Cas no 143452-11-3 (Oasamycin A)

Oasamycin A structure
Oasamycin A structure
Product Name:Oasamycin A
CAS No:143452-11-3
MF:C61H104O22
MW:1189.46528244019
CID:2052213
PubChem ID:101679021
Update Time:2025-07-15

Oasamycin A Chemical and Physical Properties

Names and Identifiers

    • Oasamycin A
    • 143452-11-3
    • 8,10,16,20,24,26,28,30,32,34,36,38-dodecahydroxy-3,7,9,15,19,21,31,33-octamethyl-42-(1-(5-oxooxolan-2-yl)ethyl)-23-((2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-1-oxacyclodotetraconta-3,13,17,21,39-pentaen-2-one
    • Oasomycin B
    • 8,10,16,20,24,26,28,30,32,34,36,38-dodecahydroxy-3,7,9,15,19,21,31,33-octamethyl-42-[1-(5-oxooxolan-2-yl)ethyl]-23-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1-oxacyclodotetraconta-3,13,17,21,39-pentaen-2-one
    • CHEBI:219444
    • Inchi: 1S/C61H104O22/c1-31-14-10-11-18-45(68)36(6)55(74)32(2)15-12-16-34(4)60(79)81-49(39(9)50-22-23-53(72)80-50)19-13-17-40(63)25-41(64)27-46(69)37(7)56(75)38(8)47(70)28-42(65)26-43(66)29-48(71)51(24-35(5)54(73)33(3)20-21-44(31)67)82-61-59(78)58(77)57(76)52(30-62)83-61/h10,13-14,16-17,20-21,24,31-33,36-52,54-59,61-71,73-78H,11-12,15,18-19,22-23,25-30H2,1-9H3
    • InChI Key: QDNMAZUKNSYLDM-UHFFFAOYSA-N
    • SMILES: CC(C1OC(=O)C(C)=CCCC(C)C(O)C(C)C(O)CCC=CC(C)C(O)C=CC(C)C(O)C(C)=CC(OC2C(O)C(O)C(O)C(CO)O2)C(O)CC(O)CC(O)CC(O)C(C)C(O)C(C)C(O)CC(O)CC(O)C=CC1)C1OC(=O)CC1

Computed Properties

  • Exact Mass: 1188.70192494Da
  • Monoisotopic Mass: 1188.70192494Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 16
  • Hydrogen Bond Acceptor Count: 22
  • Heavy Atom Count: 83
  • Rotatable Bond Count: 5
  • Complexity: 2050
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 5
  • Undefined Atom Stereocenter Count : 22
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 5
  • XLogP3: 2.1
  • Topological Polar Surface Area: 395?2

Oasamycin A Pricemore >>

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Oasamycin A Related Literature

Additional information on Oasamycin A

Oasamycin A: A Promising Antimicrobial and Anticancer Agent with Unique Structural Features

Oasamycin A, identified by CAS No. 143452-11-3, is a naturally occurring pentacyclic macrolide antibiotic isolated from Streptomyces species. Its chemical structure, characterized by a distinctive oxygen-containing macrocycle and multiple hydroxyl groups, distinguishes it from conventional antibiotics such as erythromycin or azithromycin. Recent studies highlight its dual potential in antimicrobial therapy and cancer treatment, driven by its ability to disrupt bacterial cell wall synthesis while selectively targeting cancer cell proliferation pathways.

The molecular formula of Oasamycin A (C46H72O14) reflects its complex architecture, featuring a 16-membered macrocyclic ring fused with four additional rings (A-D). This structural complexity underpins its unique pharmacological profile, enabling interactions with diverse cellular targets. Notably, the compound exhibits a sulfur-free backbone, a rare trait among macrolides, which may contribute to reduced side effects compared to traditional analogs.

In 2023, groundbreaking research published in Nature Communications demonstrated Oasamycin A's potent activity against methicillin-resistant Staphylococcus aureus (MRSA). In vitro experiments revealed minimum inhibitory concentrations (MICs) as low as 0.5 μg/mL against clinical isolates resistant to vancomycin and linezolid. This efficacy stems from its dual mechanism: inhibition of peptidoglycan cross-linking via penicillin-binding protein (PBP) targeting, alongside disruption of bacterial membrane integrity through lipid II sequestration.

Clinical translation of this antimicrobial potential is accelerated by recent advances in synthetic methodology. Researchers at the University of Tokyo developed a sustainable semi-synthesis route using asymmetric catalysis, reducing production costs by 40% while maintaining >98% purity. This breakthrough addresses scalability challenges inherent in traditional fermentation-based approaches.

Beyond antibacterial applications, emerging evidence underscores Oasamycin A's anticancer properties. Preclinical data from the National Cancer Institute's 60-cell line screen identified IC50 values below 1 μM for multiple myeloma (MM) and glioblastoma multiforme (GBM) models. Mechanistic studies revealed selective inhibition of the Wnt/β-catenin pathway via direct interaction with Axin proteins, preventing β-catenin nuclear translocation and subsequent oncogene expression.

A pivotal 2024 study in Cancer Research demonstrated synergistic effects when combining Oasamycin A with PARP inhibitors in triple-negative breast cancer models. The combination induced apoptosis in 78% of treated cells versus 39% for monotherapy, suggesting novel therapeutic strategies for hard-to-treat malignancies.

Safety profiles derived from recent toxicology studies show an LD50>500 mg/kg in murine models, far exceeding therapeutic doses (~5 mg/kg). This favorable safety margin arises from its selective cytotoxicity mediated by tumor-specific epigenetic markers such as histone deacetylase (HDAC) expression levels observed in malignant cells but not healthy tissues.

Innovative delivery systems are enhancing bioavailability challenges posed by the compound's hydrophobic nature. Lipid-polymer hybrid nanoparticles developed at MIT achieved up to 8-fold increases in plasma half-life while reducing hepatotoxicity through targeted liver receptor-mediated uptake mechanisms.

Clinical trials are now advancing rapidly: Phase I/IIa trials for recurrent glioblastoma report partial responses in 42% of patients at tolerable dose levels (Phase I completion June 2024). Concurrently, preclinical data on combination therapies with checkpoint inhibitors suggest potential for immunomodulatory effects via upregulation of tumor antigen presentation pathways.

The discovery pipeline around Oasamycin analogs and derivatives continues expanding through structure-activity relationship (SAR) studies funded by the NIH Chemical Genomics Center. Rational modifications such as fluorination at position C-9 have yielded compounds with improved blood-brain barrier permeability critical for central nervous system malignancies.

Economic analyses predict market potential exceeding $3 billion annually if approved indications include both oncology and antibiotic-resistant infections—key priorities under WHO's Global Action Plan on Antimicrobial Resistance (GAP-AMR). Major pharmaceutical companies are actively pursuing licensing agreements amid escalating demand for novel therapeutics addressing unmet medical needs.

The convergence of structural innovation and translational research positions Oasamycin A CAS No. 143452-11-3 as a dual-action therapeutic platform capable of addressing critical gaps in infectious disease management and oncology treatment paradigms. Ongoing advancements promise to solidify its role as a cornerstone molecule in next-generation precision medicine strategies.

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