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MedKoo Cat#: 112013 | Name: Amphotericin B methyl ester
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Description:

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

Amphotericin B methyl ester is a polyene antiviral and antifungal agent and a derivative of amphotericin B. It impairs viral particle production, as well as viral entry and infectivity, in HIV-1-infected TZM-bl cells when used at a concentration of 10 µM. Amphotericin B methyl ester also inhibits replication of HIV-1 clinical isolates from a variety of clades in infected human peripheral blood mononuclear cells (PBMCs; IC50s = 0.5-5.5 µM). It is active against S. cerevisiae (MIC = 0.25 µg/ml) and reduces mortality in a mouse model of C. albicans infection when administered at doses of 1 and 10 mg/kg.

Chemical Structure

Amphotericin B methyl ester
Amphotericin B methyl ester
CAS#36148-89-7 (Amphotericin B methyl ester)

Theoretical Analysis

MedKoo Cat#: 112013

Name: Amphotericin B methyl ester

CAS#: 36148-89-7 (Amphotericin B methyl ester)

Chemical Formula: C48H75NO17

Exact Mass: 937.5035

Molecular Weight: 938.12

Elemental Analysis: C, 61.46; H, 8.06; N, 1.49; O, 28.99

Price and Availability

Size Price Availability Quantity
5mg USD 260.00 2 Weeks
10mg USD 500.00 2 Weeks
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Related CAS #
1405-32-9 (Amphotericin A) 1397-89-3 (Amphotericin B) 36148-89-7 (Amphotericin B methyl ester)
Synonym
LNS-AmB methyl ester; Amphotericin B methyl ester
IUPAC/Chemical Name
methyl (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-(((2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylate
InChi Key
UAZIZEMIKKIBCA-TYVGYKFWSA-N
InChi Code
InChI=1S/C48H75NO17/c1-28-18-16-14-12-10-8-6-7-9-11-13-15-17-19-35(65-47-45(59)42(49)44(58)31(4)64-47)25-39-41(46(60)62-5)38(55)27-48(61,66-39)26-34(52)23-37(54)36(53)21-20-32(50)22-33(51)24-40(56)63-30(3)29(2)43(28)57/h6-19,28-39,41-45,47,50-55,57-59,61H,20-27,49H2,1-5H3/b7-6+,10-8+,11-9+,14-12+,15-13+,18-16+,19-17+/t28-,29-,30-,31+,32+,33+,34-,35-,36+,37+,38-,39-,41+,42-,43+,44+,45-,47-,48+/m0/s1
SMILES Code
COC([C@H]1[C@]2(O[C@@](C[C@@H](O)C[C@@H](O)[C@H](O)CC[C@@H](O)C[C@@H](O)CC(O[C@@H](C)[C@H](C)[C@H](O)[C@@H](C)/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](O[C@H]3[C@@H](O)[C@@H](N)[C@H](O)[C@@H](C)O3)C2)=O)(O)C[C@@H]1O)[H])=O
Appearance
Solid powder
Purity
>70% (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

Preparing Stock Solutions

The following data is based on the product molecular weight 938.12 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: Morgan NK, Gomes GA, Kim JC. Comparing the efficacy of stimbiotic and a combination of xylanase and beta-glucanase, in broilers fed wheat-barley based diets with high or low AME. Poult Sci. 2021 Oct;100(10):101383. doi: 10.1016/j.psj.2021.101383. Epub 2021 Jul 9. PMID: 34438325; PMCID: PMC8383100. 2: Zhang J, Xu H, Dong Y, Chen M, Zhang Y, Shangguan W, Zhao W, Feng J. Design, synthesis and biological evaluation of a novel N-aminoacyl derivative of amphotericin B methyl ester as an antifungal agent. Eur J Med Chem. 2021 Feb 5;211:113104. doi: 10.1016/j.ejmech.2020.113104. Epub 2020 Dec 17. PMID: 33360798. 3: Zhang J, Dong Y, Xu H, Chen M, Tang H, Shangguan W, Zhao W, Feng J. Synthesis and biological evaluation of esterified and acylated derivatives of NH2-(AEEA)5-amphotericin B. J Antibiot (Tokyo). 2021 Feb;74(2):133-142. doi: 10.1038/s41429-020-00365-3. Epub 2020 Sep 17. PMID: 32939075. 4: Kirui J, Freed EO. Generation and validation of a highly sensitive bioluminescent HIV-1 reporter vector that simplifies measurement of virus release. Retrovirology. 2020 May 19;17(1):12. doi: 10.1186/s12977-020-00521-5. PMID: 32430080; PMCID: PMC7235552. 5: Yamamoto T, Umegawa Y, Yamagami M, Suzuki T, Tsuchikawa H, Hanashima S, Matsumori N, Murata M. The Perpendicular Orientation of Amphotericin B Methyl Ester in Hydrated Lipid Bilayers Supports the Barrel-Stave Model. Biochemistry. 2019 Apr 30;58(17):2282-2291. doi: 10.1021/acs.biochem.9b00180. Epub 2019 Apr 18. PMID: 30973009. 6: Cavalcanti FL, Mirones CR, Paucar ER, Montes LÁ, Leal-Balbino TC, Morais MM, Martínez-Martínez L, Ocampo-Sosa AA. Mutational and acquired carbapenem resistance mechanisms in multidrug resistant Pseudomonas aeruginosa clinical isolates from Recife, Brazil. Mem Inst Oswaldo Cruz. 2015 Dec;110(8):1003-9. doi: 10.1590/0074-02760150233. Epub 2015 Dec 15. PMID: 26676375; PMCID: PMC4708020. 7: Karimi K, Shokrollahi B. Lipidemic responses of male broiler chickens to enzyme-supplemented wheat-soybean meal-based diets with various levels of metabolizable energy. Pak J Biol Sci. 2013 Nov 1;16(21):1295-302. doi: 10.3923/pjbs.2013.1295.1302. PMID: 24511737. 8: Kondo C, Aoki M, Yamamoto E, Tonomura Y, Ikeda M, Kaneto M, Yamate J, Torii M, Uehara T. Predictive genomic biomarkers for drug-induced nephrotoxicity in mice. J Toxicol Sci. 2012;37(4):723-37. doi: 10.2131/jts.37.723. PMID: 22863853. 9: Thanathanee O, Miller D, Ringel DM, Schaffner CP, Alfonso EC, O'Brien TP. Comparative in vitro antifungal susceptibility activity of amphotericin B versus amphotericin B methyl ester against Candida albicans ocular isolates. J Ocul Pharmacol Ther. 2012 Dec;28(6):589-92. doi: 10.1089/jop.2012.0048. Epub 2012 Jul 12. PMID: 22788845. 10: Jiang Y, Liu XY. [The role of structural protein Gag and related gene (protein) in late stages of the HIV-1 replication cycle and the inhibitors]. Yao Xue Xue Bao. 2010 Feb;45(2):205-14. Chinese. PMID: 21351430. 11: Waheed AA, Ablan SD, Sowder RC, Roser JD, Schaffner CP, Chertova E, Freed EO. Effect of mutations in the human immunodeficiency virus type 1 protease on cleavage of the gp41 cytoplasmic tail. J Virol. 2010 Mar;84(6):3121-6. doi: 10.1128/JVI.02002-09. Epub 2009 Dec 30. PMID: 20042499; PMCID: PMC2826043. 12: Szpilman AM, Cereghetti DM, Manthorpe JM, Wurtz NR, Carreira EM. Synthesis and biophysical studies on 35-deoxy amphotericin B methyl ester. Chemistry. 2009 Jul 20;15(29):7117-28. doi: 10.1002/chem.200900231. PMID: 19544513. 13: Waheed AA, Ablan SD, Soheilian F, Nagashima K, Ono A, Schaffner CP, Freed EO. Inhibition of human immunodeficiency virus type 1 assembly and release by the cholesterol-binding compound amphotericin B methyl ester: evidence for Vpu dependence. J Virol. 2008 Oct;82(19):9776-81. doi: 10.1128/JVI.00917-08. Epub 2008 Jul 23. PMID: 18653459; PMCID: PMC2546975. 14: Szpilman AM, Cereghetti DM, Wurtz NR, Manthorpe JM, Carreira EM. Synthesis of 35-deoxy amphotericin B methyl ester: a strategy for molecular editing. Angew Chem Int Ed Engl. 2008;47(23):4335-8. doi: 10.1002/anie.200800589. PMID: 18454441. 15: Szpilman AM, Manthorpe JM, Carreira EM. Synthesis and biological studies of 35-deoxy amphotericin B methyl ester. Angew Chem Int Ed Engl. 2008;47(23):4339-42. doi: 10.1002/anie.200800590. PMID: 18442156. 16: Waheed AA, Ablan SD, Roser JD, Sowder RC, Schaffner CP, Chertova E, Freed EO. HIV-1 escape from the entry-inhibiting effects of a cholesterol-binding compound via cleavage of gp41 by the viral protease. Proc Natl Acad Sci U S A. 2007 May 15;104(20):8467-71. doi: 10.1073/pnas.0701443104. Epub 2007 May 4. PMID: 17483482; PMCID: PMC1895973. 17: Waheed AA, Ablan SD, Mankowski MK, Cummins JE, Ptak RG, Schaffner CP, Freed EO. Inhibition of HIV-1 replication by amphotericin B methyl ester: selection for resistant variants. J Biol Chem. 2006 Sep 29;281(39):28699-711. doi: 10.1074/jbc.M603609200. Epub 2006 Aug 1. PMID: 16882663. 18: Hac-Wydro K, Dynarowicz-Łatka P, Grzybowska J, Borowski E. How does the N-acylation and esterification of amphotericin B molecule affect its interactions with cellular membrane components-the Langmuir monolayer study. Colloids Surf B Biointerfaces. 2005 Nov 25;46(1):7-19. doi: 10.1016/j.colsurfb.2005.08.008. Epub 2005 Sep 29. PMID: 16198546. 19: Hac-Wydro K, Dynarowicz-Latka P, Grzybowska J, Borowski E. N-(1-piperidinepropionyl)amphotericin B methyl ester (PAME)--a new derivative of the antifungal antibiotic amphotericin B: searching for the mechanism of its reduced toxicity. J Colloid Interface Sci. 2005 Jul 15;287(2):476-84. doi: 10.1016/j.jcis.2005.02.038. PMID: 15925613. 20: Ibragimova VKh, Alieva IN, Aliev DI. Inaktivatsiia provodimosti amfoteritsinovykh kanalov [Amphotericin B channel conductance inactivation]. Tsitologiia. 2003;45(8):804-11. Russian. PMID: 15216632.