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Piperidine CD4-Mimetic Compounds Expose Vulnerable Env Epitopes Sensitizing HIV-1-Infected Cells to ADCC.
Ding S, Tolbert WD, Zhu H, Lee D, Marchitto L, Higgins T, Zhao X, Nguyen D, Sherburn R, Richard J, Gendron-Lepage G, Medjahed H, Mohammadi M, Abrams C, Pazgier M, Smith AB 3rd, Finzi A. Ding S, et al. Viruses. 2023 May 17;15(5):1185. doi: 10.3390/v15051185. Viruses. 2023. PMID: 37243271 Free PMC article.
Small-molecule CD4 mimetics (CD4mc) based on the indane and piperidine scaffolds such as (+)-BNM-III-170 and (S)-MCG-IV-210 sensitize HIV-1-infected cells to ADCC by exposing CD4-induced (CD4i) epitopes recognized by non-neutralizing antibodies that are abund …
Small-molecule CD4 mimetics (CD4mc) based on the indane and piperidine scaffolds such as (+)-BNM-III-170 and (S)-MCG-IV …
Piperidine CD4-mimetic compounds expose vulnerable Env epitopes sensitizing HIV-1-infected cells to ADCC.
Ding S, Tolbert WD, Zhu H, Lee D, Higgins T, Zhao X, Nguyen D, Sherburn R, Richard J, Lepage GG, Medjahed H, Mohammadi M, Abrams C, Pazgier M, Smith AB 3rd, Finzi A. Ding S, et al. bioRxiv [Preprint]. 2023 Mar 24:2023.03.23.533923. doi: 10.1101/2023.03.23.533923. bioRxiv. 2023. PMID: 36993184 Free PMC article. Updated. Preprint.
Small-molecule CD4 mimetics (CD4mc) based on the indane and piperidine scaffolds such as (+)-BNM-III-170 and ( S )-MCG-IV-210 sensitize HIV-1 infected cells to ADCC by exposing CD4-induced (CD4i) epitopes recognized by non-neutralizing antibodies abundantly p …
Small-molecule CD4 mimetics (CD4mc) based on the indane and piperidine scaffolds such as (+)-BNM-III-170 and ( S )-MCG- …
Indoline CD4-mimetic compounds mediate potent and broad HIV-1 inhibition and sensitization to antibody-dependent cellular cytotoxicity.
Fritschi CJ, Anang S, Gong Z, Mohammadi M, Richard J, Bourassa C, Severino KT, Richter H, Yang D, Chen HC, Chiu TJ, Seaman MS, Madani N, Abrams C, Finzi A, Hendrickson WA, Sodroski JG, Smith AB 3rd. Fritschi CJ, et al. Proc Natl Acad Sci U S A. 2023 Mar 28;120(13):e2222073120. doi: 10.1073/pnas.2222073120. Epub 2023 Mar 24. Proc Natl Acad Sci U S A. 2023. PMID: 36961924 Free PMC article.
Here, we report the design, synthesis, and evaluation of novel CD4mcs based on an indoline scaffold. Compared with our current lead indane scaffold CD4mc, BNM-III-170, several indoline CD4mcs exhibit increased potency and breadth against HIV-1 variants from d …
Here, we report the design, synthesis, and evaluation of novel CD4mcs based on an indoline scaffold. Compared with our current lead indane s …
Structural and Functional Characterization of Indane-Core CD4-Mimetic Compounds Substituted with Heterocyclic Amines.
Chaplain C, Fritschi CJ, Anang S, Gong Z, Richard J, Bourassa C, Liang S, Mohammadi M, Park J, Finzi A, Madani N, Sodroski JG, Abrams CF, Hendrickson WA, Smith AB 3rd. Chaplain C, et al. ACS Med Chem Lett. 2022 Dec 6;14(1):51-58. doi: 10.1021/acsmedchemlett.2c00376. eCollection 2023 Jan 12. ACS Med Chem Lett. 2022. PMID: 36655122 Free PMC article.
Previous studies suggested that a C(5)-methylamino methyl moiety on a lead CD4mc, BNM-III-170, contributed to its antiviral potency. By replacing the C(5) chain with differentially substituted pyrrolidine, piperidine, and piperazine ring systems, guided by st …
Previous studies suggested that a C(5)-methylamino methyl moiety on a lead CD4mc, BNM-III-170, contributed to its antiv …
Characterization of Human Immunodeficiency Virus (HIV-1) Envelope Glycoprotein Variants Selected for Resistance to a CD4-Mimetic Compound.
