2-(2-{2-[(3-azidopropyl)amino]-3-{2-[3,3-dimethyl-1-(4-sulfobutyl)-2,3-dihydro-1H-indol-2-ylidene]ethylidene}cyclopent-1-en-1-yl}ethenyl)-3,3-dimethyl-1-(4-sulfonatobutyl)-3H-indol-1-ium

• ChemBase ID: 154781
• Molecular Formular: C40H52N6O6S2
• Molecular Mass: 777.00748
• Monoisotopic Mass: 776.33897541
• SMILES: CC1(c2ccccc2[N+](=C1/C=C/C1=C(/C(=C/C=C\2/C(c3ccccc3N2CCCCS(=O)(=O)O)(C)C)/CC1)NCCCN=[N+]=[N-])CCCCS(=O)(=O)[O-])C
• Canonical SMILES: [N-]=[N+]=NCCCNC1=C(CC/C/1=C\C=C\1/N(CCCCS(=O)(=O)O)c2c(C1(C)C)cccc2)/C=C/C1=[N+](CCCCS(=O)(=O)[O-])c2c(C1(C)C)cccc2
• InChI: InChI=1S/C40H52N6O6S2/c1-39(2)32-14-5-7-16-34(32)45(26-9-11-28-53(47,48)49)36(39)22-20-30-18-19-31(38(30)42-24-13-25-43-44-41)21-23-37-40(3,4)33-15-6-8-17-35(33)46(37)27-10-12-29-54(50,51)52/h5-8,14-17,20-23H,9-13,18-19,24-29H2,1-4H3,(H2,47,48,49,50,51,52)
• InChIKey: XEWMTEFQJKJRAZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2-{2-[(3-azidopropyl)amino]-3-{2-[3,3-dimethyl-1-(4-sulfobutyl)-2,3-dihydro-1H-indol-2-ylidene]ethylidene}cyclopent-1-en-1-yl}ethenyl)-3,3-dimethyl-1-(4-sulfonatobutyl)-3H-indol-1-ium
• IUPAC Traditional name: 2-(2-{2-[(3-azidopropyl)amino]-3-{2-[3,3-dimethyl-1-(4-sulfobutyl)indol-2-ylidene]ethylidene}cyclopent-1-en-1-yl}ethenyl)-3,3-dimethyl-1-(4-sulfonatobutyl)indol-1-ium
• Synonyms: 2-{2-{2-[(3-Azidopropyl)amino]-3-{2-[1,3-dihydro-3,3-dimethyl-1-(4-sulfobutyl)-2H-indol-2-ylidene]ethylidene}-1-cyclopenten-1-yl}ethenyl}-3,3-dimethyl-1-(4-sulfobutyl)-3H-indolium inner salt; Azide cyanine dye 728

Database IDs

• CAS Number: 1188332-22-0
• MDL Number: MFCD18452836
• PubChem SID: 162248919
• PubChem CID: 71311977

CALCULATED PROPERTIES

• Acid pKa: -1.024793
• H Acceptors: 10
• H Donor: 2
• LogD (pH = 5.5): 3.307688
• LogD (pH = 7.4): 3.280485
• Log P: 0.74565554
• Molar Refractivity: 229.6408 cm^3
• Polarizability: 82.96219 Å^3
• Polar Surface Area: 159.28 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Fluorescence: λex 670 nm; λem 728 nm in ethanol

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
• Storage Temperature: -20°C

Product Information

• Empirical Formula (Hill Notation): C40H52N6O6S2

DETAILS

Sigma Aldrich - 89524

General description
The MegaStokes dyes for ?click" biological labeling, licensed by LuminoChem are virtually covering the whole visible spectrum reaching the infra-red regime. Besides dyes that are being capable of participating in classical copper catalyzed 1,3-dipolar cycloaddition reaction with the counterparting function, we also provide dyes containing cyclooctyne moiety an alkyne derivative that enables copper free clicking to azides.These dyes are noteworthy for their large Stokes-shift (120 or 125 nm). Dyes for this kind are exceptionally useful in fluorescence resonance electron transfer (FRET) applications as they do not interfere with the spectral bands of the second fluorophore a common problem in FRET technology. Azido sugars have been used for click-labeling of surface glycoproteins, recently. We have adapted this system to demonstrate the ability of our dyes to undergo bioorthogonal labeling reaction, efficiently. Prior to labeling, Chinese hamster ovary (CHO) cells were incubated with these MegaStockesdyes to test the possible cytostatic effects of these dyes. Experimental results have shown that neither dye is toxic up to 50 μM concentration.