36536-22-8

Basic information

• Product Name: 1,1',3,3,3',3'-HEXAMETHYLINDODICARBOCYANINE IODIDE
• Synonyms: 1,3,3-TriMethyl-2-(5-(1,3,3-triMethylindolin-2-ylidene)penta-1,3-dien-1-yl)-3H-indol-1-iuM iodide;3,3-trimethyl-nyl]-iodide;3h-indolium,2-[5-(1,3-dihydro-1,3,3-trimethyl-2h-indol-2-ylidene)-1,3-pentadie;1,1',3,3,3',3'-HEXAMETHYLINDODICARBOCYANINE IODIDE;1,1,3,3,3',3'-HEXAMETHYLINDODICARBOCYANINE IODIDE;DIIC1(5);HIDC IODIDE;2-[5-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)penta-1,3-dienyl]-1,3,3-trimethyl-3H-indolium iodide
• CAS NO: 36536-22-8
• Molecular Formula: C₂₇H₃₁N₂*I
• Molecular Weight: 510.45
• EINECS: 253-091-6
• Product Categories: Cyanine
• Mol File: 36536-22-8.mol

Chemical Properties

• Melting Point: 264 °C (dec.)(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: Blue green/crystals
• Density: 1.2991 (estimate)
• Solubility: Soluble in methanol, dimethyl sulfoxide; partially soluble in wa
• CAS DataBase Reference: 1,1',3,3,3',3'-HEXAMETHYLINDODICARBOCYANINE IODIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1',3,3,3',3'-HEXAMETHYLINDODICARBOCYANINE IODIDE(36536-22-8)
• EPA Substance Registry System: 1,1',3,3,3',3'-HEXAMETHYLINDODICARBOCYANINE IODIDE(36536-22-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 24/25-36-26
• Hazardous Substances Data: 36536-22-8(Hazardous Substances Data)

Usage

Uses

Used in Photodynamic Therapy:
1,1',3,3,3',3'-HEXAMETHYLINDODICARBOCYANINE IODIDE is used as a synthetic biological stain for photodynamic therapy. It serves as a photosensitizer, which, when excited by light, generates reactive oxygen species that can cause cell death in targeted tissues. This property makes it a promising agent for the treatment of various diseases, including cancer.
Used in Antitumor Strategy:
1,1',3,3,3',3'-HEXAMETHYLINDODICARBOCYANINE IODIDE is used as a component in a novel antitumor strategy that combines a photosensitizer with a photoprotector cyanine dye. This approach aims to eradicate malignant cells expressing the multidrug-resistance phenotype, which are often resistant to conventional chemotherapy and radiation treatments. By utilizing the unique properties of Hexacyanine 2, this strategy seeks to improve the effectiveness of cancer treatment and overcome drug resistance in cancer cells.

InChI:InChI=1/C27H31N2.HI/c1-26(2)20-14-10-12-16-22(20)28(5)24(26)18-8-7-9-19-25-27(3,4)21-15-11-13-17-23(21)29(25)6;/h7-19H,1-6H3;1H/q+1;/p-1

Upstream product

• 5418-63-3 1,2,3,3-tetramethyl-3H-indolium iodide 
• 51829-35-7 2-(2-Anilino-vinyl)-1,3,3-trimethyl-3H-indolium-jodid 
• 4485-89-6 1-anilino-3-phenyliminopropene 
• 54136-24-2 5-bromo-2,3,3-trimethyl-3H-indole 
• 563-80-4 3-methyl-butan-2-one 
• 24136-92-3 1,3,3-trimethyl-2-[4-(phenylamino)-1,3-butadien-1-yl]-3H-indolium Iodide 
• 23769-16-6 phenyl[3-phenylaminoprop-2-en-1-ylidene]ammonium chloride 
• 17576-35-1 1,3,3-trimethoxypropene 
• 58467-94-0 N-((1E,3E)-3-(phenylimino)prop-1-enyl)benzenamine hydrochloride 
• 1640-39-7 2,3,3-trimethylindoleniune 
• 122-51-0 orthoformic acid triethyl ester 

Relevant articles and documents

NEAR-IR GLUCOSE SENSORS

Glucose-sensing luminescent dyes, polymers, and sensors are provided. Additionally, systems including the sensors and methods of using these sensors and systems are provided.

Charge balanced fluorescence contrast agent for high signal to background ratio and Method for imaging using the same

The present invention relates to a charge balanced fluorescence contrast agent, capable of providing a high signal to background ratio when optically observing tissues and cells using a fluorescence imaging device for image guided surgery, wherein the contrast agent emits fluorescence so that the signal to background ratio is detected to be at least 1.1 or greater, wherein the conjugate is represented by chemical formula I.COPYRIGHT KIPO 2019

Near-Infrared Illumination of Native Tissues for Image-Guided Surgery

Our initial efforts to prepare tissue-specific near-infrared (NIR) fluorescent compounds generated successful correlation between physicochemical properties and global uptake in major organs after systemic circulation and biodistribution. Herein, we focus on the effects on biodistribution based on modulating electronic influencing moieties from donating to withdrawing moieties at both the heterocyclic site and through meso-substitution of pentamethine cyanine fluorophores. These selected modifications harnessed innate biodistribution pathways through the structure-inherent targeting, resulting in effective imaging of the adrenal glands, pituitary gland, lymph nodes, pancreas, and thyroid and salivary glands. These native-tissue contrast agents will arm surgeons with a powerful and versatile arsenal for intraoperative NIR imaging in real time.

