Zarys historii syntezy leków ze szczególnym uwzględnieniem leków przeciwnowotworowych i przeciwbakteryjnych

Joanna Warguła

doi:10.56782/pps.121

Published : 2022-11-08

Vol. 20 No. 3 (2022)

Outline of the history of drug synthesis with particular emphasis on anticancer and antibacterial drugs

Joanna Warguła

DOI: https://doi.org/10.56782/pps.121

Abstract

The paper presents a historical outline of the development of drugs from the earliest times to the present, trying to take into account the path that has come from learning about the medicinal properties of the raw material, through the identification of specific active compounds isolated from it, to the identification of a biological target. On the example of the synthesis of the first chemical medicaments, the research directions and reasoning of the scientists of that time were indicated. By discussing the history of antimicrobials, the pathway from Fleming's accidental discovery to the organic synthesis of compounds with non-antimicrobial biological activity was outlined. This fact overlaps with the history of the development of anti-cancer drugs, which was discussed in terms of the main mechanisms of action.

Keywords:

synthesis, antibacterial drugs, anticancer drugs

Details

References

Statistics

Authors

Download files

PDF (Język Polski)

Citation rules

Warguła, J. (2022). Outline of the history of drug synthesis with particular emphasis on anticancer and antibacterial drugs. Prospects in Pharmaceutical Sciences, 20(3), 1–10. https://doi.org/10.56782/pps.121

Altmetric indicators

Cited by / Share

Licence

This work is licensed under a Creative Commons Attribution 4.0 International License.

References

Brzeziński, T.; Historia medycyny, Wyd. II; Wydawnictwo Lekarskie PZWL, Warszawa, Polska, 1995; ISBN 83-200-184-3.

Jesus, A.; Bonhomme, V.; Evin, A.; Ivorra, S.; Soteras, R.; Salavert, A.; Antolín, F.; Bouby L. A morphometric approach to track opium poppy domestication. Sci. Rep. 2021, 11, Art. No. 9778. https://doi.org/10.1038/s41598-021-88964-4. DOI: https://doi.org/10.1038/s41598-021-88964-4

Legrain, L. Royal Inscriptions and Fragments from Nippur and Babylon. The Museum of the University of Pennsylvania 1926, XV.

Arabas, I. Z dziejów aptekarstwa. Czy Galen był aptekarzem? Aptekarz Polski 2011, 61/39, 46–49.

Widelski, J. Medycyna arabska. Aptekarz Polski 2009, 36/14. Available online: https://www.aptekarzpolski.pl/wiedza/08-2009-mak-lekarski-i-opium/ (accessed on 13.10.2022).

Borucka, M. Wybrane osiągnięcia cywilizacji arabsko-muzułmańskiej. NURT SVD, 2013, Wydanie specjalne 2013, 85-91.

Szumowski, W. Historia medycyny filozoficznie ujęta, 1st. ed.; Wydawnictwo Marek Derewecki, Kraków, Polska, 1935.

Stawarz, N. Alchemia: klucz do wszechwiedzy. Available online: https://histmag.org/Alchemia-klucz-do-wszechwiedzy-18940 (accessed on 13.10.2022).

Małecka, E. Zanim pojawiła się chemia. Available online: http://docplayer.pl/10767070-Zanim-pojawila-sie-chemia.html (accessed on 13.10.2022).

Favier, J. Wielkie odkrycia od Aleksandra do Magellana, 1st ed.; Oficyna Wydawnicza Volumen, Warszawa, Polska, 1996.

Boyle, R. The Sceptical Chymist; 1st ed., J. Caldwell, Londyn, Anglia, 1661.

Jędrusiak, M. Kilka słów o flogistonie, czyli o tym, jak błędna teoria przyniosła nauce wiele pożytku. Available online: http://www.deltami.edu.pl/temat/roznosci/historia_i_filozofia/2016/12/27/Kilka_slow_o_flogistonie/ (accessed on 13.10.2022).

Carl-Wilhelm-Scheele. Available online: https://www.britannica.com/biography/Carl-Wilhelm-Scheele (accessed on 13.10.2022).

Marggraf Andreas Sigismund. Available online: https://encyklopedia.pwn.pl/haslo/Marggraf-Andreas-Sigismund;3937731.html (accessed on 13.10.2022).

