"Clicktophycin-52": A Bioactive Cryptophycin-52 Triazole Analogue
Nahrwold M, Bogner T, Eissler S, Verma S, Sewald N (2010)
Organic Letters 12(5): 1064-1067.
Zeitschriftenaufsatz
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Autor*in
Nahrwold, Markus;
Bogner, Tobias;
Eissler, Stefan;
Verma, Spart;
Sewald, NorbertUniBi 
Einrichtung
Abstract / Bemerkung
An endocyclic trans-amide linkage within the macrocyclic antitumor agent cryptophycin-52 was replaced by a 1,4-disubstituted 1H-1,2,3-triazole ring. Macrocyclisation of the triazole analogue was accomplished by macrolactamization as well as by Cu(I)-mediated "click"-cyclization. Compared to cryptophycin-52, in vitro cytotoxicity of "clicktophycin-52" against the multidrug resistant human cancer cell line KB-V1 is only slightly reduced.
Erscheinungsjahr
2010
Zeitschriftentitel
Organic Letters
Band
12
Ausgabe
5
Seite(n)
1064-1067
ISSN
1523-7060
eISSN
1523-7052
Page URI
https://pub.uni-bielefeld.de/record/1796707
Zitieren
Nahrwold M, Bogner T, Eissler S, Verma S, Sewald N. "Clicktophycin-52": A Bioactive Cryptophycin-52 Triazole Analogue. Organic Letters. 2010;12(5):1064-1067.
Nahrwold, M., Bogner, T., Eissler, S., Verma, S., & Sewald, N. (2010). "Clicktophycin-52": A Bioactive Cryptophycin-52 Triazole Analogue. Organic Letters, 12(5), 1064-1067. https://doi.org/10.1021/ol1000473
Nahrwold, Markus, Bogner, Tobias, Eissler, Stefan, Verma, Spart, and Sewald, Norbert. 2010. “"Clicktophycin-52": A Bioactive Cryptophycin-52 Triazole Analogue”. Organic Letters 12 (5): 1064-1067.
Nahrwold, M., Bogner, T., Eissler, S., Verma, S., and Sewald, N. (2010). "Clicktophycin-52": A Bioactive Cryptophycin-52 Triazole Analogue. Organic Letters 12, 1064-1067.
Nahrwold, M., et al., 2010. "Clicktophycin-52": A Bioactive Cryptophycin-52 Triazole Analogue. Organic Letters, 12(5), p 1064-1067.
M. Nahrwold, et al., “"Clicktophycin-52": A Bioactive Cryptophycin-52 Triazole Analogue”, Organic Letters, vol. 12, 2010, pp. 1064-1067.
Nahrwold, M., Bogner, T., Eissler, S., Verma, S., Sewald, N.: "Clicktophycin-52": A Bioactive Cryptophycin-52 Triazole Analogue. Organic Letters. 12, 1064-1067 (2010).
Nahrwold, Markus, Bogner, Tobias, Eissler, Stefan, Verma, Spart, and Sewald, Norbert. “"Clicktophycin-52": A Bioactive Cryptophycin-52 Triazole Analogue”. Organic Letters 12.5 (2010): 1064-1067.
Daten bereitgestellt von European Bioinformatics Institute (EBI)
20 Zitationen in Europe PMC
Daten bereitgestellt von Europe PubMed Central.
1,4-Disubstituted 1H-1,2,3-Triazole Containing Peptidotriazolamers: A New Class of Peptidomimetics With Interesting Foldamer Properties.
Schröder DC, Kracker O, Fröhr T, Góra J, Jewginski M, Nieß A, Antes I, Latajka R, Marion A, Sewald N., Front Chem 7(), 2019
PMID: 30972322
Schröder DC, Kracker O, Fröhr T, Góra J, Jewginski M, Nieß A, Antes I, Latajka R, Marion A, Sewald N., Front Chem 7(), 2019
PMID: 30972322
Octreotide Conjugates for Tumor Targeting and Imaging.
