Sakyomicin A
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| Category | Antibiotics |
| Catalog number | BBF-02850 |
| CAS | 86413-75-4 |
| Molecular Weight | 486.47 |
| Molecular Formula | C25H26O10 |
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Description
It is a benzoquinone antibiotic produced by the strain of Nocardia sp. M-53. It has activity against gram-positive bacteria and mycobacteria. In vivo, 10 mg/kg of Sakyomicin A had no effect against sarcoma 180A and leukemia P338 cells.
Specification
| Synonyms | Benz[A]anthracene-1,7,12(2H)-trione, 3,4,4A,12B-tetrahydro-2,3,4A,8-tetrahydroxy-3-methyl-12B-[[2R,5R,6R)-tetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl]oxy]-, (2S,3R,4as,12br)-; SKM; (2S)-3,4,4a,12b-Tetrahydro-2β,3α,4aβ,8-tetrahydroxy-3-methyl-12bβ-[[(2R,5R,6R)-tetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl]oxy]benz[a]anthracene-1,7,12(2H)-trione |
| IUPAC Name | (2S,3R,4aS,12bR)-2,3,4a,8-tetrahydroxy-12b-[(2R,5R,6R)-5-hydroxy-6-methyloxan-2-yl]oxy-3-methyl-2,4-dihydrobenzo[a]anthracene-1,7,12-trione |
| Canonical SMILES | CC1C(CCC(O1)OC23C(=O)C(C(CC2(C=CC4=C3C(=O)C5=C(C4=O)C(=CC=C5)O)O)(C)O)O)O |
| InChI | InChI=1S/C25H26O10/c1-11-14(26)6-7-16(34-11)35-25-18-13(19(28)17-12(20(18)29)4-3-5-15(17)27)8-9-24(25,33)10-23(2,32)21(30)22(25)31/h3-5,8-9,11,14,16,21,26-27,30,32-33H,6-7,10H2,1-2H3/t11-,14-,16-,21-,23-,24-,25+/m1/s1 |
| InChI Key | CKZNKYSWWCSICZ-FYJHTGLRSA-N |
Properties
| Appearance | Orange Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Mycobacteria |
| Boiling Point | 801.8°C at 760 mmHg |
| Melting Point | 205-207°C |
| Density | 1.60 g/cm3 |
| Solubility | Soluble in Methanol, Chloroform |
Reference Reading
1. Comparative studies of the inhibitory properties of antibiotics on human immunodeficiency virus and avian myeloblastosis virus reverse transcriptases and cellular DNA polymerases
Y Take, Y Inouye, S Nakamura, H S Allaudeen, A Kubo J Antibiot (Tokyo). 1989 Jan;42(1):107-15. doi: 10.7164/antibiotics.42.107.
The inhibition of human immunodeficiency virus (HIV) reverse transcriptase by certain antibiotics and related compounds was studied in comparison with that of avian myeloblastosis virus (AMV) reverse transcriptase and cellular DNA polymerases alpha and beta. In general, compounds that inhibited HIV reverse transcriptase also inhibited AMV reverse transcriptase. For example, 10 micrograms/ml of the isoquinoline quinones used in this study inhibited approximately 80% of the activity of reverse transcriptases of HIV and AMV, but did not inhibit the activity of DNA polymerases alpha and beta even at 50 micrograms/ml. AMV enzyme was more sensitive than HIV enzyme to colistin, enduracidins A and B, janiemycin, glysperin A, and thielavins A and B. The streptonigrin alkyl esters, however, inhibited HIV reverse transcriptase only. Sakyomicin A, luzopeptins, ellagic acid and suramine inhibited the activities of reverse transcriptases and cellular DNA polymerases.
2. Inhibition by sakyomicin A of avian myeloblastosis virus reverse transcriptase and proliferation of AIDS-associated virus (HTLV-III/LAV)
N Tanaka, T Okabe, N Tanaka, Y Take, Y Inouye, S Nakamura, H Nakashima, N Yamamoto Jpn J Cancer Res. 1986 Apr;77(4):324-6.
In the course of screening for inhibitors of reverse transcriptase, we have isolated an inhibitor from a strain of Nocardia and identified it as sakyomicin A. The antibiotic blocks avian myeloblastosis virus reverse transcriptase reaction: IC50 was ca. 30 micrograms/ml by the method employed. The drug affects proliferation of HTLV-III/LAV in HTLV-I-carrying MT-4 cells: ca. 60% inhibition was observed at an antibiotic concentration of 1.0 microgram/ml and ca. 20% inhibition at 0.1 microgram/ml, and there was no significant cytotoxicity.
3. Mechanism of inhibition of reverse transcriptase by quinone antibiotics. II. Dependence on putative quinone pocket on the enzyme molecule
Y Hafuri, E Takemori, K Oogose, Y Inouye, S Nakamura, Y Kitahara, S Nakahara, A Kubo J Antibiot (Tokyo). 1988 Oct;41(10):1471-8. doi: 10.7164/antibiotics.41.1471.
Inhibition of avian myeloblastosis virus (AMV) reverse transcriptase by natural and synthetic quinones including antibiotics could be accounted for by an oxidation-reduction reaction. The quinones were shown to function as electron acceptors as revealed by the catalytic oxidation of NADH by Clostridium kluyveri diaphorase which was in excellent agreement with enzyme inhibition activity. The kinetics of inhibition of AMV reverse transcriptase by three synthetic quinones with different core structures, i.e., 6-methoxy-5,8-dihydroquinoline-5,8- dione, 5,8-dihydroisoquinoline-5,8-dione and 1,4-naphthoquinone, were studied. These quinones inhibited reverse transcriptase in the same manner as streptonigrin (STN) and were shown to act at a single class of reaction site(s) on the enzyme molecule. In contrast, the quinones with bulky substituents, i.e., 7-(2-nitrophenethylamino)-5,8-dihydroisoquinoline-5,8-dione and 7-methoxy-6-methyl-3-piperidino-5,8-dihydroisoquinoline-5,8-dione, were inactive as inhibitors of reverse transcriptase, whereas they retained competent catalytic activities in the oxidation of NADH by C. kluyveri diaphorase. Based on these observations, the existence of a specific site of interaction on the enzyme molecule, referred to as a quinone pocket, was proposed. The quinone pocket might play a crucial role in the early sequence of events leading to the inhibition of reverse transcriptase by quinones including STN and sakyomicin A (SKM). Access of SKM to a quinone pocket might be restricted due to its bulky structure in the vicinity of the quinone group. This is inferred from unsuccessful inhibition of reverse transcriptase by the quinones with bulky substituents, resulting in much poorer inhibition of reverse transcriptase in spite of more potent electron acceptor activity in the oxidation-reduction system as compared with those of STN.
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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 ╳
