Tag: 1500-1600

Selective halogenation of cyclic maltose oligosaccharides in the C-6 position and synthesis of per(3,6-anhydro) cyclic maltose oligosaccharides was written by Gadelle, Andree;Defaye, Jaques. And the article was included in Angewandte Chemie in 1991.Name: Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin This article mentions the following:

Cyclic maltose oligosaccharides were treated with PPh₃ and iodine (or bromine) to give the per-6-deoxy-6-halo derivatives Treatment of per(6-deoxy-6-iodo) cyclic maltose oligosaccharide with aqueous NaOH gave the per(3,6-anhydro) derivatives In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1Name: Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin).

Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.Name: Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Improved preparation of hexakis(6-deoxy)cyclomaltohexaose and heptakis(6-deoxy)cyclomaltoheptaose was written by Baer, Hans H.;Vargas Berenguel, Antonio;Shu, Youn Y.;Defaye, Jacques;Gadelle, Andree;Santoyo Gonzalez, Francisco. And the article was included in Carbohydrate Research in 1992.HPLC of Formula: 53784-83-1 This article mentions the following:

Title compounds I (R = H; n = 6, 7) were prepared from I (R = OH) by direct halogenation with Br or iodine and DMF-PPh₃, followed by reductive dehalogenation with NaBH₄. In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1HPLC of Formula: 53784-83-1).

Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.HPLC of Formula: 53784-83-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of oligo-6-bromo-6-deoxy-β-cyclodextrins was written by Kurochkina, G. I.;Trushkin, I. Yu.;Grachev, M. K.;Nifant’ev, E. E.. And the article was included in Russian Journal of General Chemistry in 2004.Safety of Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin This article mentions the following:

Two methods of synthesis of oligo-6-bromo-6-deoxy-β-cyclodextrins, with use of the Vilsmeier-Haack reagent and via tosyl derivatives of β-cyclodextrin, were compared. The second method holds more promise, since it allows a desired number of bromine atoms to be introduced into the β-cyclodextrin mol. instead of hydroxy groups. A correlation between the decomposition onset points of oligo-6-bromo-6-deoxy-β-cyclodextrins and the number of bromine substituents in them was revealed. In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1Safety of Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin).

Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Safety of Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Phosphorescence of polynuclear aromatic hydrocarbons in heptakis(6-bromo-6-deoxy-β-cylcodextrin) was written by Femia, R. A.;Love, L. J. Cline. And the article was included in Journal of Physical Chemistry in 1985.Name: Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin This article mentions the following:

Room-temperature phosphorescence spectra and excited-state lifetimes are reported for several polynuclear aromatic hydrocarbons included within the cavity of heptakis(6-bromo-6-deoxy-β-cyclodextrin) (Br-β-CD) (synthesized by replacing β-CD’s primary hydroxyls with Br). Appreciable phosphorescence only occurs when the lumiphor is shielded from quenchers by the cyclodextrin torus and are within the realm of influence of heavy atoms. By locking the heavy atom into a fixed position on the cyclodextrin mol., the observed phosphorescence and dynamic interactions depend primarily on the entrance and exit rate constants of the lumiphor from the cyclodextrin, simplifying the kinetic scheme and data interpretation. A solvent mixture of DMF and water was employed due to the extreme water insolubility of heptakis(6-bromo-6-deoxy-β-cyclodextrin), and to assess the degree of bulk solvent hydrophobicity on the inclusion process. This latter effect was monitored by differences in phenanthrene’s Br-β-CD spectral profile relative to that in aqueous unbrominated β-CD/1,2-dibromoethane and fluorescence peak ratio variations as a function of the DMF/water ratio. Luminescence lifetime values provided indirect information on the relative exit-to-entrance rate constant ratios. The optimum DMF/water ratio for production of maximum phosphorescence intensity was 4/1, and the optimum concentration of brominated β-cyclodextrin in the 4/1 DMF/water solvent was 0.01 M. In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1Name: Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin).

Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1) belongs to organobromine compounds. Most of the natural organobromine compounds are produced by marine organisms, and several brominated metabolites with antibacterial, antitumor, antiviral, and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Name: Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis, characterization, and remarkable biological properties of cyclodextrins bearing guanidinoalkylamino and aminoalkylamino groups on their primary side was written by Mourtzis, Nikolaos;Paravatou, Maria;Mavridis, Irene M.;Roberts, Michael L.;Yannakopoulou, Konstantina. And the article was included in Chemistry – A European Journal in 2008.HPLC of Formula: 53784-83-1 This article mentions the following:

