MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 406956 | Name: Ciliobrevin A
Featured New

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ciliobrevin A, also known as HPI-4 and Hedgehog Pathway Inhibitor 4, is a Hedgehog pathway inhibitor. Treatment with HH pathway inhibitor-4 (HPI-4) could significantly decrease human chondrosarcoma cell proliferation, invasion and migration ability. Furthermore, HPI-4 could distinctly disturb HH pathway-mediated ciliogenesis and suppress primary cilia-related protein intraflagellar transport protein IFT88 expression. HH downstream effect molecular GLI2 was restrained to block parathyroid hormone-related protein and affect MAPK/ERK-regulated matrix metalloproteinases (MMP2 and MMP9). d HPI-4 could be a new therapeutic option specific to chondrosarcoma expressing elevated levels of HH pathway.

Chemical Structure

Ciliobrevin A
Ciliobrevin A
CAS#302803-72-1

Theoretical Analysis

MedKoo Cat#: 406956

Name: Ciliobrevin A

CAS#: 302803-72-1

Chemical Formula: C17H9Cl2N3O2

Exact Mass: 357.0072

Molecular Weight: 358.18

Elemental Analysis: C, 57.01; H, 2.53; Cl, 19.79; N, 11.73; O, 8.93

Price and Availability

Size Price Availability Quantity
50mg USD 450.00 2 Weeks
100mg USD 750.00 2 Weeks
200mg USD 1,150.00 2 Weeks
500mg USD 1,850.00 2 Weeks
1g USD 2,950.00 2 Weeks
2g USD 5,250.00 2 Weeks
Show More
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
302803-72-1
Synonym
Ciliobrevin A; HPI-4; HPI 4; HPI4; Hedgehog Pathway Inhibitor 4;
IUPAC/Chemical Name
(E)-3-(2,4-dichlorophenyl)-3-oxo-2-(4-oxo-3,4-dihydroquinazolin-2(1H)-ylidene)propanenitrile
InChi Key
SESYPWCSIZUIAS-FOWTUZBSSA-N
InChi Code
InChI=1S/C17H9Cl2N3O2/c18-9-5-6-10(13(19)7-9)15(23)12(8-20)16-21-14-4-2-1-3-11(14)17(24)22-16/h1-7,21H,(H,22,24)/b16-12+
SMILES Code
N#C/C(C(C1=CC=C(Cl)C=C1Cl)=O)=C(N2)/NC3=C(C=CC=C3)C2=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 358.18 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Reddy GS, Mukhopadhyay AG, Dey CS. Characterization of ciliobrevin A mediated dynein ATPase inhibition on flagellar motility of Leishmania donovani. Mol Biochem Parasitol. 2017 Jun;214:75-81. doi: 10.1016/j.molbiopara.2017.04.003. Epub 2017 Apr 5. PMID: 28389272. 2: Wada Y, Baba SA, Kamimura S. Effects of the dynein inhibitor ciliobrevin on the flagellar motility of sea urchin spermatozoa. Cytoskeleton (Hoboken). 2015 Apr;72(4):182-92. doi: 10.1002/cm.21218. Epub 2015 May 25. PMID: 25809136. 3: Tati S, Alisaraie L. Analysis of the Structural Mechanism of ATP Inhibition at the AAA1 Subunit of Cytoplasmic Dynein-1 Using a Chemical "Toolkit". Int J Mol Sci. 2021 Jul 19;22(14):7704. doi: 10.3390/ijms22147704. PMID: 34299323; PMCID: PMC8304172. 4: Pacheco MT, Morais KL, Berra CM, Demasi M, Sciani JM, Branco VG, Bosch RV, Iqbal A, Chudzinski-Tavassi AM. Specific role of cytoplasmic dynein in the mechanism of action of an antitumor molecule, Amblyomin-X. Exp Cell Res. 2016 Jan 15;340(2):248-58. doi: 10.1016/j.yexcr.2015.12.016. Epub 2015 Dec 31. PMID: 26748183. 5: Choi H, Shin JH, Kim ES, Park SJ, Bae IH, Jo YK, Jeong IY, Kim HJ, Lee Y, Park HC, Jeon HB, Kim KW, Lee TR, Cho DH. Primary Cilia Negatively Regulate Melanogenesis in Melanocytes and Pigmentation in a Human Skin Model. PLoS One. 2016 Dec 12;11(12):e0168025. doi: 10.1371/journal.pone.0168025. PMID: 27941997; PMCID: PMC5152889. 