Figueras E, Martins A, Borbély A, Le Joncour V, Cordella P, Perego R, Modena D, Pagani P, Esposito S, Auciello G, Frese M, Gallinari P, Laakkonen P, Steinkühler C, Sewald N., Pharmaceutics 11(5), 2019
PMID: 31067748
Figueras E, Martins A, Borbély A, Le Joncour V, Cordella P, Perego R, Modena D, Pagani P, Esposito S, Auciello G, Frese M, Gallinari P, Laakkonen P, Steinkühler C, Sewald N., Pharmaceutics 11(5), 2019
PMID: 31067748
1,5-Disubstituted 1,2,3-Triazole-Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics.
Kracker O, Góra J, Krzciuk-Gula J, Marion A, Neumann B, Stammler HG, Nieß A, Antes I, Latajka R, Sewald N., Chemistry 24(4), 2018
PMID: 29160605
Kracker O, Góra J, Krzciuk-Gula J, Marion A, Neumann B, Stammler HG, Nieß A, Antes I, Latajka R, Sewald N., Chemistry 24(4), 2018
PMID: 29160605
How are 1,2,3-triazoles accommodated in helical secondary structures?
Ben Haj Salah K, Das S, Ruiz N, Andreu V, Martinez J, Wenger E, Amblard M, Didierjean C, Legrand B, Inguimbert N., Org Biomol Chem 16(19), 2018
PMID: 29693098
Ben Haj Salah K, Das S, Ruiz N, Andreu V, Martinez J, Wenger E, Amblard M, Didierjean C, Legrand B, Inguimbert N., Org Biomol Chem 16(19), 2018
PMID: 29693098
Novel unit B cryptophycin analogues as payloads for targeted therapy.
Figueras E, Borbély A, Ismail M, Frese M, Sewald N., Beilstein J Org Chem 14(), 2018
PMID: 29977395
Figueras E, Borbély A, Ismail M, Frese M, Sewald N., Beilstein J Org Chem 14(), 2018
PMID: 29977395
Medicinal attributes of 1,2,3-triazoles: Current developments.
Dheer D, Singh V, Shankar R., Bioorg Chem 71(), 2017
PMID: 28126288
Dheer D, Singh V, Shankar R., Bioorg Chem 71(), 2017
PMID: 28126288
Facile access to pseudo-thio-1,2-dimannoside, a new glycomimetic DC-SIGN antagonist.
Tamburrini A, Achilli S, Vasile F, Sattin S, Vivès C, Colombo C, Fieschi F, Bernardi A., Bioorg Med Chem 25(19), 2017
PMID: 28389114
Tamburrini A, Achilli S, Vasile F, Sattin S, Vivès C, Colombo C, Fieschi F, Bernardi A., Bioorg Med Chem 25(19), 2017
PMID: 28389114
Cryptophycins: cytotoxic cyclodepsipeptides with potential for tumor targeting.
Weiss C, Figueras E, Borbely AN, Sewald N., J Pept Sci 23(7-8), 2017
PMID: 28661555
Weiss C, Figueras E, Borbely AN, Sewald N., J Pept Sci 23(7-8), 2017
PMID: 28661555
Tubulin Inhibitor-Based Antibody-Drug Conjugates for Cancer Therapy.
Chen H, Lin Z, Arnst KE, Miller DD, Li W., Molecules 22(8), 2017
PMID: 28763044
Chen H, Lin Z, Arnst KE, Miller DD, Li W., Molecules 22(8), 2017
PMID: 28763044
Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics.
Wünsch M, Schröder D, Fröhr T, Teichmann L, Hedwig S, Janson N, Belu C, Simon J, Heidemeyer S, Holtkamp P, Rudlof J, Klemme L, Hinzmann A, Neumann B, Stammler HG, Sewald N., Beilstein J Org Chem 13(), 2017
PMID: 29234470
Wünsch M, Schröder D, Fröhr T, Teichmann L, Hedwig S, Janson N, Belu C, Simon J, Heidemeyer S, Holtkamp P, Rudlof J, Klemme L, Hinzmann A, Neumann B, Stammler HG, Sewald N., Beilstein J Org Chem 13(), 2017
PMID: 29234470
Design and synthesis of a new class of cryptophycins based tubulin inhibitors.
