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MedKoo Cat#: 406348 | Name: SB-218078
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Description:

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

SB-218078 is a potent and selective indolocarbazole chk1 inhibitor.

Chemical Structure

SB-218078
SB-218078
CAS#135897-06-2

Theoretical Analysis

MedKoo Cat#: 406348

Name: SB-218078

CAS#: 135897-06-2

Chemical Formula: C24H15N3O3

Exact Mass: 393.1113

Molecular Weight: 393.40

Elemental Analysis: C, 73.27; H, 3.84; N, 10.68; O, 12.20

Price and Availability

Size Price Availability Quantity
1mg USD 500.00 2 Weeks
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Related CAS #
No Data
Synonym
SB218078; SB218078; SB218078.
IUPAC/Chemical Name
(5R,8S)-7,8-dihydro-5H-16-oxa-4b,8a,14-triaza-5,8-methanodibenzo[b,h]cycloocta[jkl]cyclopenta[e]-as-indacene-13,15(6H,14H)-dione
InChi Key
OTPNDVKVEAIXTI-IYBDPMFKSA-N
InChi Code
InChI=1S/C24H15N3O3/c28-23-19-17-11-5-1-3-7-13(11)26-15-9-10-16(30-15)27-14-8-4-2-6-12(14)18(22(27)21(17)26)20(19)24(29)25-23/h1-8,15-16H,9-10H2,(H,25,28,29)/t15-,16+
SMILES Code
O=C1NC(C(C2=C3N([C@@]4([H])CC[C@]5([H])O4)C6=CC=CC=C62)=C1C7=C3N5C8=CC=CC=C78)=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
0 – 4 C for short term (weeks to 1 month) or -20 C for long terms (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly.
Drug Formulation
Stock solution storage:
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:
SB-218078 blocks phosphorylation of cdc25 with an IC50 value of 15 nM. It inhibits cdc2 and PKC (IC50s = 250 and 1,000 nM, respectively). SB-218078 releases G2 cell cycle arrest induced by γ-irradiation or topotecan. SB-218078 enhances the cytotoxicity of DNA-damaging compounds.
In vitro activity:
When combined with SB218078, quinacrine led to enhanced apoptosis in breast cancer cells by causing G2/M cell cycle arrest, mitotic catastrophe, and increased DNA damage. These effects were accompanied by RPA level decreases. The quinacrine/SB218078 combination disrupted BER induction, offering a potential novel approach for breast cancer treatment. Reference: Biochem Pharmacol. 2016 Apr 1;105:23-33. https://pubmed.ncbi.nlm.nih.gov/26850987/
In vivo activity:
When Chk1 in was inhibited by SB-218078, the cnidarian Hydra displayed an inability to regenerate the head and maintain head-specific structures. This treatment also led to a reduction in the proportion of epithelial cells, although it did not significantly affect interstitial stem cells or their derivatives. SB-216763 had no noticeable impact on the rates of mitosis or apoptosis. Reference: Int J Dev Biol. 2021;65(10-11-12):523-536. https://pubmed.ncbi.nlm.nih.gov/34549798/
Solvent mg/mL mM
Solubility
DMF 5.0 12.71
DMSO 5.0 12.71
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 393.40 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. Preet R, Siddharth S, Satapathy SR, Das S, Nayak A, Das D, Wyatt MD, Kundu CN. Chk1 inhibitor synergizes quinacrine mediated apoptosis in breast cancer cells by compromising the base excision repair cascade. Biochem Pharmacol. 2016 Apr 1;105:23-33. doi: 10.1016/j.bcp.2016.01.017. Epub 2016 Feb 2. PMID: 26850987. 2. Akasaka T, Tsujii M, Kondo J, Hayashi Y, Ying J, Lu Y, Kato M, Yamada T, Yamamoto S, Inoue T, Tsujii Y, Maekawa A, Fujinaga T, Shiraishi E, Hiyama S, Inoue T, Shinzaki S, Watabe K, Nishida T, Iijima H, Takehara T. 5‑FU resistance abrogates the amplified cytotoxic effects induced by inhibiting checkpoint kinase 1 in p53‑mutated colon cancer cells. Int J Oncol. 2015 Jan;46(1):63-70. doi: 10.3892/ijo.2014.2693. Epub 2014 Oct 6. PMID: 25310623. 3. Lee Y, Muddaluru V, Anwar S, Wilson JY, Campos AR. A screen of kinase inhibitors reveals a potential role of Chk1 in regulating Hydra head regeneration and maintenance. Int J Dev Biol. 2021;65(10-11-12):523-536. doi: 10.1387/ijdb.210087yl. PMID: 34549798. 4. Fishler T, Li YY, Wang RH, Kim HS, Sengupta K, Vassilopoulos A, Lahusen T, Xu X, Lee MH, Liu Q, Elledge SJ, Ried T, Deng CX. Genetic instability and mammary tumor formation in mice carrying mammary-specific disruption of Chk1 and p53. Oncogene. 2010 Jul 15;29(28):4007-17. doi: 10.1038/onc.2010.163. Epub 2010 May 17. PMID: 20473325; PMCID: PMC7316381.
