fa3fb4e25175d377ef0f7689ebcce3d5 pmc_30400165.pdf ae34a66704cd10fc6aae2a6efed754f75830ed57 pmc_30400165.pdf de72bc6624bb89fdafba1e106169dfbec52001239e79e989e3032562a0f76990 pmc_30400165.pdf Title: Pentafluorosulfanyl-containing Triclocarban Analogs with Potent Antimicrobial Activity Subject: Concerns have been raised about the long-term accumulating effects of triclocarban, a polychlorinated diarylurea widely used as an antibacterial soap additive, in the environment and in human beings. Indeed, the Food and Drug Administration has recently banned it from personal care products. Herein, we report the synthesis, antibacterial activity and cytotoxicity of novel N,N'-diarylureas as triclocarban analogs, designed by reducing one or more chlorine atoms of the former and/or replacing them by the novel pentafluorosulfanyl group, a new bioisostere of the trifluoromethyl group, with growing importance in drug discovery. Interestingly, some of these pentafluorosulfanyl-bearing ureas exhibited high potency, broad spectrum of antimicrobial activity against Gram-positive bacterial pathogens, and high selectivity index, while displaying a lower spontaneous mutation frequency than triclocarban. Some lines of evidence suggest a bactericidal mode of action for this family of compounds. Keywords: antibacterial; Gram-positive; N,N'-diarylureas; pentafluorosulfanyl; Staphylococcus aureus; triclocarban Author: Eugènia Pujol, Núria Blanco-Cabra, Esther Julián, Rosana Leiva, Eduard Torrents and Santiago Vázquez Creator: LaTeX with hyperref package Producer: pdfTeX-1.40.18 CreationDate: Fri Nov 2 08:28:59 2018 CET ModDate: Fri Nov 2 08:28:59 2018 CET Tagged: no UserProperties: no Suspects: no Form: none JavaScript: no Pages: 17 Encrypted: no Page size: 595.276 x 841.89 pts (A4) Page rot: 0 File size: 1948139 bytes Optimized: no PDF version: 1.5 name type encoding emb sub uni object ID ------------------------------------ ----------------- ---------------- --- --- --- --------- GPESLR+URWPalladioL-Ital Type 1 Custom yes yes no 141 0 VKIBAI+URWPalladioL-Bold Type 1 Custom yes yes no 142 0 GTQWPK+VnURWPalladioL-Bold Type 1 Custom yes yes no 143 0 FGYQFJ+URWPalladioL-Roma Type 1 Custom yes yes no 144 0 KORLVE+VnURWPalladioL Type 1 Custom yes yes no 145 0 KOXWFM+CMSY10 Type 1 Builtin yes yes no 146 0 PUSVWS+TimesNewRomanPS-BoldItalicMT Type 1C WinAnsi yes yes no 151 0 MCBCCI+SourceSansRoman-Regular Type 1C Custom yes yes no 168 0 MCBCCM+SourceSansRoman.613wght Type 1C Custom yes yes no 169 0 MCBCCO+SourceSansRoman-Bold Type 1C Custom yes yes no 170 0 DIHANN+PalatinoLinotype CID TrueType Identity-H yes yes yes 224 0 DIHANO+PalatinoLinotype TrueType WinAnsi yes yes no 225 0 DIHBBO+PalatinoLinotype,Italic TrueType WinAnsi yes yes no 226 0 DIHBDA+PalatinoLinotype,Bold TrueType WinAnsi yes yes no 227 0 DIHBMO+TimesNewRoman TrueType WinAnsi yes yes no 228 0 DIHANN+PalatinoLinotype CID TrueType Identity-H yes yes yes 316 0 DIHCPI+Arial TrueType WinAnsi yes yes no 317 0 DIHCPK+Arial,Bold TrueType WinAnsi yes yes no 318 0 DIHANO+PalatinoLinotype TrueType WinAnsi yes yes no 319 0 DIHBBO+PalatinoLinotype,Italic TrueType WinAnsi yes yes no 320 0 DIHBDA+PalatinoLinotype,Bold TrueType WinAnsi yes yes no 321 0 DIHBMO+TimesNewRoman TrueType WinAnsi yes yes no 322 0 DIHANN+PalatinoLinotype CID TrueType Identity-H yes yes yes 361 0 DIHCPI+Arial TrueType WinAnsi yes yes no 362 0 DIHCPK+Arial,Bold TrueType WinAnsi yes yes no 363 0 DIHANO+PalatinoLinotype TrueType WinAnsi yes yes no 364 0 DIHBBO+PalatinoLinotype,Italic TrueType WinAnsi yes yes no 365 0 DIHBDA+PalatinoLinotype,Bold TrueType WinAnsi yes yes no 366 0 DIHBMO+TimesNewRoman TrueType WinAnsi yes yes no 367 0 XIRVNA+EURB10 Type 1 Builtin yes yes no 410 0 DFFBXL+URWPalladioL-BoldItal Type 1 Custom yes yes no 411 0 KCWWDP+EURM10 Type 1 Builtin yes yes no 412 0 DIHANO+PalatinoLinotype TrueType WinAnsi yes yes no 427 0 DIHBBO+PalatinoLinotype,Italic TrueType WinAnsi yes yes no 428 0 DIHBDA+PalatinoLinotype,Bold TrueType WinAnsi yes yes no 429 0 DIHBMO+TimesNewRoman TrueType WinAnsi yes yes no 430 0 DIHANN+PalatinoLinotype CID TrueType Identity-H yes yes yes 458 0 DIHGJH+TimesNewRoman,Bold TrueType WinAnsi yes yes no 459 0 DIHANO+PalatinoLinotype TrueType WinAnsi yes yes no 460 0 DIHBBO+PalatinoLinotype,Italic TrueType WinAnsi yes yes no 461 0 DIHBDA+PalatinoLinotype,Bold TrueType WinAnsi yes yes no 462 0 DIHBMO+TimesNewRoman TrueType WinAnsi yes yes no 463 0 FKPFBV+PazoMath-Italic Type 1 Builtin yes yes no 496 0 CRUZTT+VnURWPalladioL-Italic Type 1 Custom yes yes no 533 0 Jhove (Rel. 1.28.0, 2023-05-18) Date: 2024-01-19 05:41:17 CET RepresentationInformation: pmc_30400165.pdf ReportingModule: BYTESTREAM, Rel. 1.4 (2018-10-01) LastModified: 2020-08-03 03:47:09 CEST Size: 1948139 Format: bytestream Status: Well-Formed and valid SignatureMatches: PDF-hul MIMEtype: application/octet-stream Checksum: d75c5e58 Type: CRC32 Checksum: fa3fb4e25175d377ef0f7689ebcce3d5 Type: MD5 Checksum: ae34a66704cd10fc6aae2a6efed754f75830ed57 Type: SHA-1 Checksum: de72bc6624bb89fdafba1e106169dfbec52001239e79e989e3032562a0f76990 Type: SHA-256