Experimental and Theoretical Aspects of Anion Complexes with a Thiophene-Based Cryptand

Haque, Syed A.; Saeed, Musabbir A.; Jahan, Afsana; Wang, Jing; Leszczyński, Jerzy; Hossain, Md. Alamgir

doi:10.1080/02603594.2016.1171216

Cited by 6 publications

(7 citation statements)

References 73 publications

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“…The different N ··· Cl distances of such compounds range from 3.048 Å (2-fold), 3.059–3.847 Å (2-fold), and 3.197–3.941 Å (6-fold) if only distances below 4.5 Å are considered. The type of encapsulated halogen anion appears to play a crucial role in the coordination motif, as chloride anions often enforce a 2-fold coordination, as shown by the equidistant N···Cl distance of 3.048 Å, which turns into four N···Br distances of 3.471–3.998 Å with an encapsulated bromine, although water molecules and halogen anions outside of the cryptands also affect such structures . 12-fold hydrogen-bonded chlorides were only found in the single-crystal structure of a hexaaminobenzene (HAB) derivative, which is described as (HAB)Cl 2 (C 6 H 12 Cl 2 N 6 ).…”

Section: Results and Discussionmentioning

confidence: 99%

Assembly of Porous Metal Hydrogen-Bonded Organic Frameworks from Diamine-Functionalized Kuratowski Complexes

Röß-Ohlenroth

Freudig

Kraft

et al. 2021

Crystal Growth & Design

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In comparison to the vast field of porous materials, research into hydrogen-bonded organic frameworks (HOFs)and especially the subclass of metal hydrogen-bonded organic frameworks (M-HOFs), with only very few structures showing permanent porosity thus faris still in its infancy. Herein, Kuratowski coordination units, which are well-known from various complexes and metal–organic frameworks, were applied to advance this field of research with the synthesis and characterization of a novel series of M-HOFs. Synthesis of Kuratowski complexes with the 1H-benzotriazole-5,6-diamine (H-btda) ligand resulted in molecular building blocks, which initially assemble into CFA-20-Cl and CFA-20-Br M-HOFs ((2,6-lutidinium)+[Zn5X4(btda)6X]−·n(DMF); X = Cl, Br; CFA-20 = Coordination Framework Augsburg University-20, DMF = N,N-dimethylformamide). Both frameworks are isostructurally stabilized via a unique hydrogen bond framework between 12 amine functional groups of six btda ligands and a central 12-fold hydrogen bonded halogen anion, which adapts the coordination of an irregular icosahedron. Postsynthetic ligand exchange at the Kuratowski complex of CFA-20-Cl performed with Tp and Tp* ligands resulted in permanently porous CFA-20-Tp and CFA-20-Tp* M-HOFs ([Zn5Y4(btda)6]; Y = Tp (trispyrazolylborate), Tp* (tris(3,5-dimethyl-1-pyrazolyl)borate)), which, thus, constitute an important addition to the meager subclass of permanently porous M-HOFs. Crystallization of the soluble complex of CFA-20-Tp* from dimethylsulfoxide (DMSO) was additionally shown to result in a variant CFA-20-Tp*-DMSO M-HOF structure.

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Section: Results and Discussionmentioning

confidence: 99%

Assembly of Porous Metal Hydrogen-Bonded Organic Frameworks from Diamine-Functionalized Kuratowski Complexes

Röß-Ohlenroth

Freudig

Kraft

et al. 2021

Crystal Growth & Design

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“…Synthetic receptors (SR) are architecturally designed by chemists for selective recognition of a variety of substrates, mimicking many critical enzymatic activities involved in biology [ 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 ]. The unique functional groups present in such molecules can be potentially used for designing drugs to target specific activities in a human body [ 45 ].…”

Section: Introductionmentioning

confidence: 99%

Synthetic Receptors Induce Anti Angiogenic and Stress Signaling on Human First Trimester Cytotrophoblast Cells

Pantho

Price

Ashraf

et al. 2017

IJERPH

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The cytotrophoblast (CTB) cells of the human placenta have membrane receptors that bind certain cardiotonic steroids (CTS) found in blood plasma. One of these, marinobufagenin, is a key factor in the etiology of preeclampsia. Herein, we used synthetic receptors (SR) to study their effectiveness on the angiogenic profile of human first trimester CTB cells. The humanextravillous CTB cells (Sw.71) used in this study were derived from first trimester chorionic villus tissue. Culture media of CTB cells treated with ≥1 nM SR level revealed sFlt-1 (Soluble fms-like tyrosine kinase-1) was significantly increased while VEGF (vascular endothelial growth factor) was significantly decreased in the culture media (* p < 0.05 for each) The AT2 receptor (Angiotensin II receptor type 2) expression was significantly upregulated in ≥1 nM SR-treated CTB cells as compared to basal; however, the AT1 (Angiotensin II receptor, type 1) and VEGFR-1 (vascular endothelial growth factor receptor 1) receptor expression was significantly downregulated (* p < 0.05 for each). Our results show that the anti-proliferative and anti-angiogenic effects of SR on CTB cells are similar to the effects of CTS. The observed anti angiogenic activity of SR on CTB cells demonstrates that the functionalized-urea/thiourea molecules may be useful as potent inhibitors to prevent CTS-induced impairment of CTB cells.

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“…Since anions are crtical species in the environment and life, the study of anion binding with chemical receptors remains an active area of research in supramolecular chemistry . In particular, molecular compounds functionalized with urea groups have been shown to effectively bind inorganic anions under neutral conditions, allowing them to be utilized for potential applications such as extractions, transport, catalysis, and antiangiogenic activities relating to certain living cells .…”

Section: Introductionmentioning

confidence: 99%

Cleft‐Induced Ditopic Binding of Spherical Halides with a Hexaurea Receptor

et al. 2020

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A tripodal-based hexaurea receptor with two clefts (inner cleft and outer cleft) has been studied for spherical halides by 1 H NMR, UV-Vis titrations, and theoretical calculations using density functional theory (DFT). As demonstrated from experimental and computational results, the receptor exhibits cleftinduced binding for halides in a 1 : 2 binding mode, showing the binding strength in the order of fluoride > chloride > bromide > iodide. The strongest affinity for fluoride is attributed due to the best fit of two fluoride anions at the two clefts within the host's cavity. This is also supported by DFT calculations, suggesting that each anion is stabilized by six NH⋅⋅⋅F bonds -one at the inner cleft and other at the outer cleft. In addition, the synthesized receptor, as examined on HeLa cells, has been found to show good biocompatibility. Results and DiscussionSynthesis: The receptor was synthesized by following the strategy reported earlier. [15] Attempts to obtain suitable crystals for X-ray analysis were unsuccessful.

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Experimental and Theoretical Aspects of Anion Complexes with a Thiophene-Based Cryptand

Abstract: Graphical abstract

Cited by 6 publications

References 73 publications

Assembly of Porous Metal Hydrogen-Bonded Organic Frameworks from Diamine-Functionalized Kuratowski Complexes

Assembly of Porous Metal Hydrogen-Bonded Organic Frameworks from Diamine-Functionalized Kuratowski Complexes

Synthetic Receptors Induce Anti Angiogenic and Stress Signaling on Human First Trimester Cytotrophoblast Cells

Cleft‐Induced Ditopic Binding of Spherical Halides with a Hexaurea Receptor

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