New Demethylated Derivatives of Carolacton and Structure–Activity Relationship (SAR) Studies on Their Biofilm Inhibitory Properties

Jonas Ammermann; Janina Meyer; Jannik Donner; Michael Reck; Irene Wagner-Döbler; Andreas Kirschning

doi:10.1055/a-2013-9333

Synthesis, Table of Contents

Synthesis 2023; 55(13): 1961-1983
DOI: 10.1055/a-2013-9333

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New Demethylated Derivatives of Carolacton and Structure–Activity Relationship (SAR) Studies on Their Biofilm Inhibitory Properties

Authors

Jonas Ammermann

^aInstitute of Organic Chemistry, Leibniz University Hannover, Schneiderberg 1B, 30167 Hannover, Germany
Janina Meyer

^aInstitute of Organic Chemistry, Leibniz University Hannover, Schneiderberg 1B, 30167 Hannover, Germany
Jannik Donner

^bHelmholtz Centre for Infection Research, Department of Microbial Communication, Inhoffenstr. 7, 38124 Braunschweig, Germany
Michael Reck

^bHelmholtz Centre for Infection Research, Department of Microbial Communication, Inhoffenstr. 7, 38124 Braunschweig, Germany
Irene Wagner-Döbler

^bHelmholtz Centre for Infection Research, Department of Microbial Communication, Inhoffenstr. 7, 38124 Braunschweig, Germany
Andreas Kirschning ∗

^aInstitute of Organic Chemistry, Leibniz University Hannover, Schneiderberg 1B, 30167 Hannover, Germany

Abstract

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Abstract

The total synthesis of a series of new carolacton derivatives that mainly lack selected methyl substituents along the polyketide backbone is reported. Their inhibitory activity towards bacterial biofilms revealed that selective removal of the methyl group at C10 does not have a major effect on biological activity, whereas additional removal of the methyl group at C14 in carolacton results in a large decrease in antibacterial activity. A key new feature of this work is the replacement of the Nozaki–Hiyama–Kishi (NHK) vinylation with a titanium-mediated protocol for the fusion of the two main fragments.

Key words

antibiotics - biofilms - carolacton - Nozaki–Hiyama–Kishi reaction - polyketides - structure–activity relationship studies - total synthesis

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References

References
1 Jansen R, Irschik H, Huch V, Schummer D, Steinmetz H, Bock M, Schmidt T, Kirschning A, Müller R. Eur. J. Org. Chem. 2010; 1284
2 Kunze B, Reck M, Dötsch A, Lemme A, Schummer D, Irschik H, Steinmetz H, Wagner-Döbler I. BMC Microbiol. 2010; 10: 199

3a Reck M, Rutz K, Kunze B, Tomasch J, Surapaneni SK, Schulz S, Wagner-Döbler I. J. Bacteriol. 2011; 193: 5692
3b Apel C, Barg A, Rheinberg A, Conrads G, Wagner-Döbler I. Dent. Mater. 2013; 29: 1188
3c Donner J, Reck M, Bunk B, Jarek M, App C, Meier-Kolthoff J, Overmann J, Müller R, Kirschning A, Wagner-Döbler I. mSphere 2017; 2: e00375-17

4 Donner J, Reck M, Bergmann S, Kirschning A, Müller R, Wagner-Döbler I. Sci. Rep. 2016; 6: 29677

5a Schmidt T, Kirschning A. Angew. Chem. Int. Ed. 2012; 51: 1063
5b Hallside MS, Brzozowski RS, Wuest WM, Phillips AJ. Org. Lett. 2014; 16: 1148
5c Kuilya TK, Goswami RK. Org. Lett. 2017; 19: 2366

6 Stumpp N, Premnath P, Schmidt T, Ammermann J, Dräger G, Reck M, Jansen R, Stiesch M, Wagner-Döbler I, Kirschning A. Org. Biomol. Chem. 2015; 13: 5765
7 Borzilleri RM, Zheng X, Schmidt RJ, Johnson JA, Kim S.-H, DiMarco JD, Fairchild CR, Gougoutas JZ, Lee FY. F, Long BH, Vite GD. J. Am. Chem. Soc. 2000; 122: 8890
8 Hügel HM, Smith AT, Rizzacasa MA. Org. Biomol. Chem. 2016; 14: 11301
9 Ammermann J, Schmidt T, Donner J, Reck M, Wagner-Döbler I, Kirschning A. Org. Biomol. Chem. 2017; 15: 8553
10 Solinski AE, Koval AB, Brzozowski RS, Morrison KR, Fraboni AJ, Carson CE, Eshraghi AR, Zhou G, Quivey RG, Voelz VA, Buttaro BA, Wuest WM. J. Am. Chem. Soc. 2017; 139: 7188
11 Fu C, Sikandar A, Donner J, Zaburannyi N, Herrmann J, Reck M, Wagner-Döbler I, Koehnke J, Müller R. Nat. Commun. 2017; 8: 1529
12 Zhou J, Fu GC. J. Am. Chem. Soc. 2003; 125: 14726
13 Geist E, Kirschning A, Schmidt T. Nat. Prod. Rep. 2014; 31: 441
14 Ley SV, Diez E, Dixon DJ, Guy RT, Michel P, Nattrass GL, Sheppard TD. Org. Biomol. Chem. 2004; 2: 3608

