175281-76-2

Usage

Uses

Used in Chemical Synthesis:
HYDROXYETHYL PHOTOLINKER is used as a photolabile linker for the preparation of carboxylic acids. Its photolabile nature allows for the controlled release of these acids under specific conditions, making it a valuable tool in chemical synthesis processes.
Used in Solid Phase Synthesis:
In the field of solid phase synthesis, HYDROXYETHYL PHOTOLINKER is used for the preparation of photolabile linking groups. These linking groups are essential for attaching and releasing molecules from solid support materials, facilitating the synthesis of complex molecules in a controlled and efficient manner.
Used in Pharmaceutical Industry:
HYDROXYETHYL PHOTOLINKER can be employed in the pharmaceutical industry for the development of drug delivery systems. Its ability to act as a photolabile linker can be utilized to design controlled-release drug formulations, enhancing the efficacy and safety of medications.
Used in Research and Development:
In research and development, HYDROXYETHYL PHOTOLINKER can be used to study the behavior of molecules and their interactions with other compounds. Its photolabile properties make it an ideal candidate for investigating the mechanisms of various biological and chemical processes.

InChI:InChI=1/C13H17NO7/c1-8(15)9-6-11(20-2)12(7-10(9)14(18)19)21-5-3-4-13(16)17/h6-8,15H,3-5H2,1-2H3,(H,16,17)

Upstream product

• 2969-81-5 Ethyl 4-bromobutyrate 
• 498-02-2 1-(3-methoxy-4-hydroxyphenyl)ethanone 
• 188891-18-1 4-(4-acetyl-2-methoxy-5-nitrophenoxy)butanoic acid 
• 1073426-06-8 ethyl 4-(4-(1-hydroxyethyl)-2-methoxy-5-nitrophenoxy) butanoate 
• 182297-45-6 methyl 4-(4-acetyl-2-methoxy-5-nitrophenoxy)butyrate 
• 175281-79-5 methyl 4-(4-acetyl-2-methoxyphenoxy)butanoate 
• 174884-21-0 ethyl 4-(4-acetyl-2-methoxyphenoxy) butanoate 
• 198347-60-3 4-[4-(1-Hydroxy-ethyl)-2-methoxy-phenoxy]-butyric acid ethyl ester 
• 198347-61-4 4-[2-Methoxy-5-nitro-4-(1-nitrooxy-ethyl)-phenoxy]-butyric acid ethyl ester 
• 182122-16-3 methyl 4-[4-(1-hydroxyethyl)-2-methoxy-5-nitrophenoxy]butyrate 

Downstream Products

• 956347-50-5 C₃₈H₆₅N₅O₁₂ 
• 1091595-09-3 4-(4-(1-(acryloyloxy)ethyl)-2-methoxy-5-nitrophenoxy)butanoic acid 
• 1334290-05-9 4-(4-(1-hydroxyethyl)-2-methoxy-5-nitrophenoxy)butan-1-ol 
• 1269794-14-0 2-((1-(4-(4-(2-(methacryloyloxy)ethylcarbamoyloxy)butoxy)-5-methoxy-2-nitro-phenyl)ethoxy)carbonylamino)ethyl methacrylate 
• 1352127-37-7 1,1'-(4,4'-(4,4'-(ethane-1,2-diylbis(azanediyl))bis(4-oxobutane-4,1-diyl))bis(oxy)bis(5-methoxy-2-nitro-4,1-phenylene))bis(ethane-1,1-diyl)bis(2-methyl acrylate) 
• 1352127-36-6 4-(4-(1-(methacryloyloxy)ethyl)-2-methoxy-5-nitrophenoxy)butanoic acid 
• 1612262-36-8 C₃₇H₄₀N₄O₁₂ 
• 1612262-35-7 4-[4-(1-hydroxyethyl)-2-methoxy-5-nitrophenoxy]butyric acid N-(Fmoc-1,4-butanediamine) 
• 1616510-90-7 C₃₂H₅₉N₃O₁₃Si₂ 

Relevant academic research and scientific papers

Retro Diels-Alder Fragmentation of Fulvene-Maleimide Bioconjugates for Mass Spectrometric Detection of Biomolecules

Diels-Alder chemistry is a well-explored avenue for the synthesis of bioactive materials; however, its potential applications have recently expanded following the development of reactions that can be performed in buffered aqueous environments at low temperatures, including fulvene-maleimide [4 + 2] cycloadditions. In this study, we synthesized two novel amine-reactive fulvene linkers to demonstrate the application of this chemistry for generating mass spectrometry-cleavable labels (“mass tags”), which can be used for the labeling and detection of proteins. Successful conjugation of these linkers to maleimide-labeled peptides was observed at low temperatures in phosphate-buffered saline, allowing the non-destructive modification of proteins with such mass tags. The labile nature of fulvene-maleimide adducts in the gas phase also makes them suitable for both matrix-assisted laser desorption/ionization (MALDI) and electrospray ionization (ESI) mass spectrometric analysis. Unlike previous examples of MALDI mass tags, we show that fulvene-maleimide cycloaddition adducts fragment predictably upon gas-phase activation without the need for bulky photocleavable groups. Further exploration of this chemistry could therefore lead to new approaches for mass spectrometry-based bioassays.

