3,3'-Dipentyloxacarbocyanine iodide

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3,3'-Dipentyloxacarbocyanine iodide

3,3'-Dipentyloxacarbocyanine iodide | 53213-81-3

Catalog Number A16-0164
Category Cell membrane Fluorescent Probes
Molecular Formula C27H33IN2O2
Molecular Weight 544.47
Catalog Number Size Price Quantity
A16-0164 -- $--

Product Introduction

3,3'-Dipentyloxacarbocyanine iodide is a lipophilic fluorescent stain for labeling membranes.

Chemical Information

Synonyms DiOC5(3)
IUPAC Name (2Z)-3-pentyl-2-[(E)-3-(3-pentyl-1,3-benzoxazol-3-ium-2-yl)prop-2-enylidene]-1,3-benzoxazole;iodide
Canonical SMILES CCCCCN1C2=CC=CC=C2OC1=CC=CC3=[N+](C4=CC=CC=C4O3)CCCCC.[I-]
InChI InChI=1S/C27H33N2O2.HI/c1-3-5-11-20-28-22-14-7-9-16-24(22)30-26(28)18-13-19-27-29(21-12-6-4-2)23-15-8-10-17-25(23)31-27;/h7-10,13-19H,3-6,11-12,20-21H2,1-2H3;1H/q+1;/p-1
InChI Key CDLMLYASVIQVPH-UHFFFAOYSA-M
  • Product Specification
  • Application
Excitation 532
Emission 580
Signal Danger
GHS Hazard Statements H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation] H360 (100%): May damage fertility or the unborn child [Danger Reproductive toxicity]
Precautionary Statement Codes P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.)

3,3’-Dipentyloxacarbocyanine iodide, a fluorescent dye widely utilized in diverse biological and biochemical scenarios, presents numerous applications.

Cell Membrane Potential Measurement: Employing 3,3’-Dipentyloxacarbocyanine iodide for measuring alterations in membrane potential within cells showcases its utility as a potent-sensitive dye. By accumulating in cell membranes and fluorescing in response to voltage variations, this dye enables the exploration of cellular electrical activity and physiological processes in neurons, cardiac cells, and other excitable cell types.

Mitochondrial Function Assays: This versatile dye also serves in evaluating mitochondrial membrane potential, a critical gauge of mitochondrial vitality and operation. As mitochondria become energized, the dye infiltrates these organelles, emitting fluorescence that can be quantified via fluorescence microscopy or flow cytometry. This application assumes paramount importance in studying mitochondrial disorders, drug-induced toxicity, and bioenergetics.

Viability and Apoptosis Detection: 3,3’-Dipentyloxacarbocyanine iodide emerges as a valuable tool for distinguishing between live, dead, and apoptotic cells based on their membrane potential states. Whereas live cells with intact membrane potential radiate strong fluorescence, apoptotic or deceased cells exhibit subdued or altered fluorescence patterns. Such capability finds significant application in cell viability assessments and drug screening efforts.

Intracellular Tracking: Leveraging this dye for monitoring organelle movement and localization within living cells uncovers a realm of possibilities due to its fluorescence characteristics. Real-time tracking using advanced imaging methods enables a deeper understanding of intracellular dynamics and the spatial arrangement of cellular constituents, offering invaluable insights into cellular processes and architecture.

Computed Properties

Hydrogen Bond Donor Count 0
Hydrogen Bond Acceptor Count 4
Rotatable Bond Count 10
Exact Mass 544.15868 g/mol
Monoisotopic Mass 544.15868 g/mol
Topological Polar Surface Area 29.5Ų
Heavy Atom Count 32
Formal Charge 0
Complexity 554
Isotope Atom Count 0
Defined Atom Stereocenter Count 0
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 2
Undefined Bond Stereocenter Count 0
Covalently-Bonded Unit Count 2
Compound Is Canonicalized Yes
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