Reversible Covalent and Supramolecular Functionalization of Water‐Soluble Gold(I) Complexes

Kemper, Benedict; Gröning, Maximilian von; Lewe, Vanessa; Spitzer, D.; Otremba, Tobias; Stergiou, Natascha; Schollmeyer, Dieter; Schmitt, Edgar; Ravoo, Bart Jan; Besenius, Pol

doi:10.1002/chem.201700588

Cited by 18 publications

(11 citation statements)

References 129 publications

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“…[197] 152 1803,1820,1837,1849,1860,1871,1895,1904,1921,1943,1983,2013,2050 1803,1820,1837,1849,1860,1871,1895,1904,1921,1943,1983,2013,2050 The analytical data is in agreement with the data reported in literature. [198] 157 The analytical data is in agreement with the data reported in literature. [174] 198.6, 198.2, 196.8, 194.4, 194.3.…”

Section: -(4ˈ-nitrophenyl)[22]paracyclophane (70)supporting

confidence: 89%

Heterobimetallic [2.2]Paracyclophane Complexes and Their Application in Photoredox Catalysis

Knoll¹

2020

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The most important goal of current chemistry research is to provide green and sustainable routes to compounds of interest. One way of addressing this is the use of abundant and inexpensive sources of energy to drive reactions, with the prime example being visible light in photoredox catalysis. One recent promising approach is the use of heterobimetallic catalysts where two metals work in a cooperative fashion to achieve the desired transformation. However, very little is known about the exact mechanism of cooperativity. This is due to a lack of heterobimetallic compounds that can be fine-tuned to obtain very specific answers regarding for example spatial design of the catalyst in question. In this work, [2.2]paracyclophane (PCP) is presented as a new platform on which to build distance-variable heterobimetallic complexes. PCP has been described as a "super-atom" molecule for its unique ability to hold up to 16 substituents in a precise spatial relationship to each other. By using PCP as a platform, it is shown that a range of defined heterobimetallic complexes can be designed and prepared (Figure 1.1). The methods necessary for the synthetic transformations are developed and investigated for their broader synthetic applicability. 51 (10-65%) Scheme 3.8 Nickel-catalyzed Kumada arylation of PCP bromide 51. Recently, the Kumada cross-coupling was used for the heteroarylation of electron-rich para-methoxy iodo-PCP 52 with 2-pyridyl magnesium bromide (53) to form biaryl 54 (Scheme 3.9) albeit in not satisfying yields. [88] Thus, a better synthetic strategy to access valuable biaryl 54 is necessary.

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Section: -(4ˈ-nitrophenyl)[22]paracyclophane (70)supporting

confidence: 89%

Heterobimetallic [2.2]Paracyclophane Complexes and Their Application in Photoredox Catalysis

Knoll¹

2020

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“…I3MO was labeled with D-biotin (#60338ES03, YEASEN). 35 D-biotin worked as negative control. Cell lysates from MM cell lines (ARP1 and RPMI8226), and the recombinant proteins for PSME3 (P03968, Solarbio) or PSME4 (P05708, Solarbio) were incubated with I3MO-D-biotin (200 µM) at 4°C overnight, respectively.…”

Section: Methodsmentioning

confidence: 99%

Indirubin-3’-monoxime acts as proteasome inhibitor: Therapeutic application in multiple myeloma

Wei

Liu

et al. 2022

eBioMedicine

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“…Compound 1 was synthesized according to the previous literature [31] . Compounds 2 , 3 , 8 , 9 , and 10 were synthesized according to a previous report [32] . Abbreviation for reagents in the reactions: 1‐hydroxybenzotriazole (HOBt), 1‐(3‐dimethylaminopropyl)‐3‐ethylcarbodiimide hydrochloride (EDC), m ‐methylbenzene sulfonyl chloride (TsCl), triethylamine (Et 3 N), dormyl dimethylamine (DMF).…”

Section: Methodsmentioning

confidence: 99%

Self‐assembly of Amphiphilic Porphyrins To Construct Nanoparticles for Highly Efficient Photodynamic Therapy

Jiang

Liu

et al. 2021

Chemistry A European J

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Hydrophobic photosensitizers greatly affect cell permeability and enrichment in tumors, but they cannot be used directly for clinical applications because they always aggregate in water, preventing their circulation in the blood and accumulation in tumor cells. As a result, amphiphilic photosensitizers are highly desirable. Although nanomaterialbased photosensitizers can solve water solubility, they have the disadvantages of complicated operation, poor reproducibility, low drug loading, and poor stability. In this work, an efficient synthesis strategy is proposed that converts small molecules into nanoparticles in 100 % aqueous solution by molecular assembly without the addition of any foreign species. Three photosensitizers with triphenylphosphine units and ethylene glycol chains of different lengths, TPPÀ PPh 3 , TPPÀ PPh 3 À 2PEG and TPPÀ PPh 3 À 4PEG, were synthesized to improve amphiphilicity. Of the three photosensitizers, TPPÀ PPh 3 À 4PEG is the most efficient (singlet oxygen yield: 0.89) for tumor photodynamic therapy not only because of its definite constituent, but also because its amphiphilic structure allows it to self-assemble in water.

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Reversible Covalent and Supramolecular Functionalization of Water‐Soluble Gold(I) Complexes

Cited by 18 publications

References 129 publications

Heterobimetallic [2.2]Paracyclophane Complexes and Their Application in Photoredox Catalysis

Heterobimetallic [2.2]Paracyclophane Complexes and Their Application in Photoredox Catalysis

Indirubin-3’-monoxime acts as proteasome inhibitor: Therapeutic application in multiple myeloma

Self‐assembly of Amphiphilic Porphyrins To Construct Nanoparticles for Highly Efficient Photodynamic Therapy

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