Total synthesis and antimicrobial evaluation of natural albomycins against clinical pathogens

Lin, Zihua; Xu, Xiaobo; Zhao, Sheng; Yang, Xiaohong; Guo, Jingjie; Zhao, Qun; Jing, Chunmei; Chen, Shawn; He, Yun

doi:10.1038/s41467-018-05821-1

Cited by 74 publications

(88 citation statements)

References 43 publications

(36 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This hypothesis is also supported by the observation that complementation of the Δ abmJ mutant with abmJ partially restored production of 1 and 6 (Figure S13). While 1 showed antimicrobial activity against E. coli as previously reported, 1b 22 exhibited significantly reduced bacterial growth inhibition based on disc-diffusion bioassays (Figure S26). These results imply the importance of the proposed C3′-epimerization for the biological activity of albomycins.…”

supporting

confidence: 50%

“…Albomycins ( 1–3 ) are sulfur-containing sideromycin antibiotics isolated from several species of Streptomy-cetes. 1 The chemical structures of the albomycins consist of a 6′-amino-4′-thioheptose nucleoside ( 4 ) and an iron-chelating ferrichrome siderophore ( 5 ) that are connected via amide linkages to a serine residue (see Scheme 1). 2 This allows albomycins to be actively transported via the bacterial iron uptake system into bacterial cells, 3 where they are hydrolyzed by host peptidases liberating the thioheptose containing SB-217452 moiety ( 6 ) and the ferrichrome 5 .…”

mentioning

confidence: 99%

See 1 more Smart Citation

Biosynthetic Origin of the Atypical Stereochemistry in the Thioheptose Core of Albomycin Nucleoside Antibiotics

Ushimaru

Liu

2019

J. Am. Chem. Soc.

View full text Add to dashboard Cite

Albomycins are peptidyl thionucleoside natural products that display antimicrobial activity against clinically important pathogens. Their structures are characterized by a thioheptose with atypical stereo-chemistry including a D-xylofuranose ring modified with a D-amino acid moiety. Herein it is demonstrated that AbmH is a pyridoxal 5′-phosphate (PLP)-dependent transaldolase that catalyzes a threo-selective aldol-type reaction to generate the thioheptose core with a D-ribofuranose ring and an L-amino acid moiety. The conversion of L-to D-amino acid configuration is catalyzed by the PLP-dependent epimerase AbmD. The D-ribo to D-xylo conversion of the thiofuranose ring appears according to gene deletion experiments to be mediated by AbmJ, which is annotated as a radical S-adenosyl-L-methionine (SAM) enzyme. These studies establish several key steps in the assembly of the thioheptose core during the biosynthesis of albomycins.

show abstract

supporting

confidence: 50%

mentioning

confidence: 99%

Biosynthetic Origin of the Atypical Stereochemistry in the Thioheptose Core of Albomycin Nucleoside Antibiotics

Ushimaru

Liu

2019

J. Am. Chem. Soc.

View full text Add to dashboard Cite

show abstract

“…(Scheme 3b). 25 In this case, the silylating agent TMSOTf was used for electrophilic activation of the sulfoxide, conditions commonly used in combination with nucleobases. 26,27 Competitive nucleophilic addition of triethylamine was observed, motivating the use of the more hindered Hünig’s base (DIPEA).…”

Section: Sulfoxidesmentioning

confidence: 99%

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

et al. 2019

View full text Add to dashboard Cite

Organosulfur compounds have long played a vital role in organic chemistry and in the development of novel chemical structures and architectures. Prominent among these organosulfur compounds are those involving a sulfur(IV) center, which have been the subject of countless investigations over more than a hundred years. In addition to a long list of textbook sulfur-based reactions, there has been a sustained interest in the chemistry of organosulfur(IV) compounds in recent years. Of particular interest within organosulfur chemistry is the ease with which the synthetic chemist can effect a wide range of transformations through either bond formation or bond cleavage at sulfur. This review aims to cover the developments of the past decade in the chemistry of organic sulfur(IV) molecules and provide insight into both the wide range of reactions which critically rely on this versatile element and the diverse scaffolds that can thereby be synthesized.

show abstract

“…17,18 However, the ability to encapsulate only hydrophobic drugs and lower drug loadings limit their further applications. Therefore, continuing our efforts in searching for effective therapeutics, [19][20][21][22][23] we designed an oxidative responsive nanosystem mediated by NIR, which exhibited combination effect of PDT and chemotherapy. As shown in Scheme 1, a suitable proportion of PPS-PEG was used as a primary material for the nanosystem.…”

Section: Introductionmentioning

confidence: 99%

<p>Near-Infrared Laser-Triggered, Self-Immolative Smart Polymersomes for in vivo Cancer Therapy</p>

Tang

Peng

et al. 2020

IJN

Self Cite

View full text Add to dashboard Cite

Traditional chemotherapy is accompanied by significant side effects, which, in many aspects, limits its treatment efficacy and clinical applications. Herein, we report an oxidative responsive polymersome nanosystem mediated by near infrared (NIR) light which exhibited the combination effect of photodynamic therapy (PDT) and chemotherapy. Methods: In our study, poly (propylene sulfide) 20-bl-poly (ethylene glycol) 12 (PPS 20-b-PEG 12) block copolymer was synthesized and employed to prepare the polymersome. The hydrophobic photosensitizer zinc phthalocyanine (ZnPc) was loaded in the shell and the hydrophilic doxorubicin hydrochloride (DOX•HCl) in the inner aqueous space of the polymersome. Results: Under the irradiation of 660 nm NIR light, singlet oxygen 1 O 2 molecules were generated from ZnPc to oxidize the neighbouring sulfur atoms on the PPS block which eventually ruptured the intact structure of polymersomes, leading to the release of encapsulated DOX•HCl. The released DOX and the 1 O 2 could achieve a combination effect for cancer therapy if the laser activation and drug release occur at the tumoral sites. In vitro studies confirmed the generation of singlet oxygen and DOX release by NIR irradiation. In vivo studies showed that such a combined PDT-chemotherapy nanosystem could accumulate in A375 tumors efficiently, thus leading to significant inhibition on tumor growth as compared to PDT (PZ group) or chemotherapy alone (DOX group). Conclusion: In summary, this oxidation-sensitive nanosystem showed excellent anti-tumor effects by synergistic chemophotodynamic therapy, indicating that this novel drug delivery strategy could potentially provide a new means for cancer treatments in clinic.

show abstract

Total synthesis and antimicrobial evaluation of natural albomycins against clinical pathogens

Cited by 74 publications

References 43 publications

Biosynthetic Origin of the Atypical Stereochemistry in the Thioheptose Core of Albomycin Nucleoside Antibiotics

Biosynthetic Origin of the Atypical Stereochemistry in the Thioheptose Core of Albomycin Nucleoside Antibiotics

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

<p>Near-Infrared Laser-Triggered, Self-Immolative Smart Polymersomes for in vivo Cancer Therapy</p>

Contact Info

Product

Resources

About