A Novel Sensitive Colorimetric Assay for Visual Detection of Solid-Phase Bound Amines

Madder, Annemieke; Farcy, Nadia; Hosten, N.; Muynck, Hilde De; Clercq, Pierre J. De; Barry, John M.; Davis, Anthony P.

doi:10.1002/(sici)1099-0690(199911)1999:11<2787::aid-ejoc2787>3.3.co;2-4

Cited by 34 publications

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“…Identification Tests: The Kaiser colorimetric assay was used for the detection of solid-phase-bound primary amines [33], while the De Clercq test was used for secondary amines bound to solid-phase [34]. …”

Section: Methodsmentioning

confidence: 99%

Cyclic Dipeptide Shuttles as a Novel Skin Penetration Enhancement Approach: Preliminary Evaluation with Diclofenac

et al. 2016

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This study demonstrates the effectiveness of a peptide shuttle in delivering diclofenac into and through human epidermis. Diclofenac was conjugated to a novel phenylalanyl-N-methyl-naphthalenylalanine-derived diketopiperazine (DKP) shuttle and to TAT (a classical cell penetrating peptide), and topically applied to human epidermis in vitro. DKP and TAT effectively permeated into and through human epidermis. When conjugated to diclofenac, both DKP and TAT enhanced delivery into and through human epidermis, though DKP was significantly more effective. Penetration of diclofenac through human epidermis (to receptor) was increased by conjugation to the peptide shuttle and cell penetrating peptide with enhancement of 6x by DKP-diclofenac and 3x by TAT-diclofenac. In addition, the amount of diclofenac retained within the epidermis was significantly increased by peptide conjugation. COX-2 inhibition activity of diclofenac was retained when conjugated to DKP. Our study suggests that the peptide shuttle approach may offer a new strategy for targeted delivery of small therapeutic and diagnostic molecules to the skin.

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Section: Methodsmentioning

confidence: 99%

Cyclic Dipeptide Shuttles as a Novel Skin Penetration Enhancement Approach: Preliminary Evaluation with Diclofenac

et al. 2016

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“…To avoid diketopiperazine formation, the third amino acid of each sequence was incorporated by the in situ neutralization method 56. Coupling and deprotection reactions were monitored by the nynhidrin57 or p -nitrophenylester58 colorimetric tests. The linear decapeptide was cleaved from the resin by treatment with TFA/TFMSA/TIS 10:1:1 (v/v/v) (4 mL) at room temperature for 90 min and then precipitated with cold tert -butyl methyl ether.…”

Section: Methodsmentioning

confidence: 99%

Sequence Inversion and Phenylalanine Surrogates at the β-Turn Enhance the Antibiotic Activity of Gramicidin S

Solanas

Torre²,

Fernández‐Reyes³

et al. 2010

J. Med. Chem.

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A series of gramicidin S (GS) analogs have been synthesized where the Phe (i+1) and Pro (i+2) residues of the β-turn have been swapped while the respective chiralities (D-, L-) at each position are preserved, and Phe is replaced by surrogates with aromatic side chains of diverse size, orientation and flexibility. Although most analogs preserve the β-sheet structure, as assessed by NMR, their antibiotic activities turn out to be highly dependent on the bulkiness and spatial arrangement of the aromatic side chain. Significant increases in microbicidal potency against both Gram-positive and Gram-negative pathogens are observed for several analogs, resulting in improved therapeutic profiles. Data indicate that seemingly minor replacements at the GS β-turn can have significant impact on antibiotic activity, highlighting this region as a hot spot for modulating GS plasticity and activity.

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“…Finally, the solvent was removed by filtration, and the resin was washed by using DMF (10×1 min) and DCM (10×1 min). The extent of the coupling was checked by using the Ninhydrin [24], Chloranil [25] or De Clercq [26] tests (depending on the nature of the amino acid group).…”

Section: Methodsmentioning

confidence: 99%

Exploration of the One-Bead One-Compound Methodology for the Design of Prolyl Oligopeptidase Substrates

et al. 2009

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Here we describe the design, synthesis and evaluation of the first solid-phase substrates for prolyl oligopeptidase (POP), a cytosolic serine peptidase associated with schizophrenia, bipolar affective disorder and related neuropsychiatric disorders. This study seeks to contribute to the future design of a one-bead one-compound (OBOC) peptide library of POP substrates, based on an intramolecular energy transfer substrate. Unexpectedly, the enzymatic evaluation of the substrates attached on solid-phase by means of the HMBA linker were cleaved through the ester bond, thereby suggesting an unknown esterase activity of POP, in addition to its known peptidase activity. By performing multiple activity assays, we have confirmed the esterase activity of this enzyme and its capacity to process the substrates on solid-phase. Finally, we tested a new linker, compatible with both the solid-phase peptide-synthesis used and the enzymatic assay, for application in the future design of an OBOC library.

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A Novel Sensitive Colorimetric Assay for Visual Detection of Solid-Phase Bound Amines

Cited by 34 publications

References 0 publications

Cyclic Dipeptide Shuttles as a Novel Skin Penetration Enhancement Approach: Preliminary Evaluation with Diclofenac

Cyclic Dipeptide Shuttles as a Novel Skin Penetration Enhancement Approach: Preliminary Evaluation with Diclofenac

Sequence Inversion and Phenylalanine Surrogates at the β-Turn Enhance the Antibiotic Activity of Gramicidin S

Exploration of the One-Bead One-Compound Methodology for the Design of Prolyl Oligopeptidase Substrates

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