Application of a liquid chromatography-electrospray mass spectrometry (LC/MS) method to the biodistribution and excretion studies of novel 5′-chloro-2, 3-didehydroindolo (2′, 3′: 2, 3) betulinic acid (DRF-4012) in tumour-bearing mice

References

• Chen J, Korfmacher WA, Hsieh Y. (2005). Chiral liquid chromatography-tandem mass spectrometric methods for stereoisomeric pharmaceutical determinations. J Chromatogr B Analyt Technol Biomed Life Sci 820:1–8.
   PubMed Web of Science ®Google Scholar
• Deng Y, Snyder JK. (2002). Preparation of a 24-nor-1,4-dien-3-one triterpene derivative from betulin: a new route to 24-nortriterpene analogues. J Org Chem 67:2864–2873.
   Google Scholar
• Evers M, Poujade C, Soler F, Ribeill Y, James C, Lelièvre Y, Gueguen JC, Reisdorf D, Morize I, Pauwels R, De Clercq E, Hénin Y, Bousseau A, Mayaux JF, Le Pecq JB, Dereu N. (1996). Betulinic acid derivatives: a new class of human immunodeficiency virus type 1 specific inhibitors with a new mode of action. J Med Chem 39:1056–1068.
   PubMed Web of Science ®Google Scholar
• Fu I, Woolf EJ, Matuszewski BK. (1998). Effect of the sample matrix on the determination of indinavir in human urine by HPLC with turbo ion spray tandem mass spectrometric detection. J Pharm Biomed Anal 18:347–357.
   PubMed Web of Science ®Google Scholar
• Fulda S, Scaffidi C, Susin SA, Krammer PH, Kroemer G, Peter ME, Debatin KM. (1998). Activation of mitochondria and release of mitochondrial apoptogenic factors by betulinic acid. J Biol Chem 273:33942–33948.
   PubMed Web of Science ®Google Scholar
• Gabizon A, Catane R, Uziely B, Kaufman B, Safra T, Cohen R, Martin F, Huang A, Barenholz Y. (1994). Prolonged circulation time and enhanced accumulation in malignant exudates of doxorubicin encapsulated in polyethylene-glycol coated liposomes. Cancer Res 54:987–992.
   PubMed Web of Science ®Google Scholar
• Gabizon A, Papahadjopoulos D. (1988). Liposome formulations with prolonged circulation time in blood and enhanced uptake by tumors. Proc Natl Acad Sci USA 85:6949–6953.
   PubMed Web of Science ®Google Scholar
• Guidance for Industry: Bioanalytical Method Validation (2001). Rockville, MD: US Department of Health and Human Services, FDA, Center for Drug Evaluation and Research. Available at: http://www.fda.gov/cder/guidance/index.htm.
   Google Scholar
• Guo B, Li C, Deng Z, Chen S, Ji Z, Zhang J, Chen M, Xu F. (2005). A new method for measurement of (-)-sophocarpine, a candidate therapeutic for viral myocarditis, in plasma: application to a toxicokinetic study in beagle dogs. Rapid Commun Mass Spectrom 19:2840–2848.
   Google Scholar
• Jaggi M, Mukherjee R (1995). Establishment of tumorogenic cell lines from biopsies of human colon adenocarcinoma. J Appl Biomed 3:27–35.
   Google Scholar
• Jeong HJ, Chai HB, Park SY, Kim DS. (1999). Preparation of amino acid conjugates of betulinic acid with activity against human melanoma. Bioorg Med Chem Lett 9:1201–1204.
   PubMed Web of Science ®Google Scholar
• Kim YJ, Koo MH, Kim DS. (2001) Development of C-20 modified betulinic acid derivatives as antitumor agents. Bioorgan Med Chem Lett 11:2405–2408.
   PubMed Web of Science ®Google Scholar
• King R, Bonfiglio R, Fernandez-Metzler C, Miller-Stein C, Olah T. (2000). Mechanistic investigation of ionization suppression in electrospray ionization. J Am Soc Mass Spectrom 11:942–950.
   PubMed Web of Science ®Google Scholar
• Kumar V, Rani N, Aggarwal P, Sanna VK, Singh AT, Jaggi M, Joshi N, Sharma PK, Irchhaiya R, Burman AC. (2008). Synthesis and cytotoxic activity of heterocyclic ring-substituted betulinic acid derivatives. Bioorg Med Chem Lett 18:5058–5062.
   Google Scholar
• Kvasnica M, Sarek J, Klinotova E, Dzubak P, Hajduch M. (2005). Synthesis of phthalates of betulinic acid and betulin with cytotoxic activity. Bioorg Med Chem 13:3447–3454.
   PubMed Web of Science ®Google Scholar
• Liang HR, Takagaki T, Foltz RL, Bennett P. (2005). Quantitative determination of endogenous sorbitol and fructose in human nerve tissues by atmospheric-pressure chemical ionization liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom 19:2284–2294.
   PubMed Web of Science ®Google Scholar
• Mallet CR, Lu Z, Mazzeo JR. (2004). A study of ion suppression effects in electrospray ionization from mobile phase additives and solid-phase extracts. Rapid Commun Mass Spectrom 18:49–58.
   PubMed Web of Science ®Google Scholar
• Matuszewski BK, Constanzer ML, Chavez-Eng CM. (2003). Strategies for the assessment of matrix effect in quantitative bioanalytical methods based on HPLC-MS/MS. Anal Chem 75:3019–3030.
   PubMed Web of Science ®Google Scholar
• Mishra G, Singh MK, Awasthi A, Jaggi M Ahmad FJ. (2011) LC-UV detection of 5-chloro-2,3-didehydroindolo[2′,3′:2,3] betulinic acid in rat plasma and its application to a pharmacokinetic study. Chromatographia 73:281–289.
   Google Scholar
• Newman DJ, Cragg GM, Snader KM. (2003). Natural products as sources of new drugs over the period 1981-2002. J Nat Prod 66:1022–1037.
   PubMed Web of Science ®Google Scholar
• Singh SS, Patro B, Tripathi V, Srivastava A, Pandey SC, Ghosh AC. (2002) Betulinic acid and its pharmacological activity-a review. J Med Aromat Plant Sci 24:1031–1037.
   Google Scholar
• Urban M, Sarek J, Klinot J, Korinkova G, Hajduch M. (2004). Synthesis of A-seco derivatives of betulinic acid with cytotoxic activity. J Nat Prod 67:1100–1105.
   Google Scholar
• Van Hoof N, Courtheyn D, Antignac JP, Van de Wiele M, Poelmans S, Noppe H, De Brabander H. (2005). Multi-residue liquid chromatography/tandem mass spectrometric analysis of beta-agonists in urine using molecular imprinted polymers. Rapid Commun Mass Spectrom 19:2801–2808.
   Google Scholar
• Walker MA. (2001). Anti-HIV activity of betulinic acid analogue YKFH312. Drug Discov Today 6:859–861.
   Google Scholar
• You YJ, Kim Y, Nam NH, Ahn BZ. (2003). Synthesis and cytotoxic activity of A-ring modified betulinic acid derivatives. Bioorg Med Chem Lett 13:3137–3140.
   PubMed Web of Science ®Google Scholar