Sulfonic acid: key drug design elements with potent, broad-ranging pharmacological activities

Future Medicinal ChemistryVol. 15, No. 22 EditorialSulfonic acid: key drug design elements with potent, broad-ranging pharmacological activitiesLide Hu‡, Huinan Jia‡, Jiwei Zhang, Edeildo Ferreira da Silva-Júnior, Chuanfeng Liu, Xinyong Liu & Peng ZhanLide Hu‡Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Cheeloo College of Medicine, Shandong University, 44 West Culture Road, Jinan, Shandong, 250012, PR China, Huinan Jia‡Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Cheeloo College of Medicine, Shandong University, 44 West Culture Road, Jinan, Shandong, 250012, PR China, Jiwei ZhangDepartment of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Cheeloo College of Medicine, Shandong University, 44 West Culture Road, Jinan, Shandong, 250012, PR China, Edeildo Ferreira da Silva-JúniorBiological & Molecular Chemistry Research Group, Institute of Chemistry & Biotechnology, Federal University of Alagoas, Lourival Melo Mota Avenue, AC, Simoes Campus, Alagoas, Macei, 57072-970, Brazil, Chuanfeng Liu*Author for correspondence: E-mail Address: liuchuanfeng214@163.comDepartment of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Cheeloo College of Medicine, Shandong University, 44 West Culture Road, Jinan, Shandong, 250012, PR ChinaSuzhou Research Institute of Shandong University, Room 607, Building B of NUSP, NO. 388 Ruoshui Road, SIP, Suzhou, Jiangsu, 215123, PR China, Xinyong Liu**Author for correspondence: E-mail Address: xinyongl@sdu.edu.cnDepartment of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Cheeloo College of Medicine, Shandong University, 44 West Culture Road, Jinan, Shandong, 250012, PR China & Peng Zhan ***Author for correspondence: E-mail Address: zhanpeng1982@sdu.edu.cnhttps://orcid.org/0009-0003-4356-4594Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Cheeloo College of Medicine, Shandong University, 44 West Culture Road, Jinan, Shandong, 250012, PR ChinaPublished Online:6 Nov 2023https://doi.org/10.4155/fmc-2023-0257AboutSectionsView ArticleView Full TextPDF/EPUB ToolsAdd to favoritesDownload CitationsTrack CitationsPermissionsReprints ShareShare onFacebookTwitterLinkedInRedditEmail View articleKeywords: drug designmedicinal chemistrysulfonic acidReferences1. Guimond SE, Mycroft-West CJ, Gandhi NS et al. Synthetic heparan sulfate mimetic pixatimod (PG545) potently inhibits SARS-CoV-2 by disrupting the spike-ACE2 interaction. ACS Cent. Sci. 8(5), 527–545 (2022).Crossref, Medline, CAS, Google Scholar2. Bojadzic D, Alcazar O, Chen J et al. Small-Molecule inhibitors of the coronavirus spike: ACE2 protein-protein iteraction as blockers of viral attachment and entry for SARS-CoV-2. ACS Infect. Dis. 7(6), 1519–1534 (2021).Crossref, Medline, CAS, Google Scholar3. Kuroki A, Tay DJW, Chua ACY et al. Amphiphilic sulfonated polycarbonates inactivate SARS-CoV-2 in seconds. Macromolecules 56(15), 6003–6009 (2023).Crossref, CAS, Google Scholar4. Liu Y, Zhang L, Yan H et al. Design of dimeric bile acid derivatives as potent and selective human NTCP inhibitors. J. Med. Chem. 64(9), 5973–6007 (2021).Crossref, Medline, CAS, Google Scholar5. Tebas P, Powderly WG. Nelfinavir mesylate. Expert Opin. Pharmacol. 1(7), 1429–1440 (2000).Crossref, Medline, CAS, Google Scholar6. Tan GT, Wickramasinghe A, Verma S et al. Potential anti-AIDS naphthalenesulfonic acid derivatives. Synthesis and inhibition of HIV-1 induced cytopathogenesis and HIV-1 and HIV-2 reverse transcriptase activities. J. Med. Chem. 35(26), 4846–4853 (1992).Crossref, Medline, CAS, Google Scholar7. Mohan P, Wong MF, Verma S, Huang PP, Wickramasinghe A, Baba M. Structure-activity relationship studies with symmetric naphthalenesulfonic acid derivatives. Synthesis and influence of spacer and naphthalenesulfonic acid moiety on anti-HIV-1 activity. J. Med. Chem. 37(16), 2513–2519 (1994).Crossref, Medline, CAS, Google Scholar8. Sepúlveda-Crespo D, de la Mata FJ, Gómez R, Muñoz-Fernández MA. Sulfonate-ended carbosilane dendrimers with a flexible scaffold cause inactivation of HIV-1 virions and gp120 shedding. Nanoscale 