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MedKoo Cat#: 584565 | Name: Lunasine

Description:

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

Lunasine inhibits cell proliferation via apoptosis and reduces the production of proinflammatory cytokines in cultured rheumatoid arthritis synovial fibroblasts.

Chemical Structure

Lunasine
Lunasine
CAS#6901-22-0

Theoretical Analysis

MedKoo Cat#: 584565

Name: Lunasine

CAS#: 6901-22-0

Chemical Formula: C17H22NO3+

Exact Mass: 288.1594

Molecular Weight: 288.37

Elemental Analysis: C, 70.81; H, 7.69; N, 4.86; O, 16.64

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
Lunasin; Lunasine
IUPAC/Chemical Name
FURO(2,3-b)quinolinium, 2,3-dihydro-4,8-dimethoxy-9-methyl-2-(1-methylethyl)-, (2R)-
InChi Key
GUIBZZYABLMRRD-CQSZACIVSA-N
InChi Code
InChI=1S/C17H22NO3/c1-10(2)14-9-12-16(20-5)11-7-6-8-13(19-4)15(11)18(3)17(12)21-14/h6-8,10,14H,9H2,1-5H3/q+1/t14-/m1/s1
SMILES Code
CC([C@H](O1)CC2=C1[N+](C)=C3C(OC)=CC=CC3=C2OC)C
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 288.37 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: Yang X, Zhu J, Tung CY, Gardiner G, Wang Q, Chang HC, Zhou B. Lunasin alleviates allergic airway inflammation while increases antigen-specific Tregs. PLoS One. 2015 Feb 3;10(2):e0115330. doi: 10.1371/journal.pone.0115330. eCollection 2015. PubMed PMID: 25646897; PubMed Central PMCID: PMC4315393. 2: Chang HC, Lewis D, Tung CY, Han L, Henriquez SM, Voiles L, Lupov IP, Pelloso D, Sinn AL, Pollok KE, de Lumen BO, Li F, Blum JS, Srivastava S, Robertson MJ. Soypeptide lunasin in cytokine immunotherapy for lymphoma. Cancer Immunol Immunother. 2014 Mar;63(3):283-95. doi: 10.1007/s00262-013-1513-8. Epub 2013 Dec 22. PubMed PMID: 24363024; PubMed Central PMCID: PMC3928510. 3: Dinelli G, Bregola V, Bosi S, Fiori J, Gotti R, Simonetti E, Trozzi C, Leoncini E, Prata C, Massaccesi L, Malaguti M, Quinn R, Hrelia S. Lunasin in wheat: a chemical and molecular study on its presence or absence. Food Chem. 2014 May 15;151:520-5. doi: 10.1016/j.foodchem.2013.11.119. Epub 2013 Nov 27. PubMed PMID: 24423565. 4: Wołosik K, Markowska A, Kuźmicz I. [Lunasin--a novel chemopreventive peptide]. Postepy Biochem. 2014;60(1):84-9. Review. Polish. PubMed PMID: 25033546. 5: Inaba J, McConnell EJ, Davis KR. Lunasin sensitivity in non-small cell lung cancer cells is linked to suppression of integrin signaling and changes in histone acetylation. Int J Mol Sci. 2014 Dec 18;15(12):23705-24. doi: 10.3390/ijms151223705. PubMed PMID: 25530619; PubMed Central PMCID: PMC4284788. 6: Rizzello CG, Hernández-Ledesma B, Fernández-Tomé S, Curiel JA, Pinto D, Marzani B, Coda R, Gobbetti M. Italian legumes: effect of sourdough fermentation on lunasin-like polypeptides. Microb Cell Fact. 2015 Oct 22;14:168. doi: 10.1186/s12934-015-0358-6. PubMed PMID: 26494432; PubMed Central PMCID: PMC4618940. 7: Lule VK, Garg S, Pophaly SD, Hitesh, Tomar SK. "Potential health benefits of lunasin: a multifaceted soy-derived bioactive peptide". J Food Sci. 2015 Mar;80(3):R485-94. doi: 10.1111/1750-3841.12786. Epub 2015 Jan 27. Review. PubMed PMID: 25627564. 8: McConnell EJ, Devapatla B, Yaddanapudi K, Davis KR. The soybean-derived peptide lunasin inhibits non-small cell lung cancer cell proliferation by suppressing phosphorylation of the retinoblastoma protein. Oncotarget. 2015 Mar 10;6(7):4649-62. PubMed PMID: 25609198; PubMed Central PMCID: PMC4467105. 