Neamine Free Base | CAS# 3947-65-7 (free base) | synthesis of aminoglycoside antibiotics

MedKoo Cat#: 414310 | Name: Neamine Free Base

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Description:

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

Neamine Free Base is a natural degradation product of neomycin (Item No. 14287) and is a common core molecule used in the synthesis of aminoglycoside antibiotics.

Chemical Structure

Neamine Free Base

CAS#3947-65-7 (free base)

Theoretical Analysis

MedKoo Cat#: 414310

Name: Neamine Free Base

CAS#: 3947-65-7 (free base)

Chemical Formula: C12H26N4O6

Exact Mass: 322.1852

Molecular Weight: 322.36

Elemental Analysis: C, 44.71; H, 8.13; N, 17.38; O, 29.78

Price and Availability

Size	Price	Availability
1mg	USD 350.00	2 Weeks
5mg	USD 750.00	2 Weeks
10mg	USD 1,250.00	2 Weeks

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Related CAS #

3947-65-7 (free base) 15446-43-2 (HCl) 35234-28-7 (sulfate)

Synonym

Neamine Free Base; Neomycin A; BRN0026714; BRN-0026714; BRN 0026714

IUPAC/Chemical Name

(2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-(((1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl)oxy)tetrahydro-2H-pyran-3,4-diol

InChi Key

SYJXFKPQNSDJLI-HKEUSBCWSA-N

InChi Code

InChI=1S/C12H26N4O6/c13-2-5-8(18)9(19)6(16)12(21-5)22-11-4(15)1-3(14)7(17)10(11)20/h3-12,17-20H,1-2,13-16H2/t3-,4+,5-,6-,7+,8-,9-,10-,11-,12-/m1/s1

SMILES Code

NC[C@H]1O[C@@H]([C@@H]([C@H]([C@@H]1O)O)N)O[C@@H]2[C@H](C[C@H]([C@@H]([C@H]2O)O)N)N

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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:

Neamine, a degradation product of Neomycin, is a broad-spectrum aminoglycoside antibiotic.

In vitro activity:

It was found that neamine blocked nuclear translocation of angiogenin effectively and inhibited angiogenin-induced human umbilical vein endothelial cell and PC-3 cell proliferation in a dose-dependent manner. Neamine exerted a comparative antitumor effect, but lower toxicity (weight loss), in the PC-3 xenograft models treated with DDP. Reference: Oncol Lett. 2015 Jul;10(1):137-142. https://pubmed.ncbi.nlm.nih.gov/26170989/

In vivo activity:

Neamine treatment of stroke in T1DM rats significantly decreased BBB leakage and lesion volume as well as improved functional outcome compared to T1DM-control. Neamine also significantly decreased apoptosis and cleaved caspase-3 in the ischemic brain. Using immunostaining, this study found that Neamine treatment significantly decreased nuclear Angiogenin, nuclear factor kappa-light-chain-enhancer of activated B cells (NFκB) activity, advanced glycation endproducts receptor (RAGE) number, the positive area of toll-like receptor 4 (TLR4) and increased Angeopoietin-1 expression compared to T1DM-MCAo control rats. Reference: Neuroscience. 2014 Jan 17;257:76-85. https://pubmed.ncbi.nlm.nih.gov/24211797/

Preparing Stock Solutions

The following data is based on the product molecular weight 322.36 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. Zhao J, Li X, Liu J, Jiang W, Wen D, Xue H. Effect of Progranulin on Migration and Invasion of Human Colon Cancer Cells. J Coll Physicians Surg Pak. 2018 Aug;28(8):607-611. doi: 10.29271/jcpsp.2018.08.607. PMID: 30060789. 2. Liu YP, Hu GF, Wu YX. Neamine is preferential as an anti-prostate cancer reagent by inhibiting cell proliferation and angiogenesis, with lower toxicity than cis-platinum. Oncol Lett. 2015 Jul;10(1):137-142. doi: 10.3892/ol.2015.3227. Epub 2015 May 19. PMID: 26170989; PMCID: PMC4487084. 3. Wu Y, Feng Y, Li Y, Xu Y, Shi N, Hu GF, Wu Y. Sub-chronic 90-day toxicity of neamine in SD rats and its anti-liver cancer activity in vitro and in vivo. Toxicol Appl Pharmacol. 2017 Jan 15;315:50-59. doi: 10.1016/j.taap.2016.12.006. Epub 2016 Dec 9. PMID: 27940282. 4. Ning R, Chopp M, Zacharek A, Yan T, Zhang C, Roberts C, Lu M, Chen J. Neamine induces neuroprotection after acute ischemic stroke in type one diabetic rats. Neuroscience. 2014 Jan 17;257:76-85. doi: 10.1016/j.neuroscience.2013.10.071. Epub 2013 Nov 8. PMID: 24211797; PMCID: PMC3889124.