Krishnamurti, C.; Chakra Rao SSC, The isolation of morphine by Serturner. Indian J. Anaesth. 2016, 60 (11), 861–862. DOI: https://doi.org/10.4103/0019-5049.193696

Friedrich C., von Domarus C. Carl Friedrich Wilhelm Meissner (1792–1853) – Apotheker und Alkaloidforscher. Die Pharmazie 1998, 53, 67–73.

Leung, A.M.; Braverman, L.E.; Pearce, E.N. History of U.S. Iodine Fortification and Supplementation, Nutrients 2012, 4 (11), 1740–1746. doi: 10.3390/nu4111740. DOI: https://doi.org/10.3390/nu4111740

Abel, A. The history of dyes and pigments: from natural dyes to high performance pigments. In COLOUR DESIGN: THEORIES AND APPLICATIONS, 2nd ed.; Best, J. Eds.; Woodhead Publishing, Sawston, Wielka Brytania, 2012; pp. 557-587. DOI: https://doi.org/10.1016/B978-0-08-101270-3.00024-2

Kinne-Saffran, E.; Kinne, R.K. Vitalism and synthesis of urea. From Friedrich Wöhler to Hans A. Krebs. Am. J. Nephrol. 1999, 19 (2), 290-294. doi: 10.1159/000013463. DOI: https://doi.org/10.1159/000013463

van den Belt, H. Why Monopoly Failed: The Rise and Fall of Société La Fuchsie. Br. J. Hist. Sci. 1992, 25 (1), 45-63. DOI: https://doi.org/10.1017/S0007087400045325

Caro, H. XVII. On the formation of rosolic acid and rosaniline. Lond. Edinb. Dublin Philos. Mag. J. Sci. 1866, 4 (32), 126-132. https://doi.org/10.1080/14786446608644138. DOI: https://doi.org/10.1080/14786446608644138

Corbeil, M-C.; Charland, J-P.; Moffatt, E.A. The Characterization of Cobalt Violet Pigments. Stud. Conserv. 2002, 47 (4), 237-249. DOI: https://doi.org/10.1179/sic.2002.47.4.237

Kirimura, K.; Gunji, H.; Wakayama, R.; Hattori, T.; Ishii, Y. Enzymatic Kolbe-Schmitt reaction to form salicylic acid from phenol: enzymatic characterization and gene identification of a novel enzyme, Trichosporon moniliiforme salicylic acid decarboxylase. Biochem. Biophys. Res. Commun. 2010, 394 (2), 279-284. doi: 10.1016/j.bbrc.2010.02.154. DOI: https://doi.org/10.1016/j.bbrc.2010.02.154

Smith, P.W.G.; Tatchell A.R. Phenols In Aromatic Chemistry: Organic Chemistry for General Degree Students, 1st. ed., Pergamon, Oxford, Wielka Brytania, 1969; pp. 79-104. DOI: https://doi.org/10.1016/B978-0-08-012948-8.50008-5

Marson, P.; Pasero, G. The Italian contributions to the history of salicylates. Reumatismo 2006, 8 (1), 66-75. doi: 10.4081/reumatismo.2006.66. DOI: https://doi.org/10.4081/reumatismo.2006.66

Sneader, W. The discovery of aspirin: a reappraisal. BMJ 2000, 32 (7276), 1591–1594. doi: 10.1136/bmj.321.7276.1591. DOI: https://doi.org/10.1136/bmj.321.7276.1591

Rinsema, T.J. One Hundred Years of Aspiryn. Med. Hist. 1999, 43, 502-507. DOI: https://doi.org/10.1017/S0025727300065728

Renslo, A.R. Antimalarial Drug Discovery: From Quinine to the Dream of Eradication. ACS Med. Chem. Lett. 2013, 4 (12), 1126-1128. doi: 10.1021/ml4004414. DOI: https://doi.org/10.1021/ml4004414

Greenwood, D. The quinine connection. J. Antimicrob. Chemother. 1992, 30 (4), 417-427. doi: 10.1093/jac/30.4.417 DOI: https://doi.org/10.1093/jac/30.4.417

Schweitzer, H. The Influence of Sir William Henry Perkin's Discovery Upon Our Science. Science 1906, 24 (6), 481-488. DOI: https://doi.org/10.1126/science.24.616.481

Podlewski, J.K.; Chwalibogowska-Podlewska, A. Leki współczesnej terapii, 17 ed.; Split Trading, Warszawa, Polska, 2005. ISBN 83-85632-82-4.