15a Gribble G, Joyner HH, Switzer FL. Synth. Commun. 1992; 22: 2997
15b Coleman RS, Lu X, Modolo I. J. Am. Chem. Soc. 2007; 129: 3826

16 Review: Marshall JA. J. Org. Chem. 2007; 72: 8153

17a Marshall JA, Grant CM. J. Org. Chem. 1999; 64: 696
17b Marshall JA, Chobanian HR. J. Org. Chem. 2000; 65: 8357

18 Takano S, Akiyama M, Sato S, Ogasawara K. Chem. Lett. 1983; 1593
19 Duthaler RO, Herold P, Wyler-Helfer S, Riediker M. Helv. Chim. Acta 1990; 73: 659
20 Duthaler RO, Herold P, Lottenbach W, Oertle K, Riediker M. Angew. Chem. Int. Ed. Engl. 1989; 28: 495
21 Holmquist CR, Roskamp EJ. J. Org. Chem. 1989; 54: 3258
22 Corey EJ, Bakshi RK, Shibata S. J. Am. Chem. Soc. 1987; 109: 5551
23 Paterson I, Findlay AD, Florence GJ. Org. Lett. 2006; 8: 2131
24 Paterson I, Goodman JM, Isaka M. Tetrahedron Lett. 1989; 30: 7121
25 Evans DA, Chapman KT, Carreira EM. J. Am. Chem. Soc. 1988; 110: 3560
26 Li P, Li J, Arikan F, Ahlbrecht W, Dieckmann M, Menche D. J. Org. Chem. 2010; 75: 2429
27 Pietruszka J, Witt A. Synthesis 2006; 4266

28a Okude Y, Hirano S, Hiyama T, Nozaki H. J. Am. Chem. Soc. 1977; 99: 3179
28b Hiyama T, Okude Y, Kimura K, Nozaki H. Bull. Chem. Soc. Jpn. 1982; 55: 561

29 Tian Q, Zhang G. Synthesis 2016; 48: 4038
30 Kobayashi K, Fujii Y, Hayakawa I, Kigoshi H. Org. Lett. 2011; 13: 900

31a Wan Z.-K, Choi H.-W, Kang F.-A, Nakajima K, Demeke D, Kishi Y. Org. Lett. 2002; 4: 4431
31b Choi H.-W, Nakajima K, Demeke D, Kang F.-A, Jun H.-S, Wan Z.-K, Kishi Y. Org. Lett. 2002; 4: 4435

32 Bahadoor AB, Micalizio G. Org. Lett. 2006; 8: 1181
33 Hoye TR, Jeffrey CS, Shao F. Nat. Protoc. 2007; 2: 2451
34 Shiina I, Kubota M, Oshiumi H, Hashizume M. J. Org. Chem. 2004; 69: 1822
35 Inanga J, Hirata K, Saeki H, Katsuki T, Yamaguchi M. Bull. Chem. Soc. Jpn. 1979; 52: 1989

36a Boulos L, Prévost M, Barbeau B, Coallier J, Desjardins R. J. Microbiol. Methods 1999; 37: 77
36b Berney M, Hammes F, Bosshard F, Weilenmann H.-U, Egli T. Appl. Environ. Microbiol. 2007; 73: 3283

37 Ammermann J. Ph.D. Thesis. Leibniz Universität; Hannover/Germany: 2017

38a Velvadapu V, Glassford I, Lee M, Paul T, DeBrosse C, Klepacki D, Small MC, MacKerell AD. Jr, Andrade RB. ACS Med. Chem. Lett. 2012; 3: 211
38b Wagh B, Paul T, DeBrosse C, Klepacki D, Small MC, MacKerell AD. Jr, Andrade RB. ACS Med. Chem. Lett. 2013; 4: 1114

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