112247-07-1Relevant academic research and scientific papers
Microwave-assisted synthesis of calix[4]resorcinarenes
Hedidi, Madani,Hamdi, Safouane M.,Mazari, Tassadit,Boutemeur, Baya,Rabia, Cherifa,Chemat, Farid,Hamdi, Maamar
, p. 5652 - 5655 (2006)
Microwave-assisted synthesis of calix[4]resorcinarenes by cyclocondensation of various aldehydes and resorcinol catalysed by 12-tungstophosphoric acid type Keggin (H3PW12O40·13H2O) or concentrated HCl is describ
Monomeric, dimeric and hexameric resorcin[4]arene assemblies with alcohols in apolar solvents
Schnatwinkel, Bjoern,Stoll, Ion,Mix, Andreas,Rekharsky, Mikhail V.,Borovkov, Victor V.,Inoue, Yoshihisa,Mattay, Jochen
, p. 3873 - 3875 (2008)
Resorcin[4]arenes in an apolar solvent containing alcohols exist in three forms of self-assembled aggregates which have been characterised by the technique of diffusion NMR spectroscopy. The Royal Society of Chemistry.
The absolute configuration of an inherently chiral phosphonatocavitand and its use toward the enantioselective recognition of L-adrenaline
Vachon, Jerome,Harthong, Steven,Dubessy, Beatrice,Dutasta, Jean-Pierre,Vanthuyne, Nicolas,Roussel, Christian,Naubron, Jean-Valere
, p. 1534 - 1541 (2010)
An inherently chiral ABii diphosphonato cavitand (±)-4 bearing a single quinoxaline bridging moiety was synthesized and resolved by chiral HPLC. Its chiroptical properties were investigated and VCD experiments allowed the determination of its absolute con
Assembly and exchange of resorcinarene capsules monitored by fluorescence resonance energy transfer
Barrett, Elizabeth S.,Dale, Trevor J.,Rebek Jr., Julius
, p. 3818 - 3819 (2007)
Resorcinarenes were functionalized with fluorophores and fluorescence resonance energy transfer (FRET) was employed as a tool to probe the dynamic behavior of hydrogen-bonded hexameric assemblies at nanomolar concentrations. The encapsulation of a fluorescent guest inside the capsule made it possible to observe FRET across the mechanical boundary of the hexameric assembly. Copyright
Pore formation in phospholipid bilayers by amphiphilic cavitands
Elidrisi, Iman,Negin, Saeedeh,Bhatt, Pralav V.,Govender, Thavendran,Kruger, Hendrick G.,Gokel, George W.,Maguire, Glenn E. M.
, p. 4498 - 4506 (2011)
Five new cavitands were prepared that have four pendant n-undecyl chains and "headgroups" connected by 2-carbon spacers. The headgroups were ～OCH2CONH-Ala-OCH3, 1; ～OCH2CONH-Phe- OCH3, 2; ～OCH2CONH-Ala-OH, 3; ～OCH 2CONH-Phe-OH, 4; and ～OCH2CONHCH2CH 2-thyminyl, 5. Pore formation by each cavitand was studied by use of the planar bilayer conductance experiment. All five compounds were found to form pores in asolectin bialyer membranes. Compounds 1-3 behaved in a generally similar fashion and exhibited open-close dynamics. Compounds 4 and 5 formed pores more rapidly, were more dynamic, and led more quickly to membrane rupture. Differences in the ion transport activity are rationalized in terms of structure and aggregate cavitand assemblies.
Calixarene-mediated liquid-membrane transport of choline conjugates
Adhikari, Birendra Babu,Fujii, Ayu,Schramm, Michael P.
, p. 2972 - 2979 (2014)
A series of supramolecular calixarenes efficiently transport distinct molecular species through a liquid membrane when attached to a receptor-complementary choline handle. Calix[6]arene hexacarboxylic acid was highly effective at transporting different target molecules against a pH gradient. Both carboxylic-and phosphonic-acid-functionalized calix[4]arenes effect transport without requiring a pH or ion gradient. NMR binding studies, two-phase solvent extraction, and three-phase transport experiments reveal the necessary and subtle parameters to effect the transport of molecules attached to a choline "handle". On the other hand, rescorin[4]arene cavitands, which have similar guest recognition profiles, did not transport guest molecules. These developments reveal new approaches towards attempting synthetic-receptor-mediated selective small-molecule transport in vesicular and cellular systems.
Emulsification of calix[4]arenes bearing four chains and transportation of cesium ion through liquid surfactant-membrane
Koide, Yoshifumi,Sato, Hirotaka,Shosenji, Hideto,Yamada, Kimiho
, p. 315 - 319 (1996)
Resorcinol-type calix[4]arenes bearing four alkyl side chains ([4]Ar-Rn) have been applied as a liquid surfactant-membrane in the concentration process of Cs+. [4]Ar-Rn formed a highly stable water-in-oil (w/o) emulsion fo
Bolaforms with Fourteen Galactose Units: A Proposed Site-Directed Cohesion of Cancer Cells
Menger, Fredric M.,Bian, Jianwei,Sizova, Elena,Martinson, Deborah E.,Seredyuk, Victor A.
, p. 261 - 264 (2004)
(Matrix presented) The multistep synthesis of a calixarene joined to a second calixarene via a long spacer is described. Since each calixarene bears multiple galactose-based units (known to bind strongly to rat hepatoma cells), there existed the possibility of cross-linking the cancer cells into a network. The compounds did not serve this purpose, a fact potentially correctable by adjusting or rigidifying the spacer. Formation of a cancer net around a solid tumor remains a viable approach to retarding growth and/or inhibiting metastasis.
Requirements for Terpene Cyclizations inside the Supramolecular Resorcinarene Capsule: Bound Water and Its Protonation Determine the Catalytic Activity
Merget, Severin,Catti, Lorenzo,Piccini, Giovannimaria,Tiefenbacher, Konrad
, p. 4400 - 4410 (2020)
The elucidation of the requirements for efficient catalysis within supramolecular host systems is an important prerequisite for developing novel supramolecular catalysts. The resorcinarene hexamer has recently been shown to be the first supramolecular catalyst to promote the tail-to-head terpene cyclization in a biomimetic fashion. We herein present the synthesis of a number of resorcinarene-based macrocycles composed of different ratios of resorcinol and pyrogallol units capable of self-assembly and compare the corresponding assemblies regarding their catalytic activity in the cyclization of monoterpenes. The assemblies were investigated in detail with respect to a number of properties including the encapsulation of substrate and ion pairs, the structural incorporation of water, and the response to externally added acid (HCl). The results obtained strongly indicate that water incorporated into the hydrogen-bond network of the self-assembled structure plays an integral role for catalysis, effectively acting as a proton shuttle to activate the encapsulated substrate. These findings are also supported by molecular dynamics simulations, providing further insight into the protonation pathway and the relative energies of the intermediates involved.
New lipophilic macrocyclic host molecules containing multiple ferrocenyl redox-active centres
Beer, Paul D.,Smythe, Andrew C.,Tite, E. Louise,Ibbotson, Arthur
, p. C11 - C14 (1989)
The syntheses and electrochemistry of two novel lipophilic macrocyclic host molecules containing eight and twelve ferrocene redox-active centres are described.
