دورية أكاديمية
أعرض في EDS

Investigating a Boronate-Affinity-Guided Acylation Reaction for Labelling Native Antibodies.

التفاصيل البيبلوغرافية
العنوان: Investigating a Boronate-Affinity-Guided Acylation Reaction for Labelling Native Antibodies.
المؤلفون: Adak AK; Department of Chemistry, National Tsing Hua University, Hsinchu, 300, Taiwan., Huang KT; Department of Chemistry, National Tsing Hua University, Hsinchu, 300, Taiwan., Liao CY; National Institute of Cancer Research, National Health Research Institutes, Miaoli, 350, Taiwan., Lee YJ; Department of Chemistry, National Tsing Hua University, Hsinchu, 300, Taiwan., Kuo WH; Department of Chemistry, National Tsing Hua University, Hsinchu, 300, Taiwan., Huo YR; Department of Chemistry, National Tsing Hua University, Hsinchu, 300, Taiwan., Li PJ; Department of Chemistry, National Tsing Hua University, Hsinchu, 300, Taiwan., Chen YJ; Institute of Chemistry, Academia Sinica, Nankang, Taipei 115, Taiwan., Chen BS; Institute of Chemistry, Academia Sinica, Nankang, Taipei 115, Taiwan., Chen YJ; Institute of Chemistry, Academia Sinica, Nankang, Taipei 115, Taiwan., Chu Hwang K; Department of Chemistry, National Tsing Hua University, Hsinchu, 300, Taiwan., Wayne Chang WS; National Institute of Cancer Research, National Health Research Institutes, Miaoli, 350, Taiwan., Lin CC; Department of Chemistry, National Tsing Hua University, Hsinchu, 300, Taiwan.; Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung, 807, Taiwan.
المصدر: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2022 Mar 22; Vol. 28 (17), pp. e202104178. Date of Electronic Publication: 2022 Feb 19.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 9513783 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1521-3765 (Electronic) Linking ISSN: 09476539 NLM ISO Abbreviation: Chemistry Subsets: MEDLINE
أسماء مطبوعة: Original Publication: Weinheim, Germany : Wiley-VCH
مواضيع طبية MeSH: Immunoconjugates*, Acylation ; Antibodies, Monoclonal ; Azides ; Fluorescent Dyes
مستخلص: The excellent molecular recognition capabilities of monoclonal antibodies (mAbs) have opened up exciting opportunities for biotherapeutic discovery. Taking advantage of the full potential of this tool necessitates affinity ligands capable of conjugating directly with small molecules to a defined degree of biorthogonality, especially when modifying natural Abs. Herein, a bioorthogonal boronate-affinity-based Ab ligand featuring a 4-(dimethylamino)pyridine and an S-aryl thioester to label full-length Abs is reported. The photoactivatable linker in the acyl donor facilitated purification of azide-labelled Ab (N 3 -Ab) was quantitatively cleaved upon brief exposure to UV light while retaining the original Ab activity. Click reactions enabled the precise addition of biotin, a fluorophore, and a pharmacological agent to the purified N 3 -Abs. The resulting immunoconjugate showed selectivity against targeted cells. Bioorthogonal traceless design and reagentless purification allow this strategy to be a powerful tool to engineer native antibodies amenable to therapeutic intervention.
(© 2022 Wiley-VCH GmbH.)
References: G. J. Weiner, Nat. Rev. Cancer 2015, 15, 361-370.
M. X. Sliwkowski, I. Mellman, Science 2013, 341, 1192-1198.
R. V. J. Chari, M. L. Miller, W. C. Widdison, Angew. Chem. Int. Ed. 2014, 53, 3796-3827;.
Angew. Chem. 2014, 126, 3872-3904.
V. Chudasama, A. Maruani, S. Caddick, Nat. Chem. 2016, 8, 114-119.
E. A. Hoyt, P. M. S. D. Cal, B. L. Oliveira, G. J. L. Bernardes, Nat. Chem. Rev. 2019, 3, 147-171.
S. J. Walsh, J. D. Bargh, F. D. Dannheim, A. R. Hanby, H. Seki, A. J. Counsell, X. Ou, E. Fowler, N. Ashman, Y. Takada, A. I. Liobet, J. S. Parker, J. S. Carroll, D. R. Spring, Chem. Soc. Rev. 2021, 50, 1305-1353.
