{"id":41892,"date":"2021-12-30T11:16:11","date_gmt":"2021-12-30T11:16:11","guid":{"rendered":"https:\/\/biomedpharmajournal.org\/?p=41892"},"modified":"2022-01-04T07:22:29","modified_gmt":"2022-01-04T07:22:29","slug":"preparation-diagnosis-and-evaluation-of-cyclic-tryptophan-derivatives-as-anti-breast-cancer-agents","status":"publish","type":"post","link":"https:\/\/biomedpharmajournal.org\/staging\/vol14no4\/preparation-diagnosis-and-evaluation-of-cyclic-tryptophan-derivatives-as-anti-breast-cancer-agents\/","title":{"rendered":"Preparation, Diagnosis and Evaluation of Cyclic-Tryptophan Derivatives as Anti Breast Cancer Agents"},"content":{"rendered":"

Introduction<\/strong><\/p>\n

In 1901, Frederick Hopkins was able to isolate tryptophan for the first time. Hopkins extracted tryptophan from hydrolyzed casein, successfully extracting (4-8 g) of tryptophan from (600 g) of crude casein[1,2]. Tryptophan is a less common amino acid in proteins, but it plays an important structural or functional roles wherever it is found. For example, the residues tryptophan and tyrosine play special roles in ‘fixing’\u00a0membrane proteins within the cell membrane. In addition, the functions of tryptophan include being a vital precursor to compounds3-5<\/sup>., Tryptophan stimulates serotonin levels in the brain, which can treat depression and anxiety. Therefore, you can take tryptophan supplements to reduce these indications 6-8<\/sup>. Tryptophan helps increase growth hormones, so it is essential for the proper growth of children and infants. Tryptophan is used to treat insomnia, due to the presence of serotonin, which is useful for controlling sleep patterns9-11<\/sup>. People who suffer from migraines are advised to take doses of tryptophan regularly, and to\u00a0eat foods rich in tryptophan, which also helps prevent anxiety attacks, which improves a person’s reactions. It works to reduce appetite for food, because serotonin helps to make you feel satiated and reduce food intake. Thus, losing weight helps reduce diabetes and problems related to cardiovascular disease12-14<\/sup>. The body needs\u00a0tryptophan to produce niacin, which helps generate good cholesterol and lower bad cholesterol. Foods rich in tryptophan also help convert carbohydrates into energy and maintain a healthy digestive system, skin, hair and eyes15-17<\/sup>., After we absorb tryptophan from food, our bodies convert it into 5-hydroxytryptophan, an amino acid that works in the brain and central nervous system by increasing the production of the chemical\u00a0serotonin, and after our bodies convert it to this amino acid18-22<\/sup>, it then turns into serotonin, melatonin23-27<\/sup> and Vitamin B6 (nicotinamide).<\/p>\n

Some studies claim that tryptophan supplements may be effective as a sleep treatment and antidepressant. These findings are associated with its role in the synthesis of serotonin and melatonin28-30<\/sup>. Excessive\u00a0encouragement of serotonin on postsynaptic (5-HT1A and 5-HT2A) receptors at the central and peripheral levels can have negative consequences for the organism31-34<\/sup>. This is known as serotonin syndrome and can be fatal. Although this syndrome can be caused by taking medications (eg, Prozac) or using drugs (eg, LSD, MDMA, methylphenidate, bath salts…), it is not likely to be caused by the consumption of nutritional supplements35-39<\/sup>.<\/p>\n\n\n\n
\"Vol14No4_Pre_Nag_sch1\"<\/a><\/td>\nScheme 1: Trytophan<\/strong><\/p>\n

Click here to view scheme<\/a><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Experimental \u00a0Part<\/strong><\/p>\n

Because of the importance of the prepared compounds in this research that they were studied as anti-cancer agents, we were keen to provide materials with high purity and from international companies with \u00a0high technology in the production of chemicals. Also, the measurements were made on the following devices represented by \u00a0((FT-IR spectra (FT-IR 8300 Shimadzu) in \u00a0the range (400-4000) cm-1<\/sup> with KBr-discs., 1<\/sup>H.NMR\u2013Spectra with (DMSO)\u2013solvent .,besides to anti breast cancer studies.<\/p>\n

