Synthesis and evaluation of novel dolastatin 10 derivatives for versatile conjugations

Yokosaka, Shinya; Izawa, Akiko; Sakai, Chizuka; Sakurada, Eri; Morita, Yasuhiro; Nishio, Yukihiro

doi:10.1016/j.bmc.2018.02.011

Cited by 16 publications

(9 citation statements)

References 20 publications

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“…The values of IC 50 for dolastatin 13 (329) and 14 (330) against the murine P388 leukemia cell line are reported to be 14 and 20 nM, respectively [751,752]. Dolastatin 15 (331) is another linear peptide from D. auricularia widely used as a potential warhead, with an IC 50 of 3−5 nM, and with many derivatives being tested after chemical modifications, for example, replacing the C-terminal (S)-dolapyrrolidinone unit with some diverse amides while maintaining its anti-tubulin activity [756][757][758][759][760][761]. Dolastatin 15 (331) also produces microtubule depolymerization in vitro, possibly binding to the vinca domain of tubulin, and it is a classical inducer of apoptosis in cancer cells, acting as a conventional proapoptotic cytotoxic agent [762][763][764].…”

Section: Anaspideamentioning

confidence: 99%

Bioactive Compounds from Marine Heterobranchs

Ávila

Angulo‐Preckler

2020

Marine Drugs

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The natural products of heterobranch molluscs display a huge variability both in structure and in their bioactivity. Despite the considerable lack of information, it can be observed from the recent literature that this group of animals possesses an astonishing arsenal of molecules from different origins that provide the molluscs with potent chemicals that are ecologically and pharmacologically relevant. In this review, we analyze the bioactivity of more than 450 compounds from ca. 400 species of heterobranch molluscs that are useful for the snails to protect themselves in different ways and/or that may be useful to us because of their pharmacological activities. Their ecological activities include predator avoidance, toxicity, antimicrobials, antifouling, trail-following and alarm pheromones, sunscreens and UV protection, tissue regeneration, and others. The most studied ecological activity is predation avoidance, followed by toxicity. Their pharmacological activities consist of cytotoxicity and antitumoral activity; antibiotic, antiparasitic, antiviral, and anti-inflammatory activity; and activity against neurodegenerative diseases and others. The most studied pharmacological activities are cytotoxicity and anticancer activities, followed by antibiotic activity. Overall, it can be observed that heterobranch molluscs are extremely interesting in regard to the study of marine natural products in terms of both chemical ecology and biotechnology studies, providing many leads for further detailed research in these fields in the near future.

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Section: Anaspideamentioning

confidence: 99%

Bioactive Compounds from Marine Heterobranchs

Ávila

Angulo‐Preckler

2020

Marine Drugs

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“…N-Terminal modified dolastatin analog (PF-06380101) bearing a quaternary amino acid was found to have improved potency and suitable ADME properties for antibody-drug conjugates [70]. Modified dolastatins at thiazole moiety by addition of new functionalities as alcohols, amines, and thiols have also been reported [71]. These analogs also showed low IC 50 for several cancerous cell lines.…”

Section: Linear Peptidesmentioning

confidence: 99%

Thiazole Moiety: An Interesting Scaffold for Developing New Antitumoral Compounds

Ramos-Inza¹,

Aydillo²,

Sanmartín³

et al. 2020

Heterocycles - Synthesis and Biological Activities

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Currently, cancer is one of the major health problems of the human population and prominent cause of death. Thiazole ring has demonstrated many pharmacological activities including anticancer. This scaffold has been found alone or incorporated into the diversity of therapeutic active agents such as tiazofurin, dasatinib, and bleomycin, which are well-known antineoplastic drugs. Recently, most of the compounds isolated from natural sources containing thiazole moiety exhibit notable cytotoxicities and present antitumor potential. In this context, several structural changes have been made in the original structure, such as the incorporation of different substituents or the fusion with other carbo-and heterocycles, in order to increase the antitumoral potency. Related to mechanism of action of these derivatives, some of them act through kinase modulation, polymerization inhibition of microtubule, pro-matrix metalloproteinase activation, signal transducer activation of transcription 3, histone deacetylase inhibition, etc.

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“…These include curacin, apratoxins, cryptophycins, and dolastatins. A total synthesis of several bioactive cyanopeptides has been successfully elaborated, which opened new opportunities for structure-activity studies and better evaluation of their potential (White et al, 1997;Chen et al, 2014;Yokosaka et al, 2018).…”

Section: Bacteria and Archaeamentioning

confidence: 99%

The Essentials of Marine Biotechnology

Barbier²,

et al. 2021

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Coastal countries have traditionally relied on the existing marine resources (e.g., fishing, food, transport, recreation, and tourism) as well as tried to support new economic endeavors (ocean energy, desalination for water supply, and seabed mining). Modern societies and lifestyle resulted in an increased demand for dietary diversity, better health and well-being, new biomedicines, natural cosmeceuticals, environmental conservation, and sustainable energy sources. These societal needs stimulated the interest of researchers on the diverse and underexplored marine environments as promising and sustainable sources of biomolecules and biomass, and they are addressed by the emerging field of marine (blue) biotechnology. Blue biotechnology provides opportunities for a wide range of initiatives of commercial interest for the pharmaceutical, biomedical, cosmetic, nutraceutical, food, feed, agricultural, and related industries. This article synthesizes the essence, opportunities, responsibilities, and challenges encountered in marine biotechnology and outlines the attainment and valorization of directly derived or bio-inspired products from marine organisms. First, the concept of bioeconomy is introduced. Then, the diversity of marine bioresources including an overview of the most prominent marine organisms and their potential for biotechnological uses are described. This is followed by introducing methodologies for exploration of these resources and the main use case scenarios in energy, food and feed, agronomy, bioremediation and climate change, cosmeceuticals, bio-inspired materials, healthcare, and well-being sectors. The key aspects in the fields of legislation and funding are provided, with the emphasis on the importance of communication and stakeholder engagement at all levels of biotechnology development. Finally, vital overarching concepts, such as the quadruple helix and Responsible Research and Innovation principle are highlighted as important to follow within the marine biotechnology field. The authors of this review are collaborating under the European Commission-funded Cooperation in Science and Technology (COST) Action Ocean4Biotech – European transdisciplinary networking platform for marine biotechnology and focus the study on the European state of affairs.

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Synthesis and evaluation of novel dolastatin 10 derivatives for versatile conjugations

Cited by 16 publications

References 20 publications

Bioactive Compounds from Marine Heterobranchs

Bioactive Compounds from Marine Heterobranchs

Thiazole Moiety: An Interesting Scaffold for Developing New Antitumoral Compounds

The Essentials of Marine Biotechnology

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