Facile Peptide Macrocyclization and Multifunctionalization via Cyclen Installation

Tsz-Lam Cheung; Leo K. B. Tam; Wing-Sze Tam; Leilei Zhang; Hei-Yui Kai; Waygen Thor; Yue Wu; Pak-Lun Lam; Yik-Hoi Yeung; Chen Xie; Ho-Fai Chau; Wai-Sum Lo; Tao Zhang; Ka-Leung Wong

doi:10.1002/smtd.202400006

Facile Peptide Macrocyclization and Multifunctionalization via Cyclen Installation

Tsz-Lam Cheung, Leo K. B. Tam, Wing-Sze Tam, Leilei Zhang, Hei-Yui Kai, Waygen Thor, Yue Wu, Pak-Lun Lam, Yik-Hoi Yeung, Chen Xie, Ho-Fai Chau, Wai-Sum Lo, Tao Zhang^*, Ka-Leung Wong^*

^*Corresponding author for this work

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

5 Citations (Scopus)

Abstract

Cyclen-peptide bioconjugates are usually prepared in multiple steps that require individual preparation and purification of the cyclic peptide and hydrophilic cyclen derivatives. An efficient strategy is discovered for peptide cyclization and functionalization toward lanthanide probe via three components intermolecular crosslinking on solid-phase peptide synthesis with high conversion yield. Multifunctionality can be conferred by introducing different modular parts or/and metal ions on the cyclen-embedded cyclopeptide. As a proof-of-concept, a luminescent Eu³⁺ complex and a Gd³⁺-based contrasting agent for in vitro optical imaging and in vivo magnetic resonance imaging, respectively, are demonstrated through utilizing this preparation of cyclen-embedded cyclic arginylglycylaspartic acid (RGD) peptide. © 2024 The Authors. Small Methods published by Wiley-VCH GmbH.

Original language	English
Article number	2400006
Number of pages	7
Journal	Small Methods
Volume	8
Issue number	11
Online published	9 Apr 2024
DOIs	https://doi.org/10.1002/smtd.202400006
Publication status	Published - 20 Nov 2024
Externally published	Yes

Funding

All animal experiments were carried out in accordance with the National Institutes of Health (NIH) Guidelines for the Care and Use of Laboratory Animals of South China Normal University (Reference no. SCNU-BIP-2024-027). Financial assistances from the Hong Kong Research Grants Council No. 12300021, NSFC/RGC Joint Research Scheme (N_PolyU209/21), and the Centre for Medical Engineering of Molecular and Biological Probes (AoE/M-401/20) are gratefully acknowledged (K.-L. W). We also appreciate the service of high-resolution mass spectrometry (HRMS) provided by The University Research Facility in Life Sciences (ULS) and Ho-Nam Mak from the Department of Applied Biology and Chemical Technology of The Hong Kong Polytechnic University for the HRMS analysis.

Research Keywords

cyclen-peptide conjugates
lanthanides
luminescence
solid phase peptide synthesis
αvβ3 integrin

Publisher's Copyright Statement

This full text is made available under CC-BY-NC-ND 4.0. https://creativecommons.org/licenses/by-nc-nd/4.0/

RGC Funding Information

RGC-funded

Access Output

10.1002/smtd.202400006

422787238.pdfFinal Published version, 924 KBLicence: CC BY-NC-ND

Other Access Options

Check CityUHK Library

Permanent Link

Right click to copy link

Cite this

@article{d988f51d368e4f4db75bd777ad13d19c,

title = "Facile Peptide Macrocyclization and Multifunctionalization via Cyclen Installation",

abstract = "Cyclen-peptide bioconjugates are usually prepared in multiple steps that require individual preparation and purification of the cyclic peptide and hydrophilic cyclen derivatives. An efficient strategy is discovered for peptide cyclization and functionalization toward lanthanide probe via three components intermolecular crosslinking on solid-phase peptide synthesis with high conversion yield. Multifunctionality can be conferred by introducing different modular parts or/and metal ions on the cyclen-embedded cyclopeptide. As a proof-of-concept, a luminescent Eu3+ complex and a Gd3+-based contrasting agent for in vitro optical imaging and in vivo magnetic resonance imaging, respectively, are demonstrated through utilizing this preparation of cyclen-embedded cyclic arginylglycylaspartic acid (RGD) peptide. {\textcopyright} 2024 The Authors. Small Methods published by Wiley-VCH GmbH.",