Synthesis<\/strong> Progressions\u00a08-12<\/sup><\/strong><\/p>\n

Preparation Path of\u00a0 Compound {1}<\/strong><\/p>\n

Compound {1} formatted \u00a0by reaction of \u00a0tryptophan (0.01 mole) with thiosemicarbazide (0.01 mole) \u00a0in presence of (5% of NaOH) with mechanical rotation for (16 hrs) in absolute ethanol permitting to mentioned methods8-12<\/sup>\u00a0to produce precipitation that acts compound{1},the last step ,filtered ,dried ,then recrystallized to give\u00a0 pure compound.<\/p>\n

Preparation Path of\u00a0 Compound{2}<\/strong><\/p>\n

Compound {2} formatted\u00a0 by reaction of \u00a0compound{1} (0.01 mole) with chloroacetoyl chloride (0.02 mole)\u00a0 in presence of (K2<\/sub>CO3<\/sub>) with mechanical rotation for (4 hrs) permitting to methods8-12<\/sup>\u00a0to yield\u00a0 precipitation that acts\u00a0 compound{2},the last step ,filtered ,dried ,then recrystallized to give\u00a0 pure compound.<\/p>\n

Preparation Path of\u00a0 Compound{3}<\/strong><\/p>\n

Compound {3}cyclized\u00a0 by cyclization reaction of \u00a0compound{2} (0.01 mole) with in presence of (K2<\/sub>CO3<\/sub>) with mechanical rotation and\u00a0 reflux for (6 hrs) permitting to methods8-12<\/sup>\u00a0to yield\u00a0 precipitation that acts\u00a0 compound{3},the last step ,filtered ,dried ,then recrystallized to give\u00a0 pure compound.<\/p>\n

Preparation Path of\u00a0 Compound{4}<\/strong><\/p>\n

Compound {4} formatted\u00a0 by reaction of \u00a0compound {3} (0.01 mole) with benzaldehyde (0.01 mole)\u00a0 in presence of (5% of NaOH) with mechanical rotation for (12 hrs) in absolute ethanol permitting to mentioned methods8-12<\/sup>\u00a0to produce precipitation that acts\u00a0 compound{4},the last step ,filtered ,dried ,then recrystallized to give\u00a0 pure compound.<\/p>\n

Preparation Path of\u00a0 Compound{5}<\/strong><\/p>\n

Compound{5} formatted\u00a0 by reaction of \u00a0compound{3} (0.01 mole) with \u00a0m-nitrobenzaldehyde (0.01 mole)\u00a0 in presence of (5% of NaOH) with mechanical rotation for (13 hrs) in absolute ethanol permitting to mentioned methods8-12<\/sup>\u00a0to produce precipitation that acts\u00a0 compound{5},the last step ,filtered ,dried ,then recrystallized to give\u00a0 pure compound.<\/p>\n\n\n\n
\"Vol14No4_Pre_Nag_sch2\"<\/a><\/td>\nScheme 2: Synthesis of Compounds{1 ,2 ,3}<\/strong><\/p>\n

Click here to view scheme<\/a><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

 <\/p>\n\n\n\n
\"Vol14No4_Pre_Nag_sch3\"<\/a><\/td>\nScheme 3: Synthesis of Compounds{4 , 5}<\/strong><\/p>\n

Click here to view scheme<\/a><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Results\u00a0 and\u00a0 Discussion<\/strong><\/p>\n

The prepared\u00a0 tryptophan-derivatives \u00a0have been premeditated \u00a0by different\u00a0 chemical \u00a0performances\u00a0 and\u00a0 studies \u00a0against cancerous cells:<\/p>\n

Spectral \u00a0Evidences of prepared Compounds<\/strong><\/p>\n

FT.IR- Investigation of\u00a0 Manufactured Derivatives<\/strong><\/p>\n

The bands of important \u00a0groups \u00a0in\u00a0 spectra\u00a0 provided strong evidences\u00a0 for\u00a0 new synthesized\u00a0 compound via\u00a0 disappearance\u00a0 of\u00a0 bands and\u00a0 appearance\u00a0 other\u00a0 new\u00a0 bands\u00a0 that\u00a0 point to \u00a0formation of\u00a0 the new derivatives\u00a0 that represented by :<\/p>\n