Schultz, M.P. The use of amidopiryne in rheumatic fever. Arch Intern Med (Chic) 1931, 48 (6), 1138-1155. doi:10.1001/archinte.1931.00150070076006. DOI: https://doi.org/10.1001/archinte.1931.00150070076006

Otterness, I.G. The Discovery of Drugs to Treat Arthritis: A Historical View In The Search for Anti-Inflammatory Drugs, Merluzzi, V.J., Adams, J. Eds.; Birkhäuser, Szwajcaria, 2012, pp. 1-26. DOI: https://doi.org/10.1007/978-1-4615-9846-6_1

Petermann, H.; Goerig, M. History of anesthesia: From narcosis to perioperative homeostasis. Anaesthesist 2016, 65 (10), 787-808. doi: 10.1007/s00101-016-0223-y. DOI: https://doi.org/10.1007/s00101-016-0223-y

Robinson, D.H.; Toledo, A.H. Historical development of modern anesthesia. J. Invest. Surg. 2012, 25 (3), 141-149. doi: 10.3109/08941939.2012.690328. DOI: https://doi.org/10.3109/08941939.2012.690328

Butler, T.C. The introduction of chloral hydrate into medical practice. Bull. Hist. Med., 1970, 44 (2), 168-172.

Johnson, A.S. Paraldehyde for the Control of Pain and Convulsive States. N. Engl. J. Med. 1934, 210, 1065-1067. doi: 10.1056/NEJM193405172102005. DOI: https://doi.org/10.1056/NEJM193405172102005

Maruta, H. From chemotherapy to signal therapy (1909-2009): A century pioneered by Paul Ehrlich. Drug Discov. Ther. 2009, 3 (2), 37-40.

Gelpi, A.; Gilbertson, A.; Tucker, J.D. Magic bullet: Paul Ehrlich, Salvarsan and the birth of venereology. Sex. Transm. Infect. 2015, 91 (1), 68–69. doi: 10.1136/sextrans-2014-051779. DOI: https://doi.org/10.1136/sextrans-2014-051779

Farmacja Współczesna, Nr 3, Warszawa, 1938 r. online: https://jbc.bj.uj.edu.pl/Content/325241/PDF/NDIGCZAS013803_1938.pdf (accessed on 17.10.2022)

Marriott, H.L. Sulphapyridine And Pneumococcal Infections. Br. Med. J. 1939, 2 (4114), 944-947. DOI: https://doi.org/10.1136/bmj.2.4114.944

Rouf, A.; Tanyeli, C. Bioactive thiazole and benzothiazole derivatives, Eur. J. Med. Chem. 2015, 97, 911-927. doi:10.1016/j.ejmech.2014.10.058. DOI: https://doi.org/10.1016/j.ejmech.2014.10.058

Smyth, C.J.; Finkelstein, M.B.; Gould, S.E.; Koppa, M.D.; Leeder, F.S. Acute Bacillary Dysentery (Flexner): Treatment with Sulfaguanidine and Succinylsulfathiazole. J. Am. Med. Ass. 1943, 121 (17), 1325–1330. doi:10.1001/jama.1943.02840170009003. DOI: https://doi.org/10.1001/jama.1943.02840170009003

Potty, V.H.; Tamhane, D.V. Action of Sulfanilamide on Ochromonas malhamensis, J. Protozoology 1968, 15 (2), 262-268. https://doi.org/10.1111/j.1550-7408.1968.tb02120.x. DOI: https://doi.org/10.1111/j.1550-7408.1968.tb02120.x

Tan, S.Y.; Tatsumura, Y. Alexander Fleming (1881–1955): Discoverer of penicillin. Singapore Med J. 2015, 56 (7), 366–367. doi: 10.11622/smedj.2015105. DOI: https://doi.org/10.11622/smedj.2015105

Lobanovska, M.; Pilla, G. Penicillin’s Discovery and Antibiotic Resistance: Lessons for the Future? Yale J. Biol. Med. 2017, 90 (1), 135–145.

