18523-48-3Relevant academic research and scientific papers
Rhenium(I) polypyridine dibenzocyclooctyne complexes as phosphorescent bioorthogonal probes: Synthesis, characterization, emissive behavior, and biolabeling properties
Choi, Alex Wing-Tat,Liu, Hua-Wei,Lo, Kenneth Kam-Wing
, p. 2 - 10 (2015)
We report the development of rhenium(I) polypyridine complexes appended with a dibenzocyclooctyne (DIBO) moiety as bioorthogonal probes for azide-modified biomolecules. Three phosphorescent rhenium(I) polypyridine DIBO complexes [Re(N^N)(CO)3(py-C6-DIBO)][CF3SO3] (py-C6-DIBO = 3-(N-(6-(3,4:7,8-dibenzocyclooctyne-5-oxycarbonylamino)hexyl)aminocarbonyl)pyridine; N^N = 1,10-phenanthroline (phen) (1a), 3,4,7,8-tetramethyl-1,10-phenanthroline (Me4-phen) (2a), 4,7-diphenyl-1,10-phenanthroline (Ph2-phen) (3a)) and their DIBO-free counterparts [Re(N^N)(CO)3(py-C6-BOC)][CF3SO3] (py-C6-BOC = 3-(N-(6-(tert-butoxycarbonylamino)hexyl)aminocarbonyl)pyridine; N^N = phen (1b), Me4-phen (2b), Ph2-phen (3b)) were synthesized and characterized. Upon photoexcitation, all the complexes displayed intense and long-lived yellow triplet metal-to-ligand charge-transfer (3MLCT) (dπ(Re) → π?(N^N)) emission. The DIBO complexes underwent facile reactions with benzyl azide in methanol at 298 K with second-order rate constants (k2) in the range of 0.077 to 0.091 M- 1 s- 1. As revealed from SDS-PAGE analysis, the DIBO complexes can selectively label azide-modified proteins and the resulting bioconjugates displayed strong phosphorescence upon photoexcitation. Results of inductively coupled plasma mass spectrometry (ICP-MS) and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assays indicated that the DIBO complexes accumulated in Chinese Hamster Ovary (CHO) cells with considerable cytotoxic activity. Upon incubation of CHO cells with these complexes, relatively weak intracellular emission was observed. In contrast, upon pretreatment of the cells with 1,3,4,6-tetra-O-acetyl-N-azidoacetyl-d-mannosamine (Ac4ManNAz), intense emission was observed from the cell membrane and some internal compartments. The results suggest that the DIBO complexes are promising candidates for imaging azide-labeled biomolecules.
Moxifloxacin/Gatifloxacin-1,2,3-triazole-isatin Hybrids with Hydrogen-Bond Donor and Their In Vitro Anticancer Activity
Chen, Rongxing,Zhang, Hao,Ma, Tianwei,Xue, Huarui,Miao, Zhong,Chen, Liyan,Shi, Xiangkui
, p. 2691 - 2694 (2019)
A series of novel moxifloxacin/gatifloxacin-1,2,3-triazole-isatin hybrids (8a–i) were designed, synthesized, and screened for their in vitro anticancer activity in this paper. All of the synthesized hybrids were active against A549 and HepG2 cancer cell lines, whereas the parent drugs moxifloxacin and gatifloxacin were devoid of activity. Among them, hybrid 8i (IC50: 41.1–98.3 μM) showed considerable activity against A549, HepG2, and MCF-7 cancer cell lines, and it was no inferior to Vorinostat (IC50: 64.32 to >100 μM) against the three cancer cell lines. Thus, this kind of hybrids has potentiality for discovery of new anticancer candidates for clinical deployment in the control and eradication of cancers.