J. R. Junutula, H. Raab, S. Clark, S. Bhakta, D. D. Leipold, S. Weir, Y. Chen, M. Simpson, S. P. Tsai, M. S. Dennis, Y. Lu, Y. G. Meng, C. Ng, J. Yang, C. C. Lee, E. Duenas, J. Gorrell, V. Katta, A. Kim, K. McDorman, K. Flagella, R. Venook, S. Ross, S. D. Spencer, W. Lee Wong, H. B. Lowman, R. Vandlen, M. X. Sliwkowski, R. H. Scheller, P. Polakis, W. Mallet, Nat. Biotechnol. 2008, 26, 925-932.
J. Y. Axup, K. M. Bajjuri, M. Ritland, B. M. Hutchins, C. H. Kim, S. A. Kazane, R. Halder, J. S. Forsyth, A. F. Santidrian, K. Stafin, Y. Lu, H. Tran, A. J. Seller, S. L. Biroc, A. Szydlik, J. K. Pinkstaff, F. Tian, S. C. Sinha, B. Felding-Habermann, V. V. Smider, P. G. Schultz, Proc. Natl. Acad. Sci. USA 2012, 109, 16101-16106.
C. Zhang, M. Welborn, T. Zhu, N. J. Yang, M. S. Santos, T. V. Voorhis, B. L. Pentelute, Nat. Chem. 2016, 8, 120-128.
J. J. Bellucci, J. Bhattacharyya, A. Chilkoti, Angew. Chem. Int. Ed. 2015, 54, 441-445;.
Angew. Chem. 2015, 127, 451-455.
V. Siegmund, S. Schmelz, S. Dickgiesser, J. Beck, A. Ebenig, H. Fittler, H. Frauendorf, B. Piater, U. A. K. Betz, O. Avrutina, A. Scrima, H. L. Fuchsbauer, H. Kolmar, Angew. Chem. Int. Ed. 2015, 54, 13420-13424;.
Angew. Chem. 2015, 127, 13618-13623.
L. S. Witus, C. Netirojjanakul, K. S. Palla, E. M. Muehl, C.-H. Weng, A. T. Lavarone, M. B. Francis, J. Am. Chem. Soc. 2013, 135, 17223-17229.
G. Casi, N. Huguenin-Dezot, K. Zuberbühler, J. Scheuermann, D. Neri, J. Am. Chem. Soc. 2012, 134, 5887-5892.
J. N. Arnold, M. R. Wormald, R. B. Sim, P. M. Rudd, R. A. Dwek, Annu. Rev. Immunol. 2007, 25, 21-50.
X.-H. Dong, A. C. Obermeyer, B. D. Olsen, Angew. Chem. Int. Ed. 2017, 56, 1273-1277;.
Angew. Chem. 2017, 129, 1293-1297.
X. Li, T. Fang, G.-J. Boons, Angew. Chem. Int. Ed. 2014, 53, 7179-7182;.
Angew. Chem. 2014, 126, 7307-7310.
R. M. Anthony, F. Wermeling, J. V. Ravetch, Ann. N. Y. Acad. Sci. 2012, 1253, 170-180.
C. B. Rosen, A. L. B. Kodal, J. S. Nielsen, D. H. Schaffert, C. Scavenius, A. H. Okholm, N. V. Voigt, J. J. Enghild, J. Kjems, T. Tørring, K. V. Gothelf, Nat. Chem. 2014, 6, 804-809.
J. Ohata, Z. T. Ball, J. Am. Chem. Soc. 2017, 139, 12617-12622.
S. J. Walsh, S. Omarjee, W. R. J. D. Galloway, T. T.-L. Kwan, H. F. Sore, J. S. Parker, M. Hyvonen, J. S. Carroll, D. R. Spring, Chem. Sci. 2019, 10, 694-700.
A. Perols, A. E. Karlström, Bioconjugate Chem. 2014, 25, 481-488.
J. Z. Hui, S. Tamsen, Y. Song, A. Tsourkas, Bioconjugate Chem. 2015, 26, 1456-1460.
M. J. Matos, B. L. Oliveira, N. Martínez-Sáez, A. Guerreiro, P. M. S. D. Cai, J. Bertoldo, M. Maneiro, E. Perkins, J. Howard, M. J. Deery, J. M. Chalker, F. Corzana, G. Jiménez-Osés, G. J. L. Bernardes, J. Am. Chem. Soc. 2018, 140, 4004-4017.
