Identification and evaluation of antioxidant, analgesic/anti-inflammatory activity of the most active ninhydrin-phenol adducts synthesized

K.R. Prabhakar, V.P. Veerapur, P. Bansal, K.P. Vipan, K.M. Reddy, A. Barik, B.K.D. Reddy, P. Reddanna, K.I. Priyadarsini, M.K. Unnikrishnan

Research output: Contribution to journalArticle

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Abstract

Treatment of phenols with ninhydrin in acidic medium afforded 2-hydroxy-2-(ortho-hydroxy-phenyl/naphthyl)-1,3-dioxoindanes, which being unstable were isolated in their hemiketal forms. These synthesized compounds were subjected to TLC screening for radical scavenging and in vitro lipoxgenase and cycloxygenase enzyme inhibition assays. The best compound was identified and studied in detail for steady-state and time-resolved free radical kinetics, viz., DPPH, ABTS{radical dot}-, {radical dot}OH and rate constants for these reactions were evaluated. The best compound was also subjected to in vivo anti-inflammatory and analgesic activities in which the compound showed good promise for further structural optimization. © 2006 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)7113-7120
Number of pages8
JournalBioorganic and Medicinal Chemistry
Volume14
Issue number21
DOIs
Publication statusPublished - 2006

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Ninhydrin
Enzyme inhibition
Structural optimization
Phenols
Scavenging
Enzyme Assays
Non-Steroidal Anti-Inflammatory Agents
Phenol
Free Radicals
Rate constants
Assays
Screening
Antioxidants
Kinetics
2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid
In Vitro Techniques

