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MedKoo Cat#: 406115 | Name: LQB-118

Description:

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

LQB-118 is a synthetic pterocarpanquinone derivative that has demonstrated significant antitumor activity across various cancer cell lines. In vitro studies have shown that LQB-118 effectively inhibits the proliferation of leukemia, breast, and lung cancer cells by inducing apoptosis and cell cycle arrest. Notably, LQB-118 disrupts mitochondrial membrane potential, leading to the activation of caspases and subsequent programmed cell death. Additionally, this compound has been observed to modulate key signaling pathways involved in cancer progression, such as the downregulation of NF-κB activity and the inhibition of angiogenesis.

Chemical Structure

LQB-118
LQB-118
CAS#1219104-20-7

Theoretical Analysis

MedKoo Cat#: 406115

Name: LQB-118

CAS#: 1219104-20-7

Chemical Formula: C19H12O4

Exact Mass: 304.0736

Molecular Weight: 304.30

Elemental Analysis: C, 74.99; H, 3.97; O, 21.03

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
LQB118; LQB 118; LQB-118
IUPAC/Chemical Name
(7aS,12aS)-7,7a-dihydro-5H-benzo[g]benzofuro[3,2-c]chromene-5,13(12aH)-dione
InChi Key
BUEHOQICFGQBNY-ACJLOTCBSA-N
InChi Code
InChI=1S/C19H12O4/c20-16-11-6-1-2-7-12(11)17(21)19-15(16)18-13(9-22-19)10-5-3-4-8-14(10)23-18/h1-8,13,18H,9H2/t13-,18+/m1/s1
SMILES Code
O=C1C2=CC=CC=C2C(C3=C1OC[C@@]4([H])[C@]3([H])OC5=CC=CC=C54)=O
Appearance
Solid powder
Purity
>98%
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, not in water
Shelf Life
>5 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 304.30 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: Lima ÉA, Cavalcante-Silva LHA, Carvalho DCM, Soares MM, Medeiros ABA, Netto CD, Costa PRR, Rodrigues-Mascarenhas S. Immunomodulatory Effects of Pterocarpanquinone LQB-118 in Murine Peritoneal Macrophages. Immunol Invest. 2025 Jan 8:1-12. doi: 10.1080/08820139.2025.2449949. Epub ahead of print. PMID: 39780421. 2: Martino T, DE Bem GF, Santos SVM, Coelho MGP, Resende AC, Netto C, Costa PRR, Justo G, Sabino KCC. LQB-118 Suppresses Migration and Invasion of Prostate Cancer Cells by Modulating the Akt/GSK3β Pathway and MMP-9/Reck Gene Expression. Anticancer Res. 2023 Jan;43(1):359-367. doi: 10.21873/anticanres.16171. PMID: 36585169. 3: Hancio T, Mazzoccoli L, Guimarães G, Robaina M, Mendonça BDS, Nestal De Moraes G, Monte-Mor BDCR, Mayumi Gutiyama L, De Carvalho LO, Netto CD, Costa PRR, De Faria FCC, Maia RC. The pterocarpanquinone LQB‑118 compound induces apoptosis of cytarabine‑resistant acute myeloid leukemia cells. Int J Oncol. 2021 Jun;58(6):24. doi: 10.3892/ijo.2021.5204. Epub 2021 Mar 31. PMID: 33786613. 4: Lima ÉA, Cavalcante-Silva LHA, Carvalho DCM, Netto CD, Costa PRR, Rodrigues- Mascarenhas S. The pterocarpanquinone LQB 118 inhibits inflammation triggered by zymosan in vivo and in vitro. Int Immunopharmacol. 2020 Jun;83:106399. doi: 10.1016/j.intimp.2020.106399. Epub 2020 Mar 16. PMID: 32193104. 5: Bernardo PS, Guimarães GHC, De Faria FCC, Longo GMDC, Lopes GPF, Netto CD, Costa PRR, Maia RC. LQB‑118 compound inhibits migration and induces cell death in glioblastoma cells. Oncol Rep. 2020 Jan;43(1):346-357. doi: 10.3892/or.2019.7402. Epub 2019 Nov 6. PMID: 31746438. 6: Nestal De Moraes G, Pereira Castro C, Salustiano EJ, Dumas ML, Costas F, Wing-Fai Lam E, Ribeiro Costa PR, Maia RC. [Corrigendum] The pterocarpanquinone LQB-118 induces apoptosis in acute myeloid leukemia cells of distinct molecular subtypes and targets FoxO3a and FoxM1 transcription factors. Int J Oncol. 2019 Dec;55(6):1396. doi: 10.3892/ijo.2019.4874. Epub 2019 Sep 9. Erratum for: Int J Oncol. 2014 Nov;45(5):1949-58. doi: 10.3892/ijo.2014.2615. PMID: 31545420; PMCID: PMC6831192. 7: Faiões VDS, da Frota LCRM, Cunha-Junior EF, Barcellos JCF, Da Silva T, Netto CD, Da-Silva SAG, da Silva AJM, Costa PRR, Torres-Santos EC. Second-generation pterocarpanquinones: synthesis and antileishmanial activity. J Venom Anim Toxins Incl Trop Dis. 2018 Nov 29;24:35. doi: 10.1186/s40409-018-0174-7. PMID: 30519257; PMCID: PMC6263544. 