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Biomimetic Materials Lab.

Publication

Research Papers

62. Song, D.; Kim, B.; Lee, H.; Choi, J.; Muthu, R.; Shin, S.; Shin, D.; Kim, M.; Nam, H. Y.; Lee, Y.; Lee, S.; Kim, Y.*; Seo, J.* Impact of conjugation of the reactive oxygen species (ROS)-generating catalytic moiety with membrane-active antimicrobial peptoids: Promoting a multi-target mechanism and enhancing selectivity. 2023, manuscript in preparation.

61. Akber, U.; Jung, J.-H.; Yoon, H.; Seo, J.; Park, C.-S.* Depletion of CRBN alleviates synucleinopathy by activating DNAJB1 and DNAJB6. 2023, submitted.

60. Yun, M.-J.; Lee, J.; Shin, S. S.; Park, S.-J.; Choi, J.; Seo, J.; Lee, J.-H.* Ethylene glycol derivative-pendanted quaternary ammonium antibacterial polymers with low cytotoxicity. Eur. Polym. J. 2024, 206, 112772 [DOI: 10.1016/j.eurpolymj.2024.112772].

59. Park, S. -J.; Lee, M. -S.; Yoon, H.; Jeon, S.; Shin, S. S.; Yang, M.; Choi, J.; Kim, J. H.; Seo, J.*; Lee, J. -H.* Biomimetic peptoid-assisted fabrication of antibiofouling thin-film composite membranes. Chem. Eng. J. 2023, 478, 147468 ( equal contribution) [DOI: 10.1016/j.cej.2023.147468].

58. Oh, J.; Lee, Y.; Noh, G.; Park, D.; Lee, H.; Lee, J.*; Kim, C.*; Seo, J.* Chiral Display of Pyrenes on a Peptoid Backbone: Conformational Homogeneity of Peptoid Controls Excimer Chirality. Small Struct. 2023, early view 2300396 ( equal contribution) [DOI: 10.1002/sstr.202300396].

57. Lee, D.; Choi, J.; Yang, M.J.; Park, C-. J.; Seo, J.* Controlling the chameleonic behavior and membrane permeability of cyclosporine derivatives via backbone and side chain modifications. J. Med. Chem. 2023, 66, 13189-13204 [DOI: 10.1021/acs.jmedchem.3c01140].

56. Lee, Y. J.; Kim, Y.; Kim, H.; Choi, J.; Noh, G. H.; Lee, K.-S.; Lee, J.; Choi, C. H.*; Kim, S. H.*; Seo, J.* Unlocking Cu(I)-mediated catalytic pathways for efficient ROS generation by incorporating an oxazole-based histidine surrogate into Cu(II)-ATCUN complexes. Inorg. Chem. 2023, 62, 10279-10290 ( equal contribution) [DOI: 10.1021/acs.inorgchem.3c01084 ].

55. Kim, M.; Cheon, Y.; Shin, D.; Choi, J.; Nielsen, J. E.; Jeong, M. S.; Nam, H. Y.; Kim, S. H.; Lund, R.; Jenssen, H.; Barron, A. E.; Lee, S.*; Seo, J.* Real-Time Monitoring of Multitarget Antimicrobial Mechanisms of Peptoids Using Label-Free Imaging with Optical Diffraction Tomography. Adv. Sci. 2023, 10, 2302483 ( equal contribution) [DOI: 10.1002/advs.202302483 ] (selected as inside front cover).

54. Song, D.; Lee, J.-Y.; Park, E.-C.; Choi, N.-E.; Nam, H.-Y.; Seo, J.*; Lee, J.* Structure-activity relationship analysis of the activity-based probes targeting the HTRA family of serine proteases. Bioorg. Med. Chem. Lett. 2023, 87, 129259 ( equal contribution) [DOI: 10.1016/j.bmcl.2023.129259].

53. Yang, W.; Seo, J.*; Kim, J. H.* Protein-mimetic peptoid nanoarchitectures for pathogen recognition and neutralization. Nanoscale 2023, 15, 975-986 [DOI: 10.1039/D2NR05326H].

