2-(5-{5-[(2-iodoacetamido)methyl]-1,3,3-trimethyl-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: 153658
• Molecular Formular: C37H42IN3O4S
• Molecular Mass: 751.71655
• Monoisotopic Mass: 751.19407584
• SMILES: CC1(c2cc(ccc2N(/C/1=C/C=C/C=C/C1=[N+](c2ccc3ccccc3c2C1(C)C)CCCCS(=O)(=O)[O-])C)CNC(=O)CI)C
• Canonical SMILES: ICC(=O)NCc1ccc2c(c1)C(C)(C)/C(=C\C=C\C=C\C1=[N+](CCCCS(=O)(=O)[O-])c3c(C1(C)C)c1ccccc1cc3)/N2C
• InChI: InChI=1S/C37H42IN3O4S/c1-36(2)29-23-26(25-39-34(42)24-38)17-19-30(29)40(5)32(36)15-7-6-8-16-33-37(3,4)35-28-14-10-9-13-27(28)18-20-31(35)41(33)21-11-12-22-46(43,44)45/h6-10,13-20,23H,11-12,21-22,24-25H2,1-5H3,(H-,39,42,43,44,45)
• InChIKey: DSOHJESYBPIQMM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(5-{5-[(2-iodoacetamido)methyl]-1,3,3-trimethyl-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-iodoacetamido)methyl]-1,3,3-trimethylindol-2-ylidene}penta-1,3-dien-1-yl)-1,1-dimethyl-3-(4-sulfonatobutyl)benzo[e]indol-3-ium
• Synonyms: 4,5-Benzo-5′-(iodoacetaminomethyl)-1′,3,3,3′,3′-pentamethyl-1-(4-sulfobutyl)indodicarbocyanine; NIR-664-iodoacetamide

Database IDs

• CAS Number: 149021-66-9
• MDL Number: MFCD01862918
• PubChem SID: 162247797; 24847661
• PubChem CID: 71311713

CALCULATED PROPERTIES

• Acid pKa: -0.731327
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 6.057944
• LogD (pH = 7.4): 6.0580263
• Log P: 5.2013736
• Molar Refractivity: 210.0407 cm^3
• Polarizability: 76.492615 Å^3
• Polar Surface Area: 92.55 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 1-hexanol: soluble; methanol: soluble
• Fluorescence: λex 664 nm; λem 689 nm in methanol

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (HPLC)
• Suitability: suitable for fluorescence
• Empirical Formula (Hill Notation): C37H42IN3O4S

DETAILS

Sigma Aldrich - 12535

Other Notes
Cyanine label for derivatization of thiols6
Application
NIR-664-iodoacetamide, is a cyanine-based dye, which is a very efficient sensor of the chemical environment because of its strong fluorescence response to the hydrophobic nature of its immediate microenvironment 1. Such changes result in an altered equilibrium between the monomer and aggregate states of this dye, which are demonstrated by absorption peaks at 665 and 615 nm, respectively 2. A fluorescent dye which can be covalently encapsulated into silica nanoparticles to elucidate the internal architecture using the methods of fluorescence correlation spectroscopy and fluorescence lifetime measurements 3,2. This dye has a quantum efficiency of 23%, a molar absorptivity of 187,000 L mol-1 cm-1 4, and a small Stokes shift 5.