Synthesis of <scp>d</scp>-Galactose-Substituted Acylsilanes and Acylgermanes. Model Compounds for Visible Light Photoinitiators with Intriguing High Solubility

Schuh, Lukas; Müller, Philipp; Torvisco, Ana; Stueger, Harald; Wrodnigg, Tanja; Haas, Michael

doi:10.1021/acs.organomet.0c00753

Cited by 4 publications

(2 citation statements)

References 23 publications

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“…In order to adjust the absorption wavelength, a series of multi-acyl-substituted germanes have been prepared as photoinitiators. [78][79][80][81][82][83][84][85][86][87] However, in photoinduced organic reactions, only single-acyl-group-substituted germanes have been used as substrates.…”

Section: Acylgermanesmentioning

confidence: 99%

Organogermanium(iv) compounds in photo-induced radical reactions

Xiao

2022

Org. Chem. Front.

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Section: Acylgermanesmentioning

confidence: 99%

Organogermanium(iv) compounds in photo-induced radical reactions

Xiao

2022

Org. Chem. Front.

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“…It has been shown, in many studies, that the binding of a parent drug to D-galactose increases its selectivity of action and reduces its side effects. In other cases, the presence of the sugar structure ensures an improvement in the solubility and cell permeability of the parent drug, and thus in its pharmacokinetic profile [ 14 , 15 ], while keeping its pharmacodynamic characteristics intact [ 16 ].…”

Section: Introductionmentioning

confidence: 99%

Galactosylated Prodrugs: A Strategy to Improve the Profile of Nonsteroidal Anti-Inflammatory Drugs

et al. 2022

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Carbohydrates are one of the most abundant and important classes of biomolecules. The variety in their structures makes them valuable carriers that can improve the pharmaceutical phase, pharmacokinetics and pharmacodynamics of well-known drugs. D-galactose is a simple, naturally occurring monosaccharide sugar that has been extensively studied for use as a carrier and has proven to be valuable in this role. With the aim of validating the galactose-prodrug approach, we have investigated the galactosylated prodrugs ibuprofen, ketoprofen, flurbiprofen and indomethacin, which we have named IbuGAL, OkyGAL, FluGAL and IndoGAL, respectively. Their physicochemical profiles in terms of lipophilicity, solubility and chemical stability have been evaluated at different physiological pH values, as have human serum stability and serum protein binding. Ex vivo intestinal permeation experiments were performed to provide preliminary insights into the oral bioavailability of the galactosylated prodrugs. Finally, their anti-inflammatory, analgesic and ulcerogenic activities were investigated in vivo in mice after oral treatment. The present results, taken together with those of previous studies, undoubtedly validate the galactosylated prodrug strategy as a problem-solving technique that can overcome the disadvantages of NSAIDs.

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Organodigermanium Compounds: Structures and Properties

Zaitsev,

Trubachev,

Antonenko

et al. 2024

Organometallics

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A series of substituted bis(triazole) derivatives of organodigermanes (1−3) containing reactive phenolic and sugar functional groups, [1,4-C 2 HN 3 (R)GePh 2 −] 2 (R = β-(D)-glucopyranoso-C 5 H 5 O(OAc) 3 CH 2 OAc (1); R = CH 2 −1,2,3,5-(HO)C 6 H 2 (t-Bu) 2 (2); and R = CH 2 −1,2,3,5-(HO)C 6 H 2 (CHO)(t-Bu) (3)), was synthesized by the copper-catalyzed azide− alkyne cycloaddition (CuAAC) reaction. The structural features (1, XRD analysis) and optical properties (1−3, absorbance, and emission) of these digermanium heterocyclic compounds were studied. The antioxidant (DPPH test), lipoxygenase inhibitory (inhibition of LOX 1-B), and antiproliferative activities (MTT test; HCT-116, MCF-7, A-549 cancer cell lines) of differently substituted 1−6 (R = p-BrC 6 H 4 CH 2 (4); R = CH 2 COOEt (5); R = CH 2 CH 2 O-p-C 6 H 4 CHO (6)) were investigated, indicating their promising antioxidant (for 2 EC 50 103 ± 4 μM) and lipoxygenase inhibition activity (for 4 IC 50 29 ± 2 μM), moderate antiproliferative activities (for 5 IC 50 55−71 μM), and low toxic properties (WI-38, IC 50 > 36 μM). Comparison of the biological activity of the leader digermanes 2, 4, and 5 with related organic triazoles 1,4-C 2 HN 3 (R) (2a, 4a, 5a) and monogermanes 1,4-C 2 HN 3 (R)GePh 3 (2b, 4b, and 5b) indicates the influence of the Ge−Ge fragment.

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Synthesis of d-Galactose-Substituted Acylsilanes and Acylgermanes. Model Compounds for Visible Light Photoinitiators with Intriguing High Solubility

Cited by 4 publications

References 23 publications

Organogermanium(iv) compounds in photo-induced radical reactions

Organogermanium(iv) compounds in photo-induced radical reactions

Galactosylated Prodrugs: A Strategy to Improve the Profile of Nonsteroidal Anti-Inflammatory Drugs

Organodigermanium Compounds: Structures and Properties

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