Facile Solid-Phase Synthesis of Well-Defined Defect Lysine Dendrimers

Yong Liao; Yuan-Ting Chan; Vijayasimha Molakaseema; Anand Selvaraj; Hui-Ting Chen; Yun-Ming Wang; Yeun-Mun Choo; Chai-Lin Kao

doi:10.1021/acsomega.2c02708

Facile Solid-Phase Synthesis of Well-Defined Defect Lysine Dendrimers

ACS Omega. 2022 Jun 17;7(26):22896-22905. doi: 10.1021/acsomega.2c02708. eCollection 2022 Jul 5.

Authors

Yong Liao¹, Yuan-Ting Chan¹, Vijayasimha Molakaseema¹, Anand Selvaraj¹, Hui-Ting Chen², Yun-Ming Wang^{3

4

5}, Yeun-Mun Choo⁶, Chai-Lin Kao^{1

7

8

9

10}

Affiliations

¹ Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
² Department of Pharmacy, National Yang Ming Chiao Tung University, Taipei 112, Taiwan.
³ Department of Biological Science and Technology, National Yang Ming Chiao Tung University, Hsinchu 300, Taiwan.
⁴ Institute of Molecular Medicine and Bioengineering, National Yang Ming Chiao Tung University, Hsinchu 300, Taiwan.
⁵ Center for Intelligent Drug Systems and Smart Bio-devices (IDS2B), National Yang Ming Chiao Tung University, Hsinchu 300, Taiwan.
⁶ Department of Chemistry, University of Malaya, Kuala Lumpur 50603, Malaysia.
⁷ Drug Development and Value Creation Research Center, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
⁸ Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan.
⁹ Department of Chemistry, National Sun Yat-sen University, Kaohsiung 80424, Taiwan.
¹⁰ College of Professional Studies, National Pingtung University of Science and Technology, Pingtung 912, Taiwan.

Abstract

An efficient solid-phase method has been reported to prepare well-defined lysine defect dendrimers. Using orthogonally protected lysine residues, pure G2 to G4 lysine defect dendrimers were prepared with 48-95% yields within 13 h. Remarkably, high-purity products were collected via precipitation without further purification steps. This method was applied to prepare a pair of 4-carboxyphenylboronic acid-decorated defect dendrimers (16 and 17), which possessed the same number of boronic acids. The binding affinity of 16, in which the ε-amines of G1 lysine are fractured, for glucose and sorbitol was 4 times that of 17. This investigation indicated the role of allocation and distribution of peripheries for the dendrimer's properties and activity.