52. Yang, W.; Choi, J.; Choi, S. H.; Shin, S.; Park, S. M.; Lee, Y.; Seo, J.* A conjugate of chlorin and cationic amphipathic peptoid: dual antimicrobial and anticancer photodynamic therapy agent. Photochem. Photobiol. Sci. 2023, 22, 655-667 [DOI: 10.1007/s43630-022-00343-8].

51. Bak, I. G.; Chae, C.-G.; Choi, J.; Song, W.-Y.; Seo, J.*; Lee, E.*; Lee, J.-S.* Synthesis of alternating polyisocyanate copolymers by anionic polymerization for mimicking amphiphilic helical peptides. Angew. Chem. Int. Ed. 2022, 61, e202212398 [DOI: 10.1002/anie.202212398].

50. Lee, Y. J.; Kim, H.; Kim, Y.; Cho, K. H.; Hong, S.; Nam, K. T.*; Kim, S. H.*; Choi, C. H.*; Seo, J.* Repurposing a peptide antibiotic as a catalyst: multicopper-daptomycin complex as a cooperative O-O bond formation and activation catalyst. Inorg. Chem. Front. 2022, 9, 4741-4752 ( equal contribution) [DOI: 10.1039/D2QI01440H].

49. Lee, Y. J.; Park, S.; Kim, Y.; Kim, S. H.; Seo, J.* Facile synthetic method for peptoids bearing multiple azoles on side chains. Peptide Science 2023, 115, e24287 [DOI: 10.1002/pep2.24287].

48. Lee, D.; Kang, J.-A.; Lim, C.; Bae, S.; Choi, J.; Park, M.; Choi, Y.*; Park, S. -G.*; Seo, J.* Entry inhibition of hepatitis B virus using cyclosporin O derivatives with peptoid side chain incorporation. Bioorg. Med. Chem. 2022, 68, 116862 [DOI: 10.1016/j.bmc.2022.116862] (Special Issue: Richard Silverman Honor Issue].

47. Kim, S.; Lee, J.-Y.; Choi, J.; Nam, H. Y.; Seo, J.*; Lee, J.* Synthesis and structure-activity relationship of mitochondria-targeting peptoids with varying hydrophobicity and cationic charge. Peptide Science 2021, 114, e24239 ( equal contribution) [DOI: doi.org/10.1002/pep2.24239].

46. Yang, W.; Yoon, Y.; Lee, Y.; Oh, H.; Choi, J.; Shin, S.; Lee, S.; Lee, H.; Lee, Y.*; Seo, J.* Photosensitizer-peptoid conjugates for photoinactivation of gram-negative bacteria: structure-activity relationship and mechanistic studies. Org. Biomol. Chem. 2021, 19, 6546-6557 ( equal contribution) [DOI:doi.org/10.1039/D1OB00926E].

45. Lee, D.; Lee, S.; Choi, J.; Kang, J.-A.; Song, Y.-K.; Kim, M. J.; Shin, D. -S.; Bae, M. A.; Kim, Y.-C.; Park, S. -G.; Park, C. -J.*; Lee, K. -R.*; Choi, J. -H.*; Seo, J.* Interplay among conformation, intramolecular hydrogen bonds, and chameleonicity in the membrane permeability and cyclophilin A binding of macrocyclic peptide cyclosporin O derivatives. J. Med. Chem. 2021, 64, 8272-8286 [DOI: 10.1021/acs.jmedchem.1c00211].

44. Oh, J.; Kang, D.; Hong, S.; Kim, S. H.; Choi, J. -H.; Seo, J.* Formation of a tris(catecholato) iron(III) complex with a nature-inspired cyclic peptoid ligand. Dalton Trans. 2021, 50, 3459-3463 [DOI:10.1039/D1DT00091H] ( equal contribution). (Selected as Dalton Transactions HOT Articles in April 2021).

43. Shin, D.; Seo, J.* Tag-assisted liquid-phase synthesis of peptoids. Bull. Korean Chem. Soc. 2021, 42, 376-379 [DOI: 10.1002/bkcs.12223 ].