J. P. M. Antonio, R. Russo, C. P. Carvalho, P. M. S. D. Cai, P. M. P. Gois, Chem. Soc. Rev. 2019, 48, 3513-3536.
S. Chaterjee, E. V. Anslyn, A. Bandyopadhyay, Chem. Sci. 2021, 12, 1585-1599.
B. Akgun, D. G. Hall, Angew. Chem. Int. Ed. 2018, 57, 13028-13044.
Y.-L. Yang, Y.-P. Lee, Y.-L. Yang, P.-C. Lin, ACS Chem. Biol. 2014, 9, 390-397.
F. Duval, T. A. van Beek, H. Zuilhof, Analyst 2015, 140, 6467-6472.
M.-L. Chen, A. K. Adak, N.-C. Yeh, W.-B. Yang, Y.-J. Chuang, C.-H. Wong, K.-C. Hwang, J.-R. Hwu, S.-L. Hsieh, C.-C. Lin, Angew. Chem. Int. Ed. 2008, 47, 8627-8630;.
Angew. Chem. 2008, 120, 8755-8758.
P.-C. Lin, S.-H. Chen, K.-Y. Wang, M.-L. Chen, A. K. Adak, J.-R. Hwu, Y.-J. Chen, C.-C. Lin, Anal. Chem. 2009, 81, 8774-8782.
Y. Koshi, E. Nakata, M. Miyagawa, S. Tsukiji, T. Ogawa, I. Hamachi, J. Am. Chem. Soc. 2008, 130, 245-251.
P. J. LeValley, R. Neelarapu, B. P. Sutherland, S. Dasgupta, C. J. Kloxin, A. Kloxin, J. Am. Chem. Soc. 2020, 142, 4671-4679.
Z. Song, Y. Takaoka, Y. Kioi, K. Komatsu, T. Tamura, T. Miki, I. Hamachi, Chem. Lett. 2015, 44, 333-335.
A. W. T. Chiang, S. Li, P. N. Spahn, A. Richelle, C. C. Kuo, M. Samoudi, N. E. Lewis, Curr. Opin. Struct. Biol. 2016, 40, 104-111.
A. Bond, Y. Rombouts, M. H. J. Selman, P. J. Hensbergen, K. R. Reiding, J. M. W. Hazes, R. J. E. Dolhain, M. Wuthers, Mol. Cell. Proteomics 2014, 13, 3029-3039.
P. T. Kasper, J. W. Back, M. Vitale, A. F. Hartong, W. Roseboom, K. J. de Koning, J. H. van Maarseveen, A. O. Muijsers, C. G. de Koster, L. de Long, ChemBioChem 2007, 8, 1281-1292.
M. Tsushima, S. Sato, T. Niwa, H. Taguchi, H. Nakamura, Chem. Commun. 2019, 55, 13275-13278.
H. Wang, Y. Koshi, D. Minato, H. Nonaka, S. Kiyonaka, Y. Mori, S. Tsukiji, I. Hamachi, J. Am. Chem. Soc. 2011, 133, 12220-12228.
A. Pincetic, S. Bournazos, D. J. DiLillo, J. Maamary, T. T. Wang, R. Dahan, B. M. Fiebiger, J. V. Ravetch, Nat. Immunol. 2014, 15, 707-716.
S.-J. Moon, S. V. Govindan, T. M. Cardillo, C. A. D'Souza, H. J. Hansen, D. M. Goldenberg, J. Med. Chem. 2008, 51, 6916-6926.
C.-Y. Fan, S. K. Kawade, A. K. Adak, C. Cho, K.-T. Tan, C.-C. Lin, ACS Appl. Mater. Interfaces 2021, 4, 1558-1566.
H. Wang, Z. Bie, C. Lu, Z. Liu, Chem. Sci. 2013, 4, 4298-4303.
Z. Liu, H. He, Acc. Chem. Res. 2015, 50, 2185-2193.
معلومات مُعتمدة: AS-TP-108-M06 Academia Sinica; 107-2113-M-007-024-MY3 Ministry of Science and Technology; CA-109-PP-15 National Health Research Institutes
فهرسة مساهمة: Keywords: antibodies; antibody-drug conjugates; boronate affinity; boronic acid; protein modifications
المشرفين على المادة: 0 (Antibodies, Monoclonal)
0 (Azides)
0 (Fluorescent Dyes)
0 (Immunoconjugates)
تواريخ الأحداث: Date Created: 20220210 Date Completed: 20220323 Latest Revision: 20220323
رمز التحديث: 20221213
DOI: 10.1002/chem.202104178
PMID: 35143090
قاعدة البيانات: MEDLINE
الوصف
تدمد:1521-3765
DOI:10.1002/chem.202104178