Solid-phase total synthesis of cyclic pentapeptide Longicalycinin A, by using 2-chlorotrityl chloride resin

Ahmad, Waqar

doi:10.5897/jcreo2013.0102

Cited by 6 publications

(5 citation statements)

References 30 publications

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“…This is a potentially useful synergistic effect in cancer treatment, and thus is a sign of a promising prospect for this molecule to be used in combination with other chemotherapeutic drugs against cancer cells [41]. Another study reported that the cyclic peptide compound C25 (Figure 6 nine amino acid residues in the sequence Cys-Val-Pro-Met-Thr-Tyr-Arg-Al totoxicity against colon cancer cells (CT26), as shown through an in vivo stu Longicalcynin A (Figure 6b) is a cyclopeptide originally isolated from Dianthus superbus [52]; the peptide with its analogues were subsequently synthesized, as reported by Ahmad Waqar et al ( 2013) [42]. The cytotoxicity of the synthesized compounds was evaluated to obtain information on the structure-activity relationship of the cyclopeptides, which could lead to the discovery of new, safer anticancer agents.…”

Section: Cyclic Peptide For Colon Cancermentioning

confidence: 84%

“…Longicalcynin A ( Figure 6 b) is a cyclopeptide originally isolated from Dianthus superbus [ 52 ]; the peptide with its analogues were subsequently synthesized, as reported by Ahmad Waqar et al (2013) [ 42 ]. The cytotoxicity of the synthesized compounds was evaluated to obtain information on the structure–activity relationship of the cyclopeptides, which could lead to the discovery of new, safer anticancer agents.…”

Section: Cyclic Peptides For Cancermentioning

confidence: 99%

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Cyclic Peptides for the Treatment of Cancers: A Review

et al. 2022

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Cyclic peptides have been widely reported to have therapeutic abilities in the treatment of cancer. This has been proven through in vitro and in vivo studies against breast, lung, liver, colon, and prostate cancers, among others. The multitude of data available in the literature supports the potential of cyclic peptides as anticancer agents. This review summarizes the findings from previously reported studies and discusses the different cyclic peptide compounds, the sources, and their modes of action as anticancer agents. The prospects and future of cyclic peptides will also be described to give an overview on the direction of cyclic peptide development for clinical applications.

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Section: Cyclic Peptide For Colon Cancermentioning

confidence: 84%

Section: Cyclic Peptides For Cancermentioning

confidence: 99%

Cyclic Peptides for the Treatment of Cancers: A Review

et al. 2022

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“…We designed different amino acids for each position of diversities R1, R2, R3, R4 and R5 for the synthesis of eighteen Longicalycinin A analogues, based on conserving lipophilic characteristic of peptides (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18). Thus, we chose Ala, Val and Gly for position R1, Phe and Ala for position R2, Pro for position R3, Tyr (t-Bu), Ser(t-Bu) and Thr(t-Bu) for position R4 and Gly, Leu and Phe for position R5 in the first category.…”

Section: Designing Linear Peptides Of Longicalycinin a Analoguesmentioning

confidence: 99%

“…The trityl linker allows the protected compounds to be subjected to various chemical manipulations and consequently to afford pure compounds without employing numerous purification steps. [13][14][15][16][17] Oshima et al isolated a cyclic pentapeptide Longicalycinin A [cyclo-(Gly-Phe-Pro-Tyr-Phe)] from the plant Dianthus superbus var. Longicalycinus which has been used for treating carcinoma, diuretic and inflammatory diseases.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Linear and cyclic peptides analogues of Longicalycinin A and evaluation of toxicity effects on cancerous cells HepG2 and HT-29

