Kukoamine B Mesylate | CAS#164991-67-7 | Neuroprotection Compound

MedKoo Cat#: 527604 | Name: Kukoamine B Mesylate

Featured

Description:

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

Kukoamine B Mesylate is potentially for the treatment of sepsis. Kukoamines are a series of bioactive phytochemicals conjugated by a polyamine backbone and phenolic moieties. Treatment with KuB prior to H2O2 exposure effectively increased the cell viability, and restored the mitochondria membrane potential (MMP). Furthermore, KuB enhanced the antioxidant enzyme activities of superoxide dismutase (SOD), catalase (CAT), and glutathione peroxidase (GSH-Px) and decreased the malondialdehyde (MDA) content. Moreover, KuB minimized the ROS formation and inhibited mitochondria-apoptotic pathway, MAPKs (p-p38, p-JNK, p-ERK) pathways, but activated PI3K-AKT pathway.

Chemical Structure

Kukoamine B Mesylate

CAS#164991-67-7

Theoretical Analysis

MedKoo Cat#: 527604

Name: Kukoamine B Mesylate

CAS#: 164991-67-7

Chemical Formula: C28H42N4O6

Exact Mass: 530.3104

Molecular Weight: 530.67

Elemental Analysis: C, 63.37; H, 7.98; N, 10.56; O, 18.09

Price and Availability

Size	Price	Availability
5mg	USD 325.00	2 Weeks
10mg	USD 550.00	2 Weeks
25mg	USD 950.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Kukoamine B Mesylate;

IUPAC/Chemical Name

N-(3-aminopropyl)-3-(3,4-dihydroxyphenyl)-N-(4-((3-(3-(3,4-dihydroxyphenyl)propanamido)propyl)amino)butyl)propanamide

InChi Key

IWRAOCFRRTWUDF-UHFFFAOYSA-N

InChi Code

InChI=1S/C28H42N4O6/c29-13-3-18-32(28(38)12-8-22-6-10-24(34)26(36)20-22)17-2-1-14-30-15-4-16-31-27(37)11-7-21-5-9-23(33)25(35)19-21/h5-6,9-10,19-20,30,33-36H,1-4,7-8,11-18,29H2,(H,31,37)

SMILES Code

O=C(N(CCCN)CCCCNCCCNC(CCC1=CC=C(O)C(O)=C1)=O)CCC2=CC=C(O)C(O)=C2

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

>2 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:

Kukoamine B is a component of Lycii Cortex, with anti-oxidant, anti-acute inflammatory and anti-diabetic properties.

In vitro activity:

Subsequent LC-ESI-MS analysis revealed that kukoamine B (KB) formed Schiff base-derived pyridinium adducts with trans-2-nonenal. Thus, these results suggest that KB could be a potential agent that may protect HaCaT cells by forming new products with trans-2-nonenal. Reference: Plants (Basel). 2022 Dec 29;12(1):163. https://pubmed.ncbi.nlm.nih.gov/36616291/

In vivo activity:

HFDFr-fed rats showed a significant increase in body weight, fasting blood glucose, insulin, lipid accumulation and liver function enzymes. On the other hand, Kuk B (kukoamine B) significantly attenuated body weight, insulin resistance, lipid accumulation, oxidative stress and inflammation. Reference: Diabetes Metab Syndr Obes. 2020 May 26;13:1843-1853. https://pubmed.ncbi.nlm.nih.gov/32547146/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	56.53
	DMSO	30.0	56.53
	Ethanol	30.0	56.53
	PBS (pH 7.2)	10.0	18.84
	Water	62.5	117.78

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 530.67 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.

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. Kim HM, Kim JY, Kim JH, Kim CY. Kukoamine B from Lycii Radicis Cortex Protects Human Keratinocyte HaCaT Cells through Covalent Modification by Trans-2-Nonenal. Plants (Basel). 2022 Dec 29;12(1):163. doi: 10.3390/plants12010163. PMID: 36616291; PMCID: PMC9823295. 2. Jiang G, Takase M, Aihara Y, Shigemori H. Inhibitory activities of kukoamines A and B from Lycii Cortex on amyloid aggregation related to Alzheimer's disease and type 2 diabetes. J Nat Med. 2020 Jan;74(1):247-251. doi: 10.1007/s11418-019-01337-0. Epub 2019 Jul 2. PMID: 31267354. 3. Zhao Q, Li L, Zhu Y, Hou D, Li Y, Guo X, Wang Y, Olatunji OJ, Wan P, Gong K. Kukoamine B Ameliorate Insulin Resistance, Oxidative Stress, Inflammation and Other Metabolic Abnormalities in High-Fat/High-Fructose-Fed Rats. Diabetes Metab Syndr Obes. 2020 May 26;13:1843-1853. doi: 10.2147/DMSO.S247844. PMID: 32547146; PMCID: PMC7266517. 4. Park E, Kim J, Kim MC, Yeo S, Kim J, Park S, Jo M, Choi CW, Jin HS, Lee SW, Li WY, Lee JW, Park JH, Huh D, Jeong SY. Anti-Osteoporotic Effects of Kukoamine B Isolated from Lycii Radicis Cortex Extract on Osteoblast and Osteoclast Cells and Ovariectomized Osteoporosis Model Mice. Int J Mol Sci. 2019 Jun 6;20(11):2784. doi: 10.3390/ijms20112784. PMID: 31174394; PMCID: PMC6600412.