keywords = "cyclen-peptide conjugates, lanthanides, luminescence, solid phase peptide synthesis, αvβ3 integrin",

author = "Tsz-Lam Cheung and Tam, {Leo K. B.} and Wing-Sze Tam and Leilei Zhang and Hei-Yui Kai and Waygen Thor and Yue Wu and Pak-Lun Lam and Yik-Hoi Yeung and Chen Xie and Ho-Fai Chau and Wai-Sum Lo and Tao Zhang and Ka-Leung Wong",

year = "2024",

month = nov,

day = "20",

doi = "10.1002/smtd.202400006",

language = "English",

volume = "8",

number = "11",

}

TY - JOUR

T1 - Facile Peptide Macrocyclization and Multifunctionalization via Cyclen Installation

AU - Cheung, Tsz-Lam

AU - Tam, Leo K. B.

AU - Tam, Wing-Sze

AU - Zhang, Leilei

AU - Kai, Hei-Yui

AU - Thor, Waygen

AU - Wu, Yue

AU - Lam, Pak-Lun

AU - Yeung, Yik-Hoi

AU - Xie, Chen

AU - Chau, Ho-Fai

AU - Lo, Wai-Sum

AU - Zhang, Tao

AU - Wong, Ka-Leung

PY - 2024/11/20

Y1 - 2024/11/20

N2 - Cyclen-peptide bioconjugates are usually prepared in multiple steps that require individual preparation and purification of the cyclic peptide and hydrophilic cyclen derivatives. An efficient strategy is discovered for peptide cyclization and functionalization toward lanthanide probe via three components intermolecular crosslinking on solid-phase peptide synthesis with high conversion yield. Multifunctionality can be conferred by introducing different modular parts or/and metal ions on the cyclen-embedded cyclopeptide. As a proof-of-concept, a luminescent Eu3+ complex and a Gd3+-based contrasting agent for in vitro optical imaging and in vivo magnetic resonance imaging, respectively, are demonstrated through utilizing this preparation of cyclen-embedded cyclic arginylglycylaspartic acid (RGD) peptide. © 2024 The Authors. Small Methods published by Wiley-VCH GmbH.

AB - Cyclen-peptide bioconjugates are usually prepared in multiple steps that require individual preparation and purification of the cyclic peptide and hydrophilic cyclen derivatives. An efficient strategy is discovered for peptide cyclization and functionalization toward lanthanide probe via three components intermolecular crosslinking on solid-phase peptide synthesis with high conversion yield. Multifunctionality can be conferred by introducing different modular parts or/and metal ions on the cyclen-embedded cyclopeptide. As a proof-of-concept, a luminescent Eu3+ complex and a Gd3+-based contrasting agent for in vitro optical imaging and in vivo magnetic resonance imaging, respectively, are demonstrated through utilizing this preparation of cyclen-embedded cyclic arginylglycylaspartic acid (RGD) peptide. © 2024 The Authors. Small Methods published by Wiley-VCH GmbH.

KW - cyclen-peptide conjugates

KW - lanthanides

KW - luminescence

KW - solid phase peptide synthesis

KW - αvβ3 integrin

UR - http://www.scopus.com/inward/record.url?scp=85189821942&partnerID=8YFLogxK

UR - https://www.scopus.com/record/pubmetrics.uri?eid=2-s2.0-85189821942&origin=recordpage

U2 - 10.1002/smtd.202400006

DO - 10.1002/smtd.202400006

M3 - RGC 21 - Publication in refereed journal

C2 - 38593368

SN - 2366-9608

VL - 8

JO - Small Methods

JF - Small Methods

IS - 11

M1 - 2400006

ER -

Facile Peptide Macrocyclization and Multifunctionalization via Cyclen Installation

Abstract

Funding

Research Keywords

Publisher's Copyright Statement

RGC Funding Information

Access Output

Other Access Options

Permanent Link

Other Files and Links

Fingerprint

Cite this