Solvatochromic reagents for multicomponent reactions and their utility in the development of cell-permeable macrocyclic peptide vectors

Benjamin H. Rotstein; Rida Mourtada; Shana O. Kelley; Andrei K. Yudin

doi:10.1002/chem.201102096

Solvatochromic reagents for multicomponent reactions and their utility in the development of cell-permeable macrocyclic peptide vectors

Benjamin H. Rotstein, Rida Mourtada, Shana O. Kelley, Andrei K. Yudin^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

34 Scopus citations

Abstract

Sensitive scaffolds: An isocyanide equipped with an environment-sensitive fluorophore was used to synthesize peptide macrocycles. The photophysical properties of the product macrocycles are sensitive to both peptide sequence and configuration. A mitochondria-penetrating peptide was constrained within a cyclic peptide framework and showed increased uptake and localization relative to a linear control (see scheme).

Original language	English (US)
Pages (from-to)	12257-12261
Number of pages	5
Journal	Chemistry - A European Journal
Volume	17
Issue number	44
DOIs	https://doi.org/10.1002/chem.201102096
State	Published - Oct 24 2011
Externally published	Yes

Keywords

fluorescent probes
isocyanides
macrocycles
multicomponent reactions
peptides
solvatochromism

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201102096

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abstract = "Sensitive scaffolds: An isocyanide equipped with an environment-sensitive fluorophore was used to synthesize peptide macrocycles. The photophysical properties of the product macrocycles are sensitive to both peptide sequence and configuration. A mitochondria-penetrating peptide was constrained within a cyclic peptide framework and showed increased uptake and localization relative to a linear control (see scheme).",

keywords = "fluorescent probes, isocyanides, macrocycles, multicomponent reactions, peptides, solvatochromism",

author = "Rotstein, {Benjamin H.} and Rida Mourtada and Kelley, {Shana O.} and Yudin, {Andrei K.}",

year = "2011",

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AU - Rotstein, Benjamin H.

AU - Mourtada, Rida

AU - Kelley, Shana O.

AU - Yudin, Andrei K.

PY - 2011/10/24

Y1 - 2011/10/24

N2 - Sensitive scaffolds: An isocyanide equipped with an environment-sensitive fluorophore was used to synthesize peptide macrocycles. The photophysical properties of the product macrocycles are sensitive to both peptide sequence and configuration. A mitochondria-penetrating peptide was constrained within a cyclic peptide framework and showed increased uptake and localization relative to a linear control (see scheme).

AB - Sensitive scaffolds: An isocyanide equipped with an environment-sensitive fluorophore was used to synthesize peptide macrocycles. The photophysical properties of the product macrocycles are sensitive to both peptide sequence and configuration. A mitochondria-penetrating peptide was constrained within a cyclic peptide framework and showed increased uptake and localization relative to a linear control (see scheme).

KW - fluorescent probes

KW - isocyanides

KW - macrocycles

KW - multicomponent reactions

KW - peptides

KW - solvatochromism

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JF - Chemistry - A European Journal

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Solvatochromic reagents for multicomponent reactions and their utility in the development of cell-permeable macrocyclic peptide vectors

Abstract

Keywords

ASJC Scopus subject areas

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