In vitro protocol:

In vivo protocol:

1. Zhao Q, Li L, Zhu Y, Hou D, Li Y, Guo X, Wang Y, Olatunji OJ, Wan P, Gong K. Kukoamine B Ameliorate Insulin Resistance, Oxidative Stress, Inflammation and Other Metabolic Abnormalities in High-Fat/High-Fructose-Fed Rats. Diabetes Metab Syndr Obes. 2020 May 26;13:1843-1853. doi: 10.2147/DMSO.S247844. PMID: 32547146; PMCID: PMC7266517. 2. Park E, Kim J, Kim MC, Yeo S, Kim J, Park S, Jo M, Choi CW, Jin HS, Lee SW, Li WY, Lee JW, Park JH, Huh D, Jeong SY. Anti-Osteoporotic Effects of Kukoamine B Isolated from Lycii Radicis Cortex Extract on Osteoblast and Osteoclast Cells and Ovariectomized Osteoporosis Model Mice. Int J Mol Sci. 2019 Jun 6;20(11):2784. doi: 10.3390/ijms20112784. PMID: 31174394; PMCID: PMC6600412.

1: Wang Z, Zhao Q, Li L, Hu P, Dong K, Chen S, Jiang J. Development and validation of a rapid and sensitive UPLC-MS/MS method for quantification of kukoamine B in human plasma: Application to a clinical pharmacokinetic study. J Pharm Biomed Anal. 2017 Jan 5;132:1-6. doi: 10.1016/j.jpba.2016.09.032. PubMed PMID: 27693755. 2: Piletska EV, Burns R, Terry LA, Piletsky SA. Application of a molecularly imprinted polymer for the extraction of kukoamine a from potato peels. J Agric Food Chem. 2012 Jan 11;60(1):95-9. doi: 10.1021/jf203669b. PubMed PMID: 22142260. 3: Li YY, Wang H, Zhao C, Huang YQ, Tang X, Cheung HY. Identification and Characterization of Kukoamine Metabolites by Multiple Ion Monitoring Triggered Enhanced Product Ion Scan Method with a Triple-Quadruple Linear Ion Trap Mass Spectrometer. J Agric Food Chem. 2015 Dec 23;63(50):10785-90. doi: 10.1021/acs.jafc.5b04321. PubMed PMID: 26625181. 4: Zhao Q, Li L, Wang Z, Jiang J, Dong K, Chen S, Hu P. Ultra performance liquid chromatography tandem mass spectrometry assay for determination of kukoamine B in human blood and urine. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Sep 15;1031:8-14. doi: 10.1016/j.jchromb.2016.07.025. PubMed PMID: 27447928. 5: Li YY, Di R, Hsu WL, Huang YQ, Sun H, Cheung HY. Sensitivity improvement of kukoamine determination by complexation with dihydrogen phosphate anions in capillary zone electrophoresis. Electrophoresis. 2015 Aug;36(15):1801-7. doi: 10.1002/elps.201500030. PubMed PMID: 25930189. 6: Hu XL, Niu YX, Zhang Q, Tian X, Gao LY, Guo LP, Meng WH, Zhao QC. Neuroprotective effects of Kukoamine B against hydrogen peroxide-induced apoptosis and potential mechanisms in SH-SY5Y cells. Environ Toxicol Pharmacol. 2015 Jul;40(1):230-40. doi: 10.1016/j.etap.2015.06.017. PubMed PMID: 26164594. 7: Hu XL, Gao LY, Niu YX, Tian X, Wang J, Meng WH, Zhang Q, Cui C, Han L, Zhao QC. Neuroprotection by Kukoamine A against oxidative stress may involve N-methyl-D-aspartate receptors. Biochim Biophys Acta. 2015 Feb;1850(2):287-98. doi: 10.1016/j.bbagen.2014.11.006. PubMed PMID: 25445711. 8: Zhang Y, Gao L, Cheng Z, Cai J, Niu Y, Meng W, Zhao Q. Kukoamine A Prevents Radiation-Induced Neuroinflammation and Preserves Hippocampal Neurogenesis in Rats by Inhibiting Activation of NF-κB and AP-1. Neurotox Res. 2017 Feb;31(2):259-268. doi: 10.1007/s12640-016-9679-4. PubMed PMID: 27815817. 9: Liu J, Jiang X, Zhang Q, Lin S, Zhu J, Zhang Y, Du J, Hu X, Meng W, Zhao Q. Neuroprotective effects of Kukoamine A against cerebral ischemia via antioxidant and inactivation of apoptosis pathway. Neurochem Int. 2017 Jan 12. pii: S0197-0186(16)30187-5. doi: 10.1016/j.neuint.2016.12.024. [Epub ahead of print] PubMed PMID: 28088348. 