Approaches for the Synthesis of Functionalized Cryptophycins

Sammet B, Bogner T, Nahrwold M, Weiss C, Sewald N (2010)
Journal of Organic Chemistry 75(20): 6953-6960.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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DOI
Autor*in
Sammet, BenediktUniBi; Bogner, TobiasUniBi; Nahrwold, Markus; Weiss, Christine; Sewald, NorbertUniBi
Einrichtung
Fakultät für Chemie > Organische Chemie III
Centrum für Biotechnologie > Arbeitsgruppe N. Sewald
Centrum für Biotechnologie > Institut für Biochemie und Biotechnik
Abstract / Bemerkung
The first syntheses of bioactive cryptophycins functionalized at unit ID were accomplished ina one-pot Staudinger reduction/cyclization step An a/ado precursor for the lower part of the backbone was introduced to minimize protective group chemistry and enable a very convenient synthesis of cryptophycin-52 and unit D eryptophycin analogues containing an ester or a free carboxylic acid for bioconjugations Both new cryptophycin derivatives show high biological activity in cytotoxicity assays
Erscheinungsjahr
2010
Zeitschriftentitel
Journal of Organic Chemistry
Band
75
Ausgabe
20
Seite(n)
6953-6960
ISSN
0022-3263
eISSN
1520-6904
Page URI
https://pub.uni-bielefeld.de/record/1929773

Zitieren

Sammet B, Bogner T, Nahrwold M, Weiss C, Sewald N. Approaches for the Synthesis of Functionalized Cryptophycins. Journal of Organic Chemistry. 2010;75(20):6953-6960.
Sammet, B., Bogner, T., Nahrwold, M., Weiss, C., & Sewald, N. (2010). Approaches for the Synthesis of Functionalized Cryptophycins. Journal of Organic Chemistry, 75(20), 6953-6960. https://doi.org/10.1021/jo101563s
Sammet, Benedikt, Bogner, Tobias, Nahrwold, Markus, Weiss, Christine, and Sewald, Norbert. 2010. “Approaches for the Synthesis of Functionalized Cryptophycins”. Journal of Organic Chemistry 75 (20): 6953-6960.
Sammet, B., Bogner, T., Nahrwold, M., Weiss, C., and Sewald, N. (2010). Approaches for the Synthesis of Functionalized Cryptophycins. Journal of Organic Chemistry 75, 6953-6960.
Sammet, B., et al., 2010. Approaches for the Synthesis of Functionalized Cryptophycins. Journal of Organic Chemistry, 75(20), p 6953-6960.
B. Sammet, et al., “Approaches for the Synthesis of Functionalized Cryptophycins”, Journal of Organic Chemistry, vol. 75, 2010, pp. 6953-6960.
Sammet, B., Bogner, T., Nahrwold, M., Weiss, C., Sewald, N.: Approaches for the Synthesis of Functionalized Cryptophycins. Journal of Organic Chemistry. 75, 6953-6960 (2010).
Sammet, Benedikt, Bogner, Tobias, Nahrwold, Markus, Weiss, Christine, and Sewald, Norbert. “Approaches for the Synthesis of Functionalized Cryptophycins”. Journal of Organic Chemistry 75.20 (2010): 6953-6960.

19 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Synthesis and Biological Evaluation of RGD⁻Cryptophycin Conjugates for Targeted Drug Delivery.
Borbély A, Figueras E, Martins A, Esposito S, Auciello G, Monteagudo E, Di Marco A, Summa V, Cordella P, Perego R, Kemker I, Frese M, Gallinari P, Steinkühler C, Sewald N., Pharmaceutics 11(4), 2019
PMID: 30939768
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
Conjugates of Cryptophycin and RGD or isoDGR Peptidomimetics for Targeted Drug Delivery.
Borbély A, Figueras E, Martins A, Bodero L, Raposo Moreira Dias A, López Rivas P, Pina A, Arosio D, Gallinari P, Frese M, Steinkühler C, Gennari C, Piarulli U, Sewald N., ChemistryOpen 8(6), 2019
PMID: 31275795
N-Acetylborrelidin B: a new bioactive metabolite from Streptomyces mutabilis sp. MII.
Hamed A, Abdel-Razek AS, Frese M, Wibberg D, El-Haddad AF, Ibrahim TMA, Kalinowski J, Sewald N, Shaaban M., Z Naturforsch C 73(1-2), 2018
PMID: 29055178
Ecological and Phytochemical Studies on Euphorbia retusa (Forssk.) from Egyptian Habitat.
Shaaban M, Ali M, Tala MF, Hamed A, Hassan AZ., J Anal Methods Chem 2018(), 2018
PMID: 29484217
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
In Vivo Antitumor Activity of a Novel Acetazolamide-Cryptophycin Conjugate for the Treatment of Renal Cell Carcinomas.
Cazzamalli S, Figueras E, Pethő L, Borbély A, Steinkühler C, Neri D, Sewald N., ACS Omega 3(11), 2018
PMID: 30533574
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
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
Cytotoxic Compounds from Aloe megalacantha.
Abdissa N, Gohlke S, Frese M, Sewald N., Molecules 22(7), 2017
PMID: 28686200
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
Synthesis, biological activity and molecular modeling study of new Schiff bases incorporated with indole moiety.
Halawa AH, El-Gilil SMA, Bedair AH, Shaaban M, Frese M, Sewald N, Eliwa EM, El-Agrody AM., Z Naturforsch C 72(11-12), 2017
PMID: 28525356
Antimicrobial Abietane-Type Diterpenoids from Plectranthus punctatus.
Abdissa N, Frese M, Sewald N., Molecules 22(11), 2017
PMID: 29112171
Structure-Activity Relationship of Propargylamine-Based HDAC Inhibitors.
Wünsch M, Senger J, Schultheisz P, Schwarzbich S, Schmidtkunz K, Michalek C, Klaß M, Goskowitz S, Borchert P, Praetorius L, Sippl W, Jung M, Sewald N., ChemMedChem 12(24), 2017
PMID: 29120081
A new xanthone derivative from twigs of Garcinia nobilis.
Fouotsa H, Tatsimo SJ, Neumann B, Michalek C, Mbazoa CD, Nkengfack AE, Sewald N, Lannang AM., Nat Prod Res 28(14), 2014
PMID: 24697710
Cyanobacteria: potential candidates for drug discovery.
Dixit RB, Suseela MR., Antonie Van Leeuwenhoek 103(5), 2013
PMID: 23532410
Recent approaches for the synthesis of modified cryptophycins.
Weiss C, Sammet B, Sewald N., Nat Prod Rep 30(7), 2013
PMID: 23732943
Total synthesis and biological evaluation of fluorinated cryptophycins.
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

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