Self-assembly of reversed bilayer vesicles through pnictogen bonding: water-stable supramolecular nanocontainers for organic solvents

Moaven, Shiva; Watson, Brandon; Thompson, S.; Lyons, Veronica; Unruh, Daniel K.; Casadonte, Dominick J.; Pappas, Dimitri; Cozzolino, Anthony F.

doi:10.1039/d0sc00206b

Cited by 13 publications

(20 citation statements)

References 50 publications

(52 reference statements)

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“…Noncovalent interactions of this class include halogen bonds, ,− chalcogen bonds, − and tetrel bonds, − which are named after the donor atom’s group. These interactions are frequently encountered in crystal structures − and applied regularly in supramolecular assembly − as well as anion recognition. − By contrast, applications in synthetic chemistry have been less studied; only a few organocatalytic protocols have been reported on the implementation of σ-hole interactions throughout the last two decades, with most methods designed around a halogen bond. − …”

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confidence: 99%

Asymmetric Pnictogen-Bonding Catalysis: Transfer Hydrogenation by a Chiral Antimony(V) Cation/Anion Pair

et al. 2021

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Pnictogen-bonding catalysis based on σ-hole interactions has recently attracted the attention of synthetic chemists. As a proof-of-concept for asymmetric pnictogen-bonding catalysis, we report herein an enantioselective transfer hydrogenation of benzoxazines catalyzed by a novel chiral antimony cation/anion pair. The chiral pnictogen catalyst library could be rapidly accessed from triarylstibine with readily available mandelic acid analogues, and the catalyst displays remarkable efficiency and enantiocontrol potency even at 0.05 mol % loading. Moreover, the properties of the catalyst and the mechanistic insights have been investigated by nonlinear effect studies, 1H NMR, LC-MS, and control experiments.

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confidence: 99%

Asymmetric Pnictogen-Bonding Catalysis: Transfer Hydrogenation by a Chiral Antimony(V) Cation/Anion Pair

et al. 2021

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“…The S−Sb−S bond angles in the structure are in agreement with those previously reported. 54,58,59 Previously characterized As-trithiol complexes have bond angles about arsenic close to 97°. 40 The average Sb−S bond length is 2.440(8) Å, which is in agreement with the previously reported average Sb−S (2.447(7) Å) bond distance.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…40 The average Sb−S bond length is 2.440(8) Å, which is in agreement with the previously reported average Sb−S (2.447(7) Å) bond distance. 54,58,59 Selected bond distances and angles are listed in Table 2.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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A Third Generation Potentially Bifunctional Trithiol Chelate, Its ^nat,1XXSb(III) Complex, and Selective Chelation of Radioantimony (¹¹⁹Sb) from Its Sn Target

et al. 2021

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The therapeutic potential of the Meitner-Auger- and conversion-electron emitting radionuclide 119Sb remains unexplored because of the difficulty of incorporating it into biologically targeted compounds. To address this challenge, we report the development of 119Sb production from electroplated tin cyclotron targets and its complexation by a novel trithiol chelate. The chelation reaction occurs in harsh solvent conditions even in the presence of large quantities of tin, which are necessary for production on small, low energy (16 MeV) cyclotrons. The 119Sb-trithiol complex has high stability and can be purified by HPLC. The third generation trithiol chelate and the analogous stable natSb-trithiol compound were synthesized and characterized, including by single-crystal X-ray diffraction analyses.

