3,3′-Dipropylthiacarbocyanine iodide

Name: 3,3′-Dipropylthiacarbocyanine iodide
Brand: ALDRICH

98%

Synonym(s):

3-Propyl-2-[3-[3-propyl-2(3H)benzothiazolylidene]-1-propenyl]benzothiazolium iodide, DiSC₃(3)

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About This Item

Empirical Formula (Hill Notation):

C₂₃H₂₅IN₂S₂

CAS Number:

53336-12-2

Molecular Weight:

520.49

UNSPSC Code:

12171500

NACRES:

NA.47

PubChem Substance ID:

329753928

MDL number:

MFCD00013340

Beilstein/REAXYS Number:

3842440

Key Documents

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InChI

1S/C23H25N2S2.HI/c1-3-16-24-18-10-5-7-12-20(18)26-22(24)14-9-15-23-25(17-4-2)19-11-6-8-13-21(19)27-23;/h5-15H,3-4,16-17H2,1-2H3;1H/q+1;/p-1

SMILES string

[I-].CCCN1C(\Sc2ccccc12)=C\C=C\c3sc4ccccc4[n+]3CCC

InChI key

JGTCEHAVVINOPG-UHFFFAOYSA-M

assay

98%

form

crystalline powder

mp

288 °C (dec.) (lit.)

solubility

chloroform/methanol: 10 mg/mL, clear

λ_max

559 nm

ε (extinction coefficient)

163120 at 599 nm in methanol at 0.00463 g/L, 17425 at 298 nm in methanol at 0.00463 g/L, 40246 at 220 nm in methanol at 0.00463 g/L

fluorescence

λ_ex 559 nm; λ_em 575 nm in methanol

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

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1 of 4

This Item	81845	318426	P4864
Sigma-Aldrich 318434 3,3′-Dipropylthiacarbocyanine iodide	Sigma-Aldrich 81845 Propidium iodide	Sigma-Aldrich 318426 3,3′-Dihexyloxacarbocyanine iodide	Sigma-Aldrich P4864 Propidium iodide solution
fluorescence λ_ex 559 nm; λ_em 575 nm in methanol	fluorescence λ_ex 482 nm; λ_em 608 nm (pH 7.2), λ_ex 540 nm; λ_em 608 nm (bound to DNA)	fluorescence λ_ex 485 nm; λ_em 501 nm in methanol	fluorescence -
application(s) diagnostic assay manufacturing hematology histology	application(s) -	application(s) diagnostic assay manufacturing hematology histology	application(s) diagnostic assay manufacturing hematology histology
form crystalline powder	form powder	form powder or chunks	form liquid
solubility chloroform/methanol: 10 mg/mL, clear	solubility -	solubility chloroform: 25 mg/mL, clear to slightly hazy, orange	solubility water: 1 mg/mL
assay 98%	assay ≥94% (HPLC)	assay 98%	assay ≥94%
storage temp. room temp	storage temp. 2-8°C	storage temp. room temp	storage temp. 2-8°C

General description

3,3′-Dipropylthiacarbocyanine iodide is a carbocyanine fluorescent dye sensitive to membrane potential. This cyanine dye plays a vital role as an optical probe of membrane potential. An increase in the fluorescence intensity of the dye indicates depolarization of the plasma membrane potential.

Application

3,3′-Dipropylthiacarbocyanine iodide has been used to determine bacterial membrane permeability by the effect of electrochemical scaffold treatment.

Biochem/physiol Actions

The embrane potential sensitive dye, 3,3′dipropylthiacarbocyanine iodide enters only depolarized cells, where it binds reversibly to lipid-rich intracellular components.

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number

01221PW

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Augmentation of the antibacterial activities of Pt5-derived antimicrobial peptides (AMPs) by amino acid substitutions: Design of novel AMPs against MDR bacteria.

Yashuo Wang et al.

Fish & shellfish immunology, 77, 100-111 (2018-03-24)

The ever-growing concerns on multi-drug resistant (MDR) bacteria lead to urgent demands for novel antibiotics including antimicrobial peptides (AMPs). Pt5, a peptide consisting of the C-terminal 55 residues of zebrafish phosvitin, has been shown to function as an antibacterial agent.

Preserved antibacterial activity of ribosomal protein S15 during evolution.

Baozhen Qu et al.

Molecular immunology, 127, 57-66 (2020-09-15)

Conventional role of ribosomal proteins is ribosome assembly and protein translation, but some ribosomal proteins also show antimicrobial peptide (AMP) activity, though their mode of action remains ill-defined. Here we demonstrated for the first time that amphioxus RPS15, BjRPS15, was

Identification and functional characterization of ribosomal protein S23 as a new member of antimicrobial protein.

Zengyu Ma et al.

Developmental and comparative immunology, 110, 103730-103730 (2020-05-20)

Previous studies show that some ribosomal proteins possess antimicrobial peptide (AMP) activity. However, information as such remains rather fragmentary and rather limited. We showed here for the first time that amphioxus RPS23, BjRPS23, was a previously uncharacterized AMP. It not

Antimycotic Activity of Ozonized Oil in Liposome Eye Drops against Candida spp.

Giuseppe Celenza et al.

Translational vision science & technology, 9(8), 4-4 (2020-08-29)

This study aims to investigate the antifungal activity and mechanism of action of ozonized oil eye drops in liposomes (Ozodrop), commercialized as eye lubricant for the treatment of dry eye syndrome and eye inflammation. The activity was tested against four

Synthetic antimicrobial peptides of the halictines family disturb the membrane integrity of Candida cells.

Marie Kodedová et al.

Biochimica et biophysica acta, 1859(10), 1851-1858 (2017-06-11)

We compared the potency of four derivatives of the antimicrobial peptide halictine-2 against six Candida species. Observed activity was peptide and species specific. Halictines rapidly permeabilized cell membranes and caused the leakage of cytosolic components. Their killing potential was enhanced

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