Synthesis and characterization of a photoresponsive doxorubicin/combretastatin A4 hybrid prodrug

Liu, Wei; Liang, Li; Zhao, Lifeng; Tan, Huan; Wu, Jie; Qin, Qihui; Gou, Xin; Sun, Xiaohua

doi:10.1016/j.bmcl.2018.12.017

Cited by 16 publications

(8 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…designed the photoresponsive hybrid prodrug bearing both doxorubicin (DOX) and CA-4 structure (Figure 4) [119]. They found that sequential irradiation at 405 nm and 365 nm led to the release of DOX and CA-4, respectively [119]. The strictly controlled drug releases, which exert different mechanisms of action, might be most beneficial in terms of achieving a synergistic effect by different drugs.…”

Section: Modifications Of the Hydroxyl Group Of Combretastatin Corementioning

confidence: 99%

“…Ojike et al proved that polyunsaturated fatty acids (PUFAs) derivatives possess similar activity Furthermore, Liu at al. designed the photoresponsive hybrid prodrug bearing both doxorubicin (DOX) and CA-4 structure (Figure 4) [119]. They found that sequential irradiation at 405 nm and 365 nm led to the release of DOX and CA-4, respectively [119].…”

Section: Modifications Of the Hydroxyl Group Of Combretastatin Corementioning

confidence: 99%

“… The scheme presented the structure of hybrid compounds, which possess both CA-4 moiety and the additional active moiety [ 115 , 116 , 119 , 120 ]. This graph presents the general overview about combretastatin A4-basedh and does not present the detailed synthesis.…”

Section: Figurementioning

confidence: 99%

See 2 more Smart Citations

More Than Resveratrol: New Insights into Stilbene-Based Compounds

et al. 2020

View full text Add to dashboard Cite

The concept of a scaffold concerns many aspects at different steps on the drug development path. In medicinal chemistry, the choice of relevant “drug-likeness” scaffold is a starting point for the design of the structure dedicated to specific molecular targets. For many years, the chemical uniqueness of the stilbene structure has inspired scientists from different fields such as chemistry, biology, pharmacy, and medicine. In this review, we present the outstanding potential of the stilbene-based derivatives. Naturally occurring stilbenes, together with powerful synthetic chemistry possibilities, may offer an excellent approach for discovering new structures and identifying their therapeutic targets. With the development of scientific tools, sophisticated equipment, and a better understanding of the disease pathogenesis at the molecular level, the stilbene scaffold has moved innovation in science. This paper mainly focuses on the stilbene-based compounds beyond resveratrol, which are particularly attractive due to their biological activity. Given the “fresh outlook” about different stilbene-based compounds starting from stilbenoids with particular regard to isorhapontigenin and methoxy- and hydroxyl- analogues, the update about the combretastatins, and the very often overlooked and underestimated benzanilide analogues, we present a new story about this remarkable structure.

show abstract

Section: Modifications Of the Hydroxyl Group Of Combretastatin Corementioning

confidence: 99%

Section: Modifications Of the Hydroxyl Group Of Combretastatin Corementioning

confidence: 99%

See 1 more Smart Citation

More Than Resveratrol: New Insights into Stilbene-Based Compounds

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Combretastatins (e.g., combretastatin A-1 [CA1], Oxi4503, Fosbretatubulin, and Ombrabulin; reviewed in Borys et al, 2021), extractions of the Combretum caffrum tree, target the cochicine binding site of tubulin, but their development has been largely suspended due to underwhelming efficacy [ 116 ]. There is currently interest in development of photopharmacologic derivatives of combretastatins to enhance cytotoxicity, sometimes hybridized to additional cytotoxic agents [ 117 ]. Celogentin/moroidin peptides isolated from the seed of Celosia argentea have an inhibitory potency equal to or greater than vinblastine [ 118 ].…”

Section: Future Directionsmentioning

confidence: 99%

Microtubule-Interfering Drugs: Current and Future Roles in Epithelial Ovarian Cancer Treatment

Tymon‐Rosario

Adjei

Roque

et al. 2021

Cancers

View full text Add to dashboard Cite

Taxanes and epothilones are chemotherapeutic agents that ultimately lead to cell death through inhibition of normal microtubular function. This review summarizes the literature demonstrating their current use and potential promise as therapeutic agents in the treatment of epithelial ovarian cancer (EOC), as well as putative mechanisms of resistance. Historically, taxanes have become the standard of care in the front-line and recurrent treatment of epithelial ovarian cancer. In the past few years, epothilones (i.e., ixabepilone) have become of interest as they may retain activity in taxane-treated patients since they harbor several features that may overcome mechanisms of taxane resistance. Clinical data now support the use of ixabepilone in the treatment of platinum-resistant or refractory ovarian cancer. Clinical data strongly support the use of microtubule-interfering drugs alone or in combination in the treatment of epithelial ovarian cancer. Ongoing clinical trials will shed further light into the potential of making these drugs part of current standard practice.

show abstract

“…Another anticancer therapeutic agent, doxorubicin, was conjugated with CA-4 via a photoremovable protecting group to form a photoresponsive hybrid prodrug [91]. Obtained hybrid molecules exhibited increased cytotoxicity against MDA-MB-231 cells compared with individual drugs.…”

Section: Further Perspectivesmentioning

confidence: 99%

Hybrid cis-stilbene Molecules: Novel Anticancer Agents

Piekuś-Słomka

Mikstacka

Ronowicz

et al. 2019

IJMS

View full text Add to dashboard Cite

The growing interest in anticancer hybrids in the last few years has resulted in a great number of reports on hybrid design, synthesis and bioevaluation. Many novel multi-target-directed drug candidates were synthesized, and their biological activities were evaluated. For the design of anticancer hybrid compounds, the molecules of stilbenes, aromatic quinones, and heterocycles (benzimidazole, imidazole, pyrimidine, pyridine, pyrazole, quinoline, quinazoline) were applied. A distinct group of hybrids comprises the molecules built with natural compounds: Resveratrol, curcumin, coumarin, and oleanolic acid. In this review, we present the studies on bioactive hybrid molecules of a well-known tubulin polymerization inhibitor, combretastatin A-4 and its analogs with other pharmacologically active entities. The mechanism of anticancer activity of selected hybrids is discussed considering the structure-activity relationship.

show abstract

Synthesis and characterization of a photoresponsive doxorubicin/combretastatin A4 hybrid prodrug

Cited by 16 publications

References 26 publications

More Than Resveratrol: New Insights into Stilbene-Based Compounds

More Than Resveratrol: New Insights into Stilbene-Based Compounds

Microtubule-Interfering Drugs: Current and Future Roles in Epithelial Ovarian Cancer Treatment

Hybrid cis-stilbene Molecules: Novel Anticancer Agents

Contact Info

Product

Resources

About