Amphotericin B methyl ester
(Synonyms: 两性霉素B甲酯90%) 目录号 : GC60047
A polyene antiviral and antifungal agent
Cas No.:36148-89-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Amphotericin B methyl ester is a polyene antiviral and antifungal agent and a derivative of amphotericin B .1,2 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 ?M.1 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 ?M). It is active against S. cerevisiae (MIC = 0.25 ?g/ml) and reduces mortality in a mouse model of C. albicans infection when administered at doses of 1 and 10 mg/kg.2
1.Waheed, A.A., Ablan, S.D., Mankowski, M.K., et al.Inhibition of HIV-1 replication by amphotericin B methyl ester: Selection for resistant variantsJ. Biol. Chem.281(39)28699-28711(2006)
| Cas No. | 36148-89-7 | SDF | |
| 别名 | 两性霉素B甲酯90% | ||
| Canonical SMILES | COC([C@H]1[C@@]2([H])O[C@](O)(C[C@H](C[C@H]([C@@H](CC[C@H](C[C@H](CC(O[C@H]([C@@H]([C@H](O)[C@@H](C)/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](O[C@@]3([H])[C@H]([C@H]([C@H](O)[C@@H](C)O3)N)O)C2)C)C)=O)O)O)O)O)O)C[C@@H]1O)=O | ||
| 分子式 | C48H75NO17 | 分子量 | 938.11 |
| 溶解度 | DMSO : 50 mg/mL (53.30 mM; Need ultrasonic) | 储存条件 | |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 1.066 mL | 5.3299 mL | 10.6597 mL |
| 5 mM | 0.2132 mL | 1.066 mL | 2.1319 mL |
| 10 mM | 0.1066 mL | 0.533 mL | 1.066 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Stability studies with amphotericin B and Amphotericin B methyl ester
J Antibiot (Tokyo) 1975 Feb;28(2):132-5.PMID:234414DOI:10.7164/antibiotics.28.132.
In solid form, amphotericin B and Amphotericin B methyl ester free base exhibit similar stability. Acid salts of the methyl ester derivative stored under identical conditions are less stable. In solution, amphotericin B is generally more stable than its methy ester salts. However, when pH is adjusted to 6.0 and storage temperature held at 5 degrees C the methyl ester salts reflect the stability exhibited by the parent compound, amphotericin B.
Comparative toxicological studies of Amphotericin B methyl ester and amphotericin B in mice, rats, and dogs
Antimicrob Agents Chemother 1976 Oct;10(4):687-90.PMID:984803DOI:10.1128/AAC.10.4.687.
In acute and subacute toxicological studies, Amphotericin B methyl ester was shown to be much less toxic than the parent antibiotic. As a single intravenous dose in mice, the methyl ester was approximately 20 times less toxic than amphotericin B. Also, the acute toxicity of the methyl ester in mice was not enhanced by the presence of chemically induced hepatic or renal damage or by the concurrent administration of amphotericin B or flucytosine. In a 1-month intraperitoneal study in rats, the methyl ester was about one-fourth as nephrotoxic as amphotericin B. In a 1-month intravenous study in dogs, the methyl ester was about one-eighth as nephrotoxic and one-fourth to one-half as hepatotoxic as the parent compound. In addition, the methyl ester, unlike amphotericin B, produced minimal renal effects, which did not increase in severity with increasing dosage. Based on the results of these studies, it is concluded that Amphotericin B methyl ester has the potential for an improved therapeutic ratio in the treatment of systemic mycoses.
Equilibrium binding of amphotericin B and its methyl ester and borate complex to sterols
Biochim Biophys Acta 1982 Feb 23;685(2):219-24.PMID:7059605DOI:10.1016/0005-2736(82)90103-1.
Scatchard analysis of the binding of amphotericin B to sterols in egg phosphatidylcholine/sterol vesicles revealed that amphotericin B was bound to ergosterol by approximately one order of magnitude more tightly than to cholesterol. Amphotericin B methyl ester formed a tighter complex with each of the sterols investigated than did amphotericin B, but the difference in the apparent binding constants towards ergosterol and cholesterol was not as large as with amphotericin B. Amphotericin B borate formed weaker complexes with vesicle-bound sterols than amphotericin B and Amphotericin B methyl ester.
Comparison of amphotericin B and N-D-ornithyl Amphotericin B methyl ester in experimental cryptococcal meningitis and Candida albicans endocarditis with pyelonephritis
Antimicrob Agents Chemother 1985 Dec;28(6):751-5.PMID:4083860DOI:10.1128/AAC.28.6.751.
Amphotericin B and N-D-ornithyl Amphotericin B methyl ester were compared for therapeutic efficacies against experimentally induced cryptococcal meningitis and Candida albicans endocarditis with pyelonephritis in rabbits. Antifungal activity of the two polyenes in vitro was similar for the yeasts used in these experiments. N-D-ornithyl Amphotericin B methyl ester gave a slightly higher concentration in serum than amphotericin B did, but both drugs had similar elimination curves, and penetration into the cerebrospinal fluid was poor for both. Despite these similarities between the two polyenes, amphotericin B was much more effective than N-D-ornithyl Amphotericin B methyl ester in the treatment of cryptococcal meningitis in rabbits. For C. albicans endocarditis, both polyenes had similar cure rates, but in vitro measurement of fungicidal activity in serum did not predict treatment outcome. For C. albicans pyelonephritis, both polyenes showed efficacy; because higher doses of the less toxic methyl ester could be used, it sterilized the urinary tract more often than amphotericin B. These studies indicate that in vivo and in vitro experiments may be needed to predict the results of treatment with polyenes.
Antiviral effects of Amphotericin B methyl ester
Antimicrob Agents Chemother 1978 Feb;13(2):199-204.PMID:206201DOI:10.1128/AAC.13.2.199.
The methyl ester of amphotericin B (AME) is water soluble, retains antifungal activity, and is significantly less toxic in mammals than amphotericin B. In contrast to amphotericin B, which is not water soluble, AME exhibits antiviral effects against vesicular stomatitis virus, herpes simplex virus types 1 and 2, Sindbis virus, and vaccinia virus in a plaque reduction assay. No antiviral effects could be demonstrated against the unenveloped adenovirus type 4 or echovirus type 11. The extent of virus inactivation was found to be dependent upon the AME concentration, contact time, and temperature. No consistent effect of the virus concentration on the probability of plaque-forming unit inactivation could be determined. The antiviral effects of AME were partially antagonized by the presence of serum. Binding of AME to vesicular stomatitis virus was demonstrated by the comigration of drug and virus in linear sucrose gradients. AME represents a new class of antiviral agents with activity at concentrations relevant to therapeutics. Sterol components of the host cell membrane that become incorporated into the viral envelope are postulated as the site of reaction with AME.