Resorcinomycin A
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| Category | Antibiotics |
| Catalog number | BBF-02630 |
| CAS | 100234-70-6 |
| Molecular Weight | 324.33 |
| Molecular Formula | C14H20N4O5 |
| Purity | 95% |
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Description
Resorcinomycin A is produced by the strain of Streptoverticillum roseoverticillatum. It has strong anti-mycobacterium effect and weak anti-mycoplasma effect.
Specification
| Synonyms | N-(alpha-Guanidino-3,5-dihydroxy-4-isopropylphenylacetyl)glycine; S-Resorcinomycin A; (S)-(2-((diaminomethylene)amino)-2-(3,5-dihydroxy-4-isopropylphenyl)acetyl)glycine |
| IUPAC Name | 2-[[(2S)-2-(diaminomethylideneamino)-2-(3,5-dihydroxy-4-propan-2-ylphenyl)acetyl]amino]acetic acid |
| Canonical SMILES | CC(C)C1=C(C=C(C=C1O)C(C(=O)NCC(=O)O)N=C(N)N)O |
| InChI | InChI=1S/C14H20N4O5/c1-6(2)11-8(19)3-7(4-9(11)20)12(18-14(15)16)13(23)17-5-10(21)22/h3-4,6,12,19-20H,5H2,1-2H3,(H,17,23)(H,21,22)(H4,15,16,18)/t12-/m0/s1 |
| InChI Key | QMFJWJLPWNAZMH-LBPRGKRZSA-N |
Properties
| Antibiotic Activity Spectrum | mycobacteria; mycoplasma |
| Melting Point | 194-200°C |
| Density | 1.49 g/cm3 |
Reference Reading
1. Identification and analysis of the resorcinomycin biosynthetic gene cluster
Koichi Ooya, Yasushi Ogasawara, Motoyoshi Noike, Tohru Dairi Biosci Biotechnol Biochem. 2015;79(11):1833-7. doi: 10.1080/09168451.2015.1050992. Epub 2015 Jun 2.
Resorcinomycin (1) is composed of a nonproteinogenic amino acid, (S)-2-(3,5-dihydroxy-4-isopropylphenyl)-2-guanidinoacetic acid (2), and glycine. A biosynthetic gene cluster was identified in a genome database of Streptoverticillium roseoverticillatum by searching for orthologs of the genes responsible for biosynthesis of pheganomycin (3), which possesses a (2)-derivative at its N-terminus. The cluster contained a gene encoding an ATP-grasp-ligase (res5), which was suggested to catalyze the peptide bond formation between 2 and glycine. A res5-deletion mutant lost 1 productivity but accumulated 2 in the culture broth. However, recombinant RES5 did not show catalytic activity to form 1 with 2 and glycine as substrates. Moreover, heterologous expression of the cluster resulted in accumulation of only 2 and no production of 1 was observed. These results suggested that a peptide with glycine at its N-terminus may be used as a nucleophile and then maturated by a peptidase encoded by a gene outside of the cluster.
2. Enhanced intramacrophage activity of resorcinomycin A against Mycobacterium avium-Mycobacterium intracellulare complex after liposome encapsulation
R Gomez-Flores, R Hsia, R Tamez-Guerra, R T Mehta Antimicrob Agents Chemother. 1996 Nov;40(11):2545-9. doi: 10.1128/AAC.40.11.2545.
The activities of free and liposomal resorcinomycin A against Mycobacterium avium-Mycobacterium intracellulare complex (MAC) grown in broth and in murine peritoneal macrophages were evaluated. Liposomal resorcinomycin A was composed of dimyristoyl phosphatidylcholine and phosphatidylinositol at a molar ratio of 9:1. Both free resorcinomycin A and liposomal resorcinomycin A showed no toxicity to macrophages at concentrations up to 50 micrograms/ml, as determined by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) reduction assay. Minimal inhibitory concentrations of free resorcinomycin A and liposomal resorcinomycin A in broth were 6 and 12 micrograms/ml, respectively, as determined by the MTT colorimetric microassay. In macrophages, liposomal resorcinomycin A caused significantly higher intramacrophage antimycobacterial activity than the free form of the drug. At doses ranging from 6 to 50 micrograms/ml, liposomal resorcinomycin A caused 50 to 93% MAC growth inhibition, respectively (as determined by CFU), while free resorcinomycin A was associated with 33 to 62% MAC growth inhibition, respectively, 3 days after drug treatment. In addition, antimycobacterial activity of liposomal resorcinomycin A in macrophages was maintained 7 days after treatment, whereas the activity of free resorcinomycin A was reduced to negligible 3 days after treatment. In summary, liposome encapsulation of resorcinomycin A resulted in significant enhancement of antibacterial activity against intramacrophagic MAC infection.
3. Determination of MICs for Mycobacterium avium-M. intracellulare complex in liquid medium by a colorimetric method
R Gomez-Flores, S Gupta, R Tamez-Guerra, R T Mehta J Clin Microbiol. 1995 Jul;33(7):1842-6. doi: 10.1128/jcm.33.7.1842-1846.1995.
We investigated the potential of a rapid colorimetric microassay based on the reduction of dimethylthiazol-diphenyltetrazolium bromide (MTT) for determining the growth of Mycobacterium avium-M. intracellulare complex (MAC) and MICs of clofazimine, resorcinomycin A, and the quinolone PD 127391 against MAC. The reduction of MTT was directly proportional to the number of viable bacteria. A comparison of the MTT reduction test with the [3H]glycerol uptake assay showed the former to possess higher analytical sensitivity for detecting MAC growth in microtiter plates. The MIT reduction test avoids the use of radioisotopes and costly material and equipment; it is reliable, reproducible, and convenient for rapid routine susceptibility testing of MAC.
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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 ╳