Correlating molecular character of NIR imaging agents with tissue-specific uptake

Near-infrared (NIR) fluorescent contrast agents are emerging in optical imaging as sensitive, cost-effective, and nonharmful alternatives to current agents that emit harmful ionizing radiation. Developing spectrally distinct NIR fluorophores to visualize sensitive vital tissues to selectively avoid them during surgical resection of diseased tissue is of great significance. Herein, we report the synthetic variation of pentamethine cyanine fluorophores with modifications of physicochemical properties toward prompting tissue-specific uptake into sensitive tissues (i.e., endocrine glands). Tissue-specific targeting and biodistribution studies revealed localization of contrast agents in the adrenal and pituitary glands, pancreas, and lymph nodes with dependence on molecular characteristics. Incorporation of hydrophobic heterocyclic rings, alkyl groups, and halogens allowed a fine-tuning capability to the hydrophobic character and dipole moment for observing perturbation in biological activity in response to minor structural alterations. These NIR contrast agents have potential for clinical translation for intraoperative imaging in the delineation of delicate glands.

A microwave-assisted and environmentally benign approach to the synthesis of near-infrared fluorescent pentamethine cyanine dyes

A time-efficient and eco-conscious microwave methodology was developed and applied to synthesize a systematic library of pentamethine cyanine dyes and their corresponding precursors. The synthesis outlined herein drastically reduced the reaction pathway for pentamethine carbocyanine dye syntheses from days to min, as well as producing increased yields (89-98%) to the conventional heating method (18-64%). Twelve examples of pentamethine cyanine dyes were synthesized by means of microwave-assisted organic synthesis which provided excellent yield in expedited reaction time and were obtained using facile isolation methods. Furthermore, three cyanines were prepared with a novel methylene dioxy heterocyclic structure which imparted an approximately 40 nm bathochromic shift compared to unsubstituted counterparts; these results were shown to be in agreement with DFT calculations and HOMO-LUMO energy differences.

A microwave-assisted and environmentally benign approach to the synthesis of near-infrared fluorescent pentamethine cyanine dyes

A time-efficient and eco-conscious microwave methodology was developed and applied to synthesize a systematic library of pentamethine cyanine dyes and their corresponding precursors. The synthesis outlined herein drastically reduced the reaction pathway for pentamethine carbocyanine dye syntheses from days to min, as well as producing increased yields (89-98%) to the conventional heating method (18-64%). Twelve examples of pentamethine cyanine dyes were synthesized by means of microwave-assisted organic synthesis which provided excellent yield in expedited reaction time and were obtained using facile isolation methods. Furthermore, three cyanines were prepared with a novel methylene dioxy heterocyclic structure which imparted an approximately 40 nm bathochromic shift compared to unsubstituted counterparts; these results were shown to be in agreement with DFT calculations and HOMO-LUMO energy differences.

COLORED COMPOSITION, COLORED CURED FILM, AND DISPLAY ELEMENT

PROBLEM TO BE SOLVED: To provide a colored composition containing a cyanine dye as a colorant and having good storage stability. SOLUTION: The colored composition comprises (A) a colorant, (B) a binder resin, and (C) a polymerizable compound. The (A) colorant comprises a compound having a structure represented by formula (1) below and a compound having a structure represented by formula (2) below, in which the content of the compound having a structure represented by formula (2) is 0.001 mass% or more with respect to the total content of the compound having a structure represented by formula (1) and the compound having a structure represented by formula (2). In formulae (1) and (2), ring Z1, ring Z2, ring Z3, and ring Z4 each independently represent a substituted or unsubstituted heterocycle; R1 to R6 each independently represent a hydrogen atom, a halogen atom, or a substituted or unsubstituted hydrocarbon group; and when R1, R2, R4, and R5 are present in plural numbers, they can be the same or different from one another; p represents 1 or 2; and q represents an integer of 2 or more when p is 1, and represents an integer of 3 or more when p is 2. COPYRIGHT: (C)2015,JPO&INPIT

NEAR-INFRARED FLUORESCENT CONTRAST BIOIMAGING AGENTS AND METHODS OF USE THEREOF

The instant invention provides near-infrared fluorescent biological contrast agents and methods of using them.

Supramolecular control of photophysical properties of cyanine dyes

We present the results of our studies on the intramolecular complexation of cyanine dyes and cyclodextrins with the objective of modifying the photophysical behaviour of the dyes. We demonstrate that dye inclusion complex formation with cyclodextrins serves to inhibit dimer formation as well as enhance photostability of cyanines. We also show that the modification of the physicochemical properties of cyanine dyes by cyclodextrin complexation is a highly selective, structure dependent phenomenon.