The introduction of aminoalkylamino and guanidinoalkylamino substituents on the primary side of β- and γ-cyclodextrin (CDs) resulted in a series of novel compounds that were extensively characterized by NMR spectroscopy and mass spectrometry. Bromination of the primary side of β- and γ-CD, and reaction with neat alkylene diamines at a pressure of 7 atm afforded aminoalkylamino derivatives that were then guanylated at the primary amino group to give the corresponding guanidinoalkylamino-CDs. These compounds are water soluble and display pK_a values that allow them to be mostly protonated at neutral pH; for example, pK_a1 âˆ?.4 and pK_a2 âˆ?.5 for the aminoethylamino-β-CD and pK_a1 âˆ?.8 and pK_a2 âˆ?1.0 for the guanidinoethylamino-β-CD. The title CDs are rigid, cyclic α-D-glucopyranose oligomers (heptamers or octamers) with branches that resemble lysine and arginine side chains that enable multiple interactions with suitable substrates. Thus, they bear similarities to known cell-penetrating peptides. Indeed, the compounds were found to cross the membranes of HeLa cells and penetrate inside the cytoplasm quickly, the guanidinylated ones within 15 min, as shown by fluorescence microscopy using fluorescein-labeled derivatives The toxicity of the compounds, measured by performing MTT tests, ranged from 50 to 300 μM. Furthermore, some of the aminated CDs could facilitate the transfection of DNA expressing the green fluorescent protein (GFP) in HEK 293T cells, with effectiveness comparable to the com. agent Lipofectamine 2000. CD, at. force microscopy and electrophoresis experiments confirmed the strong interaction of the compounds with DNA. Because of their carbohydrate, non-peptide nature the title compounds are not anticipated to be enzymically labile or immunogenic, and thus they fulfill many of the criteria for non-hazardous transport vectors in biol. and pharmaceutical applications. In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1HPLC of Formula: 53784-83-1).

Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.HPLC of Formula: 53784-83-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Nitric Oxide-Releasing Cyclodextrins was written by Jin, Haibao;Yang, Lei;Ahonen, Mona Jasmine R.;Schoenfisch, Mark H.. And the article was included in Journal of the American Chemical Society in 2018.Synthetic Route of C42H63Br7O28 This article mentions the following:

A series of secondary amine-modified cyclodextrin (CD) derivatives were synthesized with diverse exterior terminal groups (i.e., hydroxyl, Me, methoxyl, and primary amine). Subsequent reaction with nitric oxide (NO) gas under alk. conditions yielded N-diazeniumdiolate-modified CD derivatives Adjustable NO payloads (0.6-2.4 μmol/mg) and release half-lives (0.7-4.2 h) were achieved by regulating both the amount of secondary amine precursors and the functional groups around the NO donor. The bactericidal action of these NO-releasing cyclodextrin derivatives was evaluated against Pseudomonas aeruginosa, a Gram-neg. pathogen with antibacterial activity proving dependent on both the NO payload and exterior modification. Materials containing a high d. of NO donors or primary amines exhibited the greatest ability to eradicate P. aeruginosa. Of the materials prepared, only the primary amine-terminated hepta-substituted CD derivatives exhibited toxicity against mammalian L929 mouse fibroblast cells. The NO donor-modified CD was also capable of delivering promethazine, a hydrophobic drug, thus demonstrating potential as a dual-drug releasing therapeutic. In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1Synthetic Route of C42H63Br7O28).

Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1) belongs to organobromine compounds. Most of the natural organobromine compounds are produced by marine organisms, and several brominated metabolites with antibacterial, antitumor, antiviral, and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Synthetic Route of C42H63Br7O28

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Non-ionic thiolated cyclodextrins – the next generation was written by Moghadam, Ali;Ijaz, Muhammad;Asim, Mulazim Hussain;Mahmood, Arshad;Jelkmann, Max;Matuszczak, Barbara;Bernkop-Schnuerch, Andreas. And the article was included in International Journal of Nanomedicine in 2018.Synthetic Route of C42H63Br7O28 This article mentions the following:

The current study was aimed at developing a novel mucoadhesive thiolated cyclodextrin (CD) without ionizable groups and an intact ring backbone for drug delivery. Thiolated beta CD (β-CD) was prepared through bromine substitution of its hydroxyl groups followed by replacement to thiol groups using thiourea. The thiolated β-CD was characterized in vitro via dissolution studies, cytotoxicity studies, mucoadhesion studies on freshly excised porcine intestinal mucosa, and inclusion complex formation with miconazole nitrate. Thiolated β-CDs namely β-CD-SH₆₀₀ and β-CD-SH₁₂₀₀ displayed 558.66 ± 78 and 1,163.45 ± 96 μmol thiol groups per g of polymer, resp. Stability constant (Kc) of 190 M^-1 confirmed the inclusion complex formation of miconazole nitrate with β-CD-SH. Inclusion complexes of β-CD-SH₆₀₀ and β-CD-SH₁₂₀₀ resulted in 157- and 257-fold increased solubility of miconazole nitrate, resp. In addition, more than 80% of thiol groups were stable even after 6 h at pH 5. Both β-CD-SH compounds showed at least 1.3-fold improved solubility in water. In contrast to cationic thiolated CDs of the first generation, both thiomers showed no significant cytotoxicity. The mucoadhesive properties of the new thiolated CDs were 39.73- and 46.37-fold improved, resp. These results indicate that β-CD-SH might provide a new favorable tool for delivery of poorly soluble drugs providing a prolonged residence time on mucosal surfaces. In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1Synthetic Route of C42H63Br7O28).

Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.Synthetic Route of C42H63Br7O28

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Self-Assembly of Amphiphilic Anthracene-Functionalized β-Cyclodextrin (CD-AN) through Multi-Micelle Aggregation was written by Zhang, Yuannan;Xu, Hongjie;Ma, Xiaodong;Shi, Zixing;Yin, Jie;Jiang, Xuesong. And the article was included in Macromolecular Rapid Communications in 2016.Application of 53784-83-1 This article mentions the following:

Multi-micelle aggregation (MMA) mechanism is widely acknowledged to explicate large spherical micelles self-assembly, but the process of MMA during self-assembly is hard to observe. Herein, a novel kind of strong, regular microspheres fabricated from self-assembly of amphiphilic anthracene-functionalized β-cyclodextrin (CD-AN) via Cu(I)-catalyzed azide-alkyne click reactions is reported. The obtained CD-AN amphiphiles can self-assemble in water from primary core-shell micelles to secondary aggregates with the diameter changing from several tens nm to around 600-700 nm via MMA process according to the images of SEM, transmission electron microscopy, and at. force microscopy as well as the dynamic light scattering measurements, followed by further crosslinking through photo-dimerization of anthracene. What merits special attention is that such photo-crosslinked self-assemblies are able to disaggregate reversibly into primary nanoparticles when changing the solution conditions, which is benefited from the designed regular structure of CD-AN and the rigid ranging of anthracene during assembly, thus confirming the process of MMA. In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1Application of 53784-83-1).

Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1) belongs to organobromine compounds. Many of the organo bromine compounds are relatively nonpolar. Bromine is more electronegative than carbon (2.8 vs 2.5) and hence the carbon in a carbon–bromine bond is electrophilic in nature. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Application of 53784-83-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Intrinsic Turn-On Response of Thioflavin T in Complexes was written by Kung, Jocky C. K.;Vurgun, Nesrin;Chen, JoAnn C.;Nitz, Mark;Jockusch, Rebecca A.. And the article was included in Chemistry – A European Journal in 2020.SDS of cas: 53784-83-1 This article mentions the following:

The fluorescence enhancement (“turn-on”) response of the amyloid-sensing dye thioflavin T (ThT) is examined in vacuo, where solvent interactions are absent. “Upon the complexation of ThT with a derivatized β-cyclodextrin, heptakis-[6-deoxy-6-(3-sulfanylpropanoic acid)]-β-cyclodextrin, turn-on responses in both the gas phase and solution phase were observed In contrast, turn-on response was not detected when ThT was bound to gaseous cucurbit[7]uril or human telomeric DNA 22AG, whereas clear turn-on response occurs in solution The observed difference in turn-on response in the gas phase emphasizes the key interplay between chromophore, host and solvent and demonstrates the utility of gas-phase spectroscopy to tease out the balance among intermol. forces driving the behavior of important chromophores in solution In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1SDS of cas: 53784-83-1).

Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1) belongs to organobromine compounds. Most of the natural organobromine compounds are produced by marine organisms, and several brominated metabolites with antibacterial, antitumor, antiviral, and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.SDS of cas: 53784-83-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Mechanistic Understanding of a Robust and Scalable Synthesis of Per(6-deoxy-6-halo)cyclodextrins, Versatile Intermediates for Cyclodextrin Modification was written by Zultanski, Susan L.;Kuhl, Nadine;Zhong, Wendy;Cohen, Ryan D.;Reibarkh, Mikhail;Jurica, Jon;Kim, Jungchul;Weisel, Lauren;Ekkati, Anil R.;Klapars, Artis;Gauthier, Donald R. Jr.;McCabe Dunn, Jamie M.. And the article was included in Organic Process Research & Development in 2021.Electric Literature of C42H63Br7O28 This article mentions the following:

Cyclodextrin (CD) perfunctionalization reactions are challenging to study because they proceed through a number of regioisomeric intermediates, thus warranting creative approaches to understanding the reaction mechanism. Particularly useful perfunctionalization targets are per(6-deoxy-6-halo)cyclodextrins. Their standard synthesis entails selective S_N2 halogenation at their primary alcs. using a Vilsmeier reagent, but this requires a strongly basic quench to unmask the Vilsmeier-capped secondary alcs. Herein we present an alternative and simple acidic hydrolytic quench that utilizes existing HX in the end-of-reaction solution and requires only the addition of water. We performed a detailed mechanistic investigation of the new quench, and a central feature was the use of proton sponge to develop an ¹H NMR titration method for HX in organic solvent. This method was used to both quantify and remove HX in the prequenched reaction solution The HX-free prequenched solution enabled us to (1) identify sensitive intermediates during the quench, (2) quantify all of the reaction byproducts, and (3) determine that HX is critical for hydrolysis. We then studied the halogenation reaction, wherein the new acidic quench facilitated high-throughput experimentation, using mass spectrometry as well as Design of Experiments with automated reaction profiling. Through this, we were able to establish robustness and understand the complex effects of Vilsmeier equivalent and temperature on the reaction outcome. In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1Electric Literature of C42H63Br7O28).

Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Electric Literature of C42H63Br7O28

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary