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543292

Sigma-Aldrich

IR-783

Dye content 90 %

Synonym(s):

2-[2-[2-Chloro-3-[2-[1,3-dihydro-3,3-dimethyl-1-(4-sulfobutyl)-2H-indol-2-ylidene]-ethylidene]-1-cyclohexen-1-yl]-ethenyl]-3,3-dimethyl-1-(4-sulfobutyl)-3H-indolium hydroxide, inner salt sodium salt

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About This Item

Empirical Formula (Hill Notation):
C38H46ClN2NaO6S2
CAS Number:
115970-66-6
Molecular Weight:
749.35
MDL number:
MFCD03427057
UNSPSC Code:
12352103
PubChem Substance ID:
57651464
NACRES:
NA.23

form

solid

composition

Dye content, 90%

mp

209-212 °C (lit.)

λmax

782 nm

SMILES string

[Na+].CC1(C)\C(=C\C=C2/CCCC(\C=C\C3=[N+](CCCCS([O-])(=O)=O)c4ccccc4C3(C)C)=C2Cl)N(CCCCS([O-])(=O)=O)c5ccccc15

InChI

1S/C38H47ClN2O6S2.Na/c1-37(2)30-16-5-7-18-32(30)40(24-9-11-26-48(42,43)44)34(37)22-20-28-14-13-15-29(36(28)39)21-23-35-38(3,4)31-17-6-8-19-33(31)41(35)25-10-12-27-49(45,46)47;/h5-8,16-23H,9-15,24-27H2,1-4H3,(H-,42,43,44,45,46,47);/q;+1/p-1

InChI key

QQIQAVJARACLHE-UHFFFAOYSA-M

General description

IR-783 is a near-infrared (NIR) dye with an extinction coefficient of 157000 M−1cm−1 and quantum yield of 0.11. Its excitation wavelength is in the range of 768-784 nm in saline.

Application

IR-783 can be used as a starting material in the synthesis of IR-808 dye for biological applications. It can also be used in the formation of NIR fluorescent human serum albumin nanoparticles for the detection of a tumor. It finds potential usage as a contrasting agent for the multimodal in vivo imaging.

Features and Benefits

Water soluble, laser and near-IR dye

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Markedly enhanced up-conversion luminescence by combining IR-808 dye sensitization and core-shell-shell structures
Xu J, et al.
Dalton Transactions, 46(5), 1495-1501 (2017)
Guanjun Deng et al.
Theranostics, 8(15), 4116-4128 (2018-08-22)
Near-infrared (NIR) fluorescence imaging has relied on fluorophores that emit in the 700-900 nm NIR-Ia or 1,000-1,700 nm NIR-II window for generating deep-tissue images. Up until now, there have been few fluorophores developed for the 900-1,000 nm NIR-Ib window. This
2-[2-[2-Chloro-3-[2-[1, 3-dihydro-3, 3-dimethyl-1-(4-sulfobutyl)-2H-indol-2-ylidene]-ethylidene]-1-cyclohexen-1-yl]-ethenyl]-3, 3-dimethyl-1-(4-sulfobutyl)-3H-indolium
Molecular Imaging and Contrast Agent Database (MICAD) (2010)
Synthesis and characterization of near IR fluorescent albumin nanoparticles for optical detection of colon cancer
Cohen S, et al.
Materials Science and Engineering, C, 33(2), 923-931 (2013)
Lily Yang et al.
Theranostics, 4(1), 106-118 (2014-01-08)
Complete removal of tumors by surgery is the most important prognostic factor for cancer patients with the early stage cancers. The ability to identify invasive tumor edges of the primary tumor, locally invaded small tumor lesions, and drug resistant residual
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