NIAD-4 - ≥98% , CAS No.868592-56-7

CAS: 868592-56-7 Cat. No.: N710302 Molecular Weight: 334.41

GRADE & PURITY ≥98%

Synonyms

2-((5′-(4-Hydroxyphenyl)-2,2′-bithiophen-5-yl)methylene)malononitrile | 2-[[5′-(4-Hydroxyphenyl)[2,2′-bithiophen]-5-yl]methylene]propanedinitrile | 2-[[5-[5-(4-Hydroxyphenyl)thiophen-2-yl]thiophen-2-yl]methylidene]propanedinitrile | 5’-(4-Hydroxyphenyl)-5

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

A far-red (near-infrared) fluorescent contrast agent that permeates the blood-brain barrier (BBB) ​​for highly specific in situ and in vivo staining of amyloid plaques.
NIAD-4 is a far-red (near-infrared) fluorescent contrast agent that permeates the blood-brain barrier (BBB) ​​for highly specific in situ staining of amyloid plaques (10 μM in DMSO/propylene glycol solution; coronal sections of APP mice) and in vivo staining (2 mg/kg intravenous injection in APP mice). Due to its push-pull design and significantly enhanced affinity for the thioflavin T (ThT) site (Ki = 10 nM/NIAD-4 vs 580 nM/ThT), NIAD-4 exhibits a significant red-shift in absorbance (~70 nm) and a 1.3-fold increase in extinction coefficient upon binding to aggregated amyloid-β 1-40 (4.1 μM NIAD-4 and 10 μM amyloid-β in PBS). Excitation light 450-488 nm, emission light 550-650 nm.

Specifications

Synonyms

2-((5′-(4-Hydroxyphenyl)-2, 2′-bithiophen-5-yl)methylene)malononitrile | 2-[[5′-(4-Hydroxyphenyl)[2, 2′-bithiophen]-5-yl]methylene]propanedinitrile | 2-[[5-[5-(4-Hydroxyphenyl)thiophen-2-yl]thiophen-2-yl]methylidene]propanedinitrile | 5’-(4-Hydroxyphenyl)-5

Specifications & Purity

≥98%

Storage

Protected from light, Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: C1=CC(=CC=C1C2=CC=C(S2)C3=CC=C(S3)C=C(C#N)C#N)O
• IUPAC Name: 2-[[5-[5-(4-hydroxyphenyl)thiophen-2-yl]thiophen-2-yl]methylidene]propanedinitrile
• InChIKey: KLFRZDOQQDHVSS-UHFFFAOYSA-N
• INCHI: 1S/C18H10N2OS2/c19-10-12(11-20)9-15-5-6-17(22-15)18-8-7-16(23-18)13-1-3-14(21)4-2-13/h1-9,21H
• Isomeric SMILES: C1=CC(=CC=C1C2=CC=C(S2)C3=CC=C(S3)C=C(C#N)C#N)O
• Molecular Weight: 334.41

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Bi- and oligothiophenes

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Bi- and oligothiophenes
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Bi- and oligothiophenes
• Alternative Parents: 2,5-disubstituted thiophenes 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Heteroaromatic compounds Nitriles Organooxygen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Bithiophene - 1-hydroxy-2-unsubstituted benzenoid - Phenol - 2,5-disubstituted thiophene - Monocyclic benzene moiety - Benzenoid - Thiophene - Heteroaromatic compound - Carbonitrile - Nitrile - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Organic oxygen compound - Cyanide - Hydrocarbon derivative - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as bi- and oligothiophenes. These are organic compounds containing two or more linked thiophene rings. Thiophene is a five-member aromatic ring with one sulfur and four carbon atoms.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water at 20°C
• Sensitivity: Light sensitive
• Melt Point(°C): 242-246℃
• Molecular Weight: 334.400 g/mol
• XLogP3: 4.400
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 334.023 Da
• Monoisotopic Mass: 334.023 Da
• Topological Polar Surface Area: 124.000 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 532.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1