2-(3-{4-tert-butyl-3-oxa-13-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2(7),4,8-tetraen-6-ylidene}prop-1-en-1-yl)-1-{6-[(2,5-dioxopyrrolidin-1-yl)oxy]-6-oxohexyl}-3,3-dimethyl-3H-indol-1-ium-5-sulfonate

• ChemBase ID: 156555
• Molecular Formular: C42H49N3O8S
• Molecular Mass: 755.91876
• Monoisotopic Mass: 755.32403654
• SMILES: CC1(c2cc(ccc2[N+](=C1/C=C/C=C\1/C=C(Oc2c1cc1c3c2CCCN3CCC1)C(C)(C)C)CCCCCC(=O)ON1C(=O)CCC1=O)S(=O)(=O)[O-])C
• Canonical SMILES: O=C(ON1C(=O)CCC1=O)CCCCC[N+]1=C(/C=C/C=C\2/C=C(Oc3c2cc2CCCN4c2c3CCC4)C(C)(C)C)C(c2c1ccc(c2)S(=O)(=O)[O-])(C)C
• InChI: InChI=1S/C42H49N3O8S/c1-41(2,3)35-25-27(31-24-28-13-10-21-43-22-11-14-30(39(28)43)40(31)52-35)12-9-15-34-42(4,5)32-26-29(54(49,50)51)17-18-33(32)44(34)23-8-6-7-16-38(48)53-45-36(46)19-20-37(45)47/h9,12,15,17-18,24-26H,6-8,10-11,13-14,16,19-23H2,1-5H3
• InChIKey: VRVHFNHPKUVWIW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3-{4-tert-butyl-3-oxa-13-azatetracyclo[7.7.1.0^2,^7.0^1^3,^1^7]heptadeca-1(17),2(7),4,8-tetraen-6-ylidene}prop-1-en-1-yl)-1-{6-[(2,5-dioxopyrrolidin-1-yl)oxy]-6-oxohexyl}-3,3-dimethyl-3H-indol-1-ium-5-sulfonate
• IUPAC Traditional name: 2-(3-{4-tert-butyl-3-oxa-13-azatetracyclo[7.7.1.0^2,^7.0^1^3,^1^7]heptadeca-1(17),2(7),4,8-tetraen-6-ylidene}prop-1-en-1-yl)-1-{6-[(2,5-dioxopyrrolidin-1-yl)oxy]-6-oxohexyl}-3,3-dimethylindol-1-ium-5-sulfonate
• Synonyms: 2-[3-(11-tert.-Butylpyrano[3,2-g]pyrido[3,2,1-ij]quinolin-9-ylidene)-1-propenyl]-1-[5-(succinimidooxycarbonyl)-pentyl]-3,3-dimethylindolio-5-sulfonate; Fluorescent red 635 reactive

Database IDs

• CAS Number: 350496-77-4
• MDL Number: MFCD03099336
• PubChem SID: 24864707; 162250692
• PubChem CID: 5853561

CALCULATED PROPERTIES

• Acid pKa: -1.8692477
• H Acceptors: 8
• H Donor: 0
• LogD (pH = 5.5): 6.209396
• LogD (pH = 7.4): 6.2172847
• Log P: 3.6237683
• Molar Refractivity: 220.8769 cm^3
• Polarizability: 80.05401 Å^3
• Polar Surface Area: 136.36 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMF: soluble
• Fluorescence: λex 635 nm; λem 665 nm in 0.1 M phosphate pH 7.0 (non-covalent binding to BSA enhances fluorescence emission)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Grade: for fluorescence
• Empirical Formula (Hill Notation): C42H49N3O8S

DETAILS

Sigma Aldrich - 39779

Application
Amino-reactive biolabel excited by red lasers (He-Ne; 633 nm) and diode lasers (635-650 nm). Molar absorption 200′000 1/M cm, abs: (conjugate) 650 nm, em: (conjugate) 670 nm, QY is fairly low in aqueous media, but up to 0.4 for conjugates.
Features and Benefits
Hemicyanine dye Fluorescent red 630 match excitation by He-Ne laser line at 633 nm, Argon or Argon-Krypton laser lines at 647 nm and diode lasers (635-650 nm). BenefitsIdeal match to common excitation light sourcesHigh molar absorption (200.000 M-1cm-1) Fairly low quantum yield if dissolved inaqueous media, but very strong increase by coupling to target molecule.Superior solid state fluorescence making them certainly useful to label DNA for preparation of glass arrays
General description
Fluorescent red NHS is an aminoreactive fluorescent biolabel designed for excitation by red lasers (He/Ne; 633 nm) and diode lasers (635 - 650 nm). It can be used for covalent coupling to proteins and other biomolecules containing primary amino groups like aminomodified DNA-oligomers and aminomodified biotin. The chromophore responsible for absoprtion maximum is based on a bridged hemicyanine.Fluorescent red 635-NHS exhibits a fairly low fluorescence quantum yield if dissolved in aqueous media, but after coupling to a target signal intensity can rise up to one order of magnitude as demonstrated for protein conjugates and labeled oligomers. Together with the quantum yield the fluorescence lifetime increases drastically.Within the conjugate absorption of the label shifts slightly to the red while position and shape of the emission spectrum remain nearly unchanged.