On-resin cyclization of peptide ligands of the Vascular Endothelial Growth Factor Receptor 1 by copper(I)-catalyzed 1,3-dipolar azide-alkyne cycloaddition
Goncalves, Victor,Gautier, Benoit,Regazzetti, Anne,Coric, Pascale,Bouaziz, Serge,Garbay, Christiane,Vidal, Michel,Inguimbert, Nicolas
, p. 5590 - 5594 (2007)
Cyclic peptides were obtained, on-resin, by the copper (I) catalysed 1,3-dipolar cycloaddition of azides and alkynes. The reaction led exclusively to the formation of the expected cyclomonomeric products which acted as ligands of the Vascular Endothelial Growth Factor receptor 1.
Novel N-acetyl-Glycol-split heparin biotin-conjugates endowed with anti-heparanase activity
Esposito, Emiliano,Vlodavsky, Israel,Barash, Uri,Roscilli, Giuseppe,Milazzo, Ferdinando M.,Giannini, Giuseppe,Naggi, Annamaria
, (2020)
Heparanase is regarded as a promising target for anticancer drugs and Ronepastat is one of the most promising heparanase inhibitors insert in clinical study for Multiple Myeloma Therapy. To improve its pharmacokinetic/pharmacodynamic profile, as well to have an antidote able to neutralize its activity in case of over dosages or intolerance, a new class of its derivatives was obtained inserting non-carbohydrate moieties of different length between the polysaccharide chain and biotin or its derivatives. In vitro these novel derivatives maintain the anti-heparanase activity without induced toxicity. The newly synthesized compounds retained the ability to attenuate the growth of CAG myeloma tumors in mice with potency similar, or in one case even higher than that of the reference compound Roneparstat as well as inhibited metastatic dissemination (lung colonization) of murine B16-F10 melanoma cells in vivo.
Synthesis and Properties of 3-Azido-2,2-bis(azidomethyl)propyl 2-Azidoacetate: A Potential Azido Ester Plasticizer
Wang, Yinglei,Liu, Yajing,Lu, Tingting,Gao, Fulei,Zhao, Baodong
, p. 107 - 111 (2019)
This study reports the synthesis and characterization of a novel azido ester plasticizer, 3-azido-2,2-bis(azidomethyl)propyl 2-azidoacetate (ABAMPA), with good yield and high purity. The density, impact sensitivity, friction sensitivity, thermal decomposition temperature and glass transition temperature were determined to be 1.326 g ? cm?3, 16 J, 324 N, 235.9 °C and ?50.4 °C, respectively. The plasticizing effect of ABAMPA on glycidyl azide polymer (GAP) was calculated by molecular dynamics, the solubility parameter difference value was 1.7(J ? cm?3)0.5, and the glass transition temperature of GAP was reduced from ?35 °C to ?43 °C when the weight ratio of ABAMPA and GAP was 50 : 50. The new azido ester exhibits high energy, remarkable thermostability and good compatibility with GAP, which indicates that it would have potential application in explosive and propellant formulations.
Supramolecular dendrimers: Convenient synthesis by programmed self-assembly and tunable thermoresponsivity
Ghosh, Partha S.,Hamilton, Andrew D.
, p. 2361 - 2365 (2012)
We report here the noncovalent synthesis of thermosensitive dendrimers. Short oligoguanosine strands were linked to the focal point of a dendron by using "click chemistry", and quadruplex formation was used to drive the self-assembly process in the presence of metal ions. The dynamic nature of these noncovalent assemblies can be exploited to create combinatorial libraries of dendrimers as demonstrated by the co-assembly of two components. These supramolecular dendrimers showed thermoresponsive behavior that can be tuned by varying the templating cations or the number of guanines in the oligonucleotide strand. Copyright
Light-induced tryptophan radical generation in a click modular assembly of a sensitiser-tryptophan residue
Sheth, Sujitraj,Baron, Aurelie,Herrero, Christian,Vauzeilles, Boris,Aukauloo, Ally,Leibl, Winfried
, p. 1074 - 1078 (2013)
Click chemistry was used as an efficient method to covalently attach a chromophore to an amino acid. Such easily prepared model systems allow for time-resolved studies of one-electron oxidation reactions by the excitation of the chromophore by a laser flash. The model complex ruthenium-tryptophan (Ru-Trp) has been synthesised and studied for its photophysical and electrochemical properties. Despite a small driving force of less than 100 meV, excitation with a laser flash results in fast internal electron transfer leading to the formation of the protonated radical (TrpH+). At neutral pH electron transfer is followed by deprotonation to form the neutral Trp radical with the rate depending on the concentration of water acting as the proton acceptor. The formation of the tryptophan radical was confirmed by EPR. The Royal Society of Chemistry and Owner Societies 2013.
