Nargenicin | CAS#70695-02-2 | Antibacterial

MedKoo Cat#: 208269 | Name: Nargenicin

Description:

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

Nargenicin is an antibacterial macrolide isolated from Nocardia sp. may be a potential treatment for inflammatory responses and oxidative stress, but the detailed mechanisms are still not well studied. Furthermore, nargenicin A1 showed strong protective effects against NO and ROS production in LPS-injected zebrafish larvae. In conclusion, our findings suggest that nargenicin A1 ameliorates LPS-induced anti-inflammatory and antioxidant effects by downregulating the NF-κB signaling pathway, and that nargenicin A1 can be a potential functional agent to prevent inflammatory- and oxidative-mediated damage.

Chemical Structure

Nargenicin

CAS#70695-02-2

Theoretical Analysis

MedKoo Cat#: 208269

Name: Nargenicin

CAS#: 70695-02-2

Chemical Formula: C28H37NO8

Exact Mass: 515.2519

Molecular Weight: 515.60

Elemental Analysis: C, 65.23; H, 7.23; N, 2.72; O, 24.82

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

nargenicin, Nargenicin A1

IUPAC/Chemical Name

[(1S,3R,4R,5R,6R,7S,8R,11S,13S,16S,17R,18E)-6-Hydroxy-16-[(1R)-1-hydroxyethyl]-13-methoxy-5,17,19-trimethyl-14-oxo-2,15-dioxatetracyclo[9.8.0.01,7.03,8]nonadeca-9,18-dien-4-yl] 1H-pyrrole-2-carboxylate

InChi Key

YEUSSARNQQYBKH-SIMZXIQRSA-N

InChi Code

InChI=1S/C28H37NO8/c1-13-11-14(2)28-17(12-20(34-5)27(33)35-23(13)16(4)30)8-9-18-21(28)22(31)15(3)24(25(18)37-28)36-26(32)19-7-6-10-29-19/h6-11,13,15-18,20-25,29-31H,12H2,1-5H3/b14-11+/t13-,15-,16-,17-,18-,20+,21+,22-,23+,24-,25-,28+/m1/s1

SMILES Code

O=C(C1=CC=CN1)O[C@H]([C@H](C)[C@@H](O)[C@]2([H])[C@@]3([H])C=C[C@]4([H])C[C@@H]5OC)[C@]3([H])O[C@]24/C(C)=C/[C@@H](C)[C@@H]([C@H](O)C)OC5=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

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 515.60 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

1: Pidot SJ, Rizzacasa MA. The Nargenicin Family of Oxa-Bridged Macrolide Antibiotics. Chemistry. 2020 Mar 2;26(13):2780-2792. doi: 10.1002/chem.201904053. Epub 2019 Dec 16. PMID: 31667915. 2: Kwon DH, Kim GY, Cha HJ, Kim S, Kim HS, Hwang HJ, Choi YH. Nargenicin A1 attenuates lipopolysaccharide-induced inflammatory and oxidative response by blocking the NF-κB signaling pathway. EXCLI J. 2021 May 28;20:968-982. doi: 10.17179/excli2021-3506. PMID: 34267609; PMCID: PMC8278209. 3: Pidot SJ, Herisse M, Sharkey L, Atkin L, Porter JL, Seemann T, Howden BP, Rizzacasa MA, Stinear TP. Biosynthesis and Ether-Bridge Formation in Nargenicin Macrolides. Angew Chem Int Ed Engl. 2019 Mar 18;58(12):3996-4001. doi: 10.1002/anie.201900290. Epub 2019 Feb 11. PMID: 30677204. 4: Park C, Kwon DH, Hwang SJ, Han MH, Jeong JW, Hong SH, Cha HJ, Hong SH, Kim GY, Lee HJ, Kim S, Kim HS, Choi YH. Protective Effects of Nargenicin A1 against Tacrolimus-Induced Oxidative Stress in Hirame Natural Embryo Cells. Int J Environ Res Public Health. 2019 Mar 22;16(6):1044. doi: 10.3390/ijerph16061044. PMID: 30909475; PMCID: PMC6466173. 5: Han JM, Choi YS, Dhakal D, Sohng JK, Jung HJ. Novel Nargenicin A1 Analog Inhibits Angiogenesis by Downregulating the Endothelial VEGF/VEGFR2 Signaling and Tumoral HIF-1α/VEGF Pathway. Biomedicines. 2020 Jul 29;8(8):252. doi: 10.3390/biomedicines8080252. PMID: 32751120; PMCID: PMC7460547. 6: Yoo JC, Cho HS, Park E, Park JA, Kim S, Kim DK, Kim CS, Kim SJ, Chun HS. Nargenicin attenuates lipopolysaccharide-induced inflammatory responses in BV-2 cells. Neuroreport. 2009 Jul 15;20(11):1007-12. doi: 10.1097/WNR.0b013e32832d2239. PMID: 19474767. 7: Dhakal D, Han JM, Mishra R, Pandey RP, Kim TS, Rayamajhi V, Jung HJ, Yamaguchi T, Sohng JK. Characterization of Tailoring Steps of Nargenicin A1 Biosynthesis Reveals a Novel Analogue with Anticancer Activities. ACS Chem Biol. 2020 Jun 19;15(6):1370-1380. doi: 10.1021/acschembio.9b01034. Epub 2020 Apr 3. PMID: 32208643. 8: Dhakal D, Chaudhary AK, Yi JS, Pokhrel AR, Shrestha B, Parajuli P, Shrestha A, Yamaguchi T, Jung HJ, Kim SY, Kim BG, Sohng JK. Enhanced production of nargenicin A1 and creation of a novel derivative using a synthetic biology platform. Appl Microbiol Biotechnol. 2016 Dec;100(23):9917-9931. doi: 10.1007/s00253-016-7705-3. Epub 2016 Jul 14. PMID: 27412463. 9: Dhakal D, Le TT, Pandey RP, Jha AK, Gurung R, Parajuli P, Pokhrel AR, Yoo JC, Sohng JK. Enhanced production of nargenicin A(1) and generation of novel glycosylated derivatives. Appl Biochem Biotechnol. 2015 Mar;175(6):2934-49. doi: 10.1007/s12010-014-1472-3. Epub 2015 Jan 11. PMID: 25577346. 10: Han JM, Sohng JK, Lee WH, Oh TJ, Jung HJ. Identification of Cyclophilin A as a Potential Anticancer Target of Novel Nargenicin A1 Analog in AGS Gastric Cancer Cells. Int J Mol Sci. 2021 Mar 1;22(5):2473. doi: 10.3390/ijms22052473. PMID: 33804393; PMCID: PMC7957809.