1450754-41-2

Usage

Uses

Used in Chemical Probe Synthesis:
2-(3-But-3-ynyl-3H-diazirin-3-yl)-ethanol is used as a chemical probe for the synthesis of ligands or pharmacophores. Its light-activated diazirine allows for UV light-induced covalent modification of a biological target, enabling researchers to study the interactions and effects of the probe on the target. The alkyne tag provides potential for downstream applications, such as further functionalization or conjugation to other molecules.
Used in Chemical Biology Experiments:
2-(3-But-3-ynyl-3H-diazirin-3-yl)-ethanol can be used alone or in parallel with other multi-functional building blocks to discover the optimal probe for various chemical biology experiments. Its unique structure and properties make it a valuable tool for researchers in the field of chemical biology, allowing them to explore new avenues of investigation and develop novel applications for this versatile compound.

Upstream product

• 100330-50-5 3-oxo-hept-6-ynoic acid methyl ester 
• 91798-92-4 2-(2-(but-3-yn-1-yl)-1,3-dioxolan-2-yl)ethan-1-ol 
• 91798-91-3 ethyl 2-<2-(3-butynyl)-1,3-dioxolan-2-yl>acetate 
• 35116-07-5 ethyl 3-oxo-6-heptyneoate 
• 1450754-40-1 1-hydroxy-3-ketohept-6-yne 

Downstream Products

• 1450754-54-7 C₂₇H₃₄ClN₉O₂ 
• 1450754-55-8 2-(2-fluoro-4-iodophenylamino)-N-(2-(3-(but-3-ynyl)-3H-diazirin-3-yl)ethyl)-3,4-difluorobenzamide 
• 1450754-57-0 6-(2-(3-(but-3-ynyl)-3H-diazirin-3-yl)ethoxy)-N-(3-chloro-4-fluorophenyl)-7-methoxyquinazolin-4-amine 
• 1450754-58-1 6-(4-(2-(3-(but-3-ynyl)-3H-diazirin-3-yl)ethoxy)phenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine 
• 1450754-60-5 4-(2-(4-(2-(3-(but-3-ynyl)-3H-diazirin-3-yl)ethoxy)phenyl)-5-(4-fluorophenyl)-1H-imidazol-4-yl)pyridine 
• 1450752-97-2 2-(3-(but-3-yn-1-yl)-3H-diazirin-3-yl)ethan-1-amine 
• 1450754-37-6 3-(3-(but-3-yn-1-yl)-3H-diazirin-3-yl)propanoic acid 
• 1450754-39-8 C₁₄H₁₅N₃O 
• 1450754-44-5 2-(6-(2-(3-(but-3-ynyl)-3H-diazirin-3-yl)ethylamino)-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide 
• 1450754-47-8 N-(4-(4-(2-(3-(but-3-ynyl)-3H-diazirin-3-yl)ethylamino)-6-(3-methyl-1H-pyrazol-5-ylamino)pyrimidin-2-ylthio)phenyl)cyclopropanecarboxamide 
• 1450754-51-4 C₂₇H₂₈N₈O₂ 
• 1450754-52-5 1-(4-(3-(2-(3-(but-3-ynyl)-3H-diazirin-3-yl)ethylcarbamoyl)phenoxy)phenyl)-3-(4-chloro-3-(trifluoromethyl)phenyl)urea 

Relevant academic research and scientific papers

A Whole Proteome Inventory of Background Photocrosslinker Binding

Affinity-based protein profiling (AfBPP) is a widely applied method for the target identification of bioactive molecules. Probes containing photocrosslinkers, such as benzophenones, diazirines, and aryl azides, irreversibly link the molecule of interest t

Design and synthesis of the diazirine-based clickable photo-affinity probe targeting sphingomyelin synthase 2

Background: SMS family plays a very important role in sphingolipids metabolism and is involved in the membrane mobility and signaling transduction. Methods: SMS2 subtype was related to a variety of diseases and could be regarded as a promising potential d

Exploring the potential intracellular targets of vascular normalization based on active candidates

We previously developed two candidates with potency of inducing vascular normalization, BD7 and B14. However, the definite intracellular molecular target(s) responsible for their activity remains unknown. Herein, we report the discovery and functional assessment of several multifunctional photoaffinity probes for determining the potential biological targets of active compounds. The probes bear a photoaffinity moiety and a bioorthogonal unit attached to B7 or B14 and maintained the bioactivity of the parent active molecules. Using in vitro biological assays, we preliminarily identified VEGFR-2 as a potential intracellular target for the active candidates. Our results demonstrate the utility of these multifunctional photoaffinity probes for analyzing the biological activity and subcellular localization of the intracellular target proteins of active candidates.

