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Kamptotecin

Kamptotecin
IUPAC ime
(S)-4-etil-4-hidroksi-1H-pirano[3',4':6,7]indolizino[1,2-b]
hinolin-3,14-(4H,12H)-dion
Identifikatori
CAS broj7689-03-4 ДаY
ATC kodnone
PubChemCID 2538
DrugBankDB04690 ДаY
ChemSpider22775 ДаY
UNIIXT3Z54Z28A ДаY
KEGGC01897 ДаY
ChEBICHEBI:27656 ДаY
ChEMBLCHEMBL65 ДаY
Hemijski podaci
FormulaC20H16N2O4
Molarna masa348,352 g/mol
  • O=C\1N4\C(=C/C2=C/1COC(=O)[C@]2(O)CC)c3nc5c(cc3C4)cccc5
  • InChI=1S/C20H16N2O4/c1-2-20(25)14-8-16-17-12(7-11-5-3-4-6-15(11)21-17)9-22(16)18(23)13(14)10-26-19(20)24/h3-8,25H,2,9-10H2,1H3/t20-/m0/s1 ДаY
  • Key:VSJKWCGYPAHWDS-FQEVSTJZSA-N ДаY

Kamptotecin (CPT) je citotoksični hinolinski alkaloid koji inhibira DNK enzim topoizomerazu I (topo I). Njega su otkrili M. E. Val i M. C. Vani 1966. putem sistematskog testiranja prirodnih proizvoda za lekove protiv kancera. On je izolovan iz kore i stabla Camptotheca acuminata, drveta koji se u tradicionalnoj kineskoj medicini koristi za lečenje kancera[1]. CPT je pokazao znatnu aktivnost protiv kancera u preliminarnim kliničkim ispitivanjima, međutim ovaj materijal ima nisku rastvorljivost i visoko izražene nepoželjne reakcije leka. Usled tih nedostataka putem sintetičke i medicinske hemije su razvijeni brojni sintetički analozi[2][3][4] sa poboljšanim svojstvima. Dva CPT analoga su odobrena i koriste se u hemoterapiji kancera:[5] topotekan i irinotekan.[6][7]

  1. ^ Efferth T, Fu YJ, Zu YG, Schwarz G, Konkimalla VS, Wink M (2007). „Molecular target-guided tumor therapy with natural products derived from traditional Chinese medicine.”. Current medicinal chemistry. 14 (19): 2024—32. 
  2. ^ „Curran Synthesis of Camptothecin”. Архивирано из оригинала 05. 09. 2009. г. 
  3. ^ „Comins Synthesis of Camptothecin”. Архивирано из оригинала 05. 09. 2009. г. 
  4. ^ „Rapaport Synthesis of Camptothecin”. Архивирано из оригинала 07. 09. 2009. г. 
  5. ^ Takimoto CH, Calvo E. "Principles of Oncologic Pharmacotherapy" Архивирано на сајту Wayback Machine (15. мај 2009) in Pazdur R, Wagman LD, Camphausen KA, Hoskins WJ (Eds) Cancer Management: A Multidisciplinary Approach Архивирано на сајту Wayback Machine (4. октобар 2013). 11 ed. 2008.
  6. ^ M.E. Wall, M.C.Wani, C.E. Cook, K.H.Palmer, A.I.McPhail, G.A.Sim (1966). „Plant antitumor agents. I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from camptotheca acuminate”. Journal of the American Chemical Society. 88 (16): 3888—3890. doi:10.1021/ja00968a057. 
  7. ^ G. Samuelsson (2004). Drugs of Natural Origin: a Textbook of Pharmacognosy. Swedish pharmaceutical press, Stokkholm (5 изд.). ISBN 91-974318-4-2. 

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Kamptotecin
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