Searching for Potent and Specific Antibiotics Against Pathogenic Helicobacter and Campylobacter Strains

Overview

Journal J Ind Microbiol Biotechnol

Publisher Oxford University Press

Specialty Biotechnology

Date 2018 Nov 22

PMID 30460507

Citations 3

Authors

Yasushi Ogasawara

Tohru Dairi

Affiliations

Soon will be listed here.

Abstract

Menaquinone is an obligatory component of the electron-transfer pathway in microorganisms. Its biosynthetic pathway was established by pioneering studies with Escherichia coli and it was revealed to be derived from chorismate by Men enzymes. However, we identified an alternative pathway, the futalosine pathway, operating in some microorganisms including Helicobacter pylori and Campylobacter jejuni, which cause gastric carcinoma and diarrhea, respectively. Because some useful intestinal bacteria, such as lactobacilli, use the canonical pathway, the futalosine pathway is an attractive target for development of chemotherapeutics for the abovementioned pathogens. In this mini-review, we summarize compounds that inhibit Mqn enzymes involved in the futalosine pathway discovered to date.

Citing Articles

Discovery of an alternative pathway of peptidoglycan biosynthesis: A new target for pathway specific inhibitors.

Ogasawara Y, Dairi T J Ind Microbiol Biotechnol. 2021; 48(9-10).

PMID: 34114638 PMC: 8788868. DOI: 10.1093/jimb/kuab038.

Transition State Analogues Enhanced by Fragment-Based Structural Analysis: Bacterial Methylthioadenosine Nucleosidases.

Zhang D, Burdette B, Wang Z, Karn K, Li H, Schramm V Biochemistry. 2020; 59(7):831-835.

PMID: 32022543 PMC: 10644263. DOI: 10.1021/acs.biochem.9b01092.

Antibacterial Strategy against : Inhibition of the Radical SAM Enzyme MqnE in Menaquinone Biosynthesis.

Joshi S, Fedoseyenko D, Mahanta N, Ducati R, Feng M, Schramm V ACS Med Chem Lett. 2019; 10(3):363-366.

PMID: 30891141 PMC: 6421580. DOI: 10.1021/acsmedchemlett.8b00649.

References

Takami H, Nakasone K, Takaki Y, Maeno G, Sasaki R, Masui N . Complete genome sequence of the alkaliphilic bacterium Bacillus halodurans and genomic sequence comparison with Bacillus subtilis. Nucleic Acids Res. 2000; 28(21):4317-31. PMC: 113120. DOI: 10.1093/nar/28.21.4317. View

Meganathan R . Biosynthesis of menaquinone (vitamin K2) and ubiquinone (coenzyme Q): a perspective on enzymatic mechanisms. Vitam Horm. 2001; 61:173-218. DOI: 10.1016/s0083-6729(01)61006-9. View

Lamson D, Plaza S . The anticancer effects of vitamin K. Altern Med Rev. 2003; 8(3):303-18. View

Dahlback B, Villoutreix B . Regulation of blood coagulation by the protein C anticoagulant pathway: novel insights into structure-function relationships and molecular recognition. Arterioscler Thromb Vasc Biol. 2005; 25(7):1311-20. DOI: 10.1161/01.ATV.0000168421.13467.82. View

Adams J, Pepping J . Vitamin K in the treatment and prevention of osteoporosis and arterial calcification. Am J Health Syst Pharm. 2005; 62(15):1574-81. DOI: 10.2146/ajhp040357. View

Seto H, Jinnai Y, Hiratsuka T, Fukawa M, Furihata K, Itoh N . Studies on a new biosynthetic pathway for menaquinone. J Am Chem Soc. 2008; 130(17):5614-5. DOI: 10.1021/ja710207s. View

Hiratsuka T, Furihata K, Ishikawa J, Yamashita H, Itoh N, Seto H . An alternative menaquinone biosynthetic pathway operating in microorganisms. Science. 2008; 321(5896):1670-3. DOI: 10.1126/science.1160446. View