42. Kim, H.; Shin, D.; Yang, W.; Won, D. H.; Oh, H. -S.; Chung, M. W.; Jeong, D.; Kim, S. H.; Chae, K. H.; Ryu, J. Y.; Lee, J.; Cho, S. J.; Seo, J.*; Kim, H.*; Choi, C. H.* Identification of single-atom Ni site active towards electrochemical CO2 conversion to CO. J. Am. Chem. Soc. 2021, 143, 925-933 ( equal contribution) [DOI:doi.org/10.1021/jacs.0c11008].

41. Kim, H.; Yang, W.; Lee, W. H.; Han, M. H.; Moon, J.; Jeon, C.; Kim, D.; Ji, S. G.; Chae, K. H.; Lee, K.-S.; Seo, J.; Oh, H.-S.; Kim, H.; Choi, C. H.* Operando stability of platinum electrocatalysts in ammonia oxidation reactions. ACS Catal. 2020, 10, 11674-11684 [DOI:doi.org/10.1021/acscatal.0c02413].

40. Nam, H. Y.; Choi, J.; Kuman, S. D.; Nielsen, J. E.; Kyeong, M.; Wang, S.; Kang, D.; Lee, Y.; Lee, J.; Yoon, M.-H.; Hong, S.; Lund, R.; Jenssen, H.; Shin, S. Y.*; Seo, J.* Helicity-modulation improves selectivity of antimicrobial peptoids. ACS Infect. Dis. 2020, 6, 2732-2744 [DOI: 10.1021/acsinfecdis.0c00356].

39. Nam, H. Y.; Song, D.; Eo, J.; Choi, N.-E.; Hong, J.-A.; Hong, K. T.; Lee, J. -S.; Seo, J.*; Lee, J.* Activity-based probes for the high temperature requirement A serine proteases. ACS Chem. Biol. 2020, 15, 2346-2354 ( equal contribution) [DOI: 10.1021/acschembio.0c00279].

38. Kim, D.; Lee, Y. J.; Ahn, D-H.; Song, J-W.*; Seo, J.*; Lee, H.* Peptoid-conjugated magnetic field-sensitive exciplex system at high and low solvent polarities. J. Phys. Chem. Lett. 2020, 11, 4668-4677 ( equal contribution) [DOI: doi.org/10.1021/acs.jpclett.0c00636].

37. Kim, Y.; Park, G.D.; Balamurugan, M.; Seo, J.; Min, B.K.; Nam, K.T.* Electrochemical β-selective hydrocarboxylation of styrene using CO2 and water. Adv. Sci. 2020, 7, 1900137 [DOI: doi.org/10.1002/advs.201900137].

36. Kim, S.; Nam, H. Y.; Lee, J.*; Seo, J.* Mitochondria-targeting peptides and peptidomimetics: recent progress and design principles. Biochemistry 2020, 59, 270-284 [DOI: doi.org/10.1021/acs.biochem.9b00857].

35. Yang, W.; Jo, J.; Oh, H.; Lee, H.*; Chung, W.-J.*; Seo, J.* Peptoid helix displaying flavone and porphyrin: synthesis and intramolecular energy transfer. J. Org. Chem. 2020, 85, 1392-1400 ( equal contribution) [DOI: 10.1021/acs.joc.9b02358].

34. Im, S. W.; Ha, H.; Yang, W.; Jang, J. H.; Kang, B.; Seo, D. H.; Seo, J.*; Nam, K. T.* Light polarization dependency existing in the biological photosystem and possible implications in artificial antenna systems. Photosynth. Res, 2020, 143, 205-220 ( equal contribution) [DOI: 10.1007/s11120-019-00682-1].

33. Goh, B.; Choi, J.; Kang, J.-A.; Park, S.-G.; Seo, J.*; Kim, T.-Y.* Development of a mass spectrometric screening assay for hepatitis B virus inhibitors. J. Pharmaceut. Biomed. 2020, 178, 112959 ( equal contribution) [DOI:10.1016/j.jpba.2019.112959].