A Merged Aldol Condensation, Alkene Isomerization, Cycloaddition/Cycloreversion Sequence Employing Oxazinone Intermediates for the Synthesis of Substituted Pyridines
Williamson, Jill B.,Smith, Emily R.,Scheerer, Jonathan R.
, p. 1170 - 1172 (2017)
A domino reaction sequence has been evaluated that begins with union of novel dihydrooxazinone precursors with 2-alkynyl-substituted benzaldehyde components through aldol condensation. Ensuing operations, including alkene isomerization, Diels-Alder, and retrograde Diels-Alder with loss of CO 2 occurs in the same reaction vessel to provide polysubstituted tricyclic pyridine products.
Magnetic silica nanoparticle-supported copper complex as an efficient catalyst for the synthesis of novel triazolopyrazinylacetamides with improved antibacterial activity
Asgari, Mohammad Sadegh,Sepehri, Saghi,Bahadorikhalili, Saeed,Ranjbar, Parviz Rashidi,Rahimi, Rahmatollah,Gholami, Ahmad,Kazemi, Aboozar,Khoshneviszadeh, Mehdi,Larijani, Bagher,Mahdavi, Mohammad
, p. 488 - 494 (2020)
[Figure not available: see fulltext.] A novel superparamagnetic iron oxide modified with copper via 2-aminobenzamide is synthesized by the modification of Fe3O4@SiO2 with amine, followed by the reaction with isatoic anhydride. The catalyst is fully characterized by various methods. The catalytic activity of the catalyst is evaluated in the synthesis of a series of novel N-alkyl-2-aryl-2-(6-oxo-6,7-dihydro[1,2,3]triazolo[1,5-a]pyrazin-5(4H)-yl)acetamide analogs. Antibacterial activity of the synthesized compounds is evaluated. The catalyst is recoverable and shows excellent reusability in 10 sequential runs.
Synthesis and biological evaluation of moxifloxacin-acetyl-1,2,3-1H-triazole-methylene-isatin hybrids as potential anti-tubercular agents against both drug-susceptible and drug-resistant Mycobacterium tuberculosis strains
Gao, Feng,Chen, Zijian,Ma, Long,Fan,Chen, Linjun,Lu, Guangming
, p. 648 - 655 (2019)
Herein, synthesis and biological evaluation of fourteen moxifloxacin-acetyl-1,2,3-1H-triazole-methylene-isatin hybrids as potential anti-tubercular agents against both drug-susceptible (MTB H37Rv), rifampicin-resistant and multidrug-resistant Mycobacterium tuberculosis strains were reported, and cytotoxicity towards VERO cells as well as inhibitory activity against MTB DNA gyrase were also discussed in this paper. The structure-activity relationship and structure-cytotoxicity relationship demonstrated that substituents on the C-3 and C-5/C-7 positions of isatin framework were closely related with the anti-mycobacterial activity and cytotoxicity. The most active hybrids 8h and 8l (MIC: 0.12–0.5 μg/mL) showed excellent activity which was no inferior to the parent moxifloxacin against the tested drug-susceptible, rifampicin-resistant and multidrug-resistant Mycobacterium tuberculosis strains, demonstrating their potential application as novel anti-tubercular candidates.
