Complexation Studies of Nucleotides by Tetrandrine Derivatives Bearing Anthraquinone and Acridine Groups

Moreno-Corral, Ramón; Lara, Karen Ochoa

doi:10.1080/10610270701300188

Cited by 23 publications

(19 citation statements)

References 34 publications

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“…These results are similar to those recorded for 98b, but somewhat different to those recorded in similar experiments run with 99a,b when, at low temperature, a clear separation of the signals belonging to the protons of the two types of bridges could not be obtained. Despite the specific investigations by NMR techniques (ROESY, Some other macrocyclic systems having pendant arms decorated with acridine, acridone or phenazine units were also investigated [99][100][101].…”

Section: Chart 8 Cyclophanes With Acridine and Acridinium Unitsmentioning

confidence: 99%

Macrocycles embedding phenothiazine or similar nitrogen and/or sulphur containing heterocycles

Rednic

Hădade

Bogdan

et al. 2014

J Incl Phenom Macrocycl Chem

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Macrocycles emerged as an important class of useful compounds with multiple applications ranging from selective complexation of different anions, cations or neutral molecules to the development of new sensors, materials with improved properties and biologically active compounds. In this review we focus our discussion on the synthesis and structural analysis of macrocycles containing dibenzoheterocycles with sulphur and/or nitrogen atoms in the central six-membered ring (i.e. 10H-phenothiazine, 9,10-dihydroacridine or acridane, acridone, thianthrene, phenoxathiine, acridine, phenazine). We further highlight selected application of these compounds as host molecules, DNA intercalating agents or enzyme inhibitors.

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Section: Chart 8 Cyclophanes With Acridine and Acridinium Unitsmentioning

confidence: 99%

Macrocycles embedding phenothiazine or similar nitrogen and/or sulphur containing heterocycles

Rednic

Hădade

Bogdan

et al. 2014

J Incl Phenom Macrocycl Chem

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“…Another strategy for recognition of nucleotides employs cyclophane structures that lack polyamines but nevertheless demonstrate successful nucleotide binding [28–34] . Claude, Lehn, and co‐workers reported a cyclo‐bis‐intercaland receptor informed by the propensity of DNA to bind flat, aromatic molecules via intercalation [28] .…”

Section: Nucleotidesmentioning

confidence: 99%

Mimicking Biological Recognition: Lessons in Binding Hydrophilic Guests in Water

Johns

Harrison

Stingley

et al. 2021

Chemistry A European J

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Selective molecular recognition of hydrophilic guests in water plays a fundamental role in a vast number of biological processes, but synthetic mimicry of biomolecular recognition in water still proves challenging both in terms of achieving comparable affinities and selectivities. This Review highlights strategies that have been developed in the field of supramolecular chemistry to selectively and non‐covalently bind three classes of biologically relevant molecules: nucleotides, carbohydrates, and amino acids. As several groups have systematically modified receptors for a specific guest, an evolutionary perspective is also provided in some cases. Trends in the most effective binding forces for each class are described, providing insight into selectivity and potential directions for future work.

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“…In the dicationic form, d-tubocurarine efficiently binds dianions of dicarboxylic acids (logK = 2.8 for terephthalate and 2.4 for malonate dianions) and shows significant enantioselectivity in the binding of anions of N-acylated amino acids (Table 3) [46]. Table 3: Binding constants of enantiomers of N-acetyl amino acids, free amino acids as anions, and nucleotides to bisbenzylisoquinoline macrocyclic alkaloids and their derivatives [47,51]. Affinity of anions to the neutral zwitterionic form 21 is expectedly much lower, and for N-Ac-Phe, which still shows a noticeable affinity, the enantioselectivity is inverted (Table 3) [47].…”

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confidence: 99%

“…378 Natural Product Communications Vol. 7 (3) 2012 Yatsimirsky Further development of this type of anion receptors was the synthesis of anthraquinone and acridine derivatives 24 and 25 ( Figure 7) as possible electro-active and fluorescent receptors, respectively [51]. Compared with 23, the anthraquinone receptor has significantly improved binding properties towards nucleotides (Table 3) and also binds much more strongly and with larger enantioselectivity the anionic form of phenylalanine (Table 3).…”

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confidence: 99%

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Host-Guest Chemistry of Alkaloids

Yatsimirsky

2012

Natural Product Communications

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Binding of alkaloids by different hosts (native and modified cyclodextrins, cucurbiturils, calixarenes, and metal complexes of porphyrin and Salphen-type ligands), as well as receptor properties of alkaloid based hosts are reviewed. With alkaloids as guests, the largest binding constants and most significant spectral changes, in particular strong fluorescence enhancements induced by complexation with isoquinoline alkaloids, are observed with cucurbituril hosts. Cyclodextrins are successfully employed for improvement of solubility and for chiral separation of alkaloids of different types. Receptor properties of native and modified cinchona and bisbenzylisoquinoline alkaloids have attracted considerable attention for development of chiral selectors for analysis and separation.

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Complexation Studies of Nucleotides by Tetrandrine Derivatives Bearing Anthraquinone and Acridine Groups

Cited by 23 publications

References 34 publications

Macrocycles embedding phenothiazine or similar nitrogen and/or sulphur containing heterocycles

Macrocycles embedding phenothiazine or similar nitrogen and/or sulphur containing heterocycles

Mimicking Biological Recognition: Lessons in Binding Hydrophilic Guests in Water

Host-Guest Chemistry of Alkaloids

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