32. Koo, H. B.; Seo, J.* Antimicrobial peptides under clinical investigation. Peptide Science 2019, e24122 [DOI: 10.1002/pep2.24122].

31. Lee, Y. J.; Kang, B.; Seo, J.* Metalloporphyrin dimers bridged by a peptoid helix: host-guest interaction and chiral recognition. Molecules 2018, 23, 2741 [DOI: 10.3390/molecules23112741].

30. Lee, Y.; Seo, J.* Oxopiperazine capping: formation of oxopiperazine-containing peptoids through C-terminal cyclization. Tetrahedron Lett. 2018, 59, 3946-3949. [doi.org/10.1016/j.tetlet.2018.09.047].

29. Lee, Y. J.; Kang, D.; Seo, J.* Facile method for the synthesis of triazole- and tetrazole-containing peptoids on a solid support. Tetrahedron Lett. 2018, 59, 3311-3316. [doi.org/10.1016/j.tetlet.2018.07.043] ( equal contribution).

28. Nam, H. Y.; Hong, J.-A.; Choi, J.; Shin, S.; Cho, S. K.; Seo, J.*; Lee, J.* Mitochondria targeting peptoids. Bioconjugate Chem. 2018, 29, 1669-1676. [DOI:10.1021/acs.bioconjchem.8b00148] ( equal contribution).

27. Lee, J.; Kang, D.; Choi, J.; Huang, W.; Wadman, M.; Barron, A. E.*; Seo, J.* Effect of side chain hydrophobicity and cationic charge on antimicrobial activity and cytotoxicity of helical peptoids. Bioorg. Med. Chem. Lett. 2018, 28, 170-173. [https://doi.org/10.1016/j.bmcl.2017.11.034] (* Co-corresponding authors)

26. Yang, W.; Kang, B.; Voelz, V. A.*; Seo, J.* Control of porphyrin interactions via structural changes of peptoid scaffold. Org. Biomol. Chem. 2017,15, 9670-9679.

25. Hong, J.-A.; Choi, N.-E.; La, Y. -K.; Nam, H. Y.; Seo, J.; Lee, J.* Development of a smart activity-based probe to detect subcellular activity of asparaginyl endopeptidase in living cells. Org. Biomol. Chem. 2017, 15, 8018-8022.

24. Jang, L.; Kim, S.; Seo, J.; Lee, J. Y.* Facile and Controllable Electrochemical Fabrication of Cell-Adhesive Polypyrrole Electrodes Using Pyrrole-RGD Peptides. Biofabrication 2017, 9, 045007.

23. Kang, B.; Yang, W.; Lee, S.; Mukherjee, S.; Forstater, J.; Kim, H.; Goh, B.; Kim, T.; Voelz, V. A.*; Pang, Y.*; Seo, J.* Precisely tunable energy transfer system using peptoid helix-based molecular scaffold. Sci. Rep. 2017, 7, 4786.

22. Kim, Y.; Kang, B.; Anh, H.; Seo, J.; Nam, K. T.* Plasmon enhanced fluorescence based on porphyrin-peptoid hybridized nanoparticle platform. Small 2017, 13,1700071.

21. Lee, Y. J.; Chung, S.; Ahn, Y. D.; Kang, B.; Lee, J. Y.; Seo, J.* Self-assemblying water-soluble helical rod-coil peptoid amphiphiles. Bull. Korean Chem. Soc. 2017, 38, 38-43.

20. Lee, S.; Ahn, Y.; Mun, H.; Goh, B.; Kim, T.; Seo, J.*; Kim, M.* Solid-phase synthesis of folate-chlorin conjugates for selective photodynamic therapy and the effect of linker variation. Bull. Korean Chem. Soc. 2016, 37, 2036-2040.

19. Kang, S.; Lee, S.; Yang, W.; Seo, J.; Han, M. S.* A direct assay of butyrylcholinesterase activity using a fluorescent substrate. Org. Biomol. Chem. 2016, 14, 8815-8820.