Ory, E.M; Meads, M.; Finland, M. Penicillin x: comparison with penicillin G with respect to sensitivity of pathogenic organism and serum level. JAMA 1945, 129 (4), 257-261. doi:10.1001/jama.1945.02860380015004. DOI: https://doi.org/10.1001/jama.1945.02860380015004

Oral Administration of Penicillin. N. Engl. J. Med. 1955, 253, 789-790. doi: 10.1056/NEJM195511032531811. DOI: https://doi.org/10.1056/NEJM195511032531811

Batchelor, F.R.; Doyle, F.P.; Nayler, J.H.C.; Rolinson, G.N. 6-Aminopenicillanic Acid in Penicillin Fermentations. Nature 1959, 183, 257–258. DOI: https://doi.org/10.1038/183257b0

Streptomycin. Available online: https://www.britannica.com/science/streptomycin (accessed on 09.11.2021).

Ehrlich, J.; Gottlieb, D.; Burkholder, P.R.; Anderson, L.E.; Pridham, T.G. Streptomyces venezuelae, n. sp., the source of chloromycetin. J. Bacteriol. 1948, 56 (4), 467-477. doi: 10.1128/jb.56.4.467-477.1948. DOI: https://doi.org/10.1128/jb.56.4.467-477.1948

Duggar, B.M. Aureomycin; a product of the continuing search for new antibiotics, Ann. N. Y. Acad. Sci. 1948, 51 (Art. 2), 177-181. doi: 10.1111/j.1749-6632.1948.tb27262.x. DOI: https://doi.org/10.1111/j.1749-6632.1948.tb27262.x

Boothe, J.H.; Morton, J.; Petisi, J.P.; Wilkinson, R.G.; Williams, J.H. Tetracycline. J. Am. Chem. Soc. 1953, 75 (18), 4621. https://doi.org/10.1021/ja01114a535. DOI: https://doi.org/10.1021/ja01114a535

Finlay, A.C.; Hobby, G.L.; P'an, S.Y.; Regna, P.P.; Routien, J.B.; Seeley, D.B.; Shull, G.M.; Sobin, B.A.; Solomons, I.A.; Vinson, J.W.; Kane, J.H. Terramycin, a new antibiotic. Science 1950, 111 (2874), 85. doi: 10.1126/science.111.2874.85. DOI: https://doi.org/10.1126/science.111.2874.85-a

Harned, R.L.; Hidy, P.H.; La Baw, E.K. Cycloserine. I. A preliminary report, Antibiot. Chemother. (Northfield), 1955, 5 (4), 204-205.

Umezawa, H.; Ueda, M.; Maeda, K.; Yagishita, K.; Kondō, S.; Okami, Y.; Utahara, R.; Ōsato, Y.; Nitta, K.; Takeuchi, T. Production and isolation of a new antibiotic: kanamycin. J Antibiot (Tokyo) 1957, 10 (5), 181-188.

Weinstein, M.J.; Leudemann, G.M.; Oden, E.M.; Wagman, G.H. Gentamycin, a new broad-spectrum antibiotic complex. Antimicrob. Agents Chemother. (Bethesda) 1963, 161, 1-7.

Umezawa, H.; Takeuchtti, T.; Nitta, K.; Yamamoto, T.; Yamakoka, S. Sarkomycin, an anti-tumor substance produced by streptomyces. J. Antibiot. (Tokyo) 1953, 6 (2), 101.

Bo, G. Giuseppe Brotzu and the discovery of cephalosporins. CMI Clin. Microbiol. Infect. 2000, 6 (3), 6-8. DOI: https://doi.org/10.1111/j.1469-0691.2000.tb02032.x

Lodger, B.; Newton, G.G.; Abraham, E.P. The cephalosporin C nucleus (7-aminocephalosporanic acid) and some of its derivatives. Biochem. J. 1961, 79 (2), 408-416. doi: 10.1042/bj0790408. DOI: https://doi.org/10.1042/bj0790408

