利福霉素S

利福霉素S用途

Rifamycin S 是一种醌和抗革兰氏阳性细菌 (包括 MRSA) 的抗生素。Rifamycin S 是涉及两个电子的可逆氧化还原系统的氧化形式。Rifamycin S 可以产生活性氧 (ROS) 并抑制微粒体脂质过氧化,并可用于肺结核和麻风病的研究。

利福霉素S名称

[ CAS 号 ]:
13553-79-2

[ 中文名 ]:
利福霉素-S

[ 英文名 ]:
RifamycinS

[中文别名 ]:

[英文别名 ]:

Rifamycin,1,4-dideoxy-1,4-dihydro-1,4-dioxo
UNII-PI53N820JV
rifomycin-S
rifamycin-S
NCI 144-130
EINECS 236-938-4
rifaximin S
O1,O4-didehydro-rifamycin
1,4-Dideoxy-1,4-dihydro-1,4-dioxorifamycin
RifamycinS

利福霉素S生物活性

[ 描述 ]:

[ 相关类别 ]:

研究领域 >> 感染

信号通路 >> 抗感染 >> 细菌

[ 靶点 ]

Gram-positive bacteria[3] Reactive oxygen species (ROS)[1]

[体外研究]

利福霉素SV对细菌生长的抑制作用是由于细胞内的氧化还原循环产生活性氧。金属离子Mn2+、Cu2+、Co2+诱导利福霉素SV氧化为利福霉素S。最有效的金属离子是Mn2+[2]。

[体内研究]

大鼠肝线粒体亚颗粒在NADH和利福霉素存在下也产生羟基自由基。NADH脱氢酶(复合物I)是参与利福霉素S还原的主要成分。与NADPH相比,NADH在催化这些抗生素与大鼠肝微粒体相互作用方面几乎同样有效(利福霉素S)。利福霉素S很容易被铁(II)还原成相应的对苯二酚利福霉素SV。利福霉素S形成可检测的Fe(II)-(利福霉素S)3复合物。Fe:ATP诱导的脂质过氧化被利福霉素S完全抑制。利福霉素S可与大鼠肝微粒体相互作用,进行氧化还原循环,当存在铁络合物时,随后产生羟基自由基[1]。

[参考文献]

[1]. Rao DN, et al. A comparative study of the redox-cycling of a quinone (rifamycin S) and a quinonimine (rifabutin) antibiotic by rat liver microsomes. Free Radic Biol Med. 1997;22(3):439-46.

[2]. Kono Y. Oxygen Enhancement of bactericidal activity of rifamycin SV on Escherichia coli and aerobic oxidation of rifamycin SV to rifamycin S catalyzed by manganous ions: the role of superoxide. J Biochem. 1982 Jan;91(1):381-95.

[3]. Huang H, et al. Rifamycin S and its geometric isomer produced by a newly found actinomycete, Micromonospora rifamycinica. Antonie Van Leeuwenhoek. 2009 Feb;95(2):143-8.

利福霉素S物理化学性质

[ 密度 ]:
1.3±0.1 g/cm3

[ 沸点 ]:
917.4±65.0 °C at 760 mmHg

[ 熔点 ]:
179-181ºC (dec.)

[ 分子式 ]:
C₃₇H₄₅NO₁₂

[ 分子量 ]:
695.753

[ 闪点 ]:
508.6±34.3 °C

[ 精确质量 ]:
695.294189

[ PSA ]:
194.99000

[ LogP ]:
2.87

[ 外观性状 ]:
黄色橙色结晶粉末

[ 蒸汽压 ]:
0.0±0.3 mmHg at 25°C

[ 折射率 ]:
1.605

[ 储存条件 ]:
2-8°C

利福霉素S毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: KD1925000

CHEMICAL NAME :: 2,7-(Epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b) furan-1,6,9,11(2H)-te trone, 5,17,19,21-tetrahydroxy-23-methoxy-2,4,12,16,18,20,22 -heptamethyl-, 21-acetate

CAS REGISTRY NUMBER :: 13553-79-2

LAST UPDATED :: 199612

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C37-H45-N-O12

MOLECULAR WEIGHT :: 695.83

WISWESSER LINE NOTATION :: T C6 B65-24- A D E 2BC G& AV DV GV LO NO F&VM OU B&U D&U MHT&&TJ IQ J1 M1 QO1 R1 SOV1 T1 UQ V

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >3 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EXPEAM Experientia. (Birkhaeuser Verlag, POB 133, CH-4010 Basel, Switzerland) V.1- 1945- Volume(issue)/page/year: 16,412,1960

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 258 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978 Volume(issue)/page/year: 1,865,1978

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 122 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978 Volume(issue)/page/year: 1,865,1978

利福霉素S安全信息

[ RTECS号 ]:
KD1925000

[ 海关编码 ]:
2941903000

利福霉素S合成路线

详细合成路线

利福霉素S上下游产品

利福霉素S上游产品

利福霉素S下游产品

利福霉素S海关

[ 海关编码 ]: 2941903000

利福霉素S文献

Polyketide construction via hydrohydroxyalkylation and related alcohol C-H functionalizations: reinventing the chemistry of carbonyl addition.

Nat. Prod. Rep. 31(4) , 504-13, (2014)

Despite the longstanding importance of polyketide natural products in human medicine, nearly all commercial polyketide-based drugs are prepared through fermentation or semi-synthesis. The paucity of m...

Synthesis and structure-activity relationships of novel substituted 8-amino, 8-thio, and 1,8-pyrazole congeners of antitubercular rifamycin S and rifampin.

Bioorg. Med. Chem. Lett. 21 , 6094-9, (2011)

A series of rifamycin S and rifampin analogues incorporating substituted 8-amino, 8-thio, and 1,8-pyrazole substituents has been synthesized. The compounds were made by activation of the C-8 phenol as...

Direct generation of acyclic polypropionate stereopolyads via double diastereo- and enantioselective iridium-catalyzed crotylation of 1,3-diols: beyond stepwise carbonyl addition in polyketide construction.

J. Am. Chem. Soc. 133(32) , 12795-800, (2011)

Under the conditions of transfer hydrogenation employing the cyclometalated iridium catalyst (R)-I derived from [Ir(cod)Cl](2), allyl acetate, 4-cyano-3-nitrobenzoic acid, and the chiral phosphine lig...

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