8: Rumjanek VM, Maia RC, Salustiano EJ, Costa PRR. Insights into the Biological Evaluation of Pterocarpanquinones and Carbapterocarpans with Anti-tumor Activity against MDR Leukemias. Anticancer Agents Med Chem. 2019;19(1):29-37. doi: 10.2174/1871520618666180420165128. PMID: 29692266. 9: Martino T, Kudrolli TA, Kumar B, Salviano I, Mencalha A, Coelho MGP, Justo G, Costa PRR, Sabino KCC, Lupold SE. The orally active pterocarpanquinone LQB-118 exhibits cytotoxicity in prostate cancer cell and tumor models through cellular redox stress. Prostate. 2018 Feb;78(2):140-151. doi: 10.1002/pros.23455. Epub 2017 Nov 6. PMID: 29105806; PMCID: PMC5726914. 10: Scatena GS, Cassiano NM, Netto CD, Costa PRR, Cass QB, Batista JM Jr. Preparative chiral separation and absolute configuration of the synthetic pterocarpanquinone LQB-118. Chirality. 2017 May;29(5):167-171. doi: 10.1002/chir.22696. Epub 2017 Apr 12. PMID: 28403568. 11: Riça IG, Netto CD, Rennó MN, Abreu PA, Costa PRR, da Silva AJM, Cavalcante MCM. Anti-inflammatory properties of pterocarpanquinone LQB-118 in mice. Bioorg Med Chem. 2016 Sep 15;24(18):4415-4423. doi: 10.1016/j.bmc.2016.07.046. Epub 2016 Jul 21. PMID: 27492193. 12: Salustiano EJ, Dumas ML, Silva-Santos GG, Netto CD, Costa PR, Rumjanek VM. In vitro and in vivo antineoplastic and immunological effects of pterocarpanquinone LQB-118. Invest New Drugs. 2016 Oct;34(5):541-51. doi: 10.1007/s10637-016-0359-2. Epub 2016 May 18. PMID: 27189479. 13: Cunha-Júnior EF, Martins TM, Canto-Cavalheiro MM, Marques PR, Portari EA, Coelho MG, Netto CD, Costa PR, Sabino KC, Torres-Santos EC. Preclinical Studies Evaluating Subacute Toxicity and Therapeutic Efficacy of LQB-118 in Experimental Visceral Leishmaniasis. Antimicrob Agents Chemother. 2016 May 23;60(6):3794-801. doi: 10.1128/AAC.01787-15. PMID: 27067332; PMCID: PMC4879381. 14: de Faria FC, Leal ME, Bernardo PS, Costa PR, Maia RC. NFκB pathway and microRNA-9 and -21 are involved in sensitivity to the pterocarpanquinone LQB-118 in different CML cell lines. Anticancer Agents Med Chem. 2015;15(3):345-52. doi: 10.2174/18715206113139990108. PMID: 25964959. 15: Costa L, Pinheiro RO, Dutra PM, Santos RF, Cunha-Júnior EF, Torres-Santos EC, da Silva AJ, Costa PR, Da-Silva SA. Pterocarpanquinone LQB-118 induces apoptosis in Leishmania (Viannia) braziliensis and controls lesions in infected hamsters. PLoS One. 2014 Oct 23;9(10):e109672. doi: 10.1371/journal.pone.0109672. PMID: 25340550; PMCID: PMC4207686. 16: Nestal de Moraes G, Castro CP, Salustiano EJ, Dumas ML, Costas F, Lam EW, Costa PR, Maia RC. The pterocarpanquinone LQB-118 induces apoptosis in acute myeloid leukemia cells of distinct molecular subtypes and targets FoxO3a and FoxM1 transcription factors. Int J Oncol. 2014 Nov;45(5):1949-58. doi: 10.3892/ijo.2014.2615. Epub 2014 Aug 21. Erratum in: Int J Oncol. 2019 Dec;55(6):1396. doi: 10.3892/ijo.2019.4874. PMID: 25174716. 17: Martino T, Magalhães FC, Justo GA, Coelho MG, Netto CD, Costa PR, Sabino KC. The pterocarpanquinone LQB-118 inhibits tumor cell proliferation by downregulation of c-Myc and cyclins D1 and B1 mRNA and upregulation of p21 cell cycle inhibitor expression. Bioorg Med Chem. 2014 Jun 15;22(12):3115-22. doi: 10.1016/j.bmc.2014.04.025. Epub 2014 Apr 20. PMID: 24794748. 18: Ribeiro GA, Cunha-Júnior EF, Pinheiro RO, da-Silva SA, Canto-Cavalheiro MM, da Silva AJ, Costa PR, Netto CD, Melo RC, Almeida-Amaral EE, Torres-Santos EC. LQB-118, an orally active pterocarpanquinone, induces selective oxidative stress and apoptosis in Leishmania amazonensis. J Antimicrob Chemother. 2013 Apr;68(4):789-99. doi: 10.1093/jac/dks498. Epub 2013 Jan 3. PMID: 23288404. 19: de Sá Bacelar T, da Silva AJ, Costa PR, Rumjanek VM. The pterocarpanquinone LQB 118 induces apoptosis in tumor cells through the intrinsic pathway and the endoplasmic reticulum stress pathway. Anticancer Drugs. 2013 Jan;24(1):73-83. doi: 10.1097/CAD.0b013e3283592da8. PMID: 22960938. 20: de Souza Reis FR, de Faria FC, Castro CP, de Souza PS, da Cunha Vasconcelos F, Bello RD, da Silva AJ, Costa PR, Maia RC. The therapeutical potential of a novel pterocarpanquinone LQB-118 to target inhibitor of apoptosis proteins in acute myeloid leukemia cells. Anticancer Agents Med Chem. 2013 Feb;13(2):341-51. doi: 10.2174/1871520611313020019. PMID: 22721384.