Compound {1}: appearance bands \u00a0at (3282 , 3300)Cm-1<\/sup> \u00a0due to (NH2<\/sub>) of amine group, band \u00a0at (3223)Cm-1<\/sup>\u00a0 due to (NH) of amine group in triazole\u00a0 cycle, also at \u00a0(2445)Cm-1<\/sup>\u00a0 due to (SH) of thiol group, band\u00a0 at\u00a0 (1652)Cm-1<\/sup>\u00a0due to (C=N) of endocycle\u00a0 of triazole,\u00a0 at\u00a0 (2978)Cm-1<\/sup>\u00a0 caused by (CH) aliphatic permitting to literature 16<\/sup>\u00a0.<\/p>\n

Compound {2}: appearance band \u00a0at (3369)Cm-1<\/sup>\u00a0due to (NH) of amine group in tryptophan, band\u00a0 at \u00a0(1184)Cm-1<\/sup>\u00a0due to (S-CH2<\/sub>) of sulfide group, also at (1664)Cm-1<\/sup>\u00a0caused by (C=N) of endocycle\u00a0 of triazole, band\u00a0 at\u00a0 (2918)Cm-1<\/sup>\u00a0by reason of (CH) aliphatic, at\u00a0 (792)Cm-1<\/sup>\u00a0 as a result of (C-Cl), band\u00a0 at\u00a0 (1681)Cm-1<\/sup>\u00a0 due to (C-CO) amide group.<\/p>\n

Compound {3}: appearance band at (3421)Cm-1<\/sup>\u00a0caused by (NH) of amine group in tryptophan, band\u00a0 at \u00a0(1180)Cm-1<\/sup>\u00a0due to (S-CH2<\/sub>) of sulfide group, band at (1643)Cm-1<\/sup>\u00a0down to (C=N) of endocycle\u00a0 of triazole, band at (2954)Cm-1\u00a0<\/sup>due to (CH) aliphatic, band\u00a0 at\u00a0 (1664)Cm-1<\/sup>\u00a0down to (C-CO) amide group.<\/p>\n

Compound {4}: appearance band at (3355)Cm-1<\/sup>\u00a0by reason of (NH) of amine group in tryptophan, band at (1148)Cm-1<\/sup>\u00a0due to (S-CH2<\/sub>) of sulfide group, band at (1655)Cm-1<\/sup>\u00a0due to (C=N) of endocycle\u00a0 of triazole, band\u00a0 at\u00a0 (2919)Cm-1<\/sup>\u00a0due to (CH) aliphatic, band at (1679)Cm-1<\/sup>\u00a0due to (C-CO) amide group, band\u00a0 at (3092)Cm-1<\/sup>\u00a0due to (CH=C) alkene , according to literature 16<\/sup>.<\/p>\n

Compound {5}: appearance band \u00a0at (3310)Cm-1<\/sup>\u00a0by reason of (NH) of amine group in tryptophan, band at (1133)Cm-1<\/sup>\u00a0down to (S-CH2<\/sub>) of sulfide group, at (1647)Cm-1<\/sup>\u00a0due to (C=N) of endocycle\u00a0 of triazole, band at (2906)Cm-1<\/sup>\u00a0down to (CH) aliphatic, band\u00a0 at\u00a0 (1682)Cm-1<\/sup>\u00a0down to (C-CO) amide group, band\u00a0 at (3097)Cm-1<\/sup>\u00a0down to (CH=C) alkene, bands at (1327 , 1511)Cm-1<\/sup>\u00a0 due to (NO2<\/sub>) nitro group., Other frequencies\u00a0 appeared in some figures (1 , 2) .<\/p>\n\n\n\n
\"Vol14No4_Pre_Nag_fig1\"<\/a><\/td>\nFigure 1: I.R\u00a0 Spectrum of The formatted Compound {2}<\/strong><\/p>\n

Click here to view figure<\/a><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

 <\/p>\n\n\n\n
\"Vol14No4_Pre_Nag_fig2\"<\/a><\/td>\nFigure 2: I.R -Spectrum of The formatted Compound {3}<\/strong><\/p>\n

