每周分子Molecule of the Week

Original ACS美国化学会 ACS美国化学会 2022-07-01

Molecule of the Week: Albomycin δ2

每周分子：阿波霉素δ2

阿波霉素是革兰氏阳性放线菌subtropicusbacteria产生的天然抗生素。在自然界中，它们以铁配合物的形式存在。早在20世纪50年代初，俄罗斯生物学家Georgii Frantsevich Gause就率先发现了阿波霉素，并对其抗菌性能进行了研究。

虽然至少还有其他三种存在形式，但阿波霉素最主要还是以阿波霉素δ1,δ2和ε(δ2如图所示)存在。所有的阿波霉素结构都是由六种修饰的氨基酸组成的序列。这些抗生素已显示出对特异性革兰氏阴性和革兰氏阳性病原体的活性。

几个月前，人们又想起几乎被遗忘的Gause对阿波霉素的研究。重庆大学天然产物科学家贺耘教授和他的同事们合成出了阿波霉素δ1, δ2和ε，并测试了它们在体外对几株肺炎链球菌及金黄色葡萄球菌的抗菌活性，其中一些耐甲氧西林。

阿波霉素δ2在所有结构形式中活性最强，而阿波霉素ε则没有显示任何活性。阿波霉素δ2的效果超过了被广泛使用的药物环丙沙星、万古霉素和青霉素。

因为细菌觉得阿波霉素的铁结合区是安全的，可以进入该区域，所以阿波霉素被称为“特洛伊木马”化合物。一旦细菌进入阿波霉素体内，含硫区（“弹头”）就会抑制机体的活动。

虽然铁配合物极易溶于水，因而具有生物活性，但是人们对阿波霉素δ2的化学性质和危害还知之甚少。阿波霉素δ2很难合成，因此商业化有点不切实际，但科学家们正在研究具有相似活性的更简单的类似物。

阿波霉素δ2信息速览

CAS 登记号	82113-67-5
分子式	C₃₇H₆₀N₁₂O₁₈S
摩尔质量	993.01
外观	浅黄色固体
熔点	尚未确认
水溶性	尚未确认

【关于每周分子】

自2001年以来，“每周分子”已成为广受欢迎的栏目。多数分子由读者推荐。每个结构都经由科学家审查，并以3-D和平面图像的形式显示，同时附有该分子简介。可以通过美国化学文摘社（CAS）提供的SciFinder中的CAS REGISTRY获取每周分子的更多信息。CAS REGISTRY中的每条物质信息都展示了物质的CAS登记号、索引名、通用名、商品名、书目信息等其他更多信息。发送邮件至motw@acs.org推荐您感兴趣的分子。

Albomycins are natural antibiotics produced by Gram-positive Actinomyces subtropicusbacteria. In nature, they exist as iron complexes. In the early 1950s, Russian biologist Georgii Frantsevich Gause was a pioneer in identifying albomycins and studying their antimicrobial properties.

The most abundant forms of albomycin are δ1, δ2, and ε (δ2 is shown), although at least three others exist. All albomycin structures are sequences of six modified amino acids. These antibiotics have shown activity against specific Gram-negative and Gram-positive pathogens.

Gause’s work with albomycins was largely forgotten until a few months ago. Natural products scientist Yun He and colleagues at Chongqing University (China) synthesized albomycins δ1, δ2, and ε and tested them in vitro against several strains of Streptococcus pneumoniae and Staphylococcus aureus, some of which are methicillin-resistant.

Albomycin δ2 was the most potent across the board, whereas the ε form showed no activity at all. Albomycin δ2’s potency exceeded that of the widely used drugs ciprofloxacin, vancomycin, and penicillin.

Albomycins are called “Trojan horse” compounds because bacteria sense that their iron-binding region is safe to ingest. Once inside, the sulfur-containing region (the “warhead”) inhibits the organism’s action.

Very little is known about the chemical properties and hazards of albomycin δ2, although its iron complex is highly soluble in water and therefore bioactive. Albomycin δ2 is difficult to synthesize and therefore commercially impractical, but simpler analogues that show similar activity are under investigation.

Deuterium oxide fast facts

CAS Reg. No.	82113-67-5
Empirical formula	C₃₇H₆₀N₁₂O₁₈S
Molar mass	993.01
Appearance	Yellowish solid
Melting point	Not determined
Water solubility	Not determined

*Globally Harmonized System of Classification and Labeling of Chemicals. Explanation of pictograms.

About Molecule of the Week

MOTW has been a popular feature on ACS website since 2001. Many molecules are suggested by our website visitors. Every structure is reviewed by a scientist and displayed in 3-D and flat images with a brief description. Each week’s molecule also links to a sample record from the CAS REGISTRY, which is searched using SciFinder. Each record displays the registry number, index name and synonyms, bibliographic information, and more. Send us a molecule suggestion at motw@acs.org.

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