A Stable Bis-Allyloxycarbonyl Biotin Aldehyde Derivative for Biotinylation via Reductive Alkylation:  Application to the Synthesis of a Biotinylated Doxorubicin Derivative

Allart, Brigitte; Lehtolainen, Pauliina; Ylä‐Herttuala, Seppo; Martin, John F.; Selwood, David L.

doi:10.1021/bc0255992

Cited by 13 publications

(9 citation statements)

References 20 publications

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“…677 cm -1 ; 1 H NMR (300 MHz, CDCl 3 , 25°C): δ= 4.80 (d, 3 J H,H= 6.0 Hz, 2H, -O-CH 2 -), 5.37-5.51 (m, 2H, -CH=CH 2 ), 5.96-6.09 (m, 1H, -CH=CH 2 ), 7.41 (d,3 J H,H = 9.0 Hz, 2H, m-NO 2 -Ar), 8.30 (d,3 J H,H = 9.0 Hz, 2H, o-NO 2 -Ar), in agreement with previously reported values[23] ;13 C NMR (75 MHz, CDCl 3 , 25°C): δ = 69.8 (-O-CH 2 -), 120.2 (=CH 2 ), [121.8, 125.3 and 130.6] (3°), [145.4, 152.3 and 155.5] (4°); m/z (CI) 241 [M+NH 4 ] + , 211, 194, 157, 148, 110, 108 (Found: [M+NH 4 ] + , 241.0826. C 10 H 9 NO 5 requires [M+NH 4 ] + , 241.0824) (Found: C, 53.73; H, 3.93; N, 6.19.…”

supporting

confidence: 92%

Highly regioselective decarboxylative Claisen rearrangement reactions of diallyl 2-sulfonylmalonates

Craig

Lansdell

Lewis

2007

Tetrahedron Letters

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The decarboxylative Claisen rearrangement of a range of substituted diallyl 2-sulfonylmalonates is described. The reaction displays a very high degree of regioselectivity, with allylic substituents possessing electron-rich substituents at the 3-position rearranging preferentially. The substrates are made by C-carboxylation of the corresponding allyl sulfonylacetates with allyl para-nitrophenyl carbonates. In one instance, the presence of a highly electron-withdrawing side-chain led to the competing formation of a γ-lactone by-product. The Claisen rearrangement continues to be the focus of considerable research effort. [1] Since its introduction in 1972, [2] the Ireland silyl ketene acetal variant in particular has been widely used in complex target-oriented synthesis. [3] This modified process benefits from the ease of preparation of the ketene acetal substrates and the relatively mild conditions for the sigmatropic rearrangement. In addition, it enables overall C-allylation of carboxylic acids using allylic alcohols as the surrogate electrophiles, with regiospecific allylic double-bond transposition. We recently reported [4,5] a novel variant of the Ireland-Claisen rearrangement reaction in which α-tosyl silyl keteneacetals formed in situ from allylic tosylacetates 1 in the presence of N,O-bis(trimethylsilyl)acetamide (BSA) and

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supporting

confidence: 92%

Highly regioselective decarboxylative Claisen rearrangement reactions of diallyl 2-sulfonylmalonates

Craig

Lansdell

Lewis

2007

Tetrahedron Letters

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“…MGAT1 is an enzyme for the formation of the N-glycan branch that enhances the cell surface residency of growth factor receptors. 33 Tumor invasion and metastasis may be affected by the interaction of MGAT1 with DOX. TNFAIP6 is a secret protein that contains a hyaluronan domain and is known to be involved in extracellular matrix stability and cell migration.…”

Section: Discussionmentioning

confidence: 99%

Identification of Human UMP/CMP Kinase 1 as Doxorubicin Binding Target Using Protein Microarray

Chen

Wang²,

Ye³

et al. 2017

SLAS Discovery

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Doxorubicin (DOX) is a leading anthracycline drug with exceptional efficacy; however, little is known about the molecular mechanisms of its side effects, which include heart muscle damage, noncancerous cell death, and drug resistance. A total of 17,950 human proteins expressed in HEK293 cells were screened and yielded 14 hits. Competitive and binding experiments further verified the binding of DOX to UMP/CMP kinase 1 (CMPK1), and microscale thermophoresis showed that DOX binds to CMPK1 with a K of 1216 nM. In addition, we observed that the binding of DOX to CMPK1 activated the phosphorylation of CMP, dCMP, and UMP. A significant activation was observed at the concentration of 30 µM DOX and reached plateau at the concentration of DOX 30 µM, 150 µM, and 100 µM, respectively. DOX would add up stimulation of CMPK1 by DTT and overcome inhibition of CMPK1 by NaF, EDTA. In summary, we showed that DOX might bind to the nonactive site of CMPK1 and regulate its activity with magnesium.

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“…This approach makes it possible to target even circulating cells. For cancer targeting, Scavidin and Lodavin offer a simplified protocol over previously used pre-targeting procedures, requiring only gene delivery and biotinylated drug molecule administration steps [72]. The system is flexible since the same receptor (Scavidin, Lodavin) can be used to target any desired tissue.…”

Section: The Potential Of Novel Avidin Fusion Proteins In Medical Tarmentioning

confidence: 99%

Avidin Fusion Protein Strategies in Targeted Drug and Gene Delivery

Laitinen¹,

Airenne²,

Räty³

et al. 2005

LDDD

Self Cite

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Chicken avidin is used in a wide variety of applications in the life sciences, due to its extraordinarily strong affinity for biotin. Avidin-biotin strategy has also recently established a role in medical targeting approaches for cancer treatments. An interesting new exploitation for avidin-biotin techniques is the utilization of this strong affinity in gene therapy, to target and enhance gene delivery to the appropriate target cells and tissues. In this communication, we review novel avidin fusion proteins that have been developed for enhanced gene delivery and drug targeting purposes. The principles of this approach are highlighted by the avidin fusion proteins Scavidin (fusion with the macrophage scavenger receptor class A), Lodavin (fusion with the endocytotic LDL receptor) and avidin-displaying baculovirus (Baavi). Scavidin and Lodavin are cell membrane proteins in which avidin is expressed as an extracellular portion, thereby enhancing the targeted drug and gene delivery with biotinylated drug molecules and vectors. Baavi, on the other hand, displays avidin moieties on its surface, and opens up possibilities for flexible modification of its targeting properties and other characteristics by using different biotin-conjugated molecules. Potential applications of avidin fusion proteins and future trends of targeted drug and gene delivery based on these strategies will be discussed.

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A Stable Bis-Allyloxycarbonyl Biotin Aldehyde Derivative for Biotinylation via Reductive Alkylation: Application to the Synthesis of a Biotinylated Doxorubicin Derivative

Cited by 13 publications

References 20 publications

Highly regioselective decarboxylative Claisen rearrangement reactions of diallyl 2-sulfonylmalonates

Highly regioselective decarboxylative Claisen rearrangement reactions of diallyl 2-sulfonylmalonates

Identification of Human UMP/CMP Kinase 1 as Doxorubicin Binding Target Using Protein Microarray

Avidin Fusion Protein Strategies in Targeted Drug and Gene Delivery

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