Click here to view figure\u00a0<\/a><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

1<\/sup>H.NMR- Investigation of\u00a0 Manufactured Derivatives<\/strong><\/p>\n

The signals of important \u00a0groups\u00a0 in\u00a0 spectra\u00a0 provided strong evidences\u00a0 for\u00a0 new synthesized\u00a0 compound via\u00a0 disappearance\u00a0 of\u00a0 peaks and\u00a0 appearance\u00a0 other\u00a0 new\u00a0 peaks\u00a0 that\u00a0 point to \u00a0formation of\u00a0 the new derivatives\u00a0 that represented by : signals at (4.55 to\u00a0 5.00) due to proton of amine group (NH) ,signals at (10. 12\u00a0 to\u00a0 \u00a010. 80) due to proton \u00a0of\u00a0 amide (-NH-CO), signals\u00a0 at (6. 60-7. 95) due to protons of\u00a0 phenyl\u00a0 ring in\u00a0 compounds {2 ,3 , 4, 5}respectively, signal at (3.05) due to proton of (CO-CH2<\/sub>-S) in compounds {2 ,3}respectively , signal at (4.45) due to proton of (CH=C) of\u00a0 alkene in compounds {4 ,5}respectively permitting to literature (16)<\/sup> .,Some peaks\u00a0 in some\u00a0 figures (3, 4).\u00a0\u00a0\u00a0<\/strong><\/p>\n\n\n\n
\"Vol14No4_Pre_Nag_fig3\"<\/a><\/td>\nFigure 3: H.NMR-Spectrum of Compound{2}<\/strong><\/p>\n

Click here to view figure<\/a><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

 <\/p>\n\n\n\n
\"Vol14No4_Pre_Nag_fig4\"<\/a><\/td>\nFigure 4: H.NMR-Spectrum of Compound{4}<\/strong><\/p>\n

Click here to view figure<\/a><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Some physical and Chemical characterization:<\/strong><\/p>\n

All other physical and chemical analysis besides to some description in Table (1):\u00a0<\/strong><\/p>\n

Table 1: Some\u00a0 Physical Properties\u00a0 of New Compounds<\/strong><\/p>\n\n\n\n\n\n\n\n\n
Comps <\/strong><\/td>\nProduct\u00a0 %<\/em><\/strong><\/td>\nColor<\/em><\/strong><\/td>\nM .P ( C \u00b0 )<\/em><\/strong><\/td>\nRf<\/em><\/strong><\/td>\nSolvents (TLC)<\/em><\/strong><\/td>\n<\/tr>\n
{ 1 }<\/strong><\/td>\n82<\/td>\nOrange<\/td>\n160<\/td>\n0.64<\/td>\nEthanol : Hexane<\/td>\n<\/tr>\n
{ 2 }<\/strong><\/td>\n78<\/td>\nYellowish orange<\/td>\n182<\/td>\n0.68<\/td>\nEthanol : Hexane<\/td>\n<\/tr>\n
{ 3 }<\/strong><\/td>\n70<\/td>\nDeep\u00a0 Yellow<\/td>\n194<\/td>\n0.64<\/td>\nEthanol : Hexane<\/td>\n<\/tr>\n
{ 4 }<\/strong><\/td>\n82<\/td>\nYellowish Red<\/td>\n200<\/td>\n0.58<\/td>\nEthanol : Hexane<\/td>\n<\/tr>\n
{ 5 } <\/strong><\/td>\n80<\/td>\nBill\u00a0 Orange<\/td>\n216<\/td>\n0.60<\/td>\nEthanol : Hexane<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Analysis of derivatives with \u00a0Breast Cancer<\/strong>\u00a0<\/strong><\/strong><\/p>\n

The study was conducted to test the effectiveness of medicinal derivatives through the methods listed in the references17, 18\u00a0<\/sup>.<\/p>\n

Table 2: Mean Percentage (%) for each cell line (<\/strong>Respond to Treatment<\/strong>)<\/strong> for\u00a0 Derivative{2}.<\/strong><\/p>\n\n\n\n\n\n\n\n\n\n\n\n
Concentration of Tryptophan-Derivative [2] <\/strong><\/p>\n

