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MedKoo Cat#: 563492 | Name: Robotnikinin
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Description:

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

Robotnikinin is an inhibitor of Shh signaling in a concentration-dependent manner. It acts by displaying significant repression of Shh-induced Gli1/Gli2.

Chemical Structure

Robotnikinin
Robotnikinin
CAS#1132653-79-2

Theoretical Analysis

MedKoo Cat#: 563492

Name: Robotnikinin

CAS#: 1132653-79-2

Chemical Formula: C25H27ClN2O4

Exact Mass: 454.1659

Molecular Weight: 454.95

Elemental Analysis: C, 66.00; H, 5.98; Cl, 7.79; N, 6.16; O, 14.07

Price and Availability

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1mg USD 450.00
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Related CAS #
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Synonym
Robotnikinin;
IUPAC/Chemical Name
N-[(4-Chlorophenyl)methyl]-2-[(2R,6S,8E)-5,12-dioxo-2- phenyl-1-oxa-4-azacyclododec-8-en-6-yl]acetamide
InChi Key
DRDSZZCLAHXSAE-BQIDRLATSA-N
InChi Code
InChI=1S/C25H27ClN2O4/c26-21-13-11-18(12-14-21)16-27-23(29)15-20-9-5-2-6-10-24(30)32-22(17-28-25(20)31)19-7-3-1-4-8-19/h1-5,7-8,11-14,20,22H,6,9-10,15-17H2,(H,27,29)(H,28,31)/b5-2+/t20-,22-/m0/s1
SMILES Code
O=C(NCC1=CC=C(Cl)C=C1)C[C@H](C/C=C/CC2)C(NC[C@@H](C3=CC=CC=C3)OC2=O)=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
>3 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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Robotnikinin is acts upstream of Smo, binding directly to Shh with a Kd value of 3.1 μM. Robotnikinin represses Gli-mediated transcription in primary human keratinocytes and synthetic human skin in a concentration-dependent manner.
In vitro activity:
This study reports the discovery of robotnikinin. It binds the Shh protein and blocks Shh signaling in cell lines, human primary keratinocytes and a synthetic model of human skin. Reference: Nat Chem Biol. 2009 Mar;5(3):154-6. https://pubmed.ncbi.nlm.nih.gov/19151731/
In vivo activity:
To be determined
Solvent mg/mL mM
Solubility
DMSO 10.0 21.98
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 454.95 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
Formulation protocol:
1. Skóra B, Masicz M, Nowak P, Lachowska J, Sołtysek P, Biskup J, Matuszewska P, Szychowski KA. Suppression of sonic hedgehog pathway-based proliferation in glioblastoma cells by small-size silver nanoparticles in vitro. Arch Toxicol. 2023 Sep;97(9):2385-2398. doi: 10.1007/s00204-023-03552-x. Epub 2023 Jul 5. PMID: 37407723; PMCID: PMC10404180. 2. Stanton BZ, Peng LF, Maloof N, Nakai K, Wang X, Duffner JL, Taveras KM, Hyman JM, Lee SW, Koehler AN, Chen JK, Fox JL, Mandinova A, Schreiber SL. A small molecule that binds Hedgehog and blocks its signaling in human cells. Nat Chem Biol. 2009 Mar;5(3):154-6. doi: 10.1038/nchembio.142. Epub 2009 Jan 18. PMID: 19151731; PMCID: PMC2770933.
In vitro protocol:
1. Skóra B, Masicz M, Nowak P, Lachowska J, Sołtysek P, Biskup J, Matuszewska P, Szychowski KA. Suppression of sonic hedgehog pathway-based proliferation in glioblastoma cells by small-size silver nanoparticles in vitro. Arch Toxicol. 2023 Sep;97(9):2385-2398. doi: 10.1007/s00204-023-03552-x. Epub 2023 Jul 5. PMID: 37407723; PMCID: PMC10404180. 2. Stanton BZ, Peng LF, Maloof N, Nakai K, Wang X, Duffner JL, Taveras KM, Hyman JM, Lee SW, Koehler AN, Chen JK, Fox JL, Mandinova A, Schreiber SL. A small molecule that binds Hedgehog and blocks its signaling in human cells. Nat Chem Biol. 2009 Mar;5(3):154-6. doi: 10.1038/nchembio.142. Epub 2009 Jan 18. PMID: 19151731; PMCID: PMC2770933.
In vivo protocol:
To be determined
1: Hitzenberger M, Schuster D, Hofer TS. The Binding Mode of the Sonic Hedgehog Inhibitor Robotnikinin, a Combined Docking and QM/MM MD Study. Front Chem. 2017 Oct 23;5:76. doi: 10.3389/fchem.2017.00076. eCollection 2017. PubMed PMID: 29109946; PubMed Central PMCID: PMC5660280. 2: Dockendorff C, Nagiec MM, Weïwer M, Buhrlage S, Ting A, Nag PP, Germain A, Kim HJ, Youngsaye W, Scherer C, Bennion M, Xue L, Stanton BZ, Lewis TA, Macpherson L, Palmer M, Foley MA, Perez JR, Schreiber SL. Macrocyclic Hedgehog Pathway Inhibitors: Optimization of Cellular Activity and Mode of Action Studies. ACS Med Chem Lett. 2012 Oct 11;3(10):808-813. Epub 2012 Aug 30. PubMed PMID: 23074541; PubMed Central PMCID: PMC3469069. 3: Hassounah NB, Bunch TA, McDermott KM. Molecular pathways: the role of primary cilia in cancer progression and therapeutics with a focus on Hedgehog signaling. Clin Cancer Res. 2012 May 1;18(9):2429-35. doi: 10.1158/1078-0432.CCR-11-0755. Epub 2012 Mar 13. PubMed PMID: 22415315; PubMed Central PMCID: PMC3738179. 4: Hwang S, Thangapandian S, Lee Y, Sakkiah S, John S, Lee KW. Discovery and evaluation of potential sonic hedgehog signaling pathway inhibitors using pharmacophore modeling and molecular dynamics simulations. J Bioinform Comput Biol. 2011 Dec;9 Suppl 1:15-35. PubMed PMID: 22144251. 5: Stanton BZ, Peng LF. Small-molecule modulators of the Sonic Hedgehog signaling pathway. Mol Biosyst. 2010 Jan;6(1):44-54. doi: 10.1039/b910196a. Epub 2009 Aug 27. Review. PubMed PMID: 20024066. 6: Peng LF, Stanton BZ, Maloof N, Wang X, Schreiber SL. Syntheses of aminoalcohol-derived macrocycles leading to a small-molecule binder to and inhibitor of Sonic Hedgehog. Bioorg Med Chem Lett. 2009 Nov 15;19(22):6319-25. doi: 10.1016/j.bmcl.2009.09.089. Epub 2009 Sep 25. PubMed PMID: 19819139; PubMed Central PMCID: PMC2796117. 7: Stanton BZ, Peng LF, Maloof N, Nakai K, Wang X, Duffner JL, Taveras KM, Hyman JM, Lee SW, Koehler AN, Chen JK, Fox JL, Mandinova A, Schreiber SL. A small molecule that binds Hedgehog and blocks its signaling in human cells. Nat Chem Biol. 2009 Mar;5(3):154-6. doi: 10.1038/nchembio.142. Epub 2009 Jan 18. PubMed PMID: 19151731; PubMed Central PMCID: PMC2770933.