58798-97-3 Usage
Uses
Used in Pharmaceutical Industry:
Berninamycin A is utilized as an antibiotic for its potent activity against Gram-positive bacteria. It functions by inhibiting protein biosynthesis through binding with ribosomal subunits, making it a valuable compound in the fight against bacterial infections.
Used in Research and Development:
Berninamycin A is employed as a research tool in the study of multidrug resistance in bacteria. As an inducer of the tipA gene, it helps researchers understand the mechanisms behind bacterial resistance to various antibiotics, potentially leading to the development of new strategies to combat drug-resistant infections.
Used in Oncology Research:
Due to its close relation to siomycin, an inhibitor of the oncogenic transcription factor FoxM1, berninamycin A is used in oncology research to explore its potential as a therapeutic agent against cancer. Further investigation into its properties may reveal its effectiveness in modulating oncological signaling pathways and its synergistic effects when combined with conventional chemotherapeutic drugs.
Used in Drug Delivery Systems:
Similar to gallotannin, the development of novel drug delivery systems for berninamycin A could enhance its applications and efficacy against both bacterial infections and cancer cells. Utilizing organic and metallic nanoparticles as carriers for berninamycin A delivery may improve its bioavailability and therapeutic outcomes in targeted treatments.
Biological Activity
berninamycin a is a macrocyclic thiopeptide antibiotic first isolated from s. bernensis [1]. thiopeptides are sulfur containing highly modified macrocyclic antibiotics with a central pyridine/tetrapyridine/dehydropiperidine ring with up to three thiazole substituents on positions 2, 3 and 6. thiazole antibiotics thiostrepton behaves as proteasome inhibitor in mammalian tumor cells. berninamycin showed no proteasome inhibitory activity [2]. it has been reported that the action mode of berninamycin on bacterial protein synthesis was related to that of a dissimilar compound thiostrepton. the antibiotics could bind to the complex of 23s rna with protein l11 and both affect multiple functions of the ribosomal a site [3]. berninamycin a was involved in inducing the transcriptional activator tipa in streptomyces [4].
Enzyme inhibitor
This fungal antibiotic (FW = 1146.12 g/mol; CAS 58798-97-3; Soluble in DMSO), also known as Antibiotic U27810, from Streptomyces bernensis inhibits protein biosynthesis by binding to a complex formed by ribosomal 23S and the L11 protein, thereby disrupting the function of the ribosome’s A site and inhibiting protein synthesis in Gram-positive bacteria. In this respect, it has the same mode of action as thiostrepton. Streptomyces bernensis and Streptomyces azureus, which produce berninamycin and thiostrepton, respectively, possess similar ribosomal RNA methylases that mediate specific pentose-directed methylation of 23S ribosomal RNA, rendering the modified ribosomes resistant to these antibiotics.
references
[1] lau r c m, rinehart k l. berninamycins b, c, and d, minor metabolites from streptomyces bernensis[j]. the journal of antibiotics, 1994, 47(12): 1466-1472.[2] pandit b, bhat u g, gartel a l. proteasome inhibitory activity of thiazole antibiotics[j]. cancer biology & therapy, 2011, 11(1): 43-47.[3] j. thompson, e. cundliffe and m. j. r. stark. the mode of action of berninamycin and mechanism of resistance in the producing organism, streptomyces bernensis. j.gen.microbiol. 128(4), 875-884 (1982). [4]. m. l. chiu, m. folcher, t. katoh, et al. broad spectrum thiopeptide recognition specificity of the streptomyces lividans tipal protein and its role in regulating gene expression. the journal of biological chemisty 274(29), 20578-20586 (1999).
Check Digit Verification of cas no
The CAS Registry Mumber 58798-97-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,8,7,9 and 8 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 58798-97:
(7*5)+(6*8)+(5*7)+(4*9)+(3*8)+(2*9)+(1*7)=203
203 % 10 = 3
So 58798-97-3 is a valid CAS Registry Number.
InChI:InChI=1/C51H51N15O15S/c1-13-28-49-65-34(26(10)81-49)45(76)56-21(5)40(71)66-36(51(11,12)78)46(77)58-23(7)48-64-33(25(9)80-48)44(75)55-20(4)39(70)57-22(6)47-61-30(16-79-47)35-27(50-62-31(17-82-50)42(73)63-32(24(8)67)43(74)60-28)14-15-29(59-35)41(72)54-19(3)38(69)53-18(2)37(52)68/h13-17,24,32,36,67,78H,2-7H2,1,8-12H3,(H2,52,68)(H,53,69)(H,54,72)(H,55,75)(H,56,76)(H,57,70)(H,58,77)(H,60,74)(H,63,73)(H,66,71)/b28-13-