One-Pot Synthesis of Diazirines and 15N2-Diazirines from Ketones, Aldehydes and Derivatives: Development and Mechanistic Insight

Broad scope one-pot diazirine synthesis strategies have been developed using two different oxidants depending on the nature of the starting material. In all cases, an inexpensive commercial solution of ammonia (NH3) in methanol (MeOH) was emplo

Photochemical Probe Identification of a Small-Molecule Inhibitor Binding Site in Hedgehog Acyltransferase (HHAT)**

The mammalian membrane-bound O-acyltransferase (MBOAT) superfamily is involved in biological processes including growth, development and appetite sensing. MBOATs are attractive drug targets in cancer and obesity; however, information on the binding site and molecular mechanisms underlying small-molecule inhibition is elusive. This study reports rational development of a photochemical probe to interrogate a novel small-molecule inhibitor binding site in the human MBOAT Hedgehog acyltransferase (HHAT). Structure-activity relationship investigation identified single enantiomer IMP-1575, the most potent HHAT inhibitor reported to-date, and guided design of photocrosslinking probes that maintained HHAT-inhibitory potency. Photocrosslinking and proteomic sequencing of HHAT delivered identification of the first small-molecule binding site in a mammalian MBOAT. Topology and homology data suggested a potential mechanism for HHAT inhibition which was confirmed by kinetic analysis. Our results provide an optimal HHAT tool inhibitor IMP-1575 (Ki=38 nM) and a strategy for mapping small molecule interaction sites in MBOATs.

Preparation method of amino acid compound with photo-crosslinking activity

The invention discloses a preparation method of an amino acid compound with photo-crosslinking activity, and relates to the technical field of biological medicine, and the preparation method comprises the following steps: preparing 3-(3-butyne-1-yl)-3H-bis aziridine-3-ethanol from 1-hydroxy-3-ketoheptyne; and reacting the 3-(3-butyne-1-yl)-3H-bis aziridine-3-ethanol with iodine and triphenylphosphine to generate 3-(3-alkynyl-1-butyl)-3-(2-iodoethyl)-3H-diaziridine, further reacting the 3-(3-alkynyl-1-butyl)-3-(2-iodoethyl)-3H-diaziridine with potassium cyanide to obtain 3-(3-(butyl-3-alkynyl)-3H-diaziridine-3-yl) propionitrile, obtaining 3-(3-(butyl-3-alkynyl-1-yl)-3H-diaziridine-3-yl) propionic acid in an aqueous solution of sodium hydroxide, reacting the3-(3-(butyl-3-alkynyl-1-yl)-3H-diaziridine-3-yl) propionic acid with 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride and N-hydroxysuccinimide to generate 2, 5-dioxopyrrolidine-1-yl-3-(3-(butyl 3-yn-1-yl) 3 H-diazirine 3-yl) propionate, and reacting the 2, 5-dioxopyrrolidine-1-yl-3-(3-(butyl 3-yn-1-yl) 3 H-diazirine 3-yl) propionate with amino acid molecules to generate a target product. The preparation process provided by the invention is relatively simple, and the amino acid compound contains a bis-aziridine group with relatively high photoaffinity activity.

Baicalein active probe and synthetic method and application thereof

The invention discloses a baicalein active probe, and provides a synthetic method and application of the baicalein active probe. The active probe uses baicalein as a reaction group, uses diethyleneimine as a photocrosslinking group, and uses alkynyl as a biologically orthogonal group. A structural formula is as follows: (Please see the specification for the formula). The baicalein active probe hasthe beneficial effects that (1) an anticancer mechanism based on a cell oxidative phosphorylation pathway is a novel anticancer mechanism, and is possible to achieve the effect of selectively killingcancer cells; (2) baicalein is the first discovered activator of the cell oxidative phosphorylation pathway; and (3) key proteins ATP4A(P20648), ATP5A1(P25705), ATP5F1(P24539), ATP5L(O75964), ATP6V1A(P38606), ATP6V1H(Q9UI12), ATP12A(P54707) and NDUFA13(Q9P0J0) in the cell oxidative phosphorylation pathway are targets for the development of novel anticancer drugs.

NOVEL NUCLEIC ACID MODIFIERS

The present inventions generally relate to site-specific delivery of nucleic acid modifiers and includes novel DNA-binding proteins and effectors that can be rapidly programmed to make site-specific DNA modifications. The present inventions also provide a synthetic all-in-one genome editor (SAGE) systems comprising designer DNA sequence readers and a set of small molecules that induce double-strand breaks, enhance cellular permeability, inhibit NHEJ and activate HDR, as well as methods of using and delivering such systems.

Design and synthesis of cysteine-specific labels for photo-crosslinking studies

Chemical cross-linking mass-spectrometry (XL-MS) represents a powerful methodology to map ligand/biomacromolecule interactions, particularly where conventional methods such as X-ray crystallography, nuclear magnetic resonance (NMR) spectroscopy or cryo-electron microscopy (EM) are not feasible. In this manuscript, we describe the design and synthesis of two new photo-crosslinking reagents that can be used to specifically label free thiols through either maleimido or methanethiosulfonate groups and facilitate PXL-MS workflows. Both crosslinkers are based on light sensitive diazirines-precursors of highly reactive carbenes which offer additional advantages over alternative crosslinking groups such as benzophenones and aryl nitrenes given the controlled rapid and more indiscriminate reactivity.

Cortex pseudolaricis acetic acid photoaffinity probe halogen midbody and preparation method thereof

The invention relates to a cortex pseudolaricis acetic acid photoaffinity probe halogen midbody and a preparation method thereof. The general formula of the chemical structure of the cortex pseudolaricis acetic acid photoaffinity probe halogen midbody is as shown in specifications. By designing a new synthetic route, the compound 6 with high yield and high purity can be obtained; and the compoundcan be used to continue reacting with other materials for the preparation of a cortex pseudolaricis acetic acid photoaffinity probe.