3068-32-4Relevant articles and documents
Glycosylation chemistry promoted by iodine monobromide: Efficient synthesis of glycosyl bromides from thioglycosides, and O-glycosides from 'disarmed' thioglycosides and glycosyl bromides
Kartha, K. P. Ravindranathan,Field, Robert A.
, p. 8233 - 8236 (1997)
Iodine monobromide has been found to be an efficient reagent for the conversion of both 'armed' and 'disarmed' thioglycosides (-SMe, -SPr(i), - SPh) into glycosyl bromides. This reagent is compatible with most common protecting groups, and O-glycosidic linkages. The additional potency of I- Br, compared to iodine, as an iodonium ion source also permits the glycosylation of sugar alcohols by 'disarmed' glycosyl bromides and thioglycosides.
Synthesis of glycoside derivatives of hydroxyanthraquinone with ability to dissolve and inhibit formation of crystals of calcium oxalate. Potential compounds in kidney stone therapy
Frackowiak, Anna,Skibiński, Przemys?aw,Gawe?, Wies?aw,Zaczyńska, Ewa,Czarny, Anna,Gancarz, Roman
, p. 1001 - 1007 (2010)
Synthesis of glycosyl derivatives of hydroxyanthraquinones (6-10) potentially useful for kidney stone therapy is presented. These compounds were analyzed as inhibitors of calcium oxalate crystals formation as well as substances with the ability of dissolving crystalline calcium oxalate. In addition, the effect of the compounds obtained on real kidney stones was analyzed by ex vivo tests. The tests on L929 and A545 cell lines have shown that the compounds obtained were not cytotoxic.
Probing bacterial-toxin inhibition with synthetic glycopolymers prepared by tandem post-polymerization modification: Role of linker length and carbohydrate density
Richards, Sarah-Jane,Jones, Mathew W.,Hunaban, Mark,Haddleton, David M.,Gibson, Matthew I.
, p. 7812 - 7816 (2012)
Probing the depths: A tandem post-polymerization modification strategy was used to systematically probe the multivalent inhibition of a bacterial toxin as a function of linker length (see scheme), carbohydrate density, and glycopolymer chain length. Guided by structural-biology information, the binding-pocket depth of the toxin was probed and used as a means to specifically improve inhibition of the toxin by the glycopolymer. Copyright
N-Oxyamide-linked glycoglycerolipid coated AuNPs for receptor-targeting imaging and drug delivery
Chen, Na,Yu, Zhi-Hao,Zhou, Dan,Hu, Xi-Le,Zang, Yi,He, Xiao-Peng,Li, Jia,Xie, Juan
, p. 2284 - 2287 (2016)
The synthesis of a series of new N-oxyamide-linked glycoglycerolipids and their assembly with gold nanoparticles for receptor-targeting imaging and drug delivery are reported.
Design, Synthesis, biological investigations and molecular interactions of triazole linked tacrine glycoconjugates as Acetylcholinesterase inhibitors with reduced hepatotoxicity
Ahmed, Ajaz,Bhagat, Kavita,Choudhary, Sushil,Kaur Gulati, Harmandeep,Kumar, Ajay,Kumar, Nitish,Mukherjee, Debaraj,Singh Bedi, Preet Mohinder,Singh, Atamjit,Singh, Harbinder,Vir Singh, Jatinder
, (2021/11/23)
Tacrine is a known Acetylcholinesterase (AChE) inhibitors having hepatotoxicity as main liability associated with it. The present study aims to reduce its hepatotoxicity by synthesizing tacrine linked triazole glycoconjugates via Huisgen's [3 + 2] cycloaddition of anomeric azides and terminal acetylenes derived from tacrine. A series of triazole based glycoconjugates containing both acetylated (A-1 to A-7) and free sugar hydroxyl groups (A-8 to A-14) at the amino position of tacrine were synthesized in good yield taking aid from molecular docking studies and evaluated for their in vitro AChE inhibition activity as well as hepatotoxicity. All the hybrids were found to be non-toxic on HePG2 cell line at 200 μM (100 % cell viability) as compared to tacrine (35 % cell viability) after 24 h of incubation period. Enzyme kinetic studies carried out for one of the potent hybrids in the series A-1 (IC50 0.4 μM) revealed its mixed inhibition approach. Thus, compound A-1 can be used as principle template to further explore the mechanism of action of different targets involved in Alzheimer's disease (AD) which stands as an adequate chemical probe to be launched in an AD drug discovery program.
Synthesis of malformin-A1, C, a glycan, and an aglycon analog: Potential scaffolds for targeted cancer therapy
Andreana, Peter R.,Hossain, Farzana,Nishat, Sharmeen
, (2022/02/21)
Improvement in therapeutic efficacy while reducing chemotherapeutic side effects remains a vital objective in synthetic design for cancer treatment. In keeping with the ethos of therapeutic development and inspired by the Warburg effect for augmenting biological activities of the malformin family of cyclic-peptide natural products, specifically anti-tumor activity, a β-glucoside of malformin C has been designed and synthesized utilizing precise glycosylation and solution phase peptide synthesis. We optimized several glycosylation procedures utilizing different donors and acceptors. The overarching goal of this study was to ensure a targeted delivery of a glyco-malformin C analog through the coupling of D-glucose moiety; selective transport via glucose transporters (GLUTs) into tumor cells, followed by hydrolysis in the tumor microenvironment releasing the active malformin C a glycon analog. Furthermore, total synthesis of malformin C was carried out with overall improved strategies avoiding unwanted side reactions thus increasing easier purification. We also report on an improved solid phase peptide synthesis protocol for malformin A1.
Galactose-clicked curcumin-mediated reversal of meropenem resistance among klebsiella pneumoniae by targeting its carbapenemases and the AcrAB-TolC efflux system
Yadav, Shivangi,Singh, Ashish Kumar,Agrahari, Anand K.,Pandey, Akhilesh Kumar,Gupta, Munesh Kumar,Chakravortty, Dipshikha,Tiwari, Vinod Kumar,Prakash, Pradyot
, (2021/04/23)
In over eighty years, despite successive antibiotics discoveries, the rapid advent of multidrug resistance among bacterial pathogens has jolted our misapprehension of success over them. Resistance is spreading faster than the discovery of new antibiotics/antimicrobials. Therefore, the search for better antimicrobials/additives becomes prudent. A water-soluble curcumin derivative (Curaq) was synthesised, employing a Cu (I) catalysed 1, 3-cyclo addition reaction; it has been evaluated as a potential treatment for multidrug-resistant isolates and as an antibiotic adjuvant for meropenem against hypervirulent multidrug-resistant Klebsiella pneumoniae isolates. We also investigated its solubility and effect over carbapenemase activity. Additionally, we investigated its impact on the AcrAB-TolC system. We found that Curaq inhibited bacterial growth at a minimal concentration of 16 ug/mL; at a 32 ug/mL concentration, it killed bacterial growth completely. Only nine (9.4%) Klebsiella isolates were sensitive to meropenem; however, after synergising with Curaq (8 ug/mL), 85 (88.54%) hvKP isolates became sensitive to the drug. The Curaq also inhibited the AcrAB-TolC efflux system at 1 ug/mL concentration by disrupting the membrane potential and causing depolarisation. The kinetic parameters obtained also indicated its promise as a carbapenemase inhibitor. These results suggest that Curaq can be an excellent drug candidate as a broad-spectrum antibacterial and anti-efflux agent.
