On the encapsulation and assembly of anticancer drugs in a cooperative fashion

Wang, Weikun; Wang, Han; Liu, Zhiquan; Xie, Hui; Cui, Honggang; Badjić, Jovica D.

doi:10.1039/c9sc01380f

Cited by 20 publications

(14 citation statements)

References 58 publications

(61 reference statements)

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“…)e ncompass asymmetric, concave,n onpolar,a nd functionalized spaces for accommodating targeted molecules,our methodology opens aw ay for constructing comparable interiors within artificial molecules in ap redictable and stereoselective manner. Examining chiral molecular recognition within such uniquely structured and customizable environments is to be pursued with an eye set on creating more effective supramolecular catalysts [54] or soft nanostructured materials [29] capable of sequestering toxicants [55] and delivering pharmaceuticals. [32a, 56]…”

Section: Forschungsartikel Conclusionmentioning

confidence: 99%

“…[24] Alongside these and other important advances, [25] we herein describe am ethodology for constructing ABC molecular baskets in astereoselective manner from A, B,and C building blocks (Figure 1B). So far, C 3 symmetric baskets have been used for studying gated molecular recognition [26] and allostery [27] but also probed as hosts for the encapsulation of nerve agents, [28] pharmaceuticals, [29] fullerenes, [30] hydrocarbon gases, [30][31] and other functional compounds. [32] Forthe first time, the side wall of these concave cavitands can now be selected to carry different aromatics,forming acustomizable nonpolar pocket, with desired functional groups at the rim (Figure 1B) to greatly expand the utility of basket-like hosts.…”

Section: Introductionmentioning

confidence: 99%

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Enantioselective Construction of Modular and Asymmetric Baskets

et al. 2021

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The precise positioning of functional groups about the inner space of abiotic hosts is ac hallenging task and of interest for developing more effective receptors and catalysts akin to those found in nature.T oa ddress it, we herein report as ynthetic methodology for preparing basket-like cavitands comprised of three different aromatics as side arms with orthogonal esters at the rim for further functionalization. First, enantioenriched A (borochloronorbornene), B (iodobromonorbornene), and C (boronorbornene) building blocks were obtained by stereoselective syntheses.S econd, consecutive Ato-B and then AB-to-C Suzuki-Miyaura (SM) couplings were optimizedt og ive enantioenriched ABC cavitand as the principal product. The robust synthetic protocol allowed us to prepare (a) an enantioenriched basket with three benzene sides and each holding either tBu, Et, or Me esters,( b) both enantiomers of as o-called "spiral staircase" basket with benzene, naphthalene,a nd anthracene groups surrounding the inner space,and (c) aphoto-responsive basket bearing one anthracene and two benzene arms.

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Section: Forschungsartikel Conclusionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Enantioselective Construction of Modular and Asymmetric Baskets

et al. 2021

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“…Nanosized 1 (d = 3.0 nm and V = 5 nm 3 ) is a truncated [4+4] tetrahedron 28 with four trigonal panels made of triphenyl benzenes and four vertices composed of abiotic cavitands, baskets, 29 known to act as allosteric hosts 27 capable of trapping haloalkanes, 30 cationic molecules, 31 nerve agents, 32 pesticides, 33 and anticancer drugs. 34 Accordingly, we reasoned that obtaining non-collapsible CBCs of type 1 and developing a method for their transient formation via consumption of chemical fuel will set the stage for examining temporal control of their action 17 resembling GRoEL chaperone in Figure 1C. 18 For the first time, we herein describe a method to drive the out of equilibrium formation of covalent basket cages in a tunable manner using an acidic chemical fuel in organic media.…”

Section: Introductionmentioning

confidence: 99%

Fuel-Driven Formation of Covalent Basket Cages

Badjić

Gunawardana

Finnegan

et al. 2022

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Essential functions that sustain life including reproduction, signaling and mechanical motion, persist through the consump-tion of chemical fuels. Despite recent advances in developing dissipative assemblies that mimic such systems, the fuel-driven formation of covalent organic cages with the capacity to promote catalysis, folding, delivery and sequestration has yet to be demonstrated. In this work we describe the transient formation of a nanosized, tetrahedral cage (V = 5 nm3, Mw = 6150 Da) with four molecular baskets at its vertices linked via imine bonds to four aromatic amines forming the faces. Tribromo-acetic acid (TBA) acts as the chemical fuel that drives assembly of the cage via imine metathesis in addition to controlling its formation over time. Our study sets the stage for constructing large dissipative cages with spatiotemporal modes of opera-tion resembling the action of biological molecular machines.

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“…In this regard, recent studies have shown that two limiting mechanisms are not mutually exclusive and can take place concurrently [8] . For a large variety of abiotic hosts, [2b,c, 9] only a handful of studies [10] address the two mechanistic paradigms. Raymond‐Bergman‐Toste [11] and Jiang [12] teams have recently measured kinetics by which an encapsulation equilibrium is established to find that CS dominates entrapments promoted by self‐assembled metallacages and naphthotube macrocycles with guest molecules in excess.…”

Section: Introductionmentioning

confidence: 99%

From Selection to Instruction and Back: Competing Conformational Selection and Induced Fit Pathways in Abiotic Hosts

et al. 2021

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Two limiting cases of molecular recognition, induced fit (IF) and conformational selection (CS), play a central role in allosteric regulation of natural systems. The IF paradigm states that a substrate “instructs” the host to change its shape after complexation, while CS asserts that a guest “selects” the optimal fit from an ensemble of preexisting host conformations. With no studies that quantitatively address the interplay of two limiting pathways in abiotic systems, we herein and for the first time describe the way by which twisted capsule M‐1, encompassing two conformers M‐1(+) and M‐1(−), trap CX4 (X=Cl, Br) to give CX4⊂M‐1(+) and CX4⊂M‐1(−), with all four states being in thermal equilibrium. With the assistance of 2D EXSY, we found that CBr4 would, at its lower concentrations, bind M‐1 via a M‐1(+)→M‐1(−)→CBr4⊂M‐1(−) pathway corresponding to conformational selection. For M‐1 complexing CCl4 though, data from 2D EXSY measurements and 1D NMR line‐shape analysis suggested that lower CCl4 concentrations would favor CS while the IF pathway prevailed at higher proportions of the guest. Since CS and IF are not mutually exclusive, we reason that our work sets the stage for characterizing the dynamics of a wide range of already existing hosts to broaden our fundamental understanding of their action. The objective is to master the way in which encapsulation takes place for designing novel and allosteric sequestering agents, catalysts and chemosensors akin to those found in nature.

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On the encapsulation and assembly of anticancer drugs in a cooperative fashion

Abstract: In this study, we report the remarkable recognition and assembly characteristics of D3h symmetric basket 16− containing two adjoining and nonpolar cavities with six biocompatible GABA residues at their northern and southern termini.

Cited by 20 publications

References 58 publications

Enantioselective Construction of Modular and Asymmetric Baskets

Enantioselective Construction of Modular and Asymmetric Baskets

Fuel-Driven Formation of Covalent Basket Cages

From Selection to Instruction and Back: Competing Conformational Selection and Induced Fit Pathways in Abiotic Hosts

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