Ac4ManNAz | CAS#361154-30-5 | metabolic labeling agent

MedKoo Cat#: 563796 | Name: Ac4ManNAz

Description:

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

Ac4ManNAz is a novel probe for metabolic labeling of sialoglycans, selectively imaging polysialic acids in neurons. treatment with 50 μM Ac4ManNAz led to the reduction of major cellular functions, including energy generation capacity, cellular infiltration ability and channel activity. Interestingly, 10 μM Ac4ManNAz showed the least effect on cellular systems and had a sufficient labeling efficiency for cell labeling, tracking and proteomic analysis. Based on our results, we suggest 10 μM as the optimum concentration of Ac4ManNAz for in vivo cell labeling and tracking.

Chemical Structure

Ac4ManNAz

CAS#361154-30-5

Theoretical Analysis

MedKoo Cat#: 563796

Name: Ac4ManNAz

CAS#: 361154-30-5

Chemical Formula: C16H22N4O10

Exact Mass: 430.1336

Molecular Weight: 430.37

Elemental Analysis: C, 44.65; H, 5.15; N, 13.02; O, 37.17

Price and Availability

Size	Price	Availability
10mg	USD 90.00	Ready to Ship
25mg	USD 150.00	Ready to Ship
50mg	USD 250.00	Ready to Ship
100mg	USD 450.00	Ready to Ship
200mg	USD 750.00	Ready to Ship
500mg	USD 1,650.00	Ready to Ship
1g	USD 2,950.00	Ready to Ship
2g	USD 5,250.00	Ready to Ship

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Synonym

Ac4ManNAz; Ac 4ManNAz; Ac-4ManNAz; Ac4Man-NAz; Ac4-Man-NAz; Ac4-ManNAz; N-Azidoacetylmannosamine-tetraacylated

IUPAC/Chemical Name

Peracetylated N-azidoacetyl-d-mannosamine

InChi Key

HGMISDAXLUIXKM-LIADDWGISA-N

InChi Code

InChI=1S/C16H22N4O10/c1-7(21)26-6-11-14(27-8(2)22)15(28-9(3)23)13(16(30-11)29-10(4)24)19-12(25)5-18-20-17/h11,13-16H,5-6H2,1-4H3,(H,19,25)/t11-,13+,14-,15-,16?/m1/s1

SMILES Code

O=C(C)OC[C@H]1OC(OC(C)=O)[C@@H](NC(CN=[N+]=[N-])=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

Appearance

Solid powder

Purity

>95% (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

Certificate of Analysis

View CoA: current batch, Lot#S21G03M18

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Ac4ManNAz is a novel probe for metabolic labeling of sialoglycans, selectively imaging polysialic acids in neurons.

In vitro activity:

Herein, an engineered leukocyte biomimetic colorimetric sensor was accordingly fabricated for high-efficient detection of heterogeneous CTCs. Compared with conventional leukocyte membrane coating, the sensor could covalently bound to the heterogeneous CTCs models fed with Ac4ManNAz in vitro through the synergy of bioorthogonal chemistry and metabolic glycoengineering, ignoring the phenotypic changes of heterogeneous CTCs. Reference: Li M, Jia L, Zhu A, Li J, Li J, Liu X, Xie X. Engineered Leukocyte Biomimetic Colorimetric Sensor Enables High-Efficient Detection of Tumor Cells Based on Bioorthogonal Chemistry. ACS Appl Mater Interfaces. 2024 Jul 17;16(28):36106-36116. doi: 10.1021/acsami.4c06272. Epub 2024 Jul 2. PMID: 38955781.

In vivo activity:

when we increased sialylation using N-azidoacetylmannosamine-tetraacylated (Ac4ManNAz), hTCEpi cells showed a decrease in both speed and directionality. Importantly, pretreating enucleated eyes with 3F-Neu5Ac significantly improved re-epithelialization in an ex vivo model of a corneal injury. Reference: Le B, Zhu K, Brown C, Reid B, Cressman A, Zhao M, Fierro FA. Reducing Sialylation Enhances Electrotaxis of Corneal Epithelial Cells. Int J Mol Sci. 2023 Sep 20;24(18):14327. doi: 10.3390/ijms241814327. PMID: 37762630; PMCID: PMC10531958.

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	232.36

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 430.37 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.

