2-[5-(5-{2-[(2,5-dioxopyrrolidin-1-yl)oxy]-2-oxoethyl}-1-ethyl-3,3-dimethyl-2,3-dihydro-1H-indol-2-ylidene)penta-1,3-dien-1-yl]-1,1-dimethyl-3-(4-sulfonatobutyl)-1H-benzo[e]indol-3-ium

• ChemBase ID: 153091
• Molecular Formular: C41H45N3O7S
• Molecular Mass: 723.8769
• Monoisotopic Mass: 723.2978218
• SMILES: CCN1c2ccc(cc2C(/C/1=C/C=C/C=C/C1=[N+](c2ccc3ccccc3c2C1(C)C)CCCCS(=O)(=O)[O-])(C)C)CC(=O)ON1C(=O)CCC1=O
• Canonical SMILES: CCN1c2ccc(cc2C(/C/1=C/C=C/C=C/C1=[N+](CCCCS(=O)(=O)[O-])c2c(C1(C)C)c1ccccc1cc2)(C)C)CC(=O)ON1C(=O)CCC1=O
• InChI: InChI=1S/C41H45N3O7S/c1-6-42-32-20-18-28(27-38(47)51-44-36(45)22-23-37(44)46)26-31(32)40(2,3)34(42)16-8-7-9-17-35-41(4,5)39-30-15-11-10-14-29(30)19-21-33(39)43(35)24-12-13-25-52(48,49)50/h7-11,14-21,26H,6,12-13,22-25,27H2,1-5H3
• InChIKey: OPIIZKCLUIZXHG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[5-(5-{2-[(2,5-dioxopyrrolidin-1-yl)oxy]-2-oxoethyl}-1-ethyl-3,3-dimethyl-2,3-dihydro-1H-indol-2-ylidene)penta-1,3-dien-1-yl]-1,1-dimethyl-3-(4-sulfonatobutyl)-1H-benzo[e]indol-3-ium
• IUPAC Traditional name: 2-[5-(5-{2-[(2,5-dioxopyrrolidin-1-yl)oxy]-2-oxoethyl}-1-ethyl-3,3-dimethylindol-2-ylidene)penta-1,3-dien-1-yl]-1,1-dimethyl-3-(4-sulfonatobutyl)benzo[e]indol-3-ium
• Synonyms: 4,5-Benzo-1′-ethyl-3,3,3′,3′-tetramethyl-1-(4-sulfobutyl)indodicarbocyanin-5′-acetic acid N-succinimidyl ester; 4,5-Benzo-5′-(N-succinimidyl-oxycarbonyl-methyl)-1′-ethyl-3,3,3′,3′-tetramethyl- 1-(4-sulfobutyl)indodicarbocyanine; NIR-664-N-succinimidyl ester

Database IDs

• CAS Number: 167638-53-1
• MDL Number: MFCD01862927
• Beilstein Number: 7329943
• PubChem SID: 162247231; 24847803
• PubChem CID: 6247768

CALCULATED PROPERTIES

• Acid pKa: -0.73066103
• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 5.531799
• LogD (pH = 7.4): 5.531991
• Log P: 4.34802
• Molar Refractivity: 215.6497 cm^3
• Polarizability: 79.20336 Å^3
• Polar Surface Area: 127.13 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 1-hexanol: soluble; chloroform: soluble; DMSO: soluble; isopropanol: soluble
• Fluorescence: λex 667 nm; λem 689 nm in isopropanol

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥70% (coupling to amines)
• Suitability: suitable for fluorescence
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C41H45N3O7S

DETAILS

Sigma Aldrich - 12790

Other Notes
Diode laser-induced fluorescence detection in capillary electrophoresis5
Application
3-(2-Benzothiazolyl)-7-octadecyloxycoumarin is a fluorescent compound that can be used to label proteins by reacting at the amine of the N-terminal residue on the protein of interest. Such labeling can be utilized to investigate protein interactions with other molecules (i.e. nano-materials) by monitoring changes in fluorescence 1. Utilized in the development of bifunctional fluorochrome-chelate multifunctional single attachment point’s from a dipeptide scaffold 2. Utilized in the development of near-infrared dye-doped nanoparticles and were encapsulated into the nanoparticles by using microemulsion methodology for the development of highly sensitive fluorescent immunoassays 3,4. At high pH values, NIR-664-N-succinimidyl ester is stable and at low pH (~2) it is unstable and degrades to a non-fluorescent derivative. At high concentrations, the dye molecules form complex aggregates, quenching their fluorescence. A reduction in fluorescence as a function of dye concentration can be correlated with the occurrence of homo-Förster resonance energy transfer in the nanoparticle 3. This dye has a quantum efficiency of 23%, a molar absorptivity of 187,000 L mol-1 cm-1 5, and a small Stokes shift 3.