Kahan, J.S.; Kahan, F.M.; Goegelman, R.; Currie, S.A.; Jackson, M.; Stapley, E.O.; Miller, T.W.; Miller, A.K.; Hendlin, D.; Mochales, S.; Hernandez, S.; Woodruff, H.B.; Birnbaum, J. Thienamycin, a new beta-lactam antibiotic. 1. Discovery, taxonomy, isolation ad physical properties. J. Antibiot. 1979, 32 (1), 1-12. DOI: https://doi.org/10.7164/antibiotics.32.1

Hotchkiss, R.D.; Dubos, R. Bactericidal fractions from an aerobic sporulating bacillus. J. Biol. Chem. 1940, 136 (3), 803–804. DOI: https://doi.org/10.1016/S0021-9258(18)73041-X

Waksman, S.A.; Geiger, W.B.; Reynolds, D.M. Strain Specificity and Production of Antibiotic Substances: VII. Production of Actinomycin by Different Actinomycetes. Proc. Natl. Acad. Sci. USA. 1946, 32 (5), 117-120. doi: 10.1073/pnas.32.5.117. DOI: https://doi.org/10.1073/pnas.32.5.117

Bagnicka, E.; Jóźwik, A.; Strzałkowska, N.; Krzyżewski J.; Zwierzchowski, L. Antimicrobial peptides - outline of the history of studies and mode of action. Medycyna Weterynaryjna – Vet. Med-Sci Prac. 2011, 67 (7), 444-448.

Habermann, E.; Reiz, K.G. On the biochemistry of bee venom peptides, melittin and apamin. Biochem. Z. 1965, 343 (2), 192-203.

Akari, K.; Tachibana, S.; Uchiyama, M.; Nakajima, T.; Yasuhara, T. Isolation and Structure of a New Active Peptide Xenopsin on Rat Stomach Strip and Some Biogenic Amines in the Skin of Xenopus laevis. Chem. Pharm. Bull. 1975, 23 (12), 3132-3140. https://doi.org/10.1248/cpb.23.3132. DOI: https://doi.org/10.1248/cpb.23.3132

Hultmark, D.; Engström, A.; Bennich, H.; Kapur, R.; Boman, H.G. Insect immunity: isolation and structure of cecropin D and four minor antibacterial components from Cecropia pupae. Eur. J. Biochem. 1982, 127 (1), 207-217. doi: 10.1111/j.1432-1033.1982.tb06857.x. DOI: https://doi.org/10.1111/j.1432-1033.1982.tb06857.x

Neomycin. Available online: https://www.britannica.com/science/neomycin (accessed on 10.11.2021)

Weinstein, M.J.; Marquez, J.A.; Testa, R.T.; Wagman, G.H.; Oden, E.M.; Waitz, J.A. Antibiotic 6640, a new Micromonospora-produced aminoglycoside antibiotic. J. Antibiot. 1970, 23 (11), 551–554. doi:10.7164/antibiotics.23.551. DOI: https://doi.org/10.7164/antibiotics.23.551

Fischer, J.; Ganellin, C.R. Analogue-based Drug Discovery; John Wiley & Sons, 2006. pp. 507. ISBN 9783527607495. DOI: https://doi.org/10.1002/3527608001

Doxycycline. Available online: https://go.drugbank.com/drugs/DB00254 (accessed on 13.10.2022).

Shukla, S.J.; Sakamuru, S.; Huang, R.; Moeller, T.A.; Shinn, P.; Vanleer, D.; Auld, D.S.; Austin, C.P.; Xia, M. Identification of clinically used drugs that activate pregnane X receptors. Drug Metab. Dispos. 2011, 39 (1), 151–159. DOI: https://doi.org/10.1124/dmd.110.035105

Patent US 2653899. Bunch R.L.; Mcguire J.M. Erythromycin, its salts, and method of preparation, Eli Lilly and Company.

Jelic, D.; Antolovic, R. From Erythromycin to Azithromycin and New Potential Ribosome-Binding Antimicrobials. Antibiotics (Basel) 2016, 5 (3), Art. No. 29. doi: 10.3390/antibiotics5030029. DOI: https://doi.org/10.3390/antibiotics5030029

Puri, S.K.; Lassman, H.B. Roxithromycin: a pharmacokinetic review of a macrolide. J. Antimicrob. Chemother. 1987, 20 Suppl B, 89-100. doi: 10.1093/jac/20.suppl_b.89. DOI: https://doi.org/10.1093/jac/20.suppl_B.89

Greenwood, D. Antimicrobial drugs: chronicle of a twentieth century medical triumph, 1 ed., Oxford University Press, Oxford, pp. 239. ISBN 9780199534845.

