Model Compounds of Caged Capsaicin:  Design, Synthesis, and Photoreactivity

Katritzky, Alan R.; Xu, Yong‐Jiang; Vakulenko, Anatoliy V.; Wilcox, Allan L.; Bley, Keith

doi:10.1021/jo034616t

Cited by 44 publications

(36 citation statements)

References 30 publications

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“…[18b] This bathochromic shift might be attributable to the effect of the sulfur atom placed on the TNB cage which is less electron withdrawing than the benzylic oxygen in the ONB system. [28] The photolysis of TNB cages 1 and 2 was performed by UVA exposure (365 nm), and its progress was monitored by 1 H NMR spectroscopy, UV–vis spectrometry and UPLC, each providing evidence supportive of the cleavage mechanism proposed in Figure 3a.…”

Section: Resultsmentioning

confidence: 91%

A Thioacetal Photocage Designed for Dual Release: Application in the Quantitation of Therapeutic Release by Synchronous Reporter Decaging

et al. 2016

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Despite the immense potential, application of existing photocaging technology is limited by the paucity of advanced caging tools. Here we report on the design of a novel thioacetal ortho-nitrobenzaldehyde (TNB) dual arm photocage that enables control of the simultaneous release of two payloads linked to a single TNB unit. Using this cage which was prepared in a single step from commercial 6-nitroverataldehyde, three drug-fluorophore conjugates were synthesized, Taxol-TNB-Fluorescein, Taxol-TNB-Coumarin and Doxorubicin-TNB-Coumarin, and long wavelength UVA light-triggered release experiments demonstrated that dual payload release occurred with rapid decay kinetics for each conjugate. In cell based assays in vitro, dual release could also be controlled by UV exposure, resulting in increased cellular fluorescence and cytotoxicity as potent as unmodified drug towards the KB carcinoma cell line. The extent of such dual release was quantifiable by reporter fluorescence measured in situ, and found to correlate with the extent of cytotoxicity. Thus, this novel dual-arm cage strategy provides a valuable tool which enables both active control and real-time monitoring of drug activation at the delivery site.

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Section: Resultsmentioning

confidence: 91%

A Thioacetal Photocage Designed for Dual Release: Application in the Quantitation of Therapeutic Release by Synchronous Reporter Decaging

et al. 2016

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“…The capsaicin consists of vanylamine and decanoic acid with double bond [33]. Katritzky et al [35] divided the capsaicin molecule into three parts, namely aromatic ring, amide bond and hydrophobic bond. The aromatic ring especially in 3 and 4 position bonds was easily substituted by phenol groups.…”

Section: Kinetics Of Capsaicin Degradation At Blanching-brine-calciummentioning

confidence: 99%

“…The hydrophobic bonds especially the octyl and benzyl chains were very easily substituted by the other group function. These changes played a significant role in capsaicinoid activity [35]. The change of capsaicin structure can cause vanillylamin condensation and its fatty acid derivatives that can produce vanillyl nonanoate, as depicted in Figure 5.…”

Section: Kinetics Of Capsaicin Degradation At Blanching-brine-calciummentioning

confidence: 99%

“…The change of capsaicin structure can cause vanillylamin condensation and its fatty acid derivatives that can produce vanillyl nonanoate, as depicted in Figure 5. Introduction of heat during drying process caused the change of capsaicin to be vanillyl nonanoate [35]. The vanillyl nonanoate was analog capsaicin compound that can influence low hot sensation in red chili pepper [36].…”

Section: Kinetics Of Capsaicin Degradation At Blanching-brine-calciummentioning

confidence: 99%

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Thermal Degradation Kinetics of Capsaicin on Blanching-Brine-Calcium Pretreatment Red Chili Pepper Drying

Arifin

Djaeni

2018

Bull. Chem. React. Eng. Catal.

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Post-harvest red chili pepper (Capsicum frutescens) has highly capsaicin as bioactive compound and moisture content. However, capsaicin is the responsible bioactive compound in chili for hot sensation that easy to degrade by partial oxidation caused introduction of heat in drying process. The objective of this research was to investigate kinetics of capsaicin degradation in the drying process under blanching-brine-calcium pretreatment and various temperatures. For this purposes, chili provided local farmer was pretreated using blanching-brine-calcium pretreatment. Afterward, they were dried at 40, 50, 60, and 70 o C for 8 hours. Degradation of capsaicin content was observed every 2 hours using Thin Layer Chromatography (TLC). Results showed kinetics of capsaicin degradation was categorized as second order reaction. At the same temperature and time, capsaicin retention of blanching-brinecalcium pretreated chili has highest value. The temperature dependence of the capsaicin degradation rate was analyzed using Arrhenius correlation. The activation energy for degradation rate of capsaicin during drying was around 45.10367 kJ/mol.K. It indicated the degradation rate increased as well as increased the temperature at the same time.

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“…Air-and moisture-sensitive liquids were transferred by syringe or stainless steel cannula. Organic solutions were concentrated by rotary evaporation (25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37)(38)(39)(40) at ambient temperature, unless noted otherwise. All reagents used were purchased commercially and were used as received unless noted otherwise.…”

Section: General Experimentalmentioning

confidence: 99%

End-capped poly(4,5-dichlorophthalaldehyde): a stable self-immolative poly(aldehyde) for translating specific inputs into amplified outputs, both in solution and the solid state

DiLauro

Phillips

2015

Polym. Chem.

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We recently reported that poly(4,5-dichlorophthalaldehyde) (PCl 2 PA) is an effective self-immolative CD r polymer for prototyping multi-stimuli-responsive three-dimensional polymeric materials with response properties that are inspired by the behaviour of certain biological materials in plants. In this article we detail the design and synthesis of PCl 2 PA, describe its ability to respond to specific stimuli, and compare and contrast PCl 2 PA with poly(phthalaldehyde) (PPA), which is the self-immolative CD r predecessor of this new poly(acetal). This article illustrates the favourable attributes of PCl 2 PA, including its dose-dependent solution-phase response to Pd(0). Taken together, these studies reveal the unique and useful attributes of PCl 2 PA for providing selective amplified responses to specific stimuli, both in solution and the solid state.

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Model Compounds of Caged Capsaicin: Design, Synthesis, and Photoreactivity

Cited by 44 publications

References 30 publications

A Thioacetal Photocage Designed for Dual Release: Application in the Quantitation of Therapeutic Release by Synchronous Reporter Decaging

A Thioacetal Photocage Designed for Dual Release: Application in the Quantitation of Therapeutic Release by Synchronous Reporter Decaging

Thermal Degradation Kinetics of Capsaicin on Blanching-Brine-Calcium Pretreatment Red Chili Pepper Drying

End-capped poly(4,5-dichlorophthalaldehyde): a stable self-immolative poly(aldehyde) for translating specific inputs into amplified outputs, both in solution and the solid state

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