18. Nam, H. Y.; Seo, J.* Postsynthetic modification of peptoids via the Suzuki-Miyaura cross-coupling reaction. Biopolymers (Peptide Science), 2016, 106, 82-88.

17. Lee, J.; Huang, W; Broering, J. M.; Barron, A. E.*; Seo, J.* Prostate Tumor Specific Peptide-Peptoid Hybrid Prodrugs. Bioorg. Med. Chem. Lett. 2015, 25, 2849-2852. (* Co-corresponding authors).

16. Shin, H.; Kang, C.; Yoon, M.*; Seo, J.* Peptoid Helicity Modulation: Precise Control of Peptoid Secondary Structures via Position-Specific Placement of Chiral Monomers. Chem. Comm. 2014, 50, 4465-4468. (* Co-corresponding authors).

15. Huang, W.#; Seo, J.#; Willingham, S. B.; Czyzewski, A. M.; Gonzalgo, M. L.; Weissman, I. L.; Barron, A. E. Learning from Host-Defense Peptides: Cationic, Amphipathic Peptoids with Potent Anticancer Activity. PLoS One 2014, 9, e90397 (# Authors are equally contributed to this article).

14. Kang, B.; Chung, S.; Ahn, Y.; Lee, J.; Seo, J.* Porphyrin-peptoid conjugates: Face-to-face display of porphyrins on peptoid helices. Org. Lett. 2013, 15, 1670-1673.

13. Huang, W.; Seo, J.; Lin, J. S.; Barron, A. E. Peptoid transporters: effects of cationic, amphipathic structure on their cellular uptake. Mol. Biosyst. 2012, 8, 2626-2628.

12. Seo, J.#; Ren, G.#; Liu, H.; Miao, Z.; Park, M.; Wang, Y.; Miller, T. M.; Barron, A. E.; Cheng, Z. In Vivo Biodistribution and Small Animal PET of 64Cu Labeled Antimicrobial Peptoids. Bioconjugate Chem.2012, 23, 1069-1079. (# Authors are equally contributed to this article / Evaluated Article in Faculty of 1000 Biology)

11. Seo, J.; Lee, B-C.; Zuckermann, R. N. Peptoids: Synthesis, Characterization and Nanostructures. Comprehensive Biomaterials 2011, vol.2, 53-76 (book chapters).

10. Seo, J.; Barron, A. E.; Zuckermann, R. N. Novel peptoid building blocks: Synthesis of functionalized aromatic helix-inducing submonomers. Org. Lett. 2010, 12, 492-495.

9. Seo, J.; Michaelian, N.; Owens, S. C.; Dashner, S. T.; Wong, A. J.; Barron, A. E.; Carrasco, M. R. Chemoselective and Microwave-Assisted Synthesis of Glycopeptoids. Org. Lett. 2009, 11, 5210-5213.

8. Silverman, R. B.; Lawton, G. R.; Ranaivo, H. R.; Chico, L. K.; Seo, J.; Watterson, D. M. Effect of potential amine prodrugs of selective neuronal nitric oxide synthase inhibitors on blood-brain barrier penetration. Bioorg. Med. Chem. 2009, 17, 7593-7605.

7. Dohm, M. T.; Seurynck-Servoss, S. L.; Seo, J.; Zuckermann, R. N.; Barron, A. E. Close mimicry of lung surfactant protein B by “clicked” dimers of helical, cationic peptoids. Biopolymers 2009, 92, 538-553.

6. Ji, H.; Erdal, E. P.; Litzinger, E. A.; Seo, J.; Zhu, Y.; Xue, F.; Fang, J.; Huang, J.; Silverman, R. B. Selective neuronal nitric oxide synthase inhibitors. Frontiers in Medicinal Chemistry, Reitz, A. B.; Choudhary, M. I.; Atta-ur-Rahman, Editors; Bentham Science Publishers, Volume 4, 2009, pp 842-882.