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:

In vitro protocol:

1: Li M, Jia L, Zhu A, Li J, Li J, Liu X, Xie X. Engineered Leukocyte Biomimetic Colorimetric Sensor Enables High-Efficient Detection of Tumor Cells Based on Bioorthogonal Chemistry. ACS Appl Mater Interfaces. 2024 Jul 17;16(28):36106-36116. doi: 10.1021/acsami.4c06272. Epub 2024 Jul 2. PMID: 38955781. 2: Qiao J, Tian F, Deng Y, Shang Y, Chen S, Chang E, Yao J. Bio-orthogonal click-targeting nanocomposites for chemo-photothermal synergistic therapy in breast cancer. Theranostics. 2020 Apr 6;10(12):5305-5321. doi: 10.7150/thno.42445. PMID: 32373214; PMCID: PMC7196291.

In vivo protocol:

1: Le B, Zhu K, Brown C, Reid B, Cressman A, Zhao M, Fierro FA. Reducing Sialylation Enhances Electrotaxis of Corneal Epithelial Cells. Int J Mol Sci. 2023 Sep 20;24(18):14327. doi: 10.3390/ijms241814327. PMID: 37762630; PMCID: PMC10531958.

1: Han SS, Lee DE, Shim HE, Lee S, Jung T, Oh JH, Lee HA, Moon SH, Jeon J, Yoon S, Kim K, Kang SW. Physiological Effects of Ac4ManNAz and Optimization of Metabolic Labeling for Cell Tracking. Theranostics. 2017 Mar 1;7(5):1164-1176. doi: 10.7150/thno.17711. PMID: 28435456; PMCID: PMC5399584. 2: Han SS, Shim HE, Park SJ, Kim BC, Lee DE, Chung HM, Moon SH, Kang SW. Safety and Optimization of Metabolic Labeling of Endothelial Progenitor Cells for Tracking. Sci Rep. 2018 Sep 4;8(1):13212. doi: 10.1038/s41598-018-31594-0. PMID: 30181604; PMCID: PMC6123424. 3: Qiao J, Tian F, Deng Y, Shang Y, Chen S, Chang E, Yao J. Bio-orthogonal click-targeting nanocomposites for chemo-photothermal synergistic therapy in breast cancer. Theranostics. 2020 Apr 6;10(12):5305-5321. doi: 10.7150/thno.42445. PMID: 32373214; PMCID: PMC7196291. 4: Bodnar E, Raymond C, Lopez PG, Villacrés C, Butler M, Schoenhofen IC, Durocher Y, Perreault H. Mass spectrometric analysis of products of metabolic glycan engineering with azido-modification of sialic acids. Anal Bioanal Chem. 2015 Dec;407(30):8945-58. doi: 10.1007/s00216-015-9010-x. Epub 2015 Sep 11. Erratum in: Anal Bioanal Chem. 2015 Dec;407(30):9191-3. PMID: 26362153. 5: Yoon HI, Yhee JY, Na JH, Lee S, Lee H, Kang SW, Chang H, Ryu JH, Lee S, Kwon IC, Cho YW, Kim K. Bioorthogonal Copper Free Click Chemistry for Labeling and Tracking of Chondrocytes In Vivo. Bioconjug Chem. 2016 Apr 20;27(4):927-36. doi: 10.1021/acs.bioconjchem.6b00010. Epub 2016 Mar 10. PMID: 26930274. 6: Rochefort MM, Girgis MD, Ankeny JS, Tomlinson JS. Metabolic exploitation of the sialic acid biosynthetic pathway to generate site-specifically labeled antibodies. Glycobiology. 2014 Jan;24(1):62-9. doi: 10.1093/glycob/cwt090. Epub 2013 Oct 22. PMID: 24150277. 7: Xiong DC, Zhu J, Han MJ, Luo HX, Wang C, Yu Y, Ye Y, Tai G, Ye XS. Rapid probing of sialylated glycoproteins in vitro and in vivo via metabolic oligosaccharide engineering of a minimal cyclopropene reporter. Org Biomol Chem. 2015 Apr 7;13(13):3911-7. doi: 10.1039/c5ob00069f. PMID: 25735895. 8: Parle DR, Bulat F, Fouad S, Zecchini H, Brindle KM, Neves AA, Leeper FJ. Metabolic Glycan Labeling of Cancer Cells Using Variably Acetylated Monosaccharides. Bioconjug Chem. 2022 Aug 17;33(8):1467-1473. doi: 10.1021/acs.bioconjchem.2c00169. Epub 2022 Jul 25. PMID: 35876696; PMCID: PMC9389531. 