Ciliobrevin D - ≥98% , CAS No.1370554-01-0

CAS: 1370554-01-0 Cat. No.: C414481 Molecular Weight: 392.62 PubChem CID: 136257953

GRADE & PURITY ≥98%

Synonyms

Benzenepropanenitril​e,2,​4-​dichloro-​α-​(7-​chloro-​3,​4-​dihydro-​4-​oxo-​2(1H)​-​quinazolinylidene)​-​β-​oxo-

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

Ciliobrevin D (compound 5) is a cell-permeable, reversible and specific antagonist of AAA+ (ATPases associated with diverse cellular activities) ATPase motorcytoplasmic dynein. Ciliobrevin D perturbs primary cilia formation and blocksHedgehog (Hh)signaling.

Targets

cytoplasmic dynein ; Hedgehog

In vitro

Ciliobrevin D inactivate dynein in Sertoli cells. The inactivation of dynein by ciliobrevin D also perturbs gross disruption of F-actin across the Sertoli cells in vitro. Ciliobrevin D perturbs protein trafficking within the primary cilium, leading to their malformation and Hedgehog signaling blockade. Ciliobrevin D also prevents spindle pole focusing, kinetochore-microtubule attachment, melanosome aggregation, and peroxisome motility in cultured cells.

In vivo

Ciliobrevin D inactivate dynein in the testis. The inactivation of dynein by ciliobrevin D also perturbs gross disruption of F-actin across the seminiferous epithelium illustrating there are cross talks between the two cytoskeletons in the testis.

Cell Research(from reference)

Cell lines：Sertoli cells 

Concentrations：15 µM, 30 µM 

Incubation Time：1 h 

Specifications

Synonyms

Benzenepropanenitril​e, 2, ​4-​dichloro-​α-​(7-​chloro-​3, ​4-​dihydro-​4-​oxo-​2(1H)​-​quinazolinylidene)​-​β-​oxo-

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Ciliobrevin D (compound 5) is a cell-permeable, reversible and specific antagonist of AAA+ (ATPases associated with diverse cellular activities) ATPase motor cytoplasmic dynein. Ciliobrevin D perturbs primary cilia formation and blocks Hedgehog (Hh) signa

Storage

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

• Pubchem Sid: 504773470
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504773470
• Canonical Smiles: C1=CC2=C(C=C1Cl)N=C(NC2=O)C(=C(C3=C(C=C(C=C3)Cl)Cl)O)C#N
• IUPAC Name: 2-(7-chloro-4-oxo-3H-quinazolin-2-yl)-3-(2,4-dichlorophenyl)-3-hydroxyprop-2-enenitrile
• InChIKey: HVJSIEVASHGLBF-UHFFFAOYSA-N
• INCHI: 1S/C17H8Cl3N3O2/c18-8-1-3-10(13(20)5-8)15(24)12(7-21)16-22-14-6-9(19)2-4-11(14)17(25)23-16/h1-6,24H,(H,22,23,25)
• PubChem CID: 136257953
• Molecular Weight: 392.62

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Diazanaphthalenes
      • Subclass Benzodiazines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Diazanaphthalenes
• Subclass: Benzodiazines
• Intermediate Tree Nodes: Not available
• Direct Parent: Quinazolines
• Alternative Parents: Dichlorobenzenes Pyrimidones Aryl chlorides Heteroaromatic compounds Lactams Nitriles Enols Azacyclic compounds Organopnictogen compounds Organochlorides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Quinazoline - 1,3-dichlorobenzene - Pyrimidone - Halobenzene - Chlorobenzene - Benzenoid - Pyrimidine - Monocyclic benzene moiety - Aryl halide - Aryl chloride - Heteroaromatic compound - Lactam - Azacycle - Nitrile - Carbonitrile - Enol - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as quinazolines. These are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring.
• 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

Chemical and Physical Properties

• Solubility: Solubility (25°C) In vitro DMSO: 20 mg/mL (50.93 mM); Water: Insoluble; Ethanol: Insoluble

References

1. Yunfeng Hu, Qiu Xie, Shanshan Chen, Wangxing Zhao, Xudong Zhao, Qinli Ruan, Zihui Zheng, Huanhuan Zhao, Tonghui Ma, Jun Guo, Lei Li.  (2022)  Par3 promotes breast cancer invasion and migration through pull tension and protein nanoparticle-induced osmotic pressure.  BIOMEDICINE & PHARMACOTHERAPY,      [PMID:36179489] [10.1016/j.biopha.2022.113739]

2. Ying Song, Chen Li, Yahan Fu, Qiu Xie, Jun Guo, Guangming Li, Huiwen Wu.  (2020)  Inward Tension of Talin and Integrin-related Osmotic Pressure are involved Synergetically in the Invasion and Metastasis of Non-small Cell Lung Cancer.  Journal of Cancer,      [PMID:32742451] [10.7150/jca.45494]

3. Yifan Wang, Xiaolong Zhang, Jilai Tian, Jinjun Shan, Yunfeng Hu, Yiqian Zhai, Jun Guo.  (2019)  Talin promotes integrin activation accompanied by generation of tension in talin and an increase in osmotic pressure in neurite outgrowth.  FASEB JOURNAL,  33  (5): (6311-6326).  [PMID:30768370] [10.1096/fj.201801949RR]

4. Honggang Su, Huimin Pan, Yaqiang Liu, Wei Wang, Yang Jiao, Yumo Hang, Xiahe Huang, Yong E. Zhang, Yuhang Chen, Mei Ding, Xun Huang.  (2026)  Lipid Droplet-Localized Spindle Apparatus Coiled-Coil Protein 1 Regulates Lipid Droplet Distribution.  Advanced Science,      [PMID:41487061] [10.1002/advs.202511960]