Investigation of amino acid conjugates of (S)-1-[1-(4-aminobenzoyl)-2,3-dihydro-1H-indol-6-sulfonyl]-4-phenyl-imidazolidin-2-one (DW2282) as water soluble anticancer prodrugs

Lee, Ki-Cheul; Venkateswararao, Eeda; Sharma, Vinay K.; Jung, Sang‐Hun

doi:10.1016/j.ejmech.2014.04.048

Cited by 29 publications

(8 citation statements)

References 26 publications

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“…Originally conceived as sulofenur (LY186641) analogs, some sulfonylurea derivatives showed antitubulin properties (Figure ). For instance, DW2282 displayed 0.012 µM as IC 50 against HCT116 cell line, with a quite high correlation with TPI activity (1.5 µM).…”

Section: The Sulfonamidesmentioning

confidence: 98%

Antitubulin sulfonamides: The successful combination of an established drug class and a multifaceted target

Vicente‐Blázquez

González

Álvarez

et al. 2018

Medicinal Research Reviews

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Tubulin, the microtubules and their dynamic behavior are amongst the most successful antitumor, antifungal, antiparasitic, and herbicidal drug targets. Sulfonamides are exemplary drugs with applications in the clinic, in veterinary and in the agrochemical industry. This review summarizes the actual state and recent progress of both fields looking from the double point of view of the target and its drugs, with special focus onto the structural aspects. The article starts with a brief description of tubulin structure and its dynamic assembly and disassembly into microtubules and other polymers. Posttranslational modifications and the many cellular means of regulating and modulating tubulin's biology are briefly presented in the tubulin code. Next, the structurally characterized drug binding sites, their occupying drugs and the effects they induce are described, emphasizing on the structural requirements for high potency, selectivity, and low toxicity. The second part starts with a summary of the favorable and highly tunable combination of physical-chemical and biological properties that render sulfonamides a prototypical example of privileged scaffolds with representatives in many therapeutic areas. A complete description of tubulin-binding sulfonamides is provided, covering the different species and drug sites. Some of the antimitotic sulfonamides have met with very successful Med Res Rev. 2019;39:775-830. wileyonlinelibrary.com/journal/med © 2018 Wiley Periodicals, Inc. | 775applications and others less so, thus illustrating the advances, limitations, and future perspectives of the field.All of them combine in a mechanism of action and a clinical outcome that conform efficient drugs. K E Y W O R D S molecular mechanisms, sulfonamides, tubulin binding drugs, tubulin binding sites 1 | INTRODUCTION Drugs targeting tubulin and the microtubules (tubulin binding drugs [TBDs]) are amongst the most successful antitumor, antifungal, antiparasitic, and herbicidal agents with applications in the clinic, in veterinary and in the agrochemical industry. Recently, the combination of computational methods, medicinal chemistry, biochemistry, structural biology, and cell biology is starting to unravel the intricacies of tubulin binding drugs and of the microtubules themselves, thus paving the way towards new and better TBDs. New methodological advances such as the high resolution cryo-electron microscopy, the imaging of individual microtubule dynamics, and the achievement of recombinant tubulin, altogether with more established methodologies for the study of the microtubules have combined to provide a sharper view of the structure and function of these essential cell components and their interactions with clinically important drugs. The sulfonamides are a prototypical example of privileged scaffolds, with representatives in many therapeutic areas, due to a combination of favorable and highly tunable physical-chemical and biological properties. The early discovery of the dinitroaniline herbicides, and mainly the seminal discovery o...

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Section: The Sulfonamidesmentioning

confidence: 98%

Antitubulin sulfonamides: The successful combination of an established drug class and a multifaceted target

Vicente‐Blázquez

González

Álvarez

et al. 2018

Medicinal Research Reviews

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“…Похідні імідазолідин-4-ону, в тім числі і2-сульфаніліденімідазолідин-4-ону, володіють широким спектром цінних властивостей. Зокрема, протимікробні та протиракові властивості забезпечують перспективу їх застосування в медицині [1][2][3], тоді як здатність до інгібування корозії та наявність люмінесценції із солями Cu(I) та Cu(II) сприяють їх застосуванню у техніці та промисловості [4,5]. Також 2-сульфаніліденімідазолідин-4-они широко використовують в аналітичній хімії, зокрема, як реагенти у визначенні таких металів, як Pd(II), Cu(I), Cu(II), Ag(I) та Hg(II) [6][7][8].…”

Section: одержаноunclassified

Crystal structure peculiarities of silver (I) p-toluenesulphonate complex with 3-allyl-2-sulfanylideneimidazolidin-4-one of [Ag2(L)4(CH3C6H4SO3)2] composition

Fedorchuk¹,

Kinzhybalo²,

Slyvka³

et al. 2018

Visnyk Lviv Univ. Ser. Chem.

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“…The most promising analog 36 (Figure 14) had a good reconversion rate in human plasma and good bioavailability by the oral route in mice. Moreover, this molecule was more active and approximately 36-fold more soluble than DW2282 [66].…”

Section: Amide Prodrugsmentioning

confidence: 99%

The Prodrug Approach: A Successful Tool for Improving Drug Solubility

et al. 2015

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Prodrug design is a widely known molecular modification strategy that aims to optimize the physicochemical and pharmacological properties of drugs to improve their solubility and pharmacokinetic features and decrease their toxicity. A lack of solubility is one of the main obstacles to drug development. This review aims to describe recent advances in the improvement of solubility via the prodrug approach. The main chemical carriers and examples of successful strategies will be discussed, highlighting the advances of this field in the last ten years.

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Investigation of amino acid conjugates of (S)-1-[1-(4-aminobenzoyl)-2,3-dihydro-1H-indol-6-sulfonyl]-4-phenyl-imidazolidin-2-one (DW2282) as water soluble anticancer prodrugs

Cited by 29 publications

References 26 publications

Antitubulin sulfonamides: The successful combination of an established drug class and a multifaceted target

Antitubulin sulfonamides: The successful combination of an established drug class and a multifaceted target

Crystal structure peculiarities of silver (I) p-toluenesulphonate complex with 3-allyl-2-sulfanylideneimidazolidin-4-one of [Ag2(L)4(CH3C6H4SO3)2] composition

The Prodrug Approach: A Successful Tool for Improving Drug Solubility

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