Anang S, Richard J, Bourassa C, Goyette G, Chiu TJ, Chen HC, Smith AB 3rd, Madani N, Finzi A, Sodroski J. Anang S, et al. J Virol. 2022 Sep 14;96(17):e0063622. doi: 10.1128/jvi.00636-22. Epub 2022 Aug 18. J Virol. 2022. PMID: 35980207 Free PMC article.
In cell culture, we selected and analyzed variants of the primary HIV-1(AD8) strain resistant to BNM-III-170. Two changes (S375N and I424T) in gp120 residues that flank the Phe-43 cavity each conferred an ~5-fold resistance to BNM-III-170 …
In cell culture, we selected and analyzed variants of the primary HIV-1(AD8) strain resistant to BNM-III-170. Two chang …
Identification of gp120 Residue His105 as a Novel Target for HIV-1 Neutralization by Small-Molecule CD4-Mimics.
Fritschi CJ, Liang S, Mohammadi M, Anang S, Moraca F, Chen J, Madani N, Sodroski JG, Abrams CF, Hendrickson WA, Smith AB 3rd. Fritschi CJ, et al. ACS Med Chem Lett. 2021 Oct 29;12(11):1824-1831. doi: 10.1021/acsmedchemlett.1c00437. eCollection 2021 Nov 11. ACS Med Chem Lett. 2021. PMID: 34795873 Free PMC article.
The design and synthesis of butyl chain derivatives at the indane ring 3-position of our lead CD4-mimetic compound BNM-III-170 that inhibits human immunodeficiency virus (HIV-1) infection are reported. ...Biological evaluation of 11-21 revealed that members o …
The design and synthesis of butyl chain derivatives at the indane ring 3-position of our lead CD4-mimetic compound BNM-III- …
Cryo-EM structures of HIV-1 trimer bound to CD4-mimetics BNM-III-170 and M48U1 adopt a CD4-bound open conformation.
Jette CA, Barnes CO, Kirk SM, Melillo B, Smith AB 3rd, Bjorkman PJ. Jette CA, et al. Nat Commun. 2021 Mar 29;12(1):1950. doi: 10.1038/s41467-021-21816-x. Nat Commun. 2021. PMID: 33782388 Free PMC article.
Here, we present single-particle cryo-EM structures of CD4-mimetics BNM-III-170 and M48U1 bound to a BG505 native-like Env trimer plus the CD4-induced antibody 17b at 3.7 A and 3.9 A resolution, respectively. ...
Here, we present single-particle cryo-EM structures of CD4-mimetics BNM-III-170 and M48U1 bound to a BG505 native-like …
HIV-1 Env-Dependent Cell Killing by Bifunctional Small-Molecule/Peptide Conjugates.
Gaffney A, Nangarlia A, Ang CG, Gossert S, Rashad Ahmed AA, Hossain MA, Abrams CF, Smith AB 3rd, Chaiken I. Gaffney A, et al. ACS Chem Biol. 2021 Jan 15;16(1):193-204. doi: 10.1021/acschembio.0c00888. Epub 2021 Jan 7. ACS Chem Biol. 2021. PMID: 33410670 Free PMC article.
Crucially, virolysis was found to be dependent on the covalent linkage of the BNM-III-170 and Trp3 domains, as coadministration of a mixture of the un-cross-linked components proved to be nonlytic. ...Computational modeling suggested strong membrane-binding a …
Crucially, virolysis was found to be dependent on the covalent linkage of the BNM-III-170 and Trp3 domains, as coadmini …
Development of an Effective Scalable Enantioselective Synthesis of the HIV-1 Entry Inhibitor BNM-III-170 as the Bis-Trifluoroacetate Salt.
Chen J, Park J, Kirk SM, Chen HC, Li X, Lippincott DJ, Melillo B, Smith AB 3rd. Chen J, et al. Org Process Res Dev. 2019 Nov 15;23(11):2464-2469. doi: 10.1021/acs.oprd.9b00353. Epub 2019 Oct 7. Org Process Res Dev. 2019. PMID: 33013157 Free PMC article.
We report here the development and optimization of a process synthesis for the HIV-1 entry inhibitor BNM-III-170 bis-TFA salt (1). The synthesis features a dynamic-kinetic resolution (DKR) to establish the initial stereogenicity. ...
We report here the development and optimization of a process synthesis for the HIV-1 entry inhibitor BNM-III-170 bis-TF …