9: Jia S, Zhang S, Yuan H, Chen N. Lunasin inhibits cell proliferation via apoptosis and reduces the production of proinflammatory cytokines in cultured rheumatoid arthritis synovial fibroblasts. Biomed Res Int. 2015;2015:346839. doi: 10.1155/2015/346839. Epub 2015 Jan 27. PubMed PMID: 25692134; PubMed Central PMCID: PMC4322854. 10: Tung CY, Lewis DE, Han L, Jaja M, Yao S, Li F, Robertson MJ, Zhou B, Sun J, Chang HC. Activation of dendritic cell function by soypeptide lunasin as a novel vaccine adjuvant. Vaccine. 2014 Sep 22;32(42):5411-9. doi: 10.1016/j.vaccine.2014.07.103. Epub 2014 Aug 12. PubMed PMID: 25131731. 11: Guijarro-Díez M, García MC, Crego AL, Marina ML. Off-line two dimensional isoelectrofocusing-liquid chromatography/mass spectrometry (time of flight) for the determination of the bioactive peptide lunasin. J Chromatogr A. 2014 Dec 5;1371:117-24. PubMed PMID: 25458526. 12: Cruz-Huerta E, Fernández-Tomé S, Arques MC, Amigo L, Recio I, Clemente A, Hernández-Ledesma B. The protective role of the Bowman-Birk protease inhibitor in soybean lunasin digestion: the effect of released peptides on colon cancer growth. Food Funct. 2015 Aug;6(8):2626-35. doi: 10.1039/c5fo00454c. Epub 2015 Jul 1. PubMed PMID: 26132418. 13: Shidal C, Al-Rayyan N, Yaddanapudi K, Davis KR. Lunasin is a novel therapeutic agent for targeting melanoma cancer stem cells. Oncotarget. 2016 Dec 20;7(51):84128-84141. doi: 10.18632/oncotarget.11554. PubMed PMID: 27566591; PubMed Central PMCID: PMC5356649. 14: Alaswad AA, Krishnan HB. Immunological Investigation for the Presence of Lunasin, a Chemopreventive Soybean Peptide, in the Seeds of Diverse Plants. J Agric Food Chem. 2016 Apr 13;64(14):2901-9. doi: 10.1021/acs.jafc.6b00445. Epub 2016 Apr 1. PubMed PMID: 27015324. 15: Muceniece R, Namniece J, Nakurte I, Jekabsons K, Riekstina U, Jansone B. Pharmacological research on natural substances in Latvia: Focus on lunasin, betulin, polyprenol and phlorizin. Pharmacol Res. 2016 Nov;113(Pt B):760-770. doi: 10.1016/j.phrs.2016.03.040. Epub 2016 Apr 21. Review. PubMed PMID: 27109319. 16: Aleksis R, Jaudzems K, Muceniece R, Liepinsh E. Lunasin is a redox sensitive intrinsically disordered peptide with two transiently populated α-helical regions. Peptides. 2016 Nov;85:56-62. doi: 10.1016/j.peptides.2016.09.006. Epub 2016 Sep 14. PubMed PMID: 27639324. 17: Jones G, Srivastava A. Understanding Lunasin's biology and potential as a cancer therapeutic by utilizing Drosophila genetics. Exp Biol Med (Maywood). 2014 May;239(5):519-28. doi: 10.1177/1535370214522180. Epub 2014 Mar 13. Review. PubMed PMID: 24625440. 18: Dai G, Zhang P, Ye P, Zhang M, Han N, Shuai H, Tan S. The Chemopreventive Peptide Lunasin Inhibits d-Galactose- Induced Experimental Cataract in Rats. Protein Pept Lett. 2016;23(7):619-25. PubMed PMID: 27145928. 19: Jiang Q, Pan Y, Cheng Y, Li H, Liu D, Li H. Lunasin suppresses the migration and invasion of breast cancer cells by inhibiting matrix metalloproteinase-2/-9 via the FAK/Akt/ERK and NF-κB signaling pathways. Oncol Rep. 2016 Jul;36(1):253-62. doi: 10.3892/or.2016.4798. Epub 2016 May 9. PubMed PMID: 27175819. 20: Hsieh CC, Wang CH, Huang YS. Lunasin Attenuates Obesity-Associated Metastasis of 4T1 Breast Cancer Cell through Anti-Inflammatory Property. Int J Mol Sci. 2016 Dec 15;17(12). pii: E2109. PubMed PMID: 27983683; PubMed Central PMCID: PMC5187909.

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