10: Yang D, Zheng X, Wang N, Fan S, Yang Y, Lu Y, Chen Q, Liu X, Zheng J. Kukoamine B promotes TLR4-independent lipopolysaccharide uptake in murine hepatocytes. Oncotarget. 2016 Sep 6;7(36):57498-57513. doi: 10.18632/oncotarget.11292. PubMed PMID: 27542278; PubMed Central PMCID: PMC5295368. 11: Zhang Y, Cheng Z, Wang C, Ma H, Meng W, Zhao Q. Neuroprotective Effects of Kukoamine a against Radiation-induced Rat Brain Injury through Inhibition of Oxidative Stress and Neuronal Apoptosis. Neurochem Res. 2016 Oct;41(10):2549-2558. PubMed PMID: 27241194. 12: Hu XL, Guo LP, Song Q, Zhang Q, Chen Y, Wang J, Meng WH, Zhao QC. Kukoamine B, an amide alkaloid, protects against NMDA-induced neurotoxicity and potential mechanisms in vitro. Neurochem Int. 2015 Aug;87:66-76. doi: 10.1016/j.neuint.2015.06.001. PubMed PMID: 26065936. 13: Qin WT, Wang X, Shen WC, Sun BW. A novel role of kukoamine B: Inhibition of the inflammatory response in the livers of lipopolysaccharide-induced septic mice via its unique property of combining with lipopolysaccharide. Exp Ther Med. 2015 Mar;9(3):725-732. PubMed PMID: 25667619; PubMed Central PMCID: PMC4316986. 14: Lyu W, Qin W, Zhang J, Shen W, Wang X, Sun B. [Inhibitory effects of Kukoamine B on the inflammatory response of small intestine in lipopolysaccharide-induced septic mice and its potential mechanisms]. Zhonghua Wei Zhong Bing Ji Jiu Yi Xue. 2015 Feb;27(2):121-6. doi: 10.3760/cma.j.issn.2095-4352.2015.02.009. Chinese. PubMed PMID: 25665611. 15: Wang Q, Li H, Sun Z, Dong L, Gao L, Liu C, Wang X. Kukoamine A inhibits human glioblastoma cell growth and migration through apoptosis induction and epithelial-mesenchymal transition attenuation. Sci Rep. 2016 Nov 8;6:36543. doi: 10.1038/srep36543. PubMed PMID: 27824118; PubMed Central PMCID: PMC5099904. 16: Zhang J, Qin W, Lyu W, Shen W, Wang X, Sun B. [Inhibitory effect of kukoamine B on lung inflammatory responses in mice with sepsis]. Zhonghua Wei Zhong Bing Ji Jiu Yi Xue. 2014 Jul;26(7):493-7. doi: 10.3760/cma.j.issn.2095-4352.2014.07.010. Chinese. PubMed PMID: 25027428. 17: Liu X, Zheng X, Long Y, Cao H, Wang N, Lu Y, Zhao K, Zhou H, Zheng J. Dual targets guided screening and isolation of Kukoamine B as a novel natural anti-sepsis agent from traditional Chinese herb Cortex lycii. Int Immunopharmacol. 2011 Jan;11(1):110-20. doi: 10.1016/j.intimp.2010.10.015. PubMed PMID: 21073991. 18: Liu X, Zheng X, Wang N, Cao H, Lu Y, Long Y, Zhao K, Zhou H, Zheng J. Kukoamine B, a novel dual inhibitor of LPS and CpG DNA, is a potential candidate for sepsis treatment. Br J Pharmacol. 2011 Mar;162(6):1274-90. doi: 10.1111/j.1476-5381.2010.01114.x. PubMed PMID: 21108626; PubMed Central PMCID: PMC3058161. 19: Hadjipavlou-Litina D, Garnelis T, Athanassopoulos CM, Papaioannou D. Kukoamine A analogs with lipoxygenase inhibitory activity. J Enzyme Inhib Med Chem. 2009 Oct;24(5):1188-93. doi: 10.1080/14756360902779193. PubMed PMID: 19772491. 20: Parr AJ, Mellon FA, Colquhoun IJ, Davies HV. Dihydrocaffeoyl polyamines (kukoamine and allies) in potato (Solanum tuberosum) tubers detected during metabolite profiling. J Agric Food Chem. 2005 Jun 29;53(13):5461-6. PubMed PMID: 15969534.