Towards multivalent CD1d ligands: synthesis and biological activity of homodimeric α-galactosyl ceramide analogues

Jervis, P. J.; Moulis, Marie; Jukes, John‐Paul; Ghadbane, Hemza; Cox, Liam R.; Cerundolo, Vincenzo; Besra, Gurdyal S.

doi:10.1016/j.carres.2012.02.034

Cited by 24 publications

(13 citation statements)

References 68 publications

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“…The crude product was dispersed in water (60 mL) and extracted into ethyl acetate (EtOAc; 3 × 40 mL), and then concentrated to give a yellow oil (1.0 g, 85% yield). Spectra were in accordance with data reported in literature …”

Section: Methodssupporting

confidence: 88%

Tunable, Functional Diblock Copolypeptide Hydrogels Based on Methionine Homologs

Negri

Gharakhanian

Deming

2019

Macromolecular Bioscience

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The preparation of new diblock copolypeptide hydrogels derived from homologs of l‐methionine, that is, l‐homomethionine and l‐6‐(methylthio)‐l‐norleucine is described. Compared to l‐methionine residues, use of l‐methionine homologs allow improved copolymerization with l‐leucine residues to give well‐defined block copolypeptides. These copolypeptides are subsequently modified using robust thioether alkylation reactions employing a variety of functional epoxides, which yield samples capable of forming transparent, self‐healing hydrogels in water. The facile variation of different functional epoxides for postpolymerization modification is found to allow predictable functionalization and tuning of hydrogel properties by the modification of simple precursors.

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Section: Methodssupporting

confidence: 88%

Tunable, Functional Diblock Copolypeptide Hydrogels Based on Methionine Homologs

Negri

Gharakhanian

Deming

2019

Macromolecular Bioscience

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“…1,15‐Hexadecadiyne was synthesized according to the procedure described by Jervis et al . In a 250 mL flame dried round bottom flask, lithium acetylide‐ethylenediamine (693 mg, 7.50 mmol) complex was added slowly to 1,12‐dibromododecane (1.15 g, 3.51 mmol) in DMSO (155 mL, 0.2 M) at 0 °C.…”

Section: Methodssupporting

confidence: 80%

Forming Ferrocenyl Self‐Assembled Monolayers on Si(100) Electrodes with Different Alkyl Chain Lengths for Electron Transfer Studies

2018

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The reaction of hydrogen‐terminated Si(100) with 1,8‐nonadiyne was previously shown to afford robust surfaces where oxidation of the substrate is not evident. Here, the experimental conditions required for reacting hydrogen‐terminated Si(100) with α,ω‐diynes of different lengths is explored via thermal hydrosilylation of 1,6‐heptadiyne, 1,8‐nonadiyne, 1,10‐undecadiyne and 1,15‐hexadecadiyne. X‐ray photoelectron spectroscopy indicated monolayers were successfully formed with oxide levels below the XPS detection limit for molecules with lengths varying from 7 to 11 carbons. It was observed that the apparent rate of electron transfer (ket) was affected not only by the SAM thickness, but also by hopping between ferrocene moieties where the presence of tiny oxidative defects act as electron transfer hotspots.

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“…Furthermore, the dual interaction of a dimeric agent can produce also enhanced selectivity when properly crafted, constraining the molecule in an optimal orientation for binding the second ligand [210]. As seen with dimeric diketopiperazines, several studies on naturally-occurring or synthetic dimers evidenced not only increased potency, but also high-affinity interactions and additional complementary actions [211,212,213,214,215,216].…”

Section: Discussionmentioning

confidence: 99%

Double the Chemistry, Double the Fun: Structural Diversity and Biological Activity of Marine-Derived Diketopiperazine Dimers

et al. 2019

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While several marine natural products bearing the 2,5-diketopiperazine ring have been reported to date, the unique chemistry of dimeric frameworks appears to remain neglected. Frequently reported from marine-derived strains of fungi, many naturally occurring diketopiperazine dimers have been shown to display a wide spectrum of pharmacological properties, particularly within the field of cancer and antimicrobial therapy. While their structures illustrate the unmatched power of marine biosynthetic machinery, often exhibiting unsymmetrical connections with rare linkage frameworks, enhanced binding ability to a variety of pharmacologically relevant receptors has been also witnessed. The existence of a bifunctional linker to anchor two substrates, resulting in a higher concentration of pharmacophores in proximity to recognition sites of several receptors involved in human diseases, portrays this group of metabolites as privileged lead structures for advanced pre-clinical and clinical studies. Despite the structural novelty of various marine diketopiperazine dimers and their relevant bioactive properties in several models of disease, to our knowledge, this attractive subclass of compounds is reviewed here for the first time.

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Towards multivalent CD1d ligands: synthesis and biological activity of homodimeric α-galactosyl ceramide analogues

Abstract: Graphical abstract

Cited by 24 publications

References 68 publications

Tunable, Functional Diblock Copolypeptide Hydrogels Based on Methionine Homologs

Tunable, Functional Diblock Copolypeptide Hydrogels Based on Methionine Homologs

Forming Ferrocenyl Self‐Assembled Monolayers on Si(100) Electrodes with Different Alkyl Chain Lengths for Electron Transfer Studies

Double the Chemistry, Double the Fun: Structural Diversity and Biological Activity of Marine-Derived Diketopiperazine Dimers

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