In vitro protocol:

In vivo protocol:

1. Wu Y, Feng Y, Li Y, Xu Y, Shi N, Hu GF, Wu Y. Sub-chronic 90-day toxicity of neamine in SD rats and its anti-liver cancer activity in vitro and in vivo. Toxicol Appl Pharmacol. 2017 Jan 15;315:50-59. doi: 10.1016/j.taap.2016.12.006. Epub 2016 Dec 9. PMID: 27940282. 2. Ning R, Chopp M, Zacharek A, Yan T, Zhang C, Roberts C, Lu M, Chen J. Neamine induces neuroprotection after acute ischemic stroke in type one diabetic rats. Neuroscience. 2014 Jan 17;257:76-85. doi: 10.1016/j.neuroscience.2013.10.071. Epub 2013 Nov 8. PMID: 24211797; PMCID: PMC3889124.

1: Swain J, El Khoury M, Flament A, Dezanet C, Briée F, Van Der Smissen P, Décout JL, Mingeot-Leclercq MP. Antimicrobial activity of amphiphilic neamine derivatives: Understanding the mechanism of action on Gram-positive bacteria. Biochim Biophys Acta Biomembr. 2019 Oct 1;1861(10):182998. doi: 10.1016/j.bbamem.2019.05.020. Epub 2019 May 31. PMID: 31153908. 2: Yang ZJ, Concilio MG, Ramesh V, Zhang LH. Synthesis and Evaluation of Novel Neamine-Nucleoside Conjugates as Potential Antibiotic Targets for Escherichia coli 16S Ribosomal RNA. Methods Mol Biol. 2019;1870:151-163. doi: 10.1007/978-1-4939-8808-2_11. PMID: 30539553. 3: Liu YP, Wu YL, Zhang XY, Hu GF, Wu YX. Neamine inhibits growth of pancreatic cancer cells in vitro and in vivo. J Huazhong Univ Sci Technolog Med Sci. 2016 Feb;36(1):82-87. doi: 10.1007/s11596-016-1546-2. Epub 2016 Feb 3. PMID: 26838745. 4: Liu Y, Zhang X, An S, Wu Y, Hu G, Wu Y. Pharmacokinetics of neamine in rats and anti-cervical cancer activity in vitro and in vivo. Cancer Chemother Pharmacol. 2015 Mar;75(3):465-74. doi: 10.1007/s00280-014-2658-7. Epub 2015 Jan 1. PMID: 25552400. 5: Kishimoto K, Yoshida S, Ibaragi S, Yoshioka N, Hu GF, Sasaki A. Neamine inhibits oral cancer progression by suppressing angiogenin-mediated angiogenesis and cancer cell proliferation. Anticancer Res. 2014 May;34(5):2113-21. PMID: 24778013; PMCID: PMC4757496. 6: Ning R, Chopp M, Zacharek A, Yan T, Zhang C, Roberts C, Lu M, Chen J. Neamine induces neuroprotection after acute ischemic stroke in type one diabetic rats. Neuroscience. 2014 Jan 17;257:76-85. doi: 10.1016/j.neuroscience.2013.10.071. Epub 2013 Nov 8. PMID: 24211797; PMCID: PMC3889124. 7: Liu YP, Hu GF, Wu YX. Neamine is preferential as an anti-prostate cancer reagent by inhibiting cell proliferation and angiogenesis, with lower toxicity than cis-platinum. Oncol Lett. 2015 Jul;10(1):137-142. doi: 10.3892/ol.2015.3227. Epub 2015 May 19. PMID: 26170989; PMCID: PMC4487084. 8: Prado WA, Rossaneis AC, Carvalho I, Zamoner LO, Corrado AP. Neamine and 2-deoxystreptamine neomycin derivatives exhibit antinociceptive activity in rat models of phasic, incision and neuropathic pain. J Pharm Pharmacol. 2015 Dec;67(12):1696-704. doi: 10.1111/jphp.12480. Epub 2015 Sep 17. PMID: 26376780. 9: Hirukawa S, Olson KA, Tsuji T, Hu GF. Neamine inhibits xenografic human tumor growth and angiogenesis in athymic mice. Clin Cancer Res. 2005 Dec 15;11(24 Pt 1):8745-52. doi: 10.1158/1078-0432.CCR-05-1495. PMID: 16361562. 10: Simon B, Walmsley C, Jackson VJ, Garvey EP, Slater MJ, Berrisford DJ, Gardiner JM. Evaluation of neomycin analogues for HIV-1 RRE RNA recognition identifies enhanced activity simplified neamine analogues. Bioorg Med Chem Lett. 2019 Jan 15;29(2):339-341. doi: 10.1016/j.bmcl.2018.11.004. Epub 2018 Nov 9. PMID: 30477891.