Sisomicin D
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| Category | Antibiotics |
| Catalog number | BBF-02994 |
| CAS | 53759-50-5 |
| Molecular Weight | 433.50 |
| Molecular Formula | C18H35N5O7 |
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Description
It is an aminoglycoside antibiotic produced by the strain of Micromonospora inyoensis. It has broad-spectrum antimicrobial activity.
Specification
| Synonyms | 6-O-[3-Deoxy-3-(methylamino)-β-L-arabinopyranosyl]-4-O-(2,6-diamino-2,3,4,6-tetradeoxy-α-D-glycero-hexa-4-enopyranosyl)-2-deoxy-D-streptamine; Antibiotic 66-40D; 66-40D |
| IUPAC Name | (2R,3R,4S,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-4-(methylamino)oxane-3,5-diol |
| Canonical SMILES | CNC1C(COC(C1O)OC2C(CC(C(C2O)OC3C(CC=C(O3)CN)N)N)N)O |
| InChI | InChI=1S/C18H35N5O7/c1-23-12-11(24)6-27-18(13(12)25)30-16-10(22)4-9(21)15(14(16)26)29-17-8(20)3-2-7(5-19)28-17/h2,8-18,23-26H,3-6,19-22H2,1H3/t8-,9+,10-,11+,12+,13-,14+,15-,16+,17-,18-/m1/s1 |
| InChI Key | DAKDDLIZULPEFW-JVRQZOTMSA-N |
Properties
| Appearance | Amorphous Powder |
| Boiling Point | 682.7±55.0°C at 760 mmHg |
| Melting Point | 102-103°C |
| Density | 1.4±0.1 g/cm3 |
| Solubility | Soluble in Water |
Reference Reading
1. Synthesis of Gentamicin Minor Components: Gentamicin B1 and Gentamicin X2
Parasuraman Rajasekaran, David Crich Org Lett. 2020 May 15;22(10):3850-3854. doi: 10.1021/acs.orglett.0c01107. Epub 2020 Apr 28.
The clinical aminoglycoside antibiotic gentamicin is a mixture of several difficult-to-separate major and minor components. The relative inaccessibility of the minor components in particular complicates efforts to separate antibacterial activity from nephro- and/or ototoxicity and to clarify the origin of the potentially therapeutically important read-through activity. With a view to facilitating such studies, the synthesis of a fully and selectively protected garamine-based acceptor has been developed from readily available sisomicin. Glycosylation of this acceptor with a 6-azido-6,7-dideoxy-d-glycero-d-glucoheptopyranosyl donor affords gentamicin B1 after deprotection, whereas employment of a 2-azido-2-deoxy-d-glucopyranosyl donor under N,N-dimethylformamide-directed glycosylation conditions affords gentamicin X2 after deprotection.
2. Comparison of the Anti-Inflammatory and Cytotoxic Potential of Different Corticosteroid Eye Drop Preparations
Matteo Urru, Giuseppe Ranieri, Rita Mencucci, Alberto Chiarugi Ocul Immunol Inflamm. 2020 Jul 3;28(5):839-845. doi: 10.1080/09273948.2019.1634214. Epub 2019 Sep 6.
To compare the immunosuppressive and cytotoxic effects of three anti-inflammatory eye drops formulations containing betamethasone plus chloramphenicol (B+C), dexamethasone plus netilmicin (D+N) or dexamethasone plus tobramycin (D+T).Methods: The eye drops formulations have been tested at different dilutions on cytokine synthesis by mouse or human cultured macrophages, as well as proliferation and viability of cultured human corneal cells (HCE).Results: B+C reduced IL6 and TNFα production by cultured mouse or human macrophages more potently than D+N and D+T, with the tree formulations having the same impact on IL-10 expression. We also found that the eye drops preparations reduced proliferation of HCE cells, with D+T showing the higher anti-proliferative potency and B+C showing the lower cytotoxic potential.Conclusion: Our study points out that it may be erroneous to consider routinely-used anti-inflammatory eye drops preparations with analogous formulations as readily interchangeable and of similar potency and tolerability.
3. Dissociating antibacterial from ototoxic effects of gentamicin C-subtypes
Mary E O'Sullivan, Yohan Song, Robert Greenhouse, Randy Lin, Adela Perez, Patrick J Atkinson, Jacob P MacDonald, Zehra Siddiqui, Dennis Lagasca, Kate Comstock, Markus E Huth, Alan G Cheng, Anthony J Ricci Proc Natl Acad Sci U S A. 2020 Dec 22;117(51):32423-32432. doi: 10.1073/pnas.2013065117. Epub 2020 Dec 7.
Gentamicin is a potent broad-spectrum aminoglycoside antibiotic whose use is hampered by ototoxic side-effects. Hospital gentamicin is a mixture of five gentamicin C-subtypes and several impurities of various ranges of nonexact concentrations. We developed a purification strategy enabling assaying of individual C-subtypes and impurities for ototoxicity and antimicrobial activity. We found that C-subtypes displayed broad and potent in vitro antimicrobial activities comparable to the hospital gentamicin mixture. In contrast, they showed different degrees of ototoxicity in cochlear explants, with gentamicin C2b being the least and gentamicin C2 the most ototoxic. Structure-activity relationships identified sites in the C4'-C6' region on ring I that reduced ototoxicity while preserving antimicrobial activity, thus identifying targets for future drug design and mechanisms for hair cell toxicity. Structure-activity relationship data suggested and electrophysiological data showed that the C-subtypes both bind and permeate the hair cell mechanotransducer channel, with the stronger the binding the less ototoxic the compound. Finally, both individual and reformulated mixtures of C-subtypes demonstrated decreased ototoxicity while maintaining antimicrobial activity, thereby serving as a proof-of-concept of drug reformulation to minimizing ototoxicity of gentamicin in patients.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
