Bimane: A Visible Light Induced Fluorescent Photoremovable Protecting Group for the Single and Dual Release of Carboxylic and Amino Acids

Chaudhuri, Amrita Datta; Venkatesh, Yarra; Behara, Krishna Kalyani; Singh, N. D. Pradeep

doi:10.1021/acs.orglett.7b00416

Cited by 40 publications

(43 citation statements)

References 24 publications

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“…In every case the release of alcohols, thioalcohols, and amine (0.133 ≤ Φ p ≤ 0.140) by the caged compounds was relatively faster than that of their counterpart carboxylic acids (0.097 ≤ Φ p ≤ 0.102). The photochemical quantum yield ( Φ p ) was calculated by using potassium ferrioxalate as an actinometer …”

Section: Resultsmentioning

confidence: 99%

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Bis‐Acetyl Carbazole: A Photoremovable Protecting Group for Sequential Release of Two Different Functional Groups and Its Application in Therapeutic Release

et al. 2017

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In this paper, we present fluorescent photoremovable protecting groups (FPRPG) based on bis‐acetyl carbazole for the release of two different functional groups such as carboxylic acids, alcohols, thiols, and amines in a sequential fashion. Dual‐arm caged bis‐acetyl carbazoles with different combinations of two unlike functional groups were synthesized. Photophysical studies showed that caged bis‐acetyl carbazoles are blue fluorescent and their emission properties are sensitive to the environment. Sequential photorelease of two different functional groups by bis‐acetyl carbazole was analyzed by HPLC, UV and emission spectroscopy. The mechanism of the dual release by bis‐acetyl carbazole was investigated and supported by TD‐DFT calculations. To demonstrate the applicability of the dual release ability of bis‐acetyl carbazole FPRPG, we synthesized a drug delivery system (DDS) in which one arm of bis‐acetyl carbazole is linked to the carboxylic functional group of chlorambucil (CBL) and the other arm is attached to the hydroxyl group of ferulic acid ethyl ester (FAEE). In vitro studies showed that our DDS presents excellent properties such as photoregulated dual drug delivery, cellular uptake, and biocompatibility.

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Section: Resultsmentioning

confidence: 99%

“…PRPGs based on a single chromophore for dual release are less in number than single release PRPGs . Known examples of single chromophore‐based PRPGs for dual release are thioacetal ortho ‐nitrobenzaldehyde (TNB), 3‐diethylaminobenzyl (DEABn), perylene‐3,4,9,10‐tetrayltetramethyl, and bimane …”

Section: Introductionmentioning

confidence: 99%

Bis‐Acetyl Carbazole: A Photoremovable Protecting Group for Sequential Release of Two Different Functional Groups and Its Application in Therapeutic Release

et al. 2017

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“…HPLC showed the purity of the compound is 95%: t R = 18.5 min in gradient mixture of MeOH and H 2 O. 1 13 (41). 3-Iodopropyl trimethoxysilane (0.783 g, 2.62 mmol) and NaH (94.3 mg, 3.93 mmol) were added to 0.244 g (2.62 mmol) of phenol in 50 mL of dry THF.…”

Section: Methodsmentioning

confidence: 99%

“…Photoreleased molecules are of considerable interest not only in the field of photochemistry but also in site‐specific delivery applications . Current literature on sensitizer and drug photorelease has mainly focused on the use of direct UV, visible and near‐IR light to activate the release mechanisms.…”

Section: Introductionmentioning

confidence: 99%

S,S‐Chiral Linker Induced U Shape with a Syn‐facial Sensitizer and Photocleavable Ethene Group

Ghosh

Belh

Chiemezie

et al. 2018

Photochem & Photobiology

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There is a major need for light-activated materials for the release of sensitizers and drugs. Considering the success of chiral columns for the separation of enantiomer drugs, we synthesized an S,S-chiral linker system covalently attached to silica with a sensitizer ethene near the silica surface. First, the silica surface was modified to be aromatic rich, by replacing 70% of the surface groups with (3-phenoxypropyl)silane. We then synthesized a 3-component conjugate [chlorin sensitizer, S,S-chiral cyclohexane and ethene building blocks] in 5 steps with a 13% yield, and covalently bound the conjugate to the (3-phenoxypropyl)silane-coated silica surface. We hypothesized that the chiral linker would increase exposure of the ethene site for enhanced O -based sensitizer release. However, the chiral linker caused the sensitizer conjugate to adopt a U shape due to favored 1,2-diaxial substituent orientation; resulting in a reduced efficiency of surface loading. Further accentuating the U shape was π-π stacking between the (3-phenoxypropyl)silane and sensitizer. Semiempirical calculations and singlet oxygen luminescence data provided deeper insight into the sensitizer's orientation and release. This study has lead to insight on modifications of surfaces for drug photorelease and can help lead to the development of miniaturized photodynamic devices.

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“…Such reliance on UV light has been found to be problematic due to limited capabilities for deep tissue penetration. It is worth noting that other researchers have made inroads in photorelease mechanisms with visible light , 2‐photon activation and photoinduced electron transfer techniques . Another problem that arises is the limited number of options for amine photorelease mechanisms.…”

Section: Commentarymentioning

confidence: 99%

Cyanine Modification Tuned for Amine Photorelease

Mathew

Greer

2019

Photochem & Photobiology

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Cyanines are emerging as useful agents for photoreleasing biological compounds because of their capability of utilizing near‐infrared (NIR) light. Another benefit is their ability to self‐sensitize to produce singlet oxygen for the release of aryl amines, a process that has not been as feasible in the past. Here, we highlight the paper by Schnermann et al. (https://doi.org/10.1111/php.13090), which reports on a cyanine conjugate for heterolytic photocleavage of aryl amines. This paper is timely—delving into a photorelease mechanism involving a domino rearrangement and β‐elimination triggered by NIR light.

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Bimane: A Visible Light Induced Fluorescent Photoremovable Protecting Group for the Single and Dual Release of Carboxylic and Amino Acids

Cited by 40 publications

References 24 publications

Bis‐Acetyl Carbazole: A Photoremovable Protecting Group for Sequential Release of Two Different Functional Groups and Its Application in Therapeutic Release

Bis‐Acetyl Carbazole: A Photoremovable Protecting Group for Sequential Release of Two Different Functional Groups and Its Application in Therapeutic Release

S,S‐Chiral Linker Induced U Shape with a Syn‐facial Sensitizer and Photocleavable Ethene Group

Cyanine Modification Tuned for Amine Photorelease

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