiety is stable to metabolic degradation and capable of hydrogen bonding, which could be favorable in binding biomolecular targets as

• antifungal for IFIs was amphotericin B. With the introduction of triazoles at the beginning of 1990s, the pace of drug development accelerated. Amphotericin B (AMB) was incorporated in three lipid formulations, whilst the first-generation triazoles (fluconazole (9) and itraconazole (10)) changed the

• epidemiology of Candida infections and offered new treatment options. Many of these antifungals have proven to be less toxic and in some cases more effective than amphotericin B [41]. Mechanism of action The antifungal triazoles (fluconazole (9), itraconazole (10), voriconazole (11), and currently investigated

Michael-type addition of azoles of broad-scale acidity to methyl acrylate

• Sławomir Boncel,
• Kinga Saletra,
• Barbara Hefczyc and
• Krzysztof Z. Walczak

Beilstein J. Org. Chem. 2011, 7, 173–178, doi:10.3762/bjoc.7.24

• and is used as a clinical regulator of the cardiac cycle [5]. Fluconazole (VI) 2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazol-1-yl)propan-2-ol is an antifungal drug used in the treatment and prevention of superficial and systemic fungal infections [6]. The base-catalysed Michael-type addition reaction