Literature DB >> 19053316

Monofunctional carbocyanine dyes for bio- and bioorthogonal conjugation.

Fangwei Shao1, Ralph Weissleder, Scott A Hilderbrand.   

Abstract

A facile synthetic route to prepare monofunctional carbocyanine dyes for biological application is developed. Three pentamethine carbocyanine dyes have been successfully modified with a variety of functional groups such as: carboxylic acids, azides, or alkynes. The new dyes are characterized by strong NIR fluorescence emission, high extinction coefficients and good quantum yields. The azide and alkyne dyes have potential utility as components in bioorthogonal labeling schemes via [2 + 3] dipolar cycloaddition "click" reactions. The application of one derivative, CyAM-5 alkyne, for bioorthogonal labeling is demonstrated. Fluorescence microscopy shows coupling of CyAM-5 alkyne to Chinese hamster ovary (CHO) cells preincubated with azide modified glycans.

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Year:  2008        PMID： 19053316      PMCID： PMC2656649          DOI： 10.1021/bc800417b

Source DB:  PubMed          Journal:  Bioconjug Chem        ISSN： 1043-1802            Impact factor:   4.774


  19 in total

1.  Novel near-infrared cyanine fluorochromes: synthesis, properties, and bioconjugation.

Authors:  Yuhui Lin; Ralph Weissleder; Ching-Hsuan Tung
Journal:  Bioconjug Chem       Date:  2002 May-Jun       Impact factor: 4.774

Review 2.  Shedding light onto live molecular targets.

Authors:  Ralph Weissleder; Vasilis Ntziachristos
Journal:  Nat Med       Date:  2003-01       Impact factor: 53.440

3.  A receptor-targeted near-infrared fluorescence probe for in vivo tumor imaging.

Authors:  Ching-Hsuan Tung; Yuhui Lin; Woo Kyung Moon; Ralph Weissleder
Journal:  Chembiochem       Date:  2002-08-02       Impact factor: 3.164

4.  Click imaging of biochemical processes in living systems.

Authors:  Valery V Fokin
Journal:  ACS Chem Biol       Date:  2007-12-21       Impact factor: 5.100

5.  Glycoproteomic probes for fluorescent imaging of fucosylated glycans in vivo.

Authors:  Masaaki Sawa; Tsui-Ling Hsu; Takeshi Itoh; Masakazu Sugiyama; Sarah R Hanson; Peter K Vogt; Chi-Huey Wong
Journal:  Proc Natl Acad Sci U S A       Date:  2006-08-08       Impact factor: 11.205

6.  Monofunctional near-infrared fluorochromes for imaging applications.

Authors:  Scott A Hilderbrand; Kimberley A Kelly; Ralph Weissleder; Ching-Hsuan Tung
Journal:  Bioconjug Chem       Date:  2005 Sep-Oct       Impact factor: 4.774

7.  Development of a ratiometric fluorescent zinc ion probe in near-infrared region, based on tricarbocyanine chromophore.

Authors:  Kazuki Kiyose; Hirotatsu Kojima; Yasuteru Urano; Tetsuo Nagano
Journal:  J Am Chem Soc       Date:  2006-05-24       Impact factor: 15.419

8.  Alkynyl sugar analogs for the labeling and visualization of glycoconjugates in cells.

Authors:  Tsui-Ling Hsu; Sarah R Hanson; Kuniyuki Kishikawa; Sheng-Kai Wang; Masaaki Sawa; Chi-Huey Wong
Journal:  Proc Natl Acad Sci U S A       Date:  2007-02-12       Impact factor: 11.205

9.  Cyanine-labeling reagents: sulfobenzindocyanine succinimidyl esters.

Authors:  S R Mujumdar; R B Mujumdar; C M Grant; A S Waggoner
Journal:  Bioconjug Chem       Date:  1996 May-Jun       Impact factor: 4.774

10.  IRDye78 conjugates for near-infrared fluorescence imaging.

Authors:  Atif Zaheer; Thomas E Wheat; John V Frangioni
Journal:  Mol Imaging       Date:  2002-10       Impact factor: 4.488
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  10 in total

1.  Intraoperative near-infrared fluorescent cholangiography (NIRFC) in mouse models of bile duct injury: reply.

Authors:  Jose-Luiz Figueiredo; Matthias Nahrendorf; Claudio Vinegoni; Ralph Weissleder
Journal:  World J Surg       Date:  2011-03       Impact factor: 3.352

2.  Storable arylpalladium(II) reagents for alkene labeling in aqueous media.

Authors:  Rebecca L Simmons; Robert T Yu; Andrew G Myers
Journal:  J Am Chem Soc       Date:  2011-09-15       Impact factor: 15.419

3.  NEAR-INFRARED DYES: Probe Development and Applications in Optical Molecular Imaging.

Authors:  Donald D Nolting; John C Gore; Wellington Pham
Journal:  Curr Org Synth       Date:  2011-08       Impact factor: 1.975

4.  High-yielding, two-step 18F labeling strategy for 18F-PARP1 inhibitors.

Authors:  Edmund J Keliher; Thomas Reiner; Anna Turetsky; Scott A Hilderbrand; Ralph Weissleder
Journal:  ChemMedChem       Date:  2011-01-04       Impact factor: 3.466

5.  Red Emitting Coumarins: Insights of Photophysical Properties with DFT Methods.

Authors:  Abhinav B Tathe; Lydia Rhyman; Ponnadurai Ramasami; Nagaiyan Sekar
Journal:  J Fluoresc       Date:  2015-07-03       Impact factor: 2.217

6.  Facile Synthesis of Monofunctional Pentamethine Carbocyanine Fluorophores.

Authors:  Fangwei Shao; Hushan Yuan; Lee Josephson; Ralph Weissleder; Scott A Hilderbrand
Journal:  Dyes Pigm       Date:  2011-04-01       Impact factor: 4.889

7.  Design and synthesis of a new class of membrane-permeable triazaborolopyridinium fluorescent probes.

Authors:  Sudath Hapuarachchige; Gilbert Montaño; Chinnasamy Ramesh; Delany Rodriguez; Lauren H Henson; Casey C Williams; Samuel Kadavakkollu; Dennis L Johnson; Charles B Shuster; Jeffrey B Arterburn
Journal:  J Am Chem Soc       Date:  2011-04-07       Impact factor: 15.419

Review 8.  Multimodal iron oxide nanoparticles for hybrid biomedical imaging.

Authors:  Timo Heidt; Matthias Nahrendorf
Journal:  NMR Biomed       Date:  2012-10-15       Impact factor: 4.044

9.  Semiconducting polymer dots with monofunctional groups.

Authors:  Fangmao Ye; Changfeng Wu; Wei Sun; Jiangbo Yu; Xuanjun Zhang; Yu Rong; Yue Zhang; I-Che Wu; Yang-Hsiang Chan; Daniel T Chiu
Journal:  Chem Commun (Camb)       Date:  2014-05-30       Impact factor: 6.222

10.  Bioorthogonal chemistry: fishing for selectivity in a sea of functionality.

Authors:  Ellen M Sletten; Carolyn R Bertozzi
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336
  10 in total

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