Synthesis of a new pH-sensitive folate-doxorubicin conjugate and its antitumor activity in vitro

Journal of Pharmaceutical Sciences

Volumn 102, Issue 2, 2013, Pages 530-540

  Ye, Wei Liang ^a   Teng, Zeng Hui ^a   Liu, Dao Zhou ^a   Cui, Han ^a   Liu, Miao ^a   Cheng, Ying ^a   Yang, Tie Hong ^a   Mei, Qi Bing ^a   Zhou, Si Yuan ^a  

^a FOURTH MILITARY MEDICAL UNIVERSITY   (China)

Author keywords

Cancer; Conjugation; Controlled release; Doxorubicin; Drug delivery systems; Drug targeting; Folate receptor; Folic acid; In vitro

Indexed keywords

AMINOCAPROIC ACID; DOXORUBICIN; FOLATE RECEPTOR; FOLIC ACID; FOLIC ACID AMINOCAPROIC ACI DOXORUBICIN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOLOGICAL MONITORING; CANCER CELL CULTURE; CELL STRAIN HEPG2; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DRUG CONJUGATION; DRUG DISTRIBUTION; DRUG RELEASE; DRUG SYNTHESIS; DRUG TARGETING; DRUG UPTAKE; ELECTROSPRAY MASS SPECTROMETRY; FLUORESCENCE MICROSCOPY; HUMAN; HUMAN CELL; IN VITRO STUDY; PH; PROTEIN EXPRESSION; PROTON NUCLEAR MAGNETIC RESONANCE; TANDEM MASS SPECTROMETRY;

EID: 84872497954     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.23381     Document Type: Article

References (26)

1. Minko T, Kopeckova P, Pozharov V, Kopecek J. 1998. HPMA copolymer bound adriamycin overcomes MDR1 gene en-coded resistance in a human ovarian carcinoma cell line. J Control Release 54:223-233.
2. Peterson CM, Shiah JG, Sun Y, Kopecková P, Minko T, Straight RC, Kopecek J. 2003. HPMA copolymer delivery of chemotherapy and photodynamic therapy in ovarian cancer. Adv Exp Med Biol 519:101-123.
3. Duncan R. 2003. The dawning era of polymer therapeutics. Nat Rev Drug Discov 2:347-360.
4. Mezo G, Manea M. 2010. Receptor-mediated tumor targeting based on peptide hormones. Expert Opin Drug Deliv. 7:79-96.
5. Nagy A, Schally AV, Armatis P, Szepeshazi K, Halmos G, Kovacs M, Zarandi M, Groot K, Miyazaki M, Jungwirth A, Horvath J. 1996. Cytotoxic analogs of luteinizing hormone-releasing hormone containing doxorubicin or 2-pyrrolinodoxorubicin, a derivative 500-1000 times more potent. Proc Natl Acad Sci U S A. 93:7269-7273.
6. Günthert AR, Gründker C, Bongertz T, Schlott T, Nagy A, Schally AV, Emons G. 2004. Internalization of cytotoxic analog AN-152 of luteinizing hormone-releasing hormone induces apoptosis in human endometrial and ovarian cancer cell lines independent of multidrug resistance-1 (MDR-1) system. Am J Obstet Gynecol 191:1164-1172.
7. Engel J, Emons G, Pinski J, Schally AV. 2012. AEZS-108: A targeted cytotoxic analog of LHRH for the treatment of cancers positive for LHRH receptors. Expert Opin Investig Drugs 21:891-899.
8. Leurs U, Lajkó E, Mezo G, Orbán E, Öhlschläger P, Marquardt A, Kohidai L, Manea M. 2012. GnRH-III based multifunctional drug delivery systems containing daunorubicin and methotrexate. Eur J Med Chem 52:173-183.
9. Zhao X, Li H, Lee RJ. 2008. Targeted drug delivery via folate receptors. Expert Opin Drug Deliv 5:309-319.
10. Lu Y, Low PS. 2002. Folate-mediated delivery of macromolecular anticancer therapeutic agents. Adv Drug Deliv Rev 54:675-693.
11. Han X, Liu J, Xie C, Zhan C, Gu B, Liu Y. 2009. 9-NC-loaded folate-conjugated polymer micelles as tumor targeted drug delivery system: Preparation and evaluation in vitro. Int J Pharm 372:125-131.
12. Gabizon A, Shmeeda H, Horowitz AT. 2004. Tumor cell targeting of liposome-entrapped drugs with phospholipid-anchored folic acid-PEG conjugates. Adv Drug Deliv Rev 56:1177-1192.
13. Yoo HS, Park TG. 2004. Folate-receptor-targeted delivery of doxorubicin nano-aggregates stabilized by doxorubicin-PEG-folate conjugate. J Control Release 100:247-256.
14. Antony A, Tang YS, Khan RA. 2004. Translational upregulation of folate receptors is mediated by homocysteine via RNA-heterogeneous nuclear ribonucleoprotein E1 interactions. J Clin Invest 113:285-301.
15. Orbán E, Mezo G, Schlage P, Csík G, Kulić Z, Ansorge P, Fellinger E, Möller HM, Manea M. 2011. In vitro degradation and antitumor activity of oxime bond-linked daunorubicin-GnRH-III bioconjugates and DNA-binding properties of daunorubicin-amino acid metabolites. Amino Acids 41:469-483.
16. Shmeeda H, Amitay Y, Gorin J, Tzemach D, Mak L, Gabizon A. 2010. Delivery of zoledronic acid encapsulated in folate-targeted liposome results in potent in vitro cytotoxic activity on tumor cells. J Control Release 146:76-83.
17. 67Ga-deferoxamine-folate, a potential radiopharmaceutical for tumor imaging. Bioconjug Chem 7:56-62.
18. 111In]DTPA-folate for use as a tumor-targeted radiopharmaceutical. Bioconjug Chem 8:673-679.
19. Di Stefano G, Lanza M, Kratz F. 2004. A novel method for coupling doxorubicin to lactosaminated human albumin by an acid sensitive hydrazone bond: Synthesis, characterization and preliminary biological properties of the conjugate. Eur J Pharm Sci 23:393-397.
20. Ulbrich K, Šubr V. 2004. Polymeric anticancer drugs with pH-controlled activation. Adv Drug Deliv Rev 56:1023-1050.
21. Chytil P, Etrych T, Konak C. 2006. Properties of HPMA copolymer-doxorubicin conjugates with pH-controlled activation: Effect of polymer chain modification. J Control Release 115:26-36.
22. Bareford LM, Swaan PW. 2007. Endocytic mechanisms for targeted drug delivery. Adv Drug Deliv Rev 59:748-758.
23. Midoux P, Pichon C, Yaouanc JJ, Jaffrès PA. 2009. Chemical vectors for gene delivery: A current review on polymers, peptides and lipids containing histidine or imidazole as nucleic acids carriers. Br J Pharmacol 157:166-178.
24. Gabbay EJ, Grier D, Pearce SW. 1976. Interaction specificity of the anthracyclines with DNA. Biochemistry 15:2062-2070.
25. Schlage P, Mezo G, Orbán E, Bosze S, Manea M. 2011. Anthracycline-GnRH derivative bioconjugates with different linkages: Synthesis, in vitro drug release and cytostatic effect. J Control Release 156:170-178.
26. Bareford LM, Swaan PW. 2007. Endocytic mechanisms for targeted drug delivery. Adv Drug Deliv Rev 59:748-758.