Mac Load, A.J.; Ross, H.B.; Ozere, R.L.; Digout, G.; van Rooyen, C.E. Lincomycin: A New Antibiotic Active Against Staphylococci and Other Gram-Positive Cocci: Clinical and Laboratory Studies. Can. Med. Assoc. J., 1964, 91, 1056–1960.

Smieja, M. Current indications for the use of clindamycin: A critical review. Can. J. Infect. Dis. 1998, 9 (1), 22–28. doi: 10.1155/1998/538090. DOI: https://doi.org/10.1155/1998/538090

Hall, T.C. Chemotherapy of Cancer. N. Engl. J. Med. 1962, 266, 129-134. doi: 10.1056/NEJM196201182660306. DOI: https://doi.org/10.1056/NEJM196201182660306

The Science Behind Radiation Therapy. Available online: https://www.cancer.org/content/dam/CRC/PDF/Public/6151.00.pdf (accessed on 13.10.2022).

Radium - a key element in early cancer treatment. Available online: https://www.rsc.org/images/Dronsfield_tcm18-200827.pdf (accessed on 13.11.2022).

Bonadonna, G. Does chemotherapy fulfill its expectations in cancer treatment? Ann. Oncol. 1990, 1 (1), 11-21. doi: 10.1093/oxfordjournals.annonc.a057665. DOI: https://doi.org/10.1093/oxfordjournals.annonc.a057665

Colvin, M. Alkylating Agents In Holland-Frei Cancer Medicine. 6th ed.; Kufe, D.W., Pollock, R.E., Weichselbaum, R.R., Bast, R.C.Jr., Gansler, T.S., Holland, J.F., Frei, E., Eds.; Hamilton (ON): BC Decker; Ontario, Kanada, 2003.

Goldman, R.; Egeberg, R.O.; Ware, E.R.; Evans, E.R.; Fishkin, B.G., Clinical experience with nitrogen mustard therapy. Arch. Intern. Med. (Chic) 1948, 82 (2), 125-139. doi: 10.1001/archinte.1948.00220260015002. DOI: https://doi.org/10.1001/archinte.1948.00220260015002

Spurr, C.L.; Smoth, T.R.; Block, M.; Jacobson, L.O. The role of nitrogen mustard therapy in the treatment of lymphomas and leukemias. Am. J. Med. 1950, 8 (6), 710-723. https://doi.org/10.1016/0002-9343(50)90095-7. DOI: https://doi.org/10.1016/0002-9343(50)90095-7

Goodman, J.; Walsh, V. The Story of Taxol: Nature and Politics in the Pursuit of an Anti-Cancer Drug, Cambridge University Press, Wielka Brytania, 2001. ISBN 978-0-521-56123-5.

Taxol® (NSC 125973). Available online: https://dtp.cancer.gov/timeline/flash/success_stories/s2_taxol.htm (accessed on 13.10.2022)

Malik, S.; Cusidó, R.M.; Mirjalili, M.H.; Moyano, E.; Palazón, J.; Bonfil, M. Production of the anticancer drug taxol in Taxus baccata suspension cultures: A review. Proc. Biochem. 2011, 46 (1), 23-34. https://doi.org/10.1016/j.procbio.2010.09.004. DOI: https://doi.org/10.1016/j.procbio.2010.09.004

Talebi, M.; Ghassempour, A.; Talebpour, Z.; Rassouli, A.; Dolatyari, L. Optimization of the extraction of paclitaxel from Taxus baccata L. by the use of microwave energy. J. Sep. Sci. 2004, 27 (13), 1130-1136. doi: 10.1002/jssc.200401754. DOI: https://doi.org/10.1002/jssc.200401754

van Hoesel, Q.G.C.M.; Verweij, J.; Catimel, G.; Clavel, M.; Kerbrat, P.; van Oosterom, A.T.; Kerger, J.; Tursz, T.; van Glabbeke, M.; van Pottelsberghe, C.; le Bail, N.; Mouridsen, H. Phase II study with Docetaxel (Taxotere®) in advanced soft tissue sarcomas of the adult. Ann. Oncol. 1994, 5, 539-542. DOI: https://doi.org/10.1093/oxfordjournals.annonc.a058909

Lavelle, F.; Gueritte-Voegelein, F.; Guenard, D. Taxotere: from yew's needles to clinical practice. Bull. Cancer 1993, 80 (4), 326-338.

