Amino acid conjugated antimicrobial drugs: Synthesis, lipophilicity- activity relationship, antibacterial and urease inhibition activity

Ullah, Atta; Iftikhar, Faiza Jan; Arfan, Muhammad; Kazmi, Syeda Tayyaba Batool; Anjum, Muhammad Naveed; Haq, Ihsan‐ul; Ayaz, Muhammad; Farooq, Sadia; Rashid, Umer

doi:10.1016/j.ejmech.2017.12.089

Cited by 43 publications

(18 citation statements)

References 26 publications

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“…Lack of selective cytotoxicity is the main factor that restricts the conventional chemotherapeutic agents [29,33]. Thus, to evaluate the selective antiproliferative activity of the compound 5d , the selectivity index (SI) between cancer and normal cells was calculated and the results are summarized in Table 3.…”

Section: Resultsmentioning

confidence: 99%

“…Amino acids are important organic compounds that have many functions in metabolism and are defined by their unique side chain. Due to their structural diversity, amino acids provide a balance between hydrophilicity and hydrophobicity which is necessary for the cell membrane solubility and permeability [29]. Our previous study investigated the structure-activity relationship of the antiproliferative effects of celastrol analogues.…”

Section: Introductionmentioning

confidence: 99%

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Design and Synthesis of C-19 Isosteviol Derivatives as Potent and Highly Selective Antiproliferative Agents

et al. 2018

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Six series of novel isosteviol derivatives; modified in the C-19 position; were synthesized; and their antiproliferative activity was evaluated against three human cancer cell lines (HCT-116; BEL-7402; HepG2) and the human L02 normal cell line in vitro. Most of the derivatives tested here exhibited improved antiproliferative activity with high selectivity when compared with the parent compound isosteviol and the positive control drug 5-fluorouracil. Among these derivatives; compound 5d exhibited the most potent antiproliferative activity and commendable selectivity between cancer and normal cells. In addition; compound 5d inhibited the colony formation of HCT-116 cells in a concentration-dependent manner. Further studies revealed that compound 5d arrested the HCT-116 cell cycle in the S phase; and western blot analysis demonstrated the mechanism may be correlated with a change in the expression of cyclin A; cyclin B1; and cyclin E1. Furthermore; the results of a docking study that involved placing compound 5d into the CDK2/cyclin A binding site revealed that its mode of action was possibly as a CDK2/cyclin A inhibitor.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of C-19 Isosteviol Derivatives as Potent and Highly Selective Antiproliferative Agents

et al. 2018

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“…It is noticeable that several reports have revealed that introducing some units at the C3 position with ester or ether bond significantly improved solubility and diverse physicochemical properties of diosgenin while maintaining the original advantages [22,23,24,25]. Amino acids, as an important organic compounds self-possessed of amine (-NH 2 ) and carboxylic (-COOH) functional groups along with side chain particular to each amino acid [26], possess several advantages involving enhancing the selectivity, permeability as well as solubility and reducing the toxicity when it was introduced into a insoluble compounds [27,28,29,30,31]. Besides, amino acids successfully gained our attention because of its neuroprotection.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Biological Evaluation of Diosgenin-Amino Acid Derivatives with Dual Functions of Neuroprotection and Angiogenesis

Cai

Yang

et al. 2019

Molecules

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Diosgenin, a natural product with steroidal structure, has a wide range of clinical applications in China. It also shows great potential in the treatment of blood clots and nerve damage. To enhance the bioavailability as well as efficacy of diosgenin, eighteen diosgenin-amino acid derivatives were designed and synthesized. The neuroprotective effects of these compounds were evaluated by SH-SY5Y cell line and the biosafety was evaluated by H9c2 cell line. The results displayed that part of the derivatives’ activities (EC50 < 20 μM) were higher than positive control edaravone (EC50 = 21.60 ± 3.04 μM), among which, DG-15 (EC50 = 6.86 ± 0.69 μM) exhibited the best neuroprotection. Meanwhile, biosafety evaluation showed that DG-15 had no cytotoxicity on H9c2 cell lines. Interestingly, combined neuroprotective and cytotoxic results, part of the derivatives without their protecting group were superior to compounds with protecting group. Subsequently, Giemsa staining and DAPI (4′,6-diamidino-2-phenylindole) staining indicated that DG-15 had a protective effect on damaged SH-SY5Y cells by reducing apoptosis. Moreover, DG-15 showed a higher role in promoting angiogenesis at high concentrations (4 mg/mL) on the chorioallantoic membrane model. This finding displayed that DG-15 had dual functions of neuroprotection and angiogenesis, which provided further insight into designing agent for the application in treatment of ischemic stroke.

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“…Multidrug resistant pathogens threaten human and animal health worldwide, in developed health systems and in emerging countries as well [1,2]. These strains have been considered characteristic for the hospital environment, but recently, more and more often they are also identified in community-acquired infections [3].…”

mentioning

confidence: 99%

“…This type of molecules has the potential advantage of increased potency, superior cellular permeability and improved water solubility. Insertion of amino acid fragments in biologically active molecules can be interpreted as a continuation of the magic bullet idea, conceived by Paul Erlich more than a century ago [1].…”

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confidence: 99%

Rational Synthesis of Some New para-Aminobenzoic Acid Hybrids with Thiazolidin-2,4-diones with Antimicrobial Properties. ADMET and molecular docking evaluation

Marc¹,

Oniga²,

Pı̂rnău³

et al. 2019

Rev. Chim.

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The present paper presents the synthesis, physicochemical characterization, in vitro antimicrobial activity and the molecular docking study of a series of ten new thiazolidine-2,4-dione derivatives conjugated to para-aminobenzoic acid (PABA). The lipophilicity of the new molecules was evaluated in silico. Quantitative elemental C, H, N, S analysis and spectral data (mass spectrometry, infrared and nuclear magnetic resonance) were consistent with the expected data. The results of the antimicrobial activity screening revealed that some of the synthesized compounds had moderate to good activity against E. coli ATCC 25922, S. aureus, ATCC 6538P and C. albicans ATCC 10231.

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Amino acid conjugated antimicrobial drugs: Synthesis, lipophilicity- activity relationship, antibacterial and urease inhibition activity

Cited by 43 publications

References 26 publications

Design and Synthesis of C-19 Isosteviol Derivatives as Potent and Highly Selective Antiproliferative Agents

Design and Synthesis of C-19 Isosteviol Derivatives as Potent and Highly Selective Antiproliferative Agents

Design, Synthesis and Biological Evaluation of Diosgenin-Amino Acid Derivatives with Dual Functions of Neuroprotection and Angiogenesis

Rational Synthesis of Some New para-Aminobenzoic Acid Hybrids with Thiazolidin-2,4-diones with Antimicrobial Properties. ADMET and molecular docking evaluation

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