Cite this

Prabhakar, K.R. ; Veerapur, V.P. ; Bansal, P. ; Vipan, K.P. ; Reddy, K.M. ; Barik, A. ; Reddy, B.K.D. ; Reddanna, P. ; Priyadarsini, K.I. ; Unnikrishnan, M.K. / Identification and evaluation of antioxidant, analgesic/anti-inflammatory activity of the most active ninhydrin-phenol adducts synthesized. In: Bioorganic and Medicinal Chemistry. 2006 ; Vol. 14, No. 21. pp. 7113-7120.
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abstract = "Treatment of phenols with ninhydrin in acidic medium afforded 2-hydroxy-2-(ortho-hydroxy-phenyl/naphthyl)-1,3-dioxoindanes, which being unstable were isolated in their hemiketal forms. These synthesized compounds were subjected to TLC screening for radical scavenging and in vitro lipoxgenase and cycloxygenase enzyme inhibition assays. The best compound was identified and studied in detail for steady-state and time-resolved free radical kinetics, viz., DPPH, ABTS{radical dot}-, {radical dot}OH and rate constants for these reactions were evaluated. The best compound was also subjected to in vivo anti-inflammatory and analgesic activities in which the compound showed good promise for further structural optimization. {\circledC} 2006 Elsevier Ltd. All rights reserved.",
author = "K.R. Prabhakar and V.P. Veerapur and P. Bansal and K.P. Vipan and K.M. Reddy and A. Barik and B.K.D. Reddy and P. Reddanna and K.I. Priyadarsini and M.K. Unnikrishnan",
note = "Cited By :42 Export Date: 10 November 2017 CODEN: BMECE Correspondence Address: Unnikrishnan, M.K.; Department of Pharmacology, Manipal College of Pharmaceutical Sciences, Manipal, 576 104, India; email: cheruvaloor@yahoo.com Chemicals/CAS: lipoxygenase, 9027-17-2, 9029-60-1; ninhydrin, 17596-88-2, 2462-59-1, 485-47-2, 938-24-9; phenol, 108-95-2, 3229-70-7; prostaglandin synthase, 39391-18-9, 59763-19-8, 9055-65-6; Analgesics; Anti-Inflammatory Agents; Antioxidants; Cyclooxygenase Inhibitors; Free Radicals; Lipoxygenase Inhibitors; Ninhydrin, 485-47-2; Phenol, 108-95-2 References: Ruhemann, S., (1910) Trans. Chem. Soc., 97, p. 1438; Kundu, S.K., Pramanik, A., Patra, A., (2002) Syn. lett., 5, p. 823; Klumpp, D.A., Fredrick, S., Lau, S., Jin, K.K., Bau, R., Surya Prakash, G.K., Olah, G.A., (1999) J. Org. Chem., 64, p. 5152; Kundu, S.K., Patra, A., Pramanik, A., (2004) Indian J. Chem., 43 B, p. 604; Filimonov, D.A., Poroikov, V.V., (1996) Bioactive Compound Design: Possibilities for Industrial Use, pp. 47-56. , BIOS Scientific Publishers, Oxford; Lagunin, A., Stepanchikova, A., Filimonov, D., Poroikov, V., (2000) Bioinformatics, 16, p. 747; Brooks, C.D.W., Summers, J.B., (1996) J. Med. Chem., 39, p. 2629; Lewis, R.A., Austen, K.F., (1981) Nature, 293, p. 103; Shaw, A., Krell, R.D., (1991) J. Med. Chem., 34, p. 1235; McMillan, R.M., Walker, E.R.H., (1992) Trends Pharm. Sci., 13, p. 323; Kontogiorgis, C.A., Hadjipavlou-Litina, D.J., (2002) Curr. Med. Chem., 9, p. 89; Cummings, B.S., McHowat, J., Schnellmann, R.G., (2000) J. Pharmacol. Exp. Ther., 294, p. 793; Shen, T.Y., (1980) Burger's Medicinal Chemistry, pp. 1217-1219. , Wolf M.E. (Ed), John Wiley, New York; Winter, C.A., (1965) Non-steroidal Anti-inflammatory Drugs, p. 190. , Garattini S., and Dukes M.N.G. (Eds), Excepta Medica, Amsterdam; Kuroda, T., Suzuki, F., Tamura, T., Ohmori, K., Hosoe, H., (1992) J. Med. Chem., 53, p. 1130; Reddanna, P., Whelan, J., Maddipati, K.R., Reddy, C.C., (1990) Methods Enzymol., 187, p. 268; Shimizu, T., Radmark, O., Samuelsson, B., (1984) Proc. Natl. Acad. Sci. U.S.A, 81, p. 689; Madhava Reddy, C., Bhat, V.B., Kiranmai, G., Narsa Reddy, M., Reddanna, P., Madyastha, K.M., (2000) Biochem. Biophys. Res. Commun., 277, p. 599; Copeland, R.A., Williams, J.M., Giannaras, J., Nurnberg, S., Covington, M., Pinto, D., Pick, S., Trzaskos, J.M., (1994) Proc. Natl. Acad. Sci. U.S.A., 91, p. 11202; Narla, R.S., Rao, M.N.A., (1995) J. Pharm. Pharmacol., 47, p. 623; Mishra, B., Priyadarsini, K.I., Sudheer Kumar, M., Unnikrishnan, M.K., (2003) Bioorg. Med. Chem., 11, p. 2677; Kunchandy, E., Rao, M.N.A., (1989) Int. J. Pharmaceut., 57, p. 173; Sudheer Kumar, M., Jagadish, P.C., Sridhar, R.B., Kiran, B.S., Unnikrishnan, M.K., (2003) Nahrung/Food, 47, p. 126; Kulkarni, S.K., (1984) Hand Book of Experimental Pharmacology. 3rd ed., pp. 168-171. , Vallabh Prakashan, New Delhi, India; Li, W.D., Lee, E.B., Kang, S.S., Hym, J.E., Whang, W.K., (2002) Chem. Pharm. Bull., 50, p. 900; Vogel, H.G., Vogel, W.H., (1997) Drug Discovery and Evaluation: Pharmacological Assays, p. 404. , Vogel H.G., and Vogel W.H. (Eds), Springer-Verlag, Berlin Heidelberg, Germany; Whittle, B.A., (1949) Br. J. Pharmacol., 22, p. 246",
year = "2006",
doi = "10.1016/j.bmc.2006.06.068",
language = "English",
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journal = "Bioorganic and Medicinal Chemistry",
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Prabhakar, KR, Veerapur, VP, Bansal, P, Vipan, KP, Reddy, KM, Barik, A, Reddy, BKD, Reddanna, P, Priyadarsini, KI & Unnikrishnan, MK 2006, 'Identification and evaluation of antioxidant, analgesic/anti-inflammatory activity of the most active ninhydrin-phenol adducts synthesized', Bioorganic and Medicinal Chemistry, vol. 14, no. 21, pp. 7113-7120. https://doi.org/10.1016/j.bmc.2006.06.068