Gutierrez J, Crowder T, Rinaldo-Matthis A, Ho M, Almo S, Schramm V . Transition state analogs of 5'-methylthioadenosine nucleosidase disrupt quorum sensing. Nat Chem Biol. 2009; 5(4):251-7. PMC: 2743263. DOI: 10.1038/nchembio.153. View

Tanaka R, Kunisada T, Kushida N, Yamada K, Ikeda S, Noike M . Branched fatty acids inhibit the biosynthesis of menaquinone in Helicobacter pylori. J Antibiot (Tokyo). 2010; 64(1):151-3. DOI: 10.1038/ja.2010.133. View

10.

Arakawa C, Kuratsu M, Furihata K, Hiratsuka T, Itoh N, Seto H . Diversity of the early step of the futalosine pathway. Antimicrob Agents Chemother. 2010; 55(2):913-6. PMC: 3028782. DOI: 10.1128/AAC.01362-10. View

11.

Li X, Apel D, Gaynor E, Tanner M . 5'-methylthioadenosine nucleosidase is implicated in playing a key role in a modified futalosine pathway for menaquinone biosynthesis in Campylobacter jejuni. J Biol Chem. 2011; 286(22):19392-8. PMC: 3103317. DOI: 10.1074/jbc.M111.229781. View

12.

Dairi T, Kuzuyama T, Nishiyama M, Fujii I . Convergent strategies in biosynthesis. Nat Prod Rep. 2011; 28(6):1054-86. DOI: 10.1039/c0np00047g. View

13.

Wang S, Haapalainen A, Yan F, Du Q, Tyler P, Evans G . A picomolar transition state analogue inhibitor of MTAN as a specific antibiotic for Helicobacter pylori. Biochemistry. 2012; 51(35):6892-4. PMC: 3437630. DOI: 10.1021/bi3009664. View

14.

Cooper L, Fedoseyenko D, Abdelwahed S, Kim S, Dairi T, Begley T . In vitro reconstitution of the radical S-adenosylmethionine enzyme MqnC involved in the biosynthesis of futalosine-derived menaquinone. Biochemistry. 2013; 52(27):4592-4. PMC: 3855634. DOI: 10.1021/bi400498d. View

15.

Mahanta N, Fedoseyenko D, Dairi T, Begley T . Menaquinone biosynthesis: formation of aminofutalosine requires a unique radical SAM enzyme. J Am Chem Soc. 2013; 135(41):15318-21. PMC: 3855536. DOI: 10.1021/ja408594p. View

16.

Wang S, Cameron S, Clinch K, Evans G, Wu Z, Schramm V . New Antibiotic Candidates against Helicobacter pylori. J Am Chem Soc. 2015; 137(45):14275-80. PMC: 6709534. DOI: 10.1021/jacs.5b06110. View

17.

Yamamoto T, Matsui H, Yamaji K, Takahashi T, Overby A, Nakamura M . Narrow-spectrum inhibitors targeting an alternative menaquinone biosynthetic pathway of Helicobacter pylori. J Infect Chemother. 2016; 22(9):587-92. DOI: 10.1016/j.jiac.2016.05.012. View

18.

Ogasawara Y, Kondo K, Ikeda A, Harada R, Dairi T . Identification of tirandamycins as specific inhibitors of the futalosine pathway. J Antibiot (Tokyo). 2017; 70(6):798-800. DOI: 10.1038/ja.2017.22. View

19.

Joshi S, Mahanta N, Fedoseyenko D, Williams H, Begley T . Aminofutalosine Synthase: Evidence for Captodative and Aryl Radical Intermediates Using β-Scission and S1 Trapping Reactions. J Am Chem Soc. 2017; 139(32):10952-10955. DOI: 10.1021/jacs.7b04209. View

20.

Matsui H, Takahashi T, Murayama S, Kawaguchi M, Matsuo K, Nakamura M . Protective efficacy of a hydroxy fatty acid against gastric Helicobacter infections. Helicobacter. 2017; 22(6). DOI: 10.1111/hel.12430. View