\u00a0\/ \u00a0( \u00b5 g\/Ml-1<\/sup>)<\/strong><\/td>\n

MCF-7<\/strong><\/td>\nWRL<\/strong><\/td>\n<\/tr>\n
Mean<\/strong><\/td>\nSD<\/strong><\/td>\nMean<\/strong><\/td>\nSD<\/strong><\/td>\n<\/tr>\n
400<\/td>\n50.00<\/td>\n1.34<\/td>\n49.44<\/td>\n1.14<\/td>\n<\/tr>\n
200<\/td>\n63.11<\/td>\n2.21<\/td>\n27.10<\/td>\n0.65<\/td>\n<\/tr>\n
100<\/td>\n74.12<\/td>\n5.32<\/td>\n26.41<\/td>\n2.06<\/td>\n<\/tr>\n
50<\/td>\n80.13<\/td>\n4.12<\/td>\n19.03<\/td>\n0.92<\/td>\n<\/tr>\n
25<\/td>\n89.91<\/td>\n0.87<\/td>\n10.08<\/td>\n1.58<\/td>\n<\/tr>\n
12.5<\/td>\n90.80<\/td>\n0.88<\/td>\n9.34<\/td>\n2.44<\/td>\n<\/tr>\n
6.25<\/td>\n91.24<\/td>\n0.22<\/td>\n9.04<\/td>\n1.16<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

 <\/p>\n\n\n\n
\"Vol14No4_Pre_Nag_fig5\"<\/a><\/td>\nFigure 5: Effect\u00a0 of\u00a0 Tryptophan-Derivative [2] on Breast Cancer Cells<\/strong><\/p>\n

Click here to view figure<\/a><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Conclusion<\/strong><\/p>\n

The manufactured of Tryptophan-Derivative [2]\u00a0 gave multiple strong evidences about structures of compounds were stable, and all Tryptophan-Derivatives have high solubility in ethanol , DMSO, Methanol\u00a0 and other solvents. And have good activity against\u00a0 breast breast cancer cells.<\/p>\n

Acknowledgment<\/strong><\/p>\n

we would like to express our heartfelt thanks to health-Lab for providing assistance\u00a0samples of breast cancer for studying<\/p>\n

Ethical clearance<\/strong><\/p>\n

Ethics committee refer that there is no plagiarism and there is no mistakes or wrong results\u00a0 in this work.<\/p>\n

Conflict of interest<\/strong><\/p>\n

The authors declare that there is no conflict of interest.<\/p>\n

Funding source<\/strong><\/p>\n

There are no funding sources.<\/p>\n

References<\/strong><\/p>\n

    \n
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  32. Intisar Obaid Alfatlawi, Nuha S S, Zainab M J ,Nagham Mahmood Aljamali, Intisar O A. “Synthesis of New Organic Compounds Via Three Components Reaction with Studying of (Identification, Thermal Behavior, Bioactivity on Bacteria of Teeth)”., Journal of Global Pharma Technology. 2017;11,9, 157-164.<\/li>\n
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  35. Shireen R. Rasool, Nagham Mahmood Aljamali ,Ali Jassim Al-Zuhairi., Guanine substituted heterocyclic derivatives as bioactive compounds., Biochem. Cell. Arch. Vol. 20, Supplement 2, pp. 3651-3655, 2020 ., DocID: https:\/\/connectjournals.com\/03896.2020.20.3651.
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  37. Aseel Mahmood Jawad., Nagham Mahmood Aljamali, Saher Mahmood Jawd., Development and Preparation of ciprofloxacin Drug Derivatives for Treatment of Microbial Contamination in Hospitals and Environment, Indian Journal of Forensic Medicine & Toxicology, 2020 ,14, 2, p:1115-1122.<\/li>\n
  38. S FJawad, Nagham Mahmood Aljamali , Preparation, Investigation and Study of Biological Applications of Tyrosine Derivatives against Breast Cancer Cells ., NeuroQuantology ,September 2021 ,Volume 19 , Issue 9 , Page 117-125 .,doi: 10.14704\/nq.2021.19.9.NQ21144 .
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