5. Seo, J.; Igarashi, J.; Li, H.; Martásek, P.; Roman, L. J.; Poulos, T. L.; Silverman, R. B. Structure-based design and synthesis of Nω-nitro-L-arginine-containing peptidomimetics as selective inhibitors of neuronal nitric oxide synthase. Displacement of the heme structural water. J. Med. Chem. 2007, 50, 2089-2099.

4. Seo, J.; Martásek, P.; Roman, L. J.; Silverman, R. B. Selective L-nitroargininylaminopyrrolidine and L-nitroargininylaminopiperidine neuronal nitric oxide synthase inhibitors. Bioorg. Med. Chem. 2007, 15, 1928-1938.

3. Seo, J.; Silverman, R. B. Synthesis of arginine-containing hydroxamate dipeptidomimetics. Tetrahedron Lett. 2006, 47, 4069-4073.

2. Mbadugha, B. N. A.; Seo, J.; Ji, H.; Martásek, P.; Roman, L. J.; Shea, T. M.; Li, H.; Poulos, T. L.; Silverman, R. B. Hydroxyl-terminated peptidomimetic inhibitors of neuronal nitric oxide synthase. Bioorg. Med. Chem. 2006, 14, 3681-3690.

1. Erdal, E. P.#; Litzinger, E. A.#; Seo, J.#; Zhu, Y.#; Ji, H.#; Silverman, R. B. Selective neuronal nitric oxide synthase inhibitors. Curr. Top. Med. Chem. 2005, 5, 603-624. (# Authors are equally contributed to this review article).

Patents

11. "사이클로스포린 유도체 및 이의 용도", 서지원, 김용철, 이동재, 최지은, 김윤준, 박성규, 조유리, Korean Patent (Filing Number: 10-2022-0059359), 2022.05.16.

10. "B형 간염 예방 또는 치료용 약학 조성물", 서지원, 김용철, 이동재, 최지은, 김윤준, 박성규, 조유리, Korean Patent (Filing Number: 10-2022-0056707), 2022.05.09.

9. "선택성이 개선된 항균 펩토이드 및 이를 포함하는 항균용 조성물", 서지원, 최지은, 신동민, 김민상, Korean Patent (Filing Number: 10-2022-0044371), 2022.04.11. / PCT submitted (PCT/KR2022/005387), 2022.04.14.

8. "다중 표적 항균작용을 갖는 광역학 치료용 광감작제-펩토이드 공액체", 서지원, 양우진, 최지은, Korean Patent (Filing Number: 10-2021-0025442), 2021.02.25.

7. "신규한 캡시드 조립 저해제", 김용철, 박성규, 서지원, 김우찬, 조유리, 김윤준, Korean Patent (Filing Number: 10-2020-0147948), 2020.11.06.

6. "댑토마이신을 포함하는 산소 활성화 및 전기화학적 산소 발생 반응을 위한 촉매 조성물", 서지원, 최창혁, 이연재, 김해솔, 최지은, Korean Patent (Filing Number: 10-2019-0151498), 2019. 11. 22.

5. “Antimicrobial peptoids with improved selectivity and use thereof", Seo, J.; Nam, H. Y.; Choi, J. U.S. Patent (Registration Number: 10,815,275), 2020. 10. 27.

4. "선택성이 개선된 항균 펩토이드 및 이의 용도", 서지원, 남호연, 최지은, Korean Patent (Registration Number: 10-2210934), 2021. 1. 27.

3. “Porphyrin-peptoid conjugates”, Seo, J.; Kang, B. Japanese Patent (Registration Number: 5907936), 2016. 4. 1.

2. “Porphyrin-peptoid conjugate and the preparation process thereof”, Seo, J.; Kang, B. U.S. Patent (Registration Number: 9,263,194), 2016, 2. 16.

1. “포피린-펩토이드 공액체 및 이의 제조방법”, 서지원, 강보영, Korean Patent (Registration Number: 1576850), 2015. 12. 7.

Books

1. Experiments in General Chemistry (일반화학실험), 서지원, 조춘실, 이연재, 2017.12. 28. GIST Press

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