Noncovalent Derivatization:  Green Chemistry Applications of Crystal Engineering

Cannon, Amy S.; Warner, John C.

doi:10.1021/cg0255218

Cited by 43 publications

(25 citation statements)

References 4 publications

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“…The technique of cocrystallization is a lucrative option which not only caters a drug candidate with desired physicochemical properties (Thakuria, 2018; Ueda, 2017) but also offers the right of intellectual property (IP) protection (Aakery and Salmon, 2005). Moreover, with high atom efficiency and no waste products make cocrystallization an important part of the green chemistry initiative(Cannon and Warner, 2002).…”

Section: Introductionmentioning

confidence: 99%

Daidzein cocrystals: An opportunity to improve its biopharmaceutical parameters

Bhalla

Chadha

et al. 2019

Heliyon

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The present study involves the contribution of cocrystallization towards the modification of the biopharmaceutical parameters of poorly watersoluble plant-originated isoflavone, daidzein (DAID). The cocrystals were prepared with GRAS status coformers i.e., isonicotinamide, theobromine and cytosine using mechanochemical grinding and characterized by various analytical techniques (DSC, FT-IR, PXRD and solid-state NMR). Crystal structures were obtained from PXRD data using BIOVIA Materials Studio software and compared in terms of supramolecular motifs. An additional qualitative and quantitative insight into interactions between both components of the cocrystal illustrated the presence of OH⋯N and OH⋯O=C heterosynthons and revealed a stabilizing role of hydrogen bonding. The cocrystals were further evaluated for their solubility, intrinsic dissolution and in vivo profile. Solubility and dissolution studies of pure daidzein and its cocrystals, namely daidzein-isonicotinamide (DIS), daidzein-cytosine (DCYT) and daidzein-theobromine (DTB) exhibited an almost 2-fold improvement. Evaluation of maximum concentration (Cmax) of cocrystals reveals that the DIS cocrystal shows the highest Cmax of 1848.7 ng/ml followed by DCYT cocrystal (1614.9 ng/ml) and DTB cocrystal (1326.0 ng/ml) in comparison to DAID which has a Cmax 870.5 ng/ml. Each of these cocrystals showed significant enhancement in in vivo and in vitro activities in comparison to daidzein. Thus, this report suggests cocrystallization as a viable approach to resolve the solubility and bioavailability issues that circumvent the use of a therapeutically potential isoflavone, daidzein.

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Section: Introductionmentioning

confidence: 99%

Daidzein cocrystals: An opportunity to improve its biopharmaceutical parameters

Bhalla

Chadha

et al. 2019

Heliyon

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“…A non-covalent derivative (NCD) [1] is formed when one (or more) coformer molecule(s) is incorporated into the matrix of the target molecule by way of non-covalent forces [2,3,4]. These forces can include ionic and Van der Waals forces, hydrogen bonding, lipophilic-lipophilic interactions and pi-pi interactions.…”

Section: Introductionmentioning

confidence: 99%

Non-Covalent Derivatives: Cocrystals and Eutectics

Stoler¹,

Warner²

2015

Molecules

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Non-covalent derivatives (NCDs) are formed by incorporating one (or more) coformer molecule(s) into the matrix of a parent molecule via non-covalent forces. These forces can include ionic forces, Van der Waals forces, hydrogen bonding, lipophilic-lipophilic interactions and pi-pi interactions. NCDs, in both cocrystal and eutectic forms, possess properties that are unique to their supramolecular matrix. These properties include critical product performance factors such as solubility, stability and bioavailability. NCDs have been used to tailor materials for a variety of applications and have the potential to be used in an even broader range of materials and processes. NCDs can be prepared using little or no solvent and none of the reagents typical to synthetic modifications. Thus, NCDs represent a powerfully versatile, environmentally-friendly and cost-effective opportunity.

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“…In 1968, Bent [36] published an overall review on the crystal structures of XB systems and discussed at length the structural chemistry of donor-acceptor interactions in bulk crystals, in which the XB and the hydrogen bond (HB) were compared based on their similarities, such as the short interatomic distances and high directionality. Crystal engineering is a self-assembly process in which building blocks can fabricate architectures following the laws of intermolecular interactions and shape complementarity [17,[37][38][39][40]. Many noncovalent interactions, for example, HB, XB [41], π−π stacking, metal−ligand coordination, dipole−dipole interactions, and hydrophobic interactions, were used to fabricate molecular crystals.…”

Section: The Investigation and Application Of Xb Focus On Crystal Engineeringmentioning

confidence: 99%

Halogen Bonds Fabricate 2D Molecular Self-Assembled Nanostructures by Scanning Tunneling Microscopy

2020

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Halogen bonds are currently new noncovalent interactions due to their moderate strength and high directionality, which are widely investigated in crystal engineering. The study about supramolecular two-dimensional architectures on solid surfaces fabricated by halogen bonding has been performed recently. Scanning tunneling microscopy (STM) has the advantages of realizing in situ, real-time, and atomic-level characterization. Our group has carried out molecular self-assembly induced by halogen bonds at the liquid–solid interface for about ten years. In this review, we mainly describe the concept and history of halogen bonding and the progress in the self-assembly of halogen-based organic molecules at the liquid/graphite interface in our laboratory. Our focus is mainly on (1) the effect of position, number, and type of halogen substituent on the formation of nanostructures; (2) the competition and cooperation of the halogen bond and the hydrogen bond; (3) solution concentration and solvent effects on the molecular assembly; and (4) a deep understanding of the self-assembled mechanism by density functional theory (DFT) calculations.

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Noncovalent Derivatization: Green Chemistry Applications of Crystal Engineering

Cited by 43 publications

References 4 publications

Daidzein cocrystals: An opportunity to improve its biopharmaceutical parameters

Daidzein cocrystals: An opportunity to improve its biopharmaceutical parameters

Non-Covalent Derivatives: Cocrystals and Eutectics

Halogen Bonds Fabricate 2D Molecular Self-Assembled Nanostructures by Scanning Tunneling Microscopy

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