Abstract
A new dipeptide derivative, ethyl 2-(3-(4-hydroxyphenyl)-2-(2-(4-phenyl-5-((pyridin-4-ylamino)methyl)-4H-1,2,4-triazol-3-ylthio)acetamido)propanamido)-3-(1H-indol-3-yl)propanoate (EHPTIP) was successfully synthesized and radiolabeled with 125I by the direct electrophilic substitution method. The non radiolabeled compound (EHPTIP) was tested as an antimicrobial agent and the radiolabeled derivative was tested as a new imaging agent. The study results showed a good antimicrobial activity of EHPTIP and a good in vitro and in vivo stability of 125I-EHPTIP. The biodistribution of the radiolabeled compound showed a high brain uptake of 7.60 ± 0.01 injected activity/g tissue organ at 30 min post-injection and retention in brain remained high up to 1 h, whereas the clearance from the normal mice appeared to proceed via the renal system. Such brain uptake is better than that of currently used radiopharmaceuticals for brain imaging (99mTc-ECD and 99mTc-HMPAO). As a conclusion, EHPTIP is a newly synthesized dipeptide with a good antimicrobial activity and the radioiodinated EHPTIP which is labeled with 123I could be used as a novel agent for brain SPECT.
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Dahiya R, Kumar A, Yadav R (2008) Molecules 13:958–976
Siddiqui N, Andalip BS, Ali R, Afzal O, Akhtar MJ, Azad B, Kumar R (2011) J Pharm Bioall Sci 3(20):194–212
Kumar JR (2010) Pharmacophore 1(3):167–177
Amr AG, Mohamed AM, Mohamed SF, Abdel-Hafez NA, Hammam AG (2006) Bioorg Medicinal Chem 14:5481–5488
Bart A, Jansen J, Zwan JV, Dulk H, Brouwer J, Reedijk J (2001) J Med Chem 44:245–249
Shinkai H, Ito T, Iida T, Kitao Y, Yamada H, Uchida I (2000) J Med Chem 43:4667–4677
Klimesova V, Svoboda M, Waisser K, Pour M, Kaustova J (1999) Farmaco 54:666–672
Maria GM, Valeria F, Daniele Z, Luciano V, Elena BJ (2001) Farmaco 56:587–592
Goda FE, Abdel-Aziz AAM, Attef OA (2004) Bioorg Medicinal Chem 12:1845–1852
Bhatia MS, Mulani AK, Choudhari PB, Ingale KB, Bhatia NM (2009) Int J Drug Discov 1:1–9
Muthal N, Ahirwar J, Ahriwar D, Masih P, Mahmdapure T, Sivakumar T (2010) Int J Pharm Tech Res 2(4):2450–2455
El Ashry HE, Kassem AAK, Abdel Hameed MH (2009) Carbohydr Res 344:725–733
Sztanke M, Tuzimski T, Rzymowska J, Pasternak K, Kandefer-Szerszen M (2008) Eur J Med Chem 43:404–419
Foroughifar N, Mobinikhaledi A, Ebrahimi S, Moghanian H, Fard BAM, Kalhor M (2009) Tetrahedron Lett 50:836–839
Isloor MA, Kalluraya B, Shetty P (2009) Eur J Med Chem 44:3784–3787
Qin X, Yu H, Liu J, Dai BG, Qin Z, Zhang X, Wang T, Fang J (2009) Arkivoc ii: 201–210
Khanmohammadi H, Abnosi HM, Hosseinzadeh A, Erfantalab M (2008) Spectrochim Acta A 71:1474–1480
Poojary B, Belagali SL, Kumar KH, Holla BS (2003) Farmaco 58:569–572
Levit GL, Anikina LV, Vikharev YB, Demin AM, Safin VA, Matveeva TV, Krasnov VP (2002) Pharm Chem J 36:232–236
Belagali SL, Kumar KH, Holla BS, Bhagwat A (2001) Indian J Heterocycl Chem 10:249–252
Himaja M, Rajiv RMV, Poojary B, Satyanarayana D, Subrahmanyam EV, Bhat KI (2003) Boll Chim Farm 142:450–453
Himaja M, Rajiv RMV (2002) Indian J Heterocycl Chem 12:121–124
Aboelmagd A, Ali IAI, Salem EMS, Abdel-Razik M (2011) Arkivoc ix:337–353
El-rayes SM (2010) Molecules 15:6759–6772
Bolton R (2002) J Labelled Compds Radiopharm 45:485–528
Adam MJ, Wilbur DS (2005) Chem Soc Rev 34:153–163
Amin AM, Soliman SE, Killa HM, Abd El-Aziz H (2010) J Radioanal Nucl Chem 283:273–278
El-Azony KM (2010) J Radioanal Nucl Chem 285:315–320
Newberg AB, Plössl K, Mozley PD, Stubbs JB, Wintering N, Udeshi M, Alavi A, Kauppinen T, Kung HF (2004) J Nucl Med 45:834–841
Moretti JL, Caglar M, Weinmann P (1995) J Nucl Med 36:359–363
Liu FEI, Youfeng HE, Luo Z (2004) IAEA, Austria, Technical Reports Series No 426, pp 37–52
Rhodes BA (1974) Semin J Nucl Med 4:281–293
Fathalla W, Čajan M, Pazdera P (2001) Molecules 6:557–573
Fathalla W, El Rayes SM, Ali IAI (2007) Arkivoc xvi:173–186
Ali IAI, Fathalla W, El Rayes SM (2008) Arkivoc xiii:179–188
El Rayes SM (2008) Arkivoc xvi:243–254
Hofmann K, Johl A, Furlemeier AE, Koppeler HJ (1957) J Am Chem Soc 79:1636–1641
Hofmann K, Thompson TA, Yajima H, Schwarts ET, Enouye H (1960) J Am Chem Soc 82:3715–3720
El Rayes SM, Ali IAI, Fathalla W (2008) Arkivoc xi:86–95
Bodansky M (1993) Principles of peptide synthesis, 2nd edn. Springer, Berlin, p 20
Coenen HH, Mertens J, Maziere B (2006) Radioionidation reactions for radiopharmaceuticals. Compendium for effective synthesis strategies, chap. 4. Springer, Dordrecht, p 64
Tolmachev V, Bruskin A, Sivaev I, Lundqvist H, Sjöberg S (2002) Radiochim. Acta 90:229–235
Perez C, Pauli M, Bazerque P (1990) Acta Biol Med Exp 15:113–115
Neirinckx RD, Canning LR, Piper IM, Nowotnik DP, Pickett RD, Holmes RA, Volkert WA, Forster AM, Weisner PS, Marriott JA, Chaplin SB (1987) J Nucl Med 28:191–202
Motaleb MA, El-Kolaly MT, Rashed HM, Abd El-Bary A (2011) J Radioanal Nucl Chem 289:915–921
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Abdel-Ghany, I.Y., Moustafa, K.A., Abdel-Bary, H.M. et al. Synthesis, radioiodination and biological evaluation of novel dipeptide attached to triazole-pyridine moiety. J Radioanal Nucl Chem 295, 1273–1281 (2013). https://doi.org/10.1007/s10967-012-2237-5
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DOI: https://doi.org/10.1007/s10967-012-2237-5