Identification and evaluation of antioxidant, analgesic/anti-inflammatory activity of the most active ninhydrin-phenol adducts synthesized. / Prabhakar, K.R.; Veerapur, V.P.; Bansal, P.; Vipan, K.P.; Reddy, K.M.; Barik, A.; Reddy, B.K.D.; Reddanna, P.; Priyadarsini, K.I.; Unnikrishnan, M.K.

In: Bioorganic and Medicinal Chemistry, Vol. 14, No. 21, 2006, p. 7113-7120.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Identification and evaluation of antioxidant, analgesic/anti-inflammatory activity of the most active ninhydrin-phenol adducts synthesized

AU - Prabhakar, K.R.

AU - Veerapur, V.P.

AU - Bansal, P.

AU - Vipan, K.P.

AU - Reddy, K.M.

AU - Barik, A.

AU - Reddy, B.K.D.

AU - Reddanna, P.

AU - Priyadarsini, K.I.

AU - Unnikrishnan, M.K.

N1 - Cited By :42 Export Date: 10 November 2017 CODEN: BMECE Correspondence Address: Unnikrishnan, M.K.; Department of Pharmacology, Manipal College of Pharmaceutical Sciences, Manipal, 576 104, India; email: cheruvaloor@yahoo.com Chemicals/CAS: lipoxygenase, 9027-17-2, 9029-60-1; ninhydrin, 17596-88-2, 2462-59-1, 485-47-2, 938-24-9; phenol, 108-95-2, 3229-70-7; prostaglandin synthase, 39391-18-9, 59763-19-8, 9055-65-6; Analgesics; Anti-Inflammatory Agents; Antioxidants; Cyclooxygenase Inhibitors; Free Radicals; Lipoxygenase Inhibitors; Ninhydrin, 485-47-2; Phenol, 108-95-2 References: Ruhemann, S., (1910) Trans. Chem. Soc., 97, p. 1438; Kundu, S.K., Pramanik, A., Patra, A., (2002) Syn. lett., 5, p. 823; Klumpp, D.A., Fredrick, S., Lau, S., Jin, K.K., Bau, R., Surya Prakash, G.K., Olah, G.A., (1999) J. Org. Chem., 64, p. 5152; Kundu, S.K., Patra, A., Pramanik, A., (2004) Indian J. Chem., 43 B, p. 604; Filimonov, D.A., Poroikov, V.V., (1996) Bioactive Compound Design: Possibilities for Industrial Use, pp. 47-56. , BIOS Scientific Publishers, Oxford; Lagunin, A., Stepanchikova, A., Filimonov, D., Poroikov, V., (2000) Bioinformatics, 16, p. 747; Brooks, C.D.W., Summers, J.B., (1996) J. Med. Chem., 39, p. 2629; Lewis, R.A., Austen, K.F., (1981) Nature, 293, p. 103; Shaw, A., Krell, R.D., (1991) J. Med. Chem., 34, p. 1235; McMillan, R.M., Walker, E.R.H., (1992) Trends Pharm. Sci., 13, p. 323; Kontogiorgis, C.A., Hadjipavlou-Litina, D.J., (2002) Curr. Med. Chem., 9, p. 89; Cummings, B.S., McHowat, J., Schnellmann, R.G., (2000) J. Pharmacol. Exp. Ther., 294, p. 793; Shen, T.Y., (1980) Burger's Medicinal Chemistry, pp. 1217-1219. , Wolf M.E. (Ed), John Wiley, New York; Winter, C.A., (1965) Non-steroidal Anti-inflammatory Drugs, p. 190. , Garattini S., and Dukes M.N.G. (Eds), Excepta Medica, Amsterdam; Kuroda, T., Suzuki, F., Tamura, T., Ohmori, K., Hosoe, H., (1992) J. Med. Chem., 53, p. 1130; Reddanna, P., Whelan, J., Maddipati, K.R., Reddy, C.C., (1990) Methods Enzymol., 187, p. 268; Shimizu, T., Radmark, O., Samuelsson, B., (1984) Proc. Natl. Acad. Sci. U.S.A, 81, p. 689; Madhava Reddy, C., Bhat, V.B., Kiranmai, G., Narsa Reddy, M., Reddanna, P., Madyastha, K.M., (2000) Biochem. Biophys. Res. Commun., 277, p. 599; Copeland, R.A., Williams, J.M., Giannaras, J., Nurnberg, S., Covington, M., Pinto, D., Pick, S., Trzaskos, J.M., (1994) Proc. Natl. Acad. Sci. U.S.A., 91, p. 11202; Narla, R.S., Rao, M.N.A., (1995) J. Pharm. Pharmacol., 47, p. 623; Mishra, B., Priyadarsini, K.I., Sudheer Kumar, M., Unnikrishnan, M.K., (2003) Bioorg. Med. Chem., 11, p. 2677; Kunchandy, E., Rao, M.N.A., (1989) Int. J. Pharmaceut., 57, p. 173; Sudheer Kumar, M., Jagadish, P.C., Sridhar, R.B., Kiran, B.S., Unnikrishnan, M.K., (2003) Nahrung/Food, 47, p. 126; Kulkarni, S.K., (1984) Hand Book of Experimental Pharmacology. 3rd ed., pp. 168-171. , Vallabh Prakashan, New Delhi, India; Li, W.D., Lee, E.B., Kang, S.S., Hym, J.E., Whang, W.K., (2002) Chem. Pharm. Bull., 50, p. 900; Vogel, H.G., Vogel, W.H., (1997) Drug Discovery and Evaluation: Pharmacological Assays, p. 404. , Vogel H.G., and Vogel W.H. (Eds), Springer-Verlag, Berlin Heidelberg, Germany; Whittle, B.A., (1949) Br. J. Pharmacol., 22, p. 246