Noble, R.L.; Beer, C.T.; Cutts, J.H. Role of chance observations in chemotherapy: Vinca rosea. Ann NY Acad Sci 1958, 76, 882-894. DOI: https://doi.org/10.1111/j.1749-6632.1958.tb54906.x

Svoboda, G.H.; Neuss, N.; Gorman, M. Alkaloids of Vinca rosea Linn. (Catharanthus roseus G. Don.) V. Preparation and characterization of alkaloids. J. Am. Pharm. Ass. 1959, 48 (11), 659-666. https://doi.org/10.1002/jps.3030481115. DOI: https://doi.org/10.1002/jps.3030481115

Wall, M.E.; Wani, M.C.; Cook, C.E.; Palmer, K.H.; McPhail, A.T.; Sim, G.A. Plant Antitumor Agents. I. The Isolation and Structure of Camptothecin, a Novel Alkaloidal Leukemia and Tumor Inhibitor from Camptotheca acuminate. J. Am. Chem. Soc. 1966, 88 (16), 3888–3890. https://doi.org/10.1021/ja00968a057. DOI: https://doi.org/10.1021/ja00968a057

Di Marco, A.; Gaetani, M.; Dorigotti, L; Soldati, M.; Bellini, O. Daunomycin: A New Antibiotic with Antitumor Activity. Tumori J. 1963, 49 (3), 203-217. https://doi.org/10.1177/030089166304900305. DOI: https://doi.org/10.1177/030089166304900305

Wang, J.C. Interaction between DNA and an Escherichia coli protein omega. J. Mol. Biol. 1971, 55 (3), 523-533. doi: 10.1016/0022-2836(71)90334-2. DOI: https://doi.org/10.1016/0022-2836(71)90334-2

Gellert, M.; O'Dea, M.H.; Itoh, T.; Tomizawa, J. Novobiocin and coumermycin inhibit DNA supercoiling catalyzed by DNA gyrase. Proc. Natl. Acad. Sci. USA. 1976, 73 (12), 4474-4478. doi: 10.1073/pnas.73.12.4474. DOI: https://doi.org/10.1073/pnas.73.12.4474

Mastrangelo, S.; Attina, G.; Triarico, S.; Romano, A.; Maurizi, P.; Ruggiero, A. The DNA-topoisomerase Inhibitors in Cancer Therapy. Biomed. Pharmacol. J. 2022, 15 (2), 553-562. DOI: https://doi.org/10.13005/bpj/2396

Hata, T.; Hoshi, T.; Kanamori, K.; Matsumae, A.; Sano, Y.; Shima, T.; Sugawara, R. Mitomycin, a new antibiotic from Streptomyces. I. J. Antibiot. (Tokyo) 1956, 9 (4), 141-146.

Umezawa, H.; Maeda, K.; Takeuchi, T.; Okami, Y. New antibiotics, bleomycin A and B. J. Antibiot. (Tokyo) 1966, 19 (5), 200-209.

Dubost, M.; Ganter, P.; Maral, R.; Ninet, L.; Pinnert, S.; Preudhomme, J.; Werner, G.H. Rubidomycin: a new antibiotic with cytostatic properties. C R Hebd Seances Acad. Sci. 1963, 257, 1813-1815.