9: Phelan J, Altharawi A, Chan KLA. Tracking glycosylation in live cells using FTIR spectroscopy. Talanta. 2020 May 1;211:120737. doi: 10.1016/j.talanta.2020.120737. Epub 2020 Jan 13. PMID: 32070609; PMCID: PMC7048185. 10: Mongis A, Piller F, Piller V. Coupling of Immunostimulants to Live Cells through Metabolic Glycoengineering and Bioorthogonal Click Chemistry. Bioconjug Chem. 2017 Apr 19;28(4):1151-1165. doi: 10.1021/acs.bioconjchem.7b00042. Epub 2017 Mar 28. PMID: 28297599. 11: Lee TS, Kim Y, Zhang W, Song IH, Tung CH. Facile metabolic glycan labeling strategy for exosome tracking. Biochim Biophys Acta Gen Subj. 2018 May;1862(5):1091-1100. doi: 10.1016/j.bbagen.2018.02.001. Epub 2018 Feb 2. PMID: 29410228; PMCID: PMC5866232. 12: Zhao Z, Zhang Z, Duan S, Liu X, Zhou R, Hou M, Sang Y, Zhu R, Yin L. Cytosolic protein delivery via metabolic glycoengineering and bioorthogonal click reactions. Biomater Sci. 2021 Jul 7;9(13):4639-4647. doi: 10.1039/d1bm00548k. Epub 2021 May 26. PMID: 34036971. 13: Alberti D, Grange C, Porta S, Aime S, Tei L, Geninatti Crich S. Efficient Route to Label Mesenchymal Stromal Cell-Derived Extracellular Vesicles. ACS Omega. 2018 Jul 31;3(7):8097-8103. doi: 10.1021/acsomega.8b00908. Epub 2018 Jul 19. PMID: 30087935; PMCID: PMC6072237. 14: Meghani NM, Amin HH, Park C, Park JB, Cui JH, Cao QR, Lee BJ. Design and evaluation of clickable gelatin-oleic nanoparticles using fattigation-platform for cancer therapy. Int J Pharm. 2018 Jul 10;545(1-2):101-112. doi: 10.1016/j.ijpharm.2018.04.047. Epub 2018 Apr 23. PMID: 29698822. 15: Yun WS, Shim MK, Lim S, Song S, Kim J, Yang S, Hwang HS, Kim MR, Yoon HY, Lim DK, Sun IC, Kim K. Mesenchymal Stem Cell-Mediated Deep Tumor Delivery of Gold Nanorod for Photothermal Therapy. Nanomaterials (Basel). 2022 Sep 28;12(19):3410. doi: 10.3390/nano12193410. PMID: 36234538; PMCID: PMC9565344. 16: Chen X, Qiu L, Cai R, Cui C, Li L, Jiang JH, Tan W. Aptamer-Directed Protein-Specific Multiple Modifications of Membrane Glycoproteins on Living Cells. ACS Appl Mater Interfaces. 2020 Aug 26;12(34):37845-37850. doi: 10.1021/acsami.0c07004. Epub 2020 Aug 13. PMID: 32706235. 17: Bussink AP, van Swieten PF, Ghauharali K, Scheij S, van Eijk M, Wennekes T, van der Marel GA, Boot RG, Aerts JM, Overkleeft HS. N-azidoacetylmannosamine- mediated chemical tagging of gangliosides. J Lipid Res. 2007 Jun;48(6):1417-21. doi: 10.1194/jlr.C700006-JLR200. Epub 2007 Mar 27. PMID: 17392268. 18: Chang PV, Prescher JA, Sletten EM, Baskin JM, Miller IA, Agard NJ, Lo A, Bertozzi CR. Copper-free click chemistry in living animals. Proc Natl Acad Sci U S A. 2010 Feb 2;107(5):1821-6. doi: 10.1073/pnas.0911116107. Epub 2010 Jan 14. PMID: 20080615; PMCID: PMC2836626. 19: Choi AW, Liu HW, Lo KK. Rhenium(I) polypyridine dibenzocyclooctyne complexes as phosphorescent bioorthogonal probes: Synthesis, characterization, emissive behavior, and biolabeling properties. J Inorg Biochem. 2015 Jul;148:2-10. doi: 10.1016/j.jinorgbio.2015.02.018. Epub 2015 Mar 4. PMID: 25798989. 20: Lim S, Kim W, Song S, Shim MK, Yoon HY, Kim BS, Kwon IC, Kim K. Intracellular Uptake Mechanism of Bioorthogonally Conjugated Nanoparticles on Metabolically Engineered Mesenchymal Stem Cells. Bioconjug Chem. 2021 Jan 20;32(1):199-214. doi: 10.1021/acs.bioconjchem.0c00640. Epub 2021 Jan 4. PMID: 33397092.