In vitro protocol:
1. Preet R, Siddharth S, Satapathy SR, Das S, Nayak A, Das D, Wyatt MD, Kundu CN. Chk1 inhibitor synergizes quinacrine mediated apoptosis in breast cancer cells by compromising the base excision repair cascade. Biochem Pharmacol. 2016 Apr 1;105:23-33. doi: 10.1016/j.bcp.2016.01.017. Epub 2016 Feb 2. PMID: 26850987. 2. Akasaka T, Tsujii M, Kondo J, Hayashi Y, Ying J, Lu Y, Kato M, Yamada T, Yamamoto S, Inoue T, Tsujii Y, Maekawa A, Fujinaga T, Shiraishi E, Hiyama S, Inoue T, Shinzaki S, Watabe K, Nishida T, Iijima H, Takehara T. 5‑FU resistance abrogates the amplified cytotoxic effects induced by inhibiting checkpoint kinase 1 in p53‑mutated colon cancer cells. Int J Oncol. 2015 Jan;46(1):63-70. doi: 10.3892/ijo.2014.2693. Epub 2014 Oct 6. PMID: 25310623.
In vivo protocol:
1. Lee Y, Muddaluru V, Anwar S, Wilson JY, Campos AR. A screen of kinase inhibitors reveals a potential role of Chk1 in regulating Hydra head regeneration and maintenance. Int J Dev Biol. 2021;65(10-11-12):523-536. doi: 10.1387/ijdb.210087yl. PMID: 34549798. 2. Fishler T, Li YY, Wang RH, Kim HS, Sengupta K, Vassilopoulos A, Lahusen T, Xu X, Lee MH, Liu Q, Elledge SJ, Ried T, Deng CX. Genetic instability and mammary tumor formation in mice carrying mammary-specific disruption of Chk1 and p53. Oncogene. 2010 Jul 15;29(28):4007-17. doi: 10.1038/onc.2010.163. Epub 2010 May 17. PMID: 20473325; PMCID: PMC7316381.
1: Jennings-Gee J, Pardee TS, Gmeiner WH. Replication-dependent irreversible topoisomerase 1 poisoning is responsible for FdUMP[10] anti-leukemic activity. Exp Hematol. 2013 Feb;41(2):180-188.e4. doi: 10.1016/j.exphem.2012.10.007. Epub 2012 Oct 17. PubMed PMID: 23085462; PubMed Central PMCID: PMC3660094. 2: Park JH, Kim WS, Kim JY, Park MH, Nam JH, Yun CW, Kwon YG, Jo I. Chk1 and Hsp90 cooperatively regulate phosphorylation of endothelial nitric oxide synthase at serine 1179. Free Radic Biol Med. 2011 Dec 15;51(12):2217-26. doi: 10.1016/j.freeradbiomed.2011.09.021. Epub 2011 Sep 25. PubMed PMID: 22001744. 3: Fishler T, Li YY, Wang RH, Kim HS, Sengupta K, Vassilopoulos A, Lahusen T, Xu X, Lee MH, Liu Q, Elledge SJ, Ried T, Deng CX. Genetic instability and mammary tumor formation in mice carrying mammary-specific disruption of Chk1 and p53. Oncogene. 2010 Jul 15;29(28):4007-17. doi: 10.1038/onc.2010.163. Epub 2010 May 17. PubMed PMID: 20473325. 4: Azorsa DO, Gonzales IM, Basu GD, Choudhary A, Arora S, Bisanz KM, Kiefer JA, Henderson MC, Trent JM, Von Hoff DD, Mousses S. Synthetic lethal RNAi screening identifies sensitizing targets for gemcitabine therapy in pancreatic cancer. J Transl Med. 2009 Jun 11;7:43. doi: 10.1186/1479-5876-7-43. PubMed PMID: 19519883; PubMed Central PMCID: PMC2702280. 5: Robles AI, Wright MH, Gandhi B, Feis SS, Hanigan CL, Wiestner A, Varticovski L. Schedule-dependent synergy between the heat shock protein 90 inhibitor 17-(dimethylaminoethylamino)-17-demethoxygeldanamycin and doxorubicin restores apoptosis to p53-mutant lymphoma cell lines. Clin Cancer Res. 2006 Nov 1;12(21):6547-56. PubMed PMID: 17085670. 6: Chen JS, Lin SY, Tso WL, Yeh GC, Lee WS, Tseng H, Chen LC, Ho YS. Checkpoint kinase 1-mediated phosphorylation of Cdc25C and bad proteins are involved in antitumor effects of loratadine-induced G2/M phase cell-cycle arrest and apoptosis. Mol Carcinog. 2006 Jul;45(7):461-78. PubMed PMID: 16649252. 7: Kawabe T. G2 checkpoint abrogators as anticancer drugs. Mol Cancer Ther. 2004 Apr;3(4):513-9. Review. PubMed PMID: 15078995. 8: Zhao B, Bower MJ, McDevitt PJ, Zhao H, Davis ST, Johanson KO, Green SM, Concha NO, Zhou BB. Structural basis for Chk1 inhibition by UCN-01. J Biol Chem. 2002 Nov 29;277(48):46609-15. Epub 2002 Sep 19. PubMed PMID: 12244092. 9: Jackson JR, Gilmartin A, Imburgia C, Winkler JD, Marshall LA, Roshak A. An indolocarbazole inhibitor of human checkpoint kinase (Chk1) abrogates cell cycle arrest caused by DNA damage. Cancer Res. 2000 Feb 1;60(3):566-72. PubMed PMID: 10676638.

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Hexamethonium Free Base

Hexamethonium Free Base