Amino Acids as the Potential Co-Former for Co-Crystal Development: A Review

Co-crystals are one of the most popular ways to modify the physicochemical properties of active pharmaceutical ingredients (API) without changing pharmacological activity through non-covalent interactions with one or more co-formers. A “green method” has recently prompted many researchers to develop solvent-free techniques or minimize solvents for arranging the eco-friendlier process of co-crystallization. Researchers have also been looking for less-risk co-formers that produce the desired API’s physicochemical properties. This review purposed to collect the report studies of amino acids as the safe co-former and explored their advantages. Structurally, amino acids are promising co-former candidates as they have functional groups that can form hydrogen bonds and increase stability through zwitterionic moieties, which support strong interactions. The co-crystals and deep eutectic solvent yielded from this natural compound have been proven to improve pharmaceutical performance. For example, l-glutamine could reduce the side effects of mesalamine through an acid-base stabilizing effect in the gastrointestinal fluid. In addition, some amino acids, especially l-proline, enhances API’s solubility and absorption in its natural deep eutectic solvent and co-crystals systems. Moreover, some ionic co-crystals of amino acids have also been designed to increase chiral resolution. Therefore, amino acids are safe potential co-formers, which are suitable for improving the physicochemical properties of API and prospective to be developed further in the dosage formula and solid-state syntheses.

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Labeling Preferences of Diazirines with Protein Biomolecules

10.26434/chemrxiv.13373249 ◽

2020 ◽

Author(s):

Alexander West ◽

Giovanni Muncipinto ◽

Hung-Yi Wu ◽

Andrew Huang ◽

Matthew T. Labenski ◽

...

Keyword(s):

Amino Acids ◽

Systematic Evaluation ◽

Probe Design ◽

Dependent Manner ◽

Membrane Proteome ◽

Non Covalent Interactions ◽

Acidic Proteins ◽

Cell Proteome ◽

Covalent Interactions ◽

Net Positive Charge

<p>Diazirines are widely used in photoaffinity labeling (PAL) to trap non-covalent interactions with biomolecules. However, design and interpretation of PAL experiments is challenging without a molecular understanding of the reactivity of diazirines with protein biomolecules. Here, we report a systematic evaluation of the labeling preferences of alkyl and aryl diazirines with individual amino acids, single proteins, and in the whole cell proteome. We find that aryl-fluorodiazirines react primarily through a carbene intermediate, while alkyl diazirines generate a reactive alkyl diazo intermediate on route to the carbene. The generation of a reactive diazo intermediate leads to preferential labeling of acidic amino acids in a pH-dependent manner. From a survey of 32 alkyl diazirine probes, we use this reactivity profile to rationalize why these probes preferentially enrich highly acidic proteins or those embedded in membranes and why probes with a net positive-charge tend to produce higher labeling yields. These results indicate that alkyl diazirines are an especially effective chemistry for surveying the membrane proteome, and will facilitate probe design and interpretation of biomolecular labeling experiments with diazirines.<b></b></p>

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Joining host/guest with contrary affinity at the nanoscale by chemical bonds or non-covalent interactions with organic media under diffusion: control of embedded versus exposed magnetite dispersions.

10.21203/rs.3.rs-722270/v1 ◽

2021 ◽

Author(s):

Susanna Jansat ◽

Mercè Moncusí

Keyword(s):

Alkyl Chain ◽

Fine Tuning ◽

Strong Interactions ◽

Diffusion Control ◽

Organic Media ◽

Interparticle Porosity ◽

Non Covalent Interactions ◽

Controlled Morphology ◽

Crystalline Domains ◽

Covalent Interactions

Abstract Emulating natural dynamism distributing earth minerals using diffusion and gravity, herein it is reported a strategy to unite nanostructured materials of similar size but intrinsic physical repellence, magnetite guest bestowed with C18 alkyl chain ligands and highly hydrophilic ammonium dawsonite NH4Al(OH)2CO3 host, based in electromagnetic and chemical forces. Notwithstanding augmented polarity of nanostructured surface’s carrier, has been used as fine-tuning tool in conjunction with continuum, for triggering a disseminated array of specific interactions covering entire carrier NH4+-RDW-NP periphery. Strong interactions heighten enthalpic contributions balancing unfavourable entropic penalty. Shelter adsorbs diffused guest like conventional Fe3O4-NP dispersions but additionally, whether restricts void’s access or, sinters carrier enabling isolation of a second morphology where magnetite is quantitatively embedded into cavities left between agglomerates. Reported deposition protocol extends sort of practical interactions beyond the known dipole-dipole derived ones, to ion-p and truly chemical coordination bonds, strengthening wetting interfaces that define noticeable g-Al2O3 crystalline domains at minor temperatures. Manuscript illustrates how certain organic media may assist to reliable guest depositions in, hydrotalcite to alumina carriers within controlled morphology, at the same weight level than common procedures reported for more akin host/guest. Interestingly, protocol enables practical SBET measurements for solids with significative contributions of interparticle porosity. Detrimental effects are also addressed.

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Non-covalent interactions in thermodynamic stereoselectivity of mixed-ligand copper(II)-D- or L-histidine complexes with L-amino acids. A possible model of metal ion-assisted molecular recognition

Journal of the Chemical Society Dalton Transactions ◽

10.1039/dt9900002095 ◽

1990 ◽

pp. 2095 ◽

Cited By ~ 31

Author(s):

Gianna Borghesani ◽

Ferdinando Pulidori ◽

Maurizio Remelli ◽

Roberto Purrello ◽

Enrico Rizzarelli

Keyword(s):

Amino Acids ◽

Molecular Recognition ◽

Metal Ion ◽

Mixed Ligand ◽

Non Covalent Interactions ◽

Covalent Interactions

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A functional natural deep eutectic solvent based on trehalose: Structural and physicochemical properties

Food Chemistry ◽

10.1016/j.foodchem.2016.09.012 ◽

2017 ◽

Vol 217 ◽

pp. 560-567 ◽

Cited By ~ 43

Author(s):

Ruipu Xin ◽

Suijian Qi ◽

Chaoxi Zeng ◽

Faez Iqbal Khan ◽

Bo Yang ◽

...

Keyword(s):

Physicochemical Properties ◽

Deep Eutectic Solvent ◽

Natural Deep Eutectic Solvent

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Impact of dendritic polymers on nanomaterials

Polymer Chemistry ◽

10.1039/c4py01208a ◽

2015 ◽

Vol 6 (1) ◽

pp. 10-24 ◽

Cited By ~ 29

Author(s):

R. Soleyman ◽

M. Adeli

Keyword(s):

Physicochemical Properties ◽

Dendritic Polymers ◽

Hybrid Nanomaterials ◽

Non Covalent Interactions ◽

Covalent Interactions

Primary/secondary covalent/non-covalent interactions between dendritic polymers and nanomaterials can change the physicochemical properties, such as shape, of the obtained hybrid nanomaterials.

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