Novel antibody-drug conjugate with UV-controlled cleavage mechanism for cytotoxin release

Antibody-drug conjugates (ADCs) are being developed worldwide with the potential to revolutionize current cancer treatment strategies. However, off-target toxicity caused by the instability of linkers remains one of the main issues to be resolved. Developing a novel photocontrol-ADC with good stability and photocontrolled release seemed to be an attractive and practical solution. In this study, we designed, for the first time, a novel ultraviolet (UV) light-controlled ADC by carefully integrating the UV-cleavable o-nitro-benzyl structure into the linker. Our preliminary work indicated that the ADC exhibited good stability and photocontrollability while maintaining a targeting effect similar to that of the naked antibody. Upon irradiation with UV light, the ADC rapidly released free cytotoxins and exerted significant cytotoxicity toward drug-resistant tumor cells. Compared to those of the unirradiated cells, the EC50 values of ADCs increased by up to 50-fold. Furthermore, our research confirmed that the degradation products of unirradiated ADC, Cys-1a, were relatively less toxic, thus potentially reducing the off-target toxicity caused by nonspecific uptake of ADCs. The novel design strategy of UV light-controlled ADCs may provide new perspectives for future research on ADCs and promote the development of photocontrol systems.

PEG-PEI-modified gated N-doped mesoporous carbon nanospheres for pH/NIR light-triggered drug release and cancer phototherapy

A novel hybrid drug carrier has been designed, taking N-doped mesoporous carbon (NMCS) as the core and PEG-PEI as the outer shell. NMCS was functionalized with a photocleavable nitrobenzyl-based linker following a click reaction. Gemcitabine was loaded in

Photolabile Linkers: Exploiting Labile Bond Chemistry to Control Mode and Rate of Hydrogel Degradation and Protein Release

Photolabile moieties have been utilized in applications ranging from peptide synthesis and controlled protein activation to tunable and dynamic materials. The photochromic properties of nitrobenzyl (NB) based linkers are readily tuned to respond to cytocompatible light doses and are widely utilized in cell culture and other biological applications. While widely utilized, little is known about how the microenvironment, particularly confined aqueous environments (e.g., hydrogels), affects both the mode and rate of cleavage of NB moieties, leading to unpredictable limitations in control over system properties (e.g., rapid hydrolysis or slow photolysis). To address these challenges, we synthesized and characterized the photolysis and hydrolysis of NB moieties containing different labile bonds (i.e., ester, amide, carbonate, or carbamate) that served as labile crosslinks within step-growth hydrogels. We observed that NB ester bond exhibited significant rates of both photolysis and hydrolysis, whereas, importantly, the NB carbamate bond had superior light responsiveness and resistance to hydrolysis within the hydrogel microenvironment. Exploiting this synergy and orthogonality of photolytic and hydrolytic degradation, we designed concentric cylinder hydrogels loaded with different cargoes (e.g., model protein with different fluorophores) for either combinatorial or sequential release, respectively. Overall, this work provides new facile chemical approaches for tuning the degradability of NB linkers and an innovative strategy for the construction of multimodal degradable hydrogels, which can be utilized to guide the design of not only tunable materials platforms but also controlled synthetic protocols or surface modification strategies.

MOLECULAR LOGIC GATES FOR CONTROLLED MATERIAL DEGRADATION

The present disclosure features, inter alia, a cyclic multifunctional linker, including at least two cleavable moieties; at least two connecting chains connected to the at least two cleavable moieties to provide a cyclic structure; and at least two linkin

COMPOUNDS AND METHODS FOR DETECTION AND ISOLATION OF BIOMOLECULES

A compound of general formula R1-L1-PCL-L2-R2 is disclosed wherein PCL is a photolabile group; R1 is a reactive moiety capable of modifying biomolecules without activation; L1 is a non-clea

COMPOUNDS FOR PROMOTING LIPOSOMAL AND CELLULAR ADHESION AND COMPOSITIONS AND METHODS OF USE THEREOF

The present application describes amphiphatic compounds like compound Ila below, compositions and methods for incorporating chemoselective and bio-orthogonal complementary functional groups into liposomes. Such compounds are incorporated in greater number

Photodegradable groups for tunable polymeric materials

Provided is a method that provides both spatial and temporal control of a polymer degradation process using mono- and multifunctional macromolecular monomers (“macromers”) that degrade via single- and multi-photon photolysis mechanisms over a broad range

Enzymatic- and light-degradable hybrid nanogels: Crosslinking of polyacrylamide with acrylate-functionalized Dextrans containing photocleavable linkers

Enzymatically cleavable and light-degradable hybrid nanogels were prepared by free radical inverse miniemulsion copolymerization of acrylamide (AAm) with a newly synthesized functional dextran crosslinker containing acrylate moieties attached to the backbone via a photolabile linker, that is, dextran-photolabile linker-acrylate (Dex-PL-A). The Dex-PL-A/AAm feed ratio was systematically varied to investigate the influence of the particle composition on the gel properties. The resulting hydrogel nanoparticles were examined with regard to their degradation behavior upon the appliance of the two orthogonal stimuli by turbidity measurements in combination with dynamic light scattering. Although continuous photolytic cleavage of the photolabile linkers between polyacrylamide chains and dextran molecules was found to proceed fast and quantitatively yielding completely disintegrated networks, stepwise irradiation resulted in partial degradation of crosslinking points. Thus, nanogels of a desired specific degree of swelling (DGS) can be obtained by adjusting the irradiation time accordingly. Partial enzymatic cleavage of the dextran backbones of the Dex-PL-A crosslinking molecules resulted in an increase in the DGS of the nanogels up to a constant value. Subsequent irradiation of those swollen hydrogel particles was used to fully degrade the network structure in a second step. Hence, a two-step degradation profile was realized by the combination of the two orthogonal stimuli.

Near infrared light triggered release of biomacromolecules from hydrogels loaded with upconversion nanoparticles

Using a photosensitive hybrid hydrogel loaded with upconversion nanoparticles (UCNPs), we show that continuous-wave near-infrared (NIR) light (980 nm) can be used to induce the gel-sol transition and release large, inactive biomacromolecules (protein and