Molecular Umbrellas

Janout, Václav; Lanier, Marion; Regen, Steven L.

doi:10.1021/ja953261v

Cited by 85 publications

(63 citation statements)

References 7 publications

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“…Regen's group introduced several years ago [29,30] the concept of molecular umbrellas constituted of several strerols linked together through a central scaffold to the compound of interest. When a hydrophilic compound is in a hydrophilic environment, the umbrella is in a fully exposed conformation in which the hydrophobic faces of the sterols interact together favouring hydrophilic interactions between hydrophilic faces and the solvent.…”

Section: Assisted On Delivery With "Molecular Umbrellas"mentioning

confidence: 99%

Chemical Modifications to Improve the Cellular Uptake of Oligonucleotides

Debart¹,

Abes²,

Deglane³

et al. 2007

CTMC

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Specific control of gene expression by synthetic oligonucleotides (ON) is now widely used for target validation but clinical applications are limited by ON bioavailability. Moreover, most currently used strategies for physical and chemical delivery cannot be easily implemented in vivo. This article reviews new strategies which appear promising for ON delivery. The first part deals with ON chemical modifications aiming at improving cellular uptake as for instance the grafting of cationic groups on the ON backbone. The second part concerns ON conjugation to cell penetrating peptides.

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Section: Assisted On Delivery With "Molecular Umbrellas"mentioning

confidence: 99%

Chemical Modifications to Improve the Cellular Uptake of Oligonucleotides

Debart¹,

Abes²,

Deglane³

et al. 2007

CTMC

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“…Several cholic acid derived facial amphiphiles have been reported to improve the permeability of membranes including bacterial cell wall [8]. Cholic acid and deoxycholic acid have attracted significant attention due to availability and the orientation of the hydroxy groups that may be exploited in podant-type receptors [9,10], linear dimeric hosts [11,12] or facial amphiphiles [13,14]. In addition, bile acids are natural ligands specifically recognised by hepatic cells and are amphiphilic molecules that undergo a biological recycling during enterohepatic circulation [8,15,16].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antimicrobial activity of cholic acid hydrazone analogues

Rasras

Al‐Tel

Al‐Aboudi

et al. 2010

European Journal of Medicinal Chemistry

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“…However, the vast majority are either head-to-head 18,19 or tail-to-tail 20,21 linked derivatives, and several others are linked through positions on the B or C rings, 22-25 none of which would be suitable for our purposes. A limited number of head-to-tail linked derivatives have been reported, consisting of linked bile acid components with linkers of varying lengths and functional group patterns (Figure 3), including some that are related to the linker selected in our primary design (Figure 5).…”

Section: Resultsmentioning

confidence: 99%

Design and synthesis of a crosslinker for studying intracellular steroid trafficking pathways

Byrd

Arieno

Kennelly

et al. 2015

Bioorganic & Medicinal Chemistry

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A crosslinker was designed and synthesized as a molecular tool for potential use in probing the intracellular trafficking pathways of steroids. The design was guided by computational modeling based upon a model for the transfer of cholesterol between two proteins, NPC1 and NPC2. These proteins play critical roles in the transport of low-density lipoprotein-derived cholesterol from the lumen of lysosomes to other subcellular compartments. Two modified cholesterol residues were covalently joined by a tether based on molecular modeling of the transient interaction of NPC1 and NPC2 during the transfer of cholesterol from the binding site of one of these proteins to the other. With two cholesterol molecules appropriately connected, we hypothesize that the cholesterol binding sites of both proteins will be simultaneously occupied in a manner that will stabilize the protein-protein interaction to permit detailed structural analysis of the resulting complex. A photoaffinity label has also been introduced into one of the cholesterol cores to permit covalent attachment of one of the units into its respective protein-binding pocket. The basic design of these crosslinkers should render them useful for examining interactions of the NPC1/NPC2 pair as well as other sterol transport proteins.

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Molecular Umbrellas

Cited by 85 publications

References 7 publications

Chemical Modifications to Improve the Cellular Uptake of Oligonucleotides

Chemical Modifications to Improve the Cellular Uptake of Oligonucleotides

Synthesis and antimicrobial activity of cholic acid hydrazone analogues

Design and synthesis of a crosslinker for studying intracellular steroid trafficking pathways

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