10(19), 8998–9011 (2018).Crossref, Medline, CAS, Google Scholar9. Hong BT, Cheng YE, Cheng TJ, Fang JM. Boronate, trifluoroborate, sulfone, sulfinate and sulfonate congeners of oseltamivir carboxylic acid: synthesis and anti-influenza activity. Eur. J. Med. Chem. 163, 710–721 (2019).Crossref, Medline, CAS, Google Scholar10. Razinkov V, Gazumyan A, Nikitenko A, Ellestad G, Krishnamurthy G. RFI-641 inhibits entry of respiratory syncytial virus via interactions with fusion protein. Chem. Biol. 8(7), 645–659 (2001).Crossref, Medline, CAS, Google Scholar11. He R, Wang J, Yu ZH et al. Structure-based design of active-site-directed, highly potent, selective, and orally bioavailable low-molecular-weight protein tyrosine phosphatase inhibitors. J. Med. Chem. 65(20), 13892–13909 (2022).Crossref, Medline, CAS, Google Scholar12. He R, Wang J, Yu ZH et al. Inhibition of low molecular weight protein tyrosine phosphatase by an induced-fit mechanism. J. Med. Chem. 59(19), 9094–9106 (2016).Crossref, Medline, CAS, Google Scholar13. Macedo T, Paiva-Martins F, Ferreres F et al. Anti-inflammatory effects of naringenin 8-sulphonate from parinari excelsa sabine stem bark and its semi-synthetic derivatives. Bioorg. Chem. 138, doi: 10.1016/j.bioorg.2023.106614 (2023).Crossref, Medline, Google Scholar14. Matesanz M, Mensa J. Ceftazidime-avibactam. Rev. Esp. Quimioter. 34(Suppl. 1), 38–40 (2021).Crossref, Medline, Google Scholar15. Heo YA. Imipenem/cilastatin/relebactam: a review in Gram-negative bacterial infections. Drugs 81(3), 377–388 (2021).Crossref, Medline, CAS, Google Scholar16. Büscher P, Cecchi G, Jamonneau V, Priotto G. Human african trypanosomiasis. Lancet 390(10110), 2397–2409 (2017).Crossref, Medline, Google Scholar17. Hawking F. Chemotherapy of onchocerciasis. Transactions of the Royal Society of Tropical Medicine. Hygiene 52(2), 109–111 (1958).CAS, Google Scholar18. Yahi N, Sabatier JM, Nickel P, Mabrouk K, Gonzalez-Scarano F, Fantini J. Suramin inhibits binding of the V3 region of HIV-1 envelope glycoprotein gp120 to galactosylceramide, the receptor for HIV-1 gp120 on human colon epithelial cells. J. Biol. Chem. 269(39), 24349–24353 (1994).Crossref, Medline, CAS, Google Scholar19. Sahu D, Saroha A, Roy S, Das S, Srivastava PS, Das HR. Suramin ameliorates collagen induced arthritis. Int. Immunopharmacol. 12(1), 288–293 (2012).Crossref, Medline, CAS, Google Scholar20. Williams WL. The effects of suramin (germanin), azo dyes, and vasodilators on mice with transplanted lymphosarcomas. Cancer Res. 6, 344–353 (1946).Medline, CAS, Google ScholarFiguresReferencesRelatedDetails Vol. 15, No. 22 STAY CONNECTED Metrics Downloaded 25 times History Received 1 September 2023 Accepted 15 September 2023 Published online 6 November 2023 Published in print November 2023 Information© 2023 Newlands PressKeywordsdrug designmedicinal chemistrysulfonic acidAuthor contributionsThe writing of the first draft was initiated by C Liu, L Hu and H Jia. E Ferreira da Silva-Júnior, X Liu and P Zhan edited the manuscript. P Zhan reviewed and approved the final manuscript.Financial disclosureThe authors have received financial support from the National Natural Science Foundation of China (NSFC nos. 82173677, 82211530493), and the Science Foundation for Outstanding Young Scholars of Shandong Province (ZR2020JQ31). Natural Science Foundation of Jiangsu Province (SBK2023041680); China Postdoctoral Science Foundation (2022M711938). The authors have no other relevant affiliations or financial involvement with any organization or entity with a financial interest in or financial conflict with the subject matter or materials discussed in the manuscript apart from those disclosed.Competing interests disclosureThe authors have no competing interests or relevant affiliations with any organization or entity with the subject matter or materials discussed in the manuscript. This includes employment, consultancies, honoraria, stock ownership or options, expert testimony, grants or patents received or pending, or royalties.Writing disclosureNo writing assistance was utilized in the production of this manuscript.PDF download