6: Gweon B, Jang TK, Thuy PX, Moon EY. Primary Cilium by Polyinosinic:Polycytidylic Acid Regulates the Regenerative Migration of Beas-2B Bronchial Epithelial Cells. Biomol Ther (Seoul). 2022 Mar 1;30(2):170-178. doi: 10.4062/biomolther.2022.009. PMID: 35221299; PMCID: PMC8902458. 7: Li CG, Zeng QZ, Chen MY, Xu LH, Zhang CC, Mai FY, Zeng CY, He XH, Ouyang DY. Evodiamine Augments NLRP3 Inflammasome Activation and Anti-bacterial Responses Through Inducing α-Tubulin Acetylation. Front Pharmacol. 2019 Mar 26;10:290. doi: 10.3389/fphar.2019.00290. PMID: 30971927; PMCID: PMC6443907. 8: Clippinger AJ, Alwine JC. Dynein mediates the localization and activation of mTOR in normal and human cytomegalovirus-infected cells. Genes Dev. 2012 Sep 15;26(18):2015-26. doi: 10.1101/gad.196147.112. PMID: 22987636; PMCID: PMC3444728. 9: Mukhopadhyay AG, Dey CS. Effect of inhibition of axonemal dynein ATPases on the regulation of flagellar and ciliary waveforms in Leishmania parasites. Mol Biochem Parasitol. 2018 Oct;225:27-37. doi: 10.1016/j.molbiopara.2018.08.002. Epub 2018 Aug 23. PMID: 30145318. 10: Lee JW, Cho JY, Thuy PX, Moon EY. HeLa Cervical Cancer Cells Are Maintained by Nephronophthisis 3-Associated Primary Cilium Formation via ROS-Induced ERK and HIF-1α Activation under Serum-Deprived Normoxic Condition. Int J Mol Sci. 2022 Nov 22;23(23):14500. doi: 10.3390/ijms232314500. PMID: 36498831; PMCID: PMC9739938. 11: Gibbs KL, Kalmar B, Rhymes ER, Fellows AD, Ahmed M, Whiting P, Davies CH, Greensmith L, Schiavo G. Inhibiting p38 MAPK alpha rescues axonal retrograde transport defects in a mouse model of ALS. Cell Death Dis. 2018 May 22;9(6):596. doi: 10.1038/s41419-018-0624-8. PMID: 29789529; PMCID: PMC5964181. 12: Keller S, Berghoff K, Kress H. Phagosomal transport depends strongly on phagosome size. Sci Rep. 2017 Dec 6;7(1):17068. doi: 10.1038/s41598-017-17183-7. PMID: 29213131; PMCID: PMC5719076. 13: Lee JW, Thuy PX, Koo JH, Moon EY. Nuclear factor (erythroid-derived 2)-like 2 counter-regulates thymosin beta-4 expression and primary cilium formation for HeLa cervical cancer cell survival. Sci Rep. 2022 Nov 23;12(1):20170. doi: 10.1038/s41598-022-24596-6. PMID: 36424462; PMCID: PMC9691707. 14: Lee JW, Thuy PX, Han HK, Moon EY. Di-(2-ethylhexyl) phthalate-induced tumor growth is regulated by primary cilium formation via the axis of H2O2 production-thymosin beta-4 gene expression. Int J Med Sci. 2021 Jan 14;18(5):1247-1258. doi: 10.7150/ijms.53595. PMID: 33526986; PMCID: PMC7847613. 15: Falcón-Urrutia P, Carrasco CM, Lois P, Palma V, Roth AD. Shh Signaling through the Primary Cilium Modulates Rat Oligodendrocyte Differentiation. PLoS One. 2015 Jul 28;10(7):e0133567. doi: 10.1371/journal.pone.0133567. PMID: 26218245; PMCID: PMC4517900. 16: Xiang W, Jiang T, Guo F, Gong C, Yang K, Wu Y, Huang X, Cheng W, Xu K. Hedgehog pathway inhibitor-4 suppresses malignant properties of chondrosarcoma cells by disturbing tumor ciliogenesis. Oncol Rep. 2014 Oct;32(4):1622-30. doi: 10.3892/or.2014.3372. Epub 2014 Jul 31. PMID: 25110171. 17: Villani A, Cappello M, Costa C, Fabbrocini G, Scalvenzi M. Advanced basal cell carcinoma treated with vismodegib: impact on the lives of patients and their families. Clin Exp Dermatol. 2020 Dec;45(8):1044-1046. doi: 10.1111/ced.14287. Epub 2020 Aug 26. PMID: 32415864.