Daunorubicin. Available online: https://go.drugbank.com/drugs/DB00694 (accessed on 17.10.2022)

Nakano, I.; Soe, C.Z.; Codd, R. Isolation of doxorubicin from a bacterial culture using immobilised metal ion affinity chromatography. RSC Advances, 2015, 5(58), 46437-46442. DOI: https://doi.org/10.1039/C5RA07639K

Bonfante, V.; Bonadonna, G.; Villani, F.; Mrtini, A. Preliminary clinical experience with 4-epidoxorubicin in advanced human neoplasia. Rec. Res. Cancer Res. 1980, 74, 192-199. doi:10.1007/978-3-642-81488-4_24. DOI: https://doi.org/10.1007/978-3-642-81488-4_24

Buckley, M.M.; Lamb, H.M. Oral idarubicin. A review of its pharmacological properties and clinical efficacy in the treatment of haematological malignancies and advanced breast cancer. Drugs Aging 1997, 11 (1), 61-86. doi: 10.2165/00002512-199711010-0000. DOI: https://doi.org/10.2165/00002512-199711010-00006

White, R.J.; Durr, F.E. Development of mitoxantrone. Invest. New Drugs 1985, 3 (2), 85-93. doi: 10.1007/BF00174154. DOI: https://doi.org/10.1007/BF00174154

Farber, S.; Diamond, L.K.; Mercer, R.D.; Sylvester, R.F. Jr.; Wolff, J.A. Temporary Remissions in Acute Leukemia in Children Produced by Folic Acid Antagonist, 4-Aminopteroyl-Glutamic Acid (Aminopterin). N. Engl. J. Med. 1948, 238, 787-793. doi: 10.1056/NEJM194806032382301. DOI: https://doi.org/10.1056/NEJM194806032382301

Weinblatt, M.E. Methotrexate in Rheumatoid Arthritis: A Quarter Century of Development. Trans. Am. Clin. Climatol. Assoc. 2013, 124, 16–25.

Huennekens, F.M. The methotrexate story: a paradigm for development of cancer chemotherapeutic agents. Adv. Enzyme Regul. 1994, 34, 397-419. doi: 10.1016/0065-2571(94)90025-6. DOI: https://doi.org/10.1016/0065-2571(94)90025-6

Manegold, C. Pemetrexed (Alimta, MTA, multitargeted antifolate, LY231514) for malignant pleural mesothelioma. Semin. Oncol. 2003, 30 (4 Suppl 10), 32–36. doi:10.1016/S0093-7754(03)00283-5. DOI: https://doi.org/10.1016/S0093-7754(03)00283-5

Rossi, A.; Ricciardi, S.; Maione, P.; de Marinis, F.; Gridelli, C. Pemetrexed in the treatment of advanced non-squamous lung cancer. Lung Cancer 2009, 66 (2), 141–149. doi:10.1016/j.lungcan.2009.06.006. DOI: https://doi.org/10.1016/j.lungcan.2009.06.006

Vardanyan, R.; Hruby, V. Immunopharmacological Drugs In Synthesis of Best-Seller Drugs, 1st ed., Academic Press, USA, 2016, pp. 549-572. DOI: https://doi.org/10.1016/B978-0-12-411492-0.00029-8

Antimetabolites for Cancer: Effects, Benefits, Risks. Available online: https://www.webmd.com/cancer/antimetabolite-medications-overview (accessed on 10.11.2021).

Schwartz, R.; Stack, J.; Dameshek, W. Effect of 6-mercaptopurine on antibody production. Proc. Soc. Exp. Biol. Med. 1958, 99 (1), 164–167. doi:10.3181/00379727-99-24281. DOI: https://doi.org/10.3181/00379727-99-24281

Calne, R.Y. The rejection of renal homografts. The Lancet 1960, 275 (7121), 417–418. doi:10.1016/S0140-6736(60)90343-3. DOI: https://doi.org/10.1016/S0140-6736(60)90343-3

Elion, G. The purine path to chemotherapy. Science 1989, 244 (4900), 41–47. doi:10.1126/science.2649979. DOI: https://doi.org/10.1126/science.2649979

Patel, A.A.; Swerlick, R.A.; McCall, C.O. Azathioprine in dermatology. The past, the present, and the future. J. Am. Acad. Dermatol. 2006, 55 (3), 369–389. doi:10.1016/j.jaad.2005.07.059. DOI: https://doi.org/10.1016/j.jaad.2005.07.059

Chemical structure of DNA discovered. Available online: https://www.history.com/this-day-in-history/watson-and-crick-discover-chemical-structure-of-dna (accessed on 14.10.2022).

The Discovery of the Double Helix, 1951-1953. Available online: https://profiles.nlm.nih.gov/spotlight/sc/feature/doublehelix (accessed on 14.10.2022).