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Literature DB >> 20857920

Approaches for the synthesis of functionalized cryptophycins.

Benedikt Sammet¹, Tobias Bogner, Markus Nahrwold, Christine Weiss, Norbert Sewald.

Abstract

The first syntheses of bioactive cryptophycins functionalized at unit D were accomplished in a one-pot Staudinger reduction/cyclization step. An azido 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 cryptophycin analogues containing an ester or a free carboxylic acid for bioconjugations. Both new cryptophycin derivatives show high biological activity in cytotoxicity assays.

Entities: Chemical Disease

Mesh：

Substances：

Year: 2010 PMID： 20857920 DOI： 10.1021/jo101563s

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

13 in total

1. A two step synthesis of a key unit B precursor of cryptophycins by asymmetric hydrogenation.

Authors: Benedikt Sammet; Mathilde Brax; Norbert Sewald
Journal: Beilstein J Org Chem Date: 2011-02-22 Impact factor: 2.883

2. Cytotoxic Compounds from Aloe megalacantha.

Authors: Negera Abdissa; Sebastian Gohlke; Marcel Frese; Norbert Sewald
Journal: Molecules Date: 2017-07-07 Impact factor: 4.411

3. Novel unit B cryptophycin analogues as payloads for targeted therapy.

Authors: Eduard Figueras; Adina Borbély; Mohamed Ismail; Marcel Frese; Norbert Sewald
Journal: Beilstein J Org Chem Date: 2018-06-01 Impact factor: 2.883

4. In Vivo Antitumor Activity of a Novel Acetazolamide-Cryptophycin Conjugate for the Treatment of Renal Cell Carcinomas.

Authors: Samuele Cazzamalli; Eduard Figueras; Lilla Pethő; Adina Borbély; Christian Steinkühler; Dario Neri; Norbert Sewald
Journal: ACS Omega Date: 2018-11-02

5. Octreotide Conjugates for Tumor Targeting and Imaging.

Authors: Eduard Figueras; Ana Martins; Adina Borbély; Vadim Le Joncour; Paola Cordella; Raffaella Perego; Daniela Modena; Paolo Pagani; Simone Esposito; Giulio Auciello; Marcel Frese; Paola Gallinari; Pirjo Laakkonen; Christian Steinkühler; Norbert Sewald
Journal: Pharmaceutics Date: 2019-05-07 Impact factor: 6.321

6. Conjugates of Cryptophycin and RGD or isoDGR Peptidomimetics for Targeted Drug Delivery.

Authors: Adina Borbély; Eduard Figueras; Ana Martins; Lizeth Bodero; André Raposo Moreira Dias; Paula López Rivas; Arianna Pina; Daniela Arosio; Paola Gallinari; Marcel Frese; Christian Steinkühler; Cesare Gennari; Umberto Piarulli; Norbert Sewald
Journal: ChemistryOpen Date: 2019-06-07 Impact factor: 2.911

Approaches for the synthesis of functionalized cryptophycins.

1. A two step synthesis of a key unit B precursor of cryptophycins by asymmetric hydrogenation.

2. Cytotoxic Compounds from Aloe megalacantha.

3. Novel unit B cryptophycin analogues as payloads for targeted therapy.

4. In Vivo Antitumor Activity of a Novel Acetazolamide-Cryptophycin Conjugate for the Treatment of Renal Cell Carcinomas.

5. Octreotide Conjugates for Tumor Targeting and Imaging.

6. Conjugates of Cryptophycin and RGD or isoDGR Peptidomimetics for Targeted Drug Delivery.

7. Total synthesis and biological evaluation of fluorinated cryptophycins.

8. Ecological and Phytochemical Studies on Euphorbia retusa (Forssk.) from Egyptian Habitat.

Review 9. Tubulin Inhibitor-Based Antibody-Drug Conjugates for Cancer Therapy.

10. Antimicrobial Abietane-Type Diterpenoids from Plectranthus punctatus.