Kumar A, Kumar M, Sharma S, Guru SK, Bhushan S, Shah BA., Eur J Med Chem 93(), 2015
PMID: 25647428
Kumar A, Kumar M, Sharma S, Guru SK, Bhushan S, Shah BA., Eur J Med Chem 93(), 2015
PMID: 25647428
A diversity-oriented synthesis strategy enabling the combinatorial-type variation of macrocyclic peptidomimetic scaffolds.
Isidro-Llobet A, Hadje Georgiou K, Galloway WR, Giacomini E, Hansen MR, Méndez-Abt G, Tan YS, Carro L, Sore HF, Spring DR., Org Biomol Chem 13(15), 2015
PMID: 25778821
Isidro-Llobet A, Hadje Georgiou K, Galloway WR, Giacomini E, Hansen MR, Méndez-Abt G, Tan YS, Carro L, Sore HF, Spring DR., Org Biomol Chem 13(15), 2015
PMID: 25778821
Design and synthesis of anti-cancer cyclopeptides containing triazole skeleton.
Tahoori F, Balalaie S, Sheikhnejad R, Sadjadi M, Boloori P., Amino Acids 46(4), 2014
PMID: 24420338
Tahoori F, Balalaie S, Sheikhnejad R, Sadjadi M, Boloori P., Amino Acids 46(4), 2014
PMID: 24420338
Macrocyclic drugs and synthetic methodologies toward macrocycles.
Yu X, Sun D., Molecules 18(6), 2013
PMID: 23708234
Yu X, Sun D., Molecules 18(6), 2013
PMID: 23708234
Recent approaches for the synthesis of modified cryptophycins.
Weiss C, Sammet B, Sewald N., Nat Prod Rep 30(7), 2013
PMID: 23732943
Weiss C, Sammet B, Sewald N., Nat Prod Rep 30(7), 2013
PMID: 23732943
Braces for the peptide backbone: insights into structure-activity relationships of protease inhibitor mimics with locked amide conformations.
Tischler M, Nasu D, Empting M, Schmelz S, Heinz DW, Rottmann P, Kolmar H, Buntkowsky G, Tietze D, Avrutina O., Angew Chem Int Ed Engl 51(15), 2012
PMID: 22374650
Tischler M, Nasu D, Empting M, Schmelz S, Heinz DW, Rottmann P, Kolmar H, Buntkowsky G, Tietze D, Avrutina O., Angew Chem Int Ed Engl 51(15), 2012
PMID: 22374650
Total synthesis and biological evaluation of fluorinated cryptophycins.
Weiß C, Bogner T, Sammet B, Sewald N., Beilstein J Org Chem 8(), 2012
PMID: 23209540
Weiß C, Bogner T, Sammet B, Sewald N., Beilstein J Org Chem 8(), 2012
PMID: 23209540
A two step synthesis of a key unit B precursor of cryptophycins by asymmetric hydrogenation.
Sammet B, Brax M, Sewald N., Beilstein J Org Chem 7(), 2011
PMID: 21448253
Sammet B, Brax M, Sewald N., Beilstein J Org Chem 7(), 2011
PMID: 21448253
Diversity-oriented synthesis of macrocyclic peptidomimetics.
Isidro-Llobet A, Murillo T, Bello P, Cilibrizzi A, Hodgkinson JT, Galloway WR, Bender A, Welch M, Spring DR., Proc Natl Acad Sci U S A 108(17), 2011
PMID: 21383137
Isidro-Llobet A, Murillo T, Bello P, Cilibrizzi A, Hodgkinson JT, Galloway WR, Bender A, Welch M, Spring DR., Proc Natl Acad Sci U S A 108(17), 2011
PMID: 21383137
"Triazole bridge": disulfide-bond replacement by ruthenium-catalyzed formation of 1,5-disubstituted 1,2,3-triazoles.
Empting M, Avrutina O, Meusinger R, Fabritz S, Reinwarth M, Biesalski M, Voigt S, Buntkowsky G, Kolmar H., Angew Chem Int Ed Engl 50(22), 2011
PMID: 21544910
Empting M, Avrutina O, Meusinger R, Fabritz S, Reinwarth M, Biesalski M, Voigt S, Buntkowsky G, Kolmar H., Angew Chem Int Ed Engl 50(22), 2011
PMID: 21544910
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