Gholibeikian,

HoushdarTehrani,

Bamoniri

2022

IJID

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In this work, linear and cyclic peptides analogues of Longicalycinin A, known as a natural cyclopeptide anticancer agent, have been designed and successfully synthesized by solid phase peptide synthesis methodology of Fmoc/t-Bu. 2-Chlorotrityl chloride resin (2-CTC) was used as solid support. The synthesized linear (Ot-Bu) Longicalycinin A analogues were cleavaged by the method of partial cleavage for the separation of the solid phase. The final deprotection was performed by treatment with TFA 95% containing scavengers to achieve deprotected linear Longicalycinin A analogues. Macrocyclization of deprotected cyclic Longicalycinin A analogues were characterized by different instrumental methods using FT-IR, LC-MS, 1H-NMR and 13C-NMR. Deprotected linear and cyclic analogues, synthesized as such, were evaluated for their toxic activity against cell lines of HepG2 (human liver cancer cell line) and HT-29 (human colorectal adenocarcinoma cell line) using MTT assay. The synthetic linear and cyclic analogues showed relatively good activity against cell lines of HepG2 and HT-29 with IC50 values from 8.76 to 17.2 µg/mL and 9.06 to 17.34µg/mL, respectively, in comparison to standard drug 5-fluorouracil (5-FU). Safety profile of the synthesized liner and cyclic analogues of Longicalycinin A were also examined using skin Fibroblast cells. Among the linear peptides, linear compounds 1, 8, 12, 13 and 14, showed a considerable toxicity activity on cancer cell lines HT-29 than HepG2 along with a high safety on normal cells and among the cyclic peptides, compound 5, considering the property of toxicity action good enough on cancerous cell lines along with high safety profile on normal skin cells, can be good candidates for developing new anticancer agents

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“…This compound had been successfully synthesized by the solid-phase methodology. When acting against in vitro Dalton’s lymphoma ascites (DLA) and Enrlich’s ascites carcinoma (EAC) cells, CTC 50 values were determined to be 2.62 and 6.17 µM, respectively [ 132 ]. In the study of Tehrani et al, they demonstrated that the synthesized linear and cyclic disulfide heptapeptides of longicalycinin A showed similar inhibitory effect against HepG2 (IC 50 = 16.97 and 16.91 µM, respectively) and HT29 (IC 50 = 20.38 and 27.68 µM, respectively) cells.…”

Section: Terrestrial Plant-derived Anticancer Cyclopeptidesmentioning

confidence: 99%

Natural Cyclopeptides as Anticancer Agents in the Last 20 Years

Zhang

Xia

Zhang

2021

IJMS

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Cyclopeptides or cyclic peptides are polypeptides formed by ring closing of terminal amino acids. A large number of natural cyclopeptides have been reported to be highly effective against different cancer cells, some of which are renowned for their clinical uses. Compared to linear peptides, cyclopeptides have absolute advantages of structural rigidity, biochemical stability, binding affinity as well as membrane permeability, which contribute greatly to their anticancer potency. Therefore, the discovery and development of natural cyclopeptides as anticancer agents remains attractive to academic researchers and pharmaceutical companies. Herein, we provide an overview of anticancer cyclopeptides that were discovered in the past 20 years. The present review mainly focuses on the anticancer efficacies, mechanisms of action and chemical structures of cyclopeptides with natural origins. Additionally, studies of the structure–activity relationship, total synthetic strategies as well as bioactivities of natural cyclopeptides are also included in this article. In conclusion, due to their characteristic structural features, natural cyclopeptides have great potential to be developed as anticancer agents. Indeed, they can also serve as excellent scaffolds for the synthesis of novel derivatives for combating cancerous pathologies.

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Solid-phase total synthesis of cyclic pentapeptide Longicalycinin A, by using 2-chlorotrityl chloride resin

Cited by 6 publications

References 30 publications

Cyclic Peptides for the Treatment of Cancers: A Review

Cyclic Peptides for the Treatment of Cancers: A Review

Synthesis of Linear and cyclic peptides analogues of Longicalycinin A and evaluation of toxicity effects on cancerous cells HepG2 and HT-29

Natural Cyclopeptides as Anticancer Agents in the Last 20 Years

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