Inverse Polyamidoamine (i‐PAMAM) Dendrimer Antimicrobials

Bonvin, Etienne; Reymond, Jean-Louis (2023). Inverse Polyamidoamine (i‐PAMAM) Dendrimer Antimicrobials. Helvetica chimica acta, 106(6) Wiley 10.1002/hlca.202300035

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Here we redesigned the branches of polyamidoamine (PAMAM) dendrimers by moving the amide carbonyl group on the other side of the amide nitrogen atom, transforming the β-alaninyl-amidoethylamine branch, which easily undergoes retro-Michael reactions and renders PAMAMs intrinsically unstable, into a more stable glycyl-amidopropylamine branch. The resulting inverse PAMAM (i-PAMAM) dendrimers have the same carbon framework as PAMAMs and only differ by the position of the carbonyl group. In contrast to PAMAMs which are prepared in solution and are difficult to purify, we synthesize i-PAMAMs using high-temperature solid-phase peptide synthesis by iterative coupling and deprotection of the commercially available N,N-bis(N′-Fmoc-3-aminopropyl)glycine and purify them preparative reverse phase HPLC. Our i-PAMAM dendrimers show no detectable degradation over time. We demonstrate this new class of dendrimers with the synthesis of antimicrobial dendrimers with potent yet non-membrane disruptive activities against both Gram-negative and Gram-positive bacteria.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP)

UniBE Contributor:

Bonvin, Etienne, Reymond, Jean-Louis

Subjects:

600 Technology > 610 Medicine & health

ISSN:

0018-019X

Publisher:

Wiley

Language:

English

Submitter:

Sandra Tanja Zbinden Di Biase

Date Deposited:

11 Jan 2024 10:11

Last Modified:

14 Sep 2024 00:03

Publisher DOI:

10.1002/hlca.202300035

BORIS DOI:

10.48350/191466

URI:

https://boris.unibe.ch/id/eprint/191466

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