Heptamethine dyes

Hep tafluoropropane, 13 726t Heptafluorozirconate(IV), 7 578t Heptafulvalene, 21 148 Heptaldehyde. See Heptanal Heptamethine dyes, 9 505 Heptamolybdate, 17 21 Heptanal, physical properties of, 2 6 It Heptane... 

Dye-aptamer complexes can be used also to develop high specific and selective colorimetric chemosensors. For example, the displacement of the heptamethine dye 26b... 

A similar reaction with l,5,5-triethoxy-l,3-pentadiene failed to give the expected heptamethine dye ... 

Our group in Lyon developed heptamethine dyes with promising TPA cross sections in the range 1400-1600 nm [69]. Anl (Fig. 12) exhibits a crjpA value of 792 GM at 1445 nm these molecules, have many promising properties in terms of synthesis, stability and solubility and may have potential for practical applications in biology and optical limiting. 

Fig. 14.5 S) nthetic route to s) mmetrical indolium heptamethine dyes.

X. Tan, et al., A NIR heptamethine dye with intrinsic cancer targeting, imaging and photosensitizing properties. Biomaterials 33 (7)... 

In WORM disks, pentamethine and heptamethine are the materials of choice (see Cyanine dyes Polymethine dyes). 

An interesting imaging probe Id that can selectively target bacteria was recently reported by Smith et al. [31] also based on a heptamethine chromophore. The probe is composed of a bacterial affinity group, which is a synthetic zinc (II) coordination complex that targets the anionic surfaces of bacterial cells and a near infrared dye. The probe allowed detection of Staphylococcus aureus in a mouse leg infection model using whole animal near-infrared fluorescence imaging. 

Narayanan N, Strekowski L, Lipowska M, Patonay G (1995) A new method for the synthesis of heptamethine cyanine dyes synthesis of new near infrared fluorescent labels. J Org Chem 60 2391-2395... 

A 2 1-fold increase in fluorescence intensity was demonstrated for the long-wavelength hydrophilic bis-trimethine label 29 (original silver nanoparticles coated with a cryolite spacer [96], A 20-fold increase of fluorescence intensity and a sixfold decrease of the mean decay time were obtained for heptamethine cyanine dye 30 on silver nanoparticles [97],... 

Yau CMS, Pascu SI, Odom SA, Warren JE, Klotz EJF, Frampton MJ, Williams CC, Coropceanu V, Kuimova MK, Phillips D, Barlow S, Bredas JL, Marder SR, Millar V, Anderson HL (2008) Stabilisation of a heptamethine cyanine dye by rotaxane encapsulation. Chem Commun 25 2897-2899... 

L. Strekowski, M. Lipowska, and G. Patonay, Facile derivatizations of heptamethine cyanine dyes. Synth. Comm. 22(17), 2593-2598 (1992). 

Scheme 1. Principle of cyanine dye synthesis leading to trimethine (n = l), pentamethine (n = 2) and heptamethine (n = 3) chromophores. Structures comprising indolic subunits are usually named indocarbocyanine, indodicarbocyanine and indotricarbocyanine, respectively. Formic acid, malonic aldehyde, glutaconic aldehyde are used in their protected dianUide or orthoester form. They can be applied as substituted derivatives to introduce residues into the polymethine unit. The indolic substructure might bear further residues or annelated aromatic rings...

Fig. 3 Electropherograms illustrating the competitive binding of ketoprofen and quinidine to noncovalently dye-labeled human serum albumin. 100 nM heptamethine cyanine dye and (A) 50 nM human serum albumin, (B) 50 nM human serum albumin, 50 nM quinidine, (C) 50 nM human serum albumin, 50 nM ketoprofen. (Reprinted with permission from Ref. 47. Copyright 2001 Wiley-VCH.)...

The classical synthetic route to symmetrical indolium heptamethine cyanine dyes by the Strekowski approach [72] is represented in Fig. 14.5. Introduction of an iso-thiocyanato (-NGS) functionality into the dye is accomplished by facile nucleophilic displacement of the meso-chloro substituent in the intermediate product 22. This method provides amino-reactive cyanines with absorption in the 770-800 nm region. 

A similar approach also supplies heptamethine cyanine dyes with altered spectroscopic properties for more specific applications. For example, Flanagan et al. incorporated fluorine and heavy atoms such as I, Br, and G1 into polymethine dyes, as shown in Fig. 14.6, to alter the fluorescence lifetime of the dye without disturbing the other spectroscopic properties [73]. The fluorine or heavy-atom modified... 

Lee SK, Richter MM, Strekowski L, Bard AJ (1997) Electrogenerated chemiluminescence. 61. Near-IR electrogenerated chemiluminescence, electrochemistry, and spectroscopic properties of a heptamethine cyanine dye in MeCN. Anal Chem 69(20) 4126-4133... 

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