SAG hydrochloride
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MedKoo CAT#: 407942

CAS#: 2095432-58-7 (HCl)

Description: SAG is a potent Smoothened (Smo) receptor agonist (Kd = 59 nM); sag antagonizes cyclopamine action at the Smo receptor. SAG potently activates the Hedgehog signaling pathway in Shh-light 2 cells (EC50 ~ 3 nM). SAG induces pathway activation independently of Ptch proteins. The Smoothened receptor (SMO) mediates signal transduction in the hedgehog pathway, which is implicated in normal development and carcinogenesis. SMO antagonists can suppress the growth of some tumours.


Price and Availability

Size
Price

100mg
USD 850
1g
USD 3250
Size
Price

200mg
USD 1450
2g
USD 5250
Size
Price

500mg
USD 2250
5g
USD 8450

SAG hydrochloride, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 407942
Name: SAG hydrochloride
CAS#: 2095432-58-7 (HCl)
Chemical Formula: C28H29Cl2N3OS
Exact Mass:
Molecular Weight: 526.52
Elemental Analysis: C, 63.87; H, 5.55; Cl, 13.47; N, 7.98; O, 3.04; S, 6.09


Related CAS #: 2095432-58-7 (HCl)   912545-86-9 (free base)    

Synonym: SAG hydrochloride; SAG; SAG (Smo agonist);

IUPAC/Chemical Name: 3-chloro-N-((1r,4r)-4-(methylamino)cyclohexyl)-N-(3-(pyridin-4-yl)benzyl)benzo[b]thiophene-2-carboxamide hydrochloride

InChi Key: CRWTYWYPPITOOZ-HFSDZXIBSA-N

InChi Code: InChI=1S/C28H28ClN3OS.ClH/c1-30-22-9-11-23(12-10-22)32(28(33)27-26(29)24-7-2-3-8-25(24)34-27)18-19-5-4-6-21(17-19)20-13-15-31-16-14-20;/h2-8,13-17,22-23,30H,9-12,18H2,1H3;1H/t22-,23-;

SMILES Code: O=C(C1=C(Cl)C2=CC=CC=C2S1)N([C@H]3CC[C@H](NC)CC3)CC4=CC=CC(C5=CC=NC=C5)=C4.[H]Cl


Technical Data

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).

Harmonized System Code:
2934.99.03.00


References

1: Geyer N, Ridzewski R, Bauer J, Kuzyakova M, Dittmann K, Dullin C, Rosenberger A, Schildhaus HU, Uhmann A, Fulda S, Hahn H. Different Response of Ptch Mutant and Ptch Wildtype Rhabdomyosarcoma Toward SMO and PI3K Inhibitors. Front Oncol. 2018 Sep 25;8:396. doi: 10.3389/fonc.2018.00396. eCollection 2018. PubMed PMID: 30319965; PubMed Central PMCID: PMC6168716.

2: Guerrini G, Criscuoli M, Filippi I, Naldini A, Carraro F. Inhibition of smoothened in breast cancer cells reduces CAXII expression and cell migration. J Cell Physiol. 2018 Dec;233(12):9799-9811. doi: 10.1002/jcp.26947. Epub 2018 Aug 21. PubMed PMID: 30132883.

3: Gigante ED, Long AB, Ben-Ami J, Caspary T. Hypomorphic Smo mutant with inefficient ciliary enrichment disrupts the highest level of vertebrate Hedgehog response. Dev Biol. 2018 May 15;437(2):152-162. doi: 10.1016/j.ydbio.2018.03.019. Epub 2018 Mar 20. PubMed PMID: 29571613; PubMed Central PMCID: PMC5903954.

4: Zhang F, Hao M, Jin H, Yao Z, Lian N, Wu L, Shao J, Chen A, Zheng S. Canonical hedgehog signalling regulates hepatic stellate cell-mediated angiogenesis in liver fibrosis. Br J Pharmacol. 2017 Mar;174(5):409-423. doi: 10.1111/bph.13701. Epub 2017 Jan 31. PubMed PMID: 28052321; PubMed Central PMCID: PMC5301045.

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. eCollection 2016. PubMed PMID: 27941997; PubMed Central PMCID: PMC5152889.

6: Fish EW, Parnell SE, Sulik KK, Baker LK, Murdaugh LB, Lamson D, Williams KP. Preaxial polydactyly following early gestational exposure to the smoothened agonist, SAG, in C57BL/6J mice. Birth Defects Res. 2017 Jan 20;109(1):49-54. doi: 10.1002/bdra.23571. PubMed PMID: 27801979; PubMed Central PMCID: PMC5388559.

7: Lubik AA, Nouri M, Truong S, Ghaffari M, Adomat HH, Corey E, Cox ME, Li N, Guns ES, Yenki P, Pham S, Buttyan R. Paracrine sonic hedgehog signaling contributes significantly to acquired steroidogenesis in the prostate tumor microenvironment. Int J Cancer. 2017 Jan 15;140(2):358-369. doi: 10.1002/ijc.30450. Epub 2016 Oct 20. PubMed PMID: 27672740.

8: Wang LC, Almazan G. Role of Sonic Hedgehog Signaling in Oligodendrocyte Differentiation. Neurochem Res. 2016 Dec;41(12):3289-3299. Epub 2016 Sep 17. PubMed PMID: 27639396.