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“…Pnictogen exchangers 3 , 25 5 , 64 8 , 25 10 , 65 12 , 43 13 , 25 and 15 ( 66 ) and transporter 21 ( 58 ) were prepared by the reported procedures. Synthetic procedures and characterization of 2 , 6 , 7 , 9 , 11 , 14 , and 20 are given in the Supporting Information .…”

Section: Methodsmentioning

confidence: 99%

Pnictogen-Centered Cascade Exchangers for Thiol-Mediated Uptake: As(III)-, Sb(III)-, and Bi(III)-Expanded Cyclic Disulfides as Inhibitors of Cytosolic Delivery and Viral Entry

Lim

Kato

Besnard

et al. 2022

JACS Au

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Dynamic covalent exchange cascades with cellular thiols are of interest to deliver substrates to the cytosol and to inhibit the entry of viruses. The best transporters and inhibitors known today are cyclic cascade exchangers (CAXs), producing a new exchanger with every exchange, mostly cyclic oligochalcogenides, particularly disulfides. The objective of this study was to expand the dynamic covalent chalcogen exchange cascades in thiol-mediated uptake by inserting pnictogen relays. A family of pnictogen-expanded cyclic disulfides covering As(III), Sb(III), and Bi(III) is introduced. Their ability to inhibit thiol-mediated cytosolic delivery is explored with fluorescently labeled CAXs as transporters. The promise of inhibiting viral entry is assessed with SARS-CoV-2 lentiviral vectors. Oxygen-bridged seven-membered 1,3,2-dithiabismepane rings are identified as privileged scaffolds. The same holds for six-membered 1,3,2-dithiarsinane rings made from asparagusic acid and para -aminophenylarsine oxide, which are inactive or toxic when used alone. These chemically complementary Bi(III) and As(III) cascade exchangers inhibit both thiol-mediated cytosolic delivery and SARS-CoV-2 lentivector uptake at concentrations of 10 μM or lower. Crystal structures, computational models, and exchange kinetics support that lentivector entry inhibition of the contracted dithiarsinane and the expanded dithiabismepane rings coincides with exchange cascades that occur without the release of the pnictogen relay and benefit from noncovalent pnictogen bonds. The identified leads open perspectives regarding drug delivery as well as unorthodox approaches toward dynamic covalent inhibition of cellular entry.

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Self-assembly of reversed bilayer vesicles through pnictogen bonding: water-stable supramolecular nanocontainers for organic solvents

Abstract: A new air and moisture stable antimony thiolate compound has been prepared that spontaneously forms stable hollow vesicles.

Cited by 13 publications

References 50 publications

Asymmetric Pnictogen-Bonding Catalysis: Transfer Hydrogenation by a Chiral Antimony(V) Cation/Anion Pair

Asymmetric Pnictogen-Bonding Catalysis: Transfer Hydrogenation by a Chiral Antimony(V) Cation/Anion Pair

A Third Generation Potentially Bifunctional Trithiol Chelate, Its ^nat,1XXSb(III) Complex, and Selective Chelation of Radioantimony (¹¹⁹Sb) from Its Sn Target

Pnictogen-Centered Cascade Exchangers for Thiol-Mediated Uptake: As(III)-, Sb(III)-, and Bi(III)-Expanded Cyclic Disulfides as Inhibitors of Cytosolic Delivery and Viral Entry

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Self-assembly of reversed bilayer vesicles through pnictogen bonding: water-stable supramolecular nanocontainers for organic solvents

Abstract: A new air and moisture stable antimony thiolate compound has been prepared that spontaneously forms stable hollow vesicles.

Cited by 13 publications

References 50 publications

Asymmetric Pnictogen-Bonding Catalysis: Transfer Hydrogenation by a Chiral Antimony(V) Cation/Anion Pair

Asymmetric Pnictogen-Bonding Catalysis: Transfer Hydrogenation by a Chiral Antimony(V) Cation/Anion Pair

A Third Generation Potentially Bifunctional Trithiol Chelate, Its nat,1XXSb(III) Complex, and Selective Chelation of Radioantimony (119Sb) from Its Sn Target

Pnictogen-Centered Cascade Exchangers for Thiol-Mediated Uptake: As(III)-, Sb(III)-, and Bi(III)-Expanded Cyclic Disulfides as Inhibitors of Cytosolic Delivery and Viral Entry

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A Third Generation Potentially Bifunctional Trithiol Chelate, Its ^nat,1XXSb(III) Complex, and Selective Chelation of Radioantimony (¹¹⁹Sb) from Its Sn Target