PY - 2006

Y1 - 2006

N2 - Treatment of phenols with ninhydrin in acidic medium afforded 2-hydroxy-2-(ortho-hydroxy-phenyl/naphthyl)-1,3-dioxoindanes, which being unstable were isolated in their hemiketal forms. These synthesized compounds were subjected to TLC screening for radical scavenging and in vitro lipoxgenase and cycloxygenase enzyme inhibition assays. The best compound was identified and studied in detail for steady-state and time-resolved free radical kinetics, viz., DPPH, ABTS{radical dot}-, {radical dot}OH and rate constants for these reactions were evaluated. The best compound was also subjected to in vivo anti-inflammatory and analgesic activities in which the compound showed good promise for further structural optimization. © 2006 Elsevier Ltd. All rights reserved.

AB - Treatment of phenols with ninhydrin in acidic medium afforded 2-hydroxy-2-(ortho-hydroxy-phenyl/naphthyl)-1,3-dioxoindanes, which being unstable were isolated in their hemiketal forms. These synthesized compounds were subjected to TLC screening for radical scavenging and in vitro lipoxgenase and cycloxygenase enzyme inhibition assays. The best compound was identified and studied in detail for steady-state and time-resolved free radical kinetics, viz., DPPH, ABTS{radical dot}-, {radical dot}OH and rate constants for these reactions were evaluated. The best compound was also subjected to in vivo anti-inflammatory and analgesic activities in which the compound showed good promise for further structural optimization. © 2006 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.bmc.2006.06.068

DO - 10.1016/j.bmc.2006.06.068

M3 - Article

VL - 14

SP - 7113

EP - 7120

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

SN - 0968-0896

IS - 21

ER -