71418-44-5

Usage

Uses

1. Used in Chemical Analysis:
Monobromobimane is used as a detection agent for identifying and quantifying compounds with reactive sulfur or thiol groups, such as H2S, glutathione, proteins, and nucleotides.
2. Used in Cellular Studies:
Monobromobimane is used as a fluorescent probe for tracing cell-lineages, neuronal tracing, and transplantation due to its ability to generate a stable fluorescent signal upon reaction with thiol groups.
3. Used in Protein Studies:
Monobromobimane is used as a detection tool for identifying the distribution of protein thiols in cells before and after the chemical reduction of disulfides.
4. Used in Drug Delivery Systems:
Monobromobimane is used as a carrier for low molecular weight thiols, including glutathione, mercaptopurine, peptides, and plasma thiols, as well as with carboxylic acids, to improve their delivery, bioavailability, and therapeutic outcomes.
5. Used in Research and Development:
Monobromobimane is used as a research tool for studying the interactions of various organic and metallic nanoparticles with thiol groups, which can be beneficial in developing novel drug delivery systems and understanding cellular processes.

InChI:InChI=1/C10H11BrN2O2/c1-5-7(3)12-8(4-11)6(2)10(15)13(12)9(5)14/h4H2,1-3H3

Upstream product

• 68654-22-8 9,10-dioxa-syn-(methyl,methyl)bimane 
• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 6628-22-4 3,4-dimethyl-4-chloro-2-pyrazolin-5-one 
• 68654-32-0 3,4-dimethyl-4-chloro-2-pyrazolin-5-one 
• 76421-69-7 3-(hydroxymethyl)-2,5,6-trimethylpyrazolo[1,2-a]pyrazole-1,7-dione 

Downstream Products

• 76421-90-4 9,10-dioxa-syn-(aminomethyl,methyl)(methyl,methyl)bimane 
• 76421-91-5 9,10-dioxa-syn-(cyano,methyl)(methyl,methyl)bimane 
• 119843-35-5 9,10-dioxa-syn-(carboxymethylthiomethyl, methyl)(methyl, methyl)-bimane 
• 87623-39-0 C₁₃H₁₇N₃O₄S 
• 76421-73-3 Monochlorobimane 
• 158761-05-8 1-D-myo-inosityl-2-deoxy-2-(N-acetamido-L-cysteinamido)-α-D-glucopyranoside 
• 76421-84-6 9,10-dioxa-syn-(1-propylthiomethyl,methyl)(methyl,methyl)bimane 
• 68654-22-8 9,10-dioxa-syn-(methyl,methyl)bimane 
• 418785-19-0 diethylphophoryl cyanide 

Relevant academic research and scientific papers

A β-hairpin peptide with pH-controlled affinity for tumor cells

Considering that the pH in the tumor microenvironment is dysregulated, we designed a β-hairpin peptide (SSRFEWEFESSDPRGDPSSRFEWEFESS). The configuration of the peptide switched from a flexible linear to a rigid loop structure under weakly acidic conditions. The peptide internalized by tumor cells increased significantly under weakly acidic conditions.

Dihalogen and Solvent-Free Preparation of syn- Bimane

Fluorescent bimanes are low molecular weight and low toxicity molecules with applications ranging from biology to LASER dyes. The widespread use of these molecular probes has presumably been stalled by the hazards involved in their current synthetic preparation which involve handling of dangerous halogens like chlorine (gas) and bromine (liq.). The accessibility achieved by the simple and safe dihalogen and solvent-free methodologies described here open the floodgates to additional future practical applications of bimanes.

Visible Light Activation of Nucleophilic Thiol-X Addition via Thioether Bimane Photocleavage for Polymer Cross-Linking

On-demand photo-uncaging of reactive thiols have been employed in engineering biomaterial scaffolds for regulation of cellular activities. A drawback of the current photo-uncaging chemistry is the utilization of high energy UV light or 2-photon laser light, which may be harmful to cells and cause undesired side reactions within the biological environment. We introduce an effective approach for the caging of thiol using monobromobimane, which can be removed under irradiation of light at = 420 nm and in the presence of electrophiles, such as acrylate, propiolate and maleimide, for trapping of the newly release thiol. This chemical approach can be used in visible light-induced polymer coupling and cross-linking for the preparation of cell-laden hydrogels.

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

A series of ester conjugates of carboxylic and amino acids were synthesized based on bimane fluorescent photoremovable protecting group (FPRPG). The photorelease of single and dual (same as well as different) carboxylic and amino acids is demonstrated from a single bimane molecule on irradiation with visible light (λ ≥ 410 nm). The detailed mechanistic study of photorelease revealed that the release of two caged acids is simultaneous but in a stepwise pathway.

Bimanes. 6. Reactive halogen derivatives of syn- and anti-1,5-diazabicyclo[3.3.0]octadienediones (9,10-dioxabimanes)

The preparation of reactive halogen derivatives of syn- and anti-1,5-diazabicyclo[3.3.0]octadienediones (9,10-dioxabimanes) is accomplished through the intermediate monobromo- and dibromobimanes previously described. Mono- and dihydroxy compounds are produced from the bromides by reaction with wet sodium trifluoroacetate in CH3CN and are used to prepare the (a) monochlorides and dichlorides (SOCl2) and (b) the monofluorides and difluorides (Et2NSF3). Monofunctional halides react with nucleophiles (amines, thiols, carboxylates) to yield direct substitution products, with some reduction accompanying the thiol reaction. Difunctional halides react with excess nucleophile to give direct disubstitution products. syn-Dihalides react with difunctional nucleophiles (actual or potential, e.g., RNH2, S2-, (CN)2C2,CH3)B are markedly affected by the nature of X. Most syn-bromobimanes are nonfluorescent and are moderately photosensitive, due to thermally reversible isomerizations and additional irreversible reactions. syra-Chlorobimanes are nonfluorescent to weakly fluorescent. syn-Monofluoro- and difluorobimanes are strongly fluorescent. At 77 K, the halogenated compounds are all phosphorescent to some extent and many of the syn derivatives are strongly fluorescent.