9: Fleury A, Hoch L, Martinez MC, Faure H, Taddei M, Petricci E, Manetti F, Girard N, Mann A, Jacques C, Larghero J, Ruat M, Andriantsitohaina R, Le Lay S. Hedgehog associated to microparticles inhibits adipocyte differentiation via a non-canonical pathway. Sci Rep. 2016 Mar 24;6:23479. doi: 10.1038/srep23479. PubMed PMID: 27010359; PubMed Central PMCID: PMC4806302.

10: Chapouly C, Yao Q, Vandierdonck S, Larrieu-Lahargue F, Mariani JN, Gadeau AP, Renault MA. Impaired Hedgehog signalling-induced endothelial dysfunction is sufficient to induce neuropathy: implication in diabetes. Cardiovasc Res. 2016 Feb 1;109(2):217-27. doi: 10.1093/cvr/cvv263. Epub 2015 Dec 8. PubMed PMID: 26645982.

11: Kharebava G, Rashid MA, Lee JW, Sarkar S, Kevala K, Kim HY. N-docosahexaenoylethanolamine regulates Hedgehog signaling and promotes growth of cortical axons. Biol Open. 2015 Nov 6;4(12):1660-70. doi: 10.1242/bio.013425. PubMed PMID: 26545965; PubMed Central PMCID: PMC4736029.

12: Spann AL, Yuan K, Goliwas KF, Steg AD, Kaushik DD, Kwon YJ, Frost AR. The presence of primary cilia in cancer cells does not predict responsiveness to modulation of smoothened activity. Int J Oncol. 2015 Jul;47(1):269-79. doi: 10.3892/ijo.2015.3006. Epub 2015 May 15. PubMed PMID: 25997440.

13: Lian N, Jiang Y, Zhang F, Jin H, Lu C, Wu X, Lu Y, Zheng S. Curcumin regulates cell fate and metabolism by inhibiting hedgehog signaling in hepatic stellate cells. Lab Invest. 2015 Jul;95(7):790-803. doi: 10.1038/labinvest.2015.59. Epub 2015 May 4. PubMed PMID: 25938627.

14: Wang C, Wu H, Evron T, Vardy E, Han GW, Huang XP, Hufeisen SJ, Mangano TJ, Urban DJ, Katritch V, Cherezov V, Caron MG, Roth BL, Stevens RC. Structural basis for Smoothened receptor modulation and chemoresistance to anticancer drugs. Nat Commun. 2014 Jul 10;5:4355. doi: 10.1038/ncomms5355. PubMed PMID: 25008467; PubMed Central PMCID: PMC4198951.

15: Huang JG, Shen CB, Wu WB, Ren JW, Xu L, Liu S, Yang Q. Primary cilia mediate sonic hedgehog signaling to regulate neuronal-like differentiation of bone mesenchymal stem cells for resveratrol induction in vitro. J Neurosci Res. 2014 May;92(5):587-96. doi: 10.1002/jnr.23343. Epub 2014 Jan 24. PubMed PMID: 24464877.

16: Werminghaus P, Haase M, Hornsby PJ, Schinner S, Schott M, Malendowicz LK, Lammers BJ, Goretzki PE, Müller-Mattheis V, Markus Giessing, Willenberg HS. Hedgehog-signaling is upregulated in non-producing human adrenal adenomas and antagonism of hedgehog-signaling inhibits proliferation of NCI-H295R cells and an immortalized primary human adrenal cell line. J Steroid Biochem Mol Biol. 2014 Jan;139:7-15. doi: 10.1016/j.jsbmb.2013.09.007. Epub 2013 Sep 21. PubMed PMID: 24063979.

17: Gorojankina T, Hoch L, Faure H, Roudaut H, Traiffort E, Schoenfelder A, Girard N, Mann A, Manetti F, Solinas A, Petricci E, Taddei M, Ruat M. Discovery, molecular and pharmacological characterization of GSA-10, a novel small-molecule positive modulator of Smoothened. Mol Pharmacol. 2013 May;83(5):1020-9. doi: 10.1124/mol.112.084590. Epub 2013 Feb 28. Erratum in: Mol Pharmacol. 2013 Aug;84(2):303. PubMed PMID: 23448715.

18: Luo QF, Chen W, Zhang ST. Identification of Nedd4 as a novel regulator in Hedgehog signaling. Chin Med J (Engl). 2012 Nov;125(21):3851-5. PubMed PMID: 23106887.

19: Caparrós-Martín JA, Valencia M, Reytor E, Pacheco M, Fernandez M, Perez-Aytes A, Gean E, Lapunzina P, Peters H, Goodship JA, Ruiz-Perez VL. The ciliary Evc/Evc2 complex interacts with Smo and controls Hedgehog pathway activity in chondrocytes by regulating Sufu/Gli3 dissociation and Gli3 trafficking in primary cilia. Hum Mol Genet. 2013 Jan 1;22(1):124-39. doi: 10.1093/hmg/dds409. Epub 2012 Oct 1. PubMed PMID: 23026747.

20: Yang S, Wang C. The intraflagellar transport protein IFT80 is required for cilia formation and osteogenesis. Bone. 2012 Sep;51(3):407-17. doi: 10.1016/j.bone.2012.06.021. Epub 2012 Jul 4. PubMed PMID: 22771375; PubMed Central PMCID: PMC3412883.