Novel unit B cryptophycin analogues as payloads for targeted therapy

Figueras Agustí E, Borbély AN, Ismail M, Frese M, Sewald N (2018)
Beilstein Journal of Organic Chemistry 14: 1281-1286.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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DOI
Autor*in
Figueras Agustí, EduardUniBi; Borbély, Adina NoémiUniBi; Ismail, MohamedUniBi; Frese, MarcelUniBi ; Sewald, NorbertUniBi
Einrichtung
Centrum für Biotechnologie > Arbeitsgruppe N. Sewald
Fakultät für Chemie > Organische Chemie III
Abstract / Bemerkung
Cryptophycins are naturally occurring cytotoxins with great potential for chemotherapy. Since targeted therapy provides new perspectives for treatment of cancer, new potent analogues of cytotoxic agents containing functional groups for conjugation to homing devices are required. We describe the design, synthesis and biological evaluation of three new unit B cryptophycin analogues. The O-methyl group of the unit B D-tyrosine analogue was replaced by an O-(allyloxyethyl) moiety, an O-(hydroxyethyl) group, or an O-(((azidoethoxy) ethoxy) ethoyxethyl) substituent. While the former two maintain cytotoxicity in the subnanomolar range, the attachment of the triethylene glycol spacer with a terminal azide results in a complete loss of activity. Docking studies of the novel cryptophycin analogues to beta-tubulin provided a rationale for the observed cytotoxicities.
Stichworte
cryptophycin; cytotoxic agents; novel payloads; tubulin inhibitors; tumour targeting
Erscheinungsjahr
2018
Zeitschriftentitel
Beilstein Journal of Organic Chemistry
Band
14
Seite(n)
1281-1286
ISSN
1860-5397
Page URI
https://pub.uni-bielefeld.de/record/2920953

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Figueras Agustí E, Borbély AN, Ismail M, Frese M, Sewald N. Novel unit B cryptophycin analogues as payloads for targeted therapy. Beilstein Journal of Organic Chemistry. 2018;14:1281-1286.
Figueras Agustí, E., Borbély, A. N., Ismail, M., Frese, M., & Sewald, N. (2018). Novel unit B cryptophycin analogues as payloads for targeted therapy. Beilstein Journal of Organic Chemistry, 14, 1281-1286. https://doi.org/10.3762/bjoc.14.109
Figueras Agustí, Eduard, Borbély, Adina Noémi, Ismail, Mohamed, Frese, Marcel, and Sewald, Norbert. 2018. “Novel unit B cryptophycin analogues as payloads for targeted therapy”. Beilstein Journal of Organic Chemistry 14: 1281-1286.
Figueras Agustí, E., Borbély, A. N., Ismail, M., Frese, M., and Sewald, N. (2018). Novel unit B cryptophycin analogues as payloads for targeted therapy. Beilstein Journal of Organic Chemistry 14, 1281-1286.
Figueras Agustí, E., et al., 2018. Novel unit B cryptophycin analogues as payloads for targeted therapy. Beilstein Journal of Organic Chemistry, 14, p 1281-1286.
E. Figueras Agustí, et al., “Novel unit B cryptophycin analogues as payloads for targeted therapy”, Beilstein Journal of Organic Chemistry, vol. 14, 2018, pp. 1281-1286.
Figueras Agustí, E., Borbély, A.N., Ismail, M., Frese, M., Sewald, N.: Novel unit B cryptophycin analogues as payloads for targeted therapy. Beilstein Journal of Organic Chemistry. 14, 1281-1286 (2018).
Figueras Agustí, Eduard, Borbély, Adina Noémi, Ismail, Mohamed, Frese, Marcel, and Sewald, Norbert. “Novel unit B cryptophycin analogues as payloads for targeted therapy”. Beilstein Journal of Organic Chemistry 14 (2018): 1281-1286.

4 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
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

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