Combining aminocyanine dyes with polyamide dendrons: A promising strategy for imaging in the near-infrared region

Cátia Ornelas, Rachelle Lodescar, Alexander Durandin, James Canary, Ryan Pennell, Leonard F. Liebes, Marcus Weck

Research output: Contribution to journalArticle

Abstract

Cyanine dyes are known for their fluorescence in the near-IR (NIR) region, which is desirable for biological applications. We report the synthesis of a series of aminocyanine dyes containing terminal functional groups such as acid, azide, and cyclooctyne groups for further functionalization through, for example, click chemistry. These aminocyanine dyes can be attached to polyfunctional dendrons by copper-catalyzed azide alkyne cycloaddition (CuAAC), strain-promoted azide alkyne cycloaddition (SPAAC), peptide coupling, or direct S NR1 reactions. The resulting dendron-dye conjugates were obtained in high yields and displayed high chemical stability and photostability. The optical properties of the new compounds were studied by UV/Vis and fluorescence spectroscopy. All compounds show large Stokes shifts and strong fluorescence in the NIR region with high quantum yields, which are optimal properties for in vivo optical imaging.

Original languageEnglish (US)
Pages (from-to)3619-3629
Number of pages11
JournalChemistry - A European Journal
Volume17
Issue number13
DOIs
StatePublished - Mar 21 2011

Fingerprint

Dendrimers
Nylons
Polyamides
Azides
Coloring Agents
Dyes
Infrared radiation
Imaging techniques
Alkynes
Cycloaddition
Fluorescence
Chemical stability
Fluorescence spectroscopy
Quantum yield
Ultraviolet spectroscopy
Functional groups
Peptides
Copper
Optical properties
Acids

Keywords

  • CuAAC
  • cycloaddition
  • dendrimers
  • dendrons
  • dyes/pigments
  • imaging agent
  • SPAAC

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Combining aminocyanine dyes with polyamide dendrons : A promising strategy for imaging in the near-infrared region. / Ornelas, Cátia; Lodescar, Rachelle; Durandin, Alexander; Canary, James; Pennell, Ryan; Liebes, Leonard F.; Weck, Marcus.

In: Chemistry - A European Journal, Vol. 17, No. 13, 21.03.2011, p. 3619-3629.

Research output: Contribution to journalArticle

Ornelas, Cátia ; Lodescar, Rachelle ; Durandin, Alexander ; Canary, James ; Pennell, Ryan ; Liebes, Leonard F. ; Weck, Marcus. / Combining aminocyanine dyes with polyamide dendrons : A promising strategy for imaging in the near-infrared region. In: Chemistry - A European Journal. 2011 ; Vol. 17, No. 13. pp. 3619-3629.
@article{97250e8b4f6c414389264949289875d5,
title = "Combining aminocyanine dyes with polyamide dendrons: A promising strategy for imaging in the near-infrared region",
abstract = "Cyanine dyes are known for their fluorescence in the near-IR (NIR) region, which is desirable for biological applications. We report the synthesis of a series of aminocyanine dyes containing terminal functional groups such as acid, azide, and cyclooctyne groups for further functionalization through, for example, click chemistry. These aminocyanine dyes can be attached to polyfunctional dendrons by copper-catalyzed azide alkyne cycloaddition (CuAAC), strain-promoted azide alkyne cycloaddition (SPAAC), peptide coupling, or direct S NR1 reactions. The resulting dendron-dye conjugates were obtained in high yields and displayed high chemical stability and photostability. The optical properties of the new compounds were studied by UV/Vis and fluorescence spectroscopy. All compounds show large Stokes shifts and strong fluorescence in the NIR region with high quantum yields, which are optimal properties for in vivo optical imaging.",
keywords = "CuAAC, cycloaddition, dendrimers, dendrons, dyes/pigments, imaging agent, SPAAC",
author = "C{\'a}tia Ornelas and Rachelle Lodescar and Alexander Durandin and James Canary and Ryan Pennell and Liebes, {Leonard F.} and Marcus Weck",
year = "2011",
month = "3",
day = "21",
doi = "10.1002/chem.201002268",
language = "English (US)",
volume = "17",
pages = "3619--3629",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "13",

}

TY - JOUR

T1 - Combining aminocyanine dyes with polyamide dendrons

T2 - A promising strategy for imaging in the near-infrared region

AU - Ornelas, Cátia

AU - Lodescar, Rachelle

AU - Durandin, Alexander

AU - Canary, James

AU - Pennell, Ryan

AU - Liebes, Leonard F.

AU - Weck, Marcus

PY - 2011/3/21

Y1 - 2011/3/21

N2 - Cyanine dyes are known for their fluorescence in the near-IR (NIR) region, which is desirable for biological applications. We report the synthesis of a series of aminocyanine dyes containing terminal functional groups such as acid, azide, and cyclooctyne groups for further functionalization through, for example, click chemistry. These aminocyanine dyes can be attached to polyfunctional dendrons by copper-catalyzed azide alkyne cycloaddition (CuAAC), strain-promoted azide alkyne cycloaddition (SPAAC), peptide coupling, or direct S NR1 reactions. The resulting dendron-dye conjugates were obtained in high yields and displayed high chemical stability and photostability. The optical properties of the new compounds were studied by UV/Vis and fluorescence spectroscopy. All compounds show large Stokes shifts and strong fluorescence in the NIR region with high quantum yields, which are optimal properties for in vivo optical imaging.

AB - Cyanine dyes are known for their fluorescence in the near-IR (NIR) region, which is desirable for biological applications. We report the synthesis of a series of aminocyanine dyes containing terminal functional groups such as acid, azide, and cyclooctyne groups for further functionalization through, for example, click chemistry. These aminocyanine dyes can be attached to polyfunctional dendrons by copper-catalyzed azide alkyne cycloaddition (CuAAC), strain-promoted azide alkyne cycloaddition (SPAAC), peptide coupling, or direct S NR1 reactions. The resulting dendron-dye conjugates were obtained in high yields and displayed high chemical stability and photostability. The optical properties of the new compounds were studied by UV/Vis and fluorescence spectroscopy. All compounds show large Stokes shifts and strong fluorescence in the NIR region with high quantum yields, which are optimal properties for in vivo optical imaging.

KW - CuAAC

KW - cycloaddition

KW - dendrimers

KW - dendrons

KW - dyes/pigments

KW - imaging agent

KW - SPAAC

UR - http://www.scopus.com/inward/record.url?scp=79952583432&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79952583432&partnerID=8YFLogxK

U2 - 10.1002/chem.201002268

DO - 10.1002/chem.201002268

M3 - Article

C2 - 21337432

AN - SCOPUS:79952583432

VL - 17

SP - 3619

EP - 3629

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 13

ER -