Gas-Phase Acidity Studies of Dual Hydrogen-Bonding Organic Silanols and Organocatalysts

Liu, Min; Tran, Ngon T.; Franz, Annaliese K.; Lee, Jeehiun K.

doi:10.1021/jo201214x

Cited by 48 publications

(35 citation statements)

References 61 publications

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“…[26,27] However in the actual film these terminal hydroxyl moieties crosslink to form siloxane bonds during the curing process. Part A is a viscous silicone polymer with terminal hydroxyl groups.…”

Section: Dtx Stability In Silicone Kit Componentsmentioning

confidence: 99%

Docetaxel epimerization in silicone films: a case of drug excipient incompatibility

Shaikh

Arellano

Choudhury

et al. 2014

Drug Testing and Analysis

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Docetaxel (DTX) is an anti-cancer compound derived from 10-deacetyl baccatin III which is indicated for treatment of breast, lung, prostate, gastro-esophageal, and head and neck cancers. Epimerization of DTX at the C-7 hydroxyl position has intrigued chemists and has been implicated in loss of potency, as well as in the development of resistance in tumour cells. For localized controlled delivery of this agent, silicone films were prepared from a commercially available silicone kit. High levels of epimeric degradants were unexpectedly found in the in vitro release media. Herein, we discuss this anomalous DTX degradation to epimeric impurities, and discuss the possible reasons for degradation. Systematic stability studies were performed on the release media and the silicone kit components. It was found that release media and tin-based catalyst present in the silicone kit could be responsible for the epimeric conversion. This unusual case of chemical incompatibility can affect product performance and can even lead to development of resistance in tumour cells towards DTX.

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Section: Dtx Stability In Silicone Kit Componentsmentioning

confidence: 99%

Docetaxel epimerization in silicone films: a case of drug excipient incompatibility

Shaikh

Arellano

Choudhury

et al. 2014

Drug Testing and Analysis

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“…Although disiloxanediols are recognized for their hydrogen‐bonding and anion‐recognition capabilities, they have not been previously reported as anion‐binding catalysts . Anion‐binding catalysis has been identified as an important new mode of catalysis that proceeds by activation of electrophilic ionic substrates by hydrogen bonding to their counter anions .…”

Section: Introductionmentioning

confidence: 99%

“…[10b] Although disiloxanediols are recognized for their hydrogenbondinga nd anion-recognition capabilities, they have not been previouslyr eported as anion-bindingc atalysts. [11] Anionbinding catalysis has been identified asa ni mportant new mode of catalysis that proceeds by activation of electrophilic ionic substrates by hydrogen bonding to their counter anions. [12] Here, we report the synthesis of structurally varied disiloxanediols and the first example of disiloxanediols as an ew class of anion-binding catalysts.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Structurally Varied 1,3‐Disiloxanediols and Their Activity as Anion‐Binding Catalysts

Diemoz

Wilson

Franz

2016

Chemistry A European J

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A series of new 1,3-disiloxanediols has been synthesized, including naphthyl-substituted and unsymmetrical siloxanes, and demonstrated as a new class of anion-binding catalysts. In the absence of anions, diffusion-ordered spectroscopy (DOSY) displays self-association of 1,3-disiloxanediols through hydrogen-bonding interactions. Binding constants determined for 1,3-disiloxanediol catalysts indicate strong hydrogen-bonding and anion-binding abilities with unsymmetrical siloxanes displaying different hydrogen-bonding abilities for each silanol group.

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“…More recently, Kondo and co‐workers found that certain silanediols fluoresce in the presence of anions 51. In work related to Kondo's reports, the Franz group also explored gas‐phase acidities of several organocatalysts and silanols52 as well as NMR and X‐ray crystallography studies of hydrogen bonding in amide‐containing silanediols 53…”

Section: Silanediol Catalysismentioning

confidence: 99%

Discovery of a Highly Selective PLD2 Inhibitor (ML395): A New Probe with Improved Physiochemical Properties and Broad‐Spectrum Antiviral Activity against Influenza Strains

et al. 2014

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Further chemical optimization of the halopemide-derived family of dual PLD1/2 inhibitors afforded ML395 (VU0468809), a potent, >80-fold PLD2 selective allosteric inhibitor (cellular PLD1, IC50 >30,000 nM, cellular PLD2, IC50 = 360 nM). Moreover, ML395 possesses an attractive in vitro DMPK profile, improved physiochemical properties, ancillary pharmacology (Eurofins Panel) cleaner than any other reported PLD inhibitor, and has been found to possess interesting activity as an antiviral agent in cellular assays against a range of influenza strains (H1, H3, H5 and H7).

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Gas-Phase Acidity Studies of Dual Hydrogen-Bonding Organic Silanols and Organocatalysts

Cited by 48 publications

References 61 publications

Docetaxel epimerization in silicone films: a case of drug excipient incompatibility

Docetaxel epimerization in silicone films: a case of drug excipient incompatibility

Synthesis of Structurally Varied 1,3‐Disiloxanediols and Their Activity as Anion‐Binding Catalysts

Discovery of a Highly Selective PLD2 Inhibitor (ML395): A New Probe with Improved Physiochemical Properties